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class="vector-toc-numb">2</span> <span>Complexes of porphyrins</span> </div> </a> <ul id="toc-Complexes_of_porphyrins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ancient_porphyrins" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ancient_porphyrins"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Ancient porphyrins</span> </div> </a> <ul id="toc-Ancient_porphyrins-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory_synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Laboratory_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Laboratory synthesis</span> </div> </a> <ul id="toc-Laboratory_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Potential_applications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Potential_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Potential applications</span> </div> </a> <button aria-controls="toc-Potential_applications-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Potential applications subsection</span> </button> <ul id="toc-Potential_applications-sublist" class="vector-toc-list"> <li id="toc-Photodynamic_therapy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Photodynamic_therapy"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Photodynamic therapy</span> </div> </a> <ul id="toc-Photodynamic_therapy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Molecular_electronics_and_sensors" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Molecular_electronics_and_sensors"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Molecular electronics and sensors</span> </div> </a> <ul id="toc-Molecular_electronics_and_sensors-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_applications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biological_applications"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Biological applications</span> </div> </a> <ul id="toc-Biological_applications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Toxicology</span> </div> </a> <ul id="toc-Toxicology-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Gallery" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Gallery"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Gallery</span> </div> </a> <ul id="toc-Gallery-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Related_species" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Related_species"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Related species</span> </div> </a> <button aria-controls="toc-Related_species-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Related species subsection</span> </button> <ul id="toc-Related_species-sublist" class="vector-toc-list"> <li id="toc-In_nature" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_nature"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>In nature</span> </div> </a> <ul id="toc-In_nature-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Synthetic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Synthetic"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2</span> <span>Synthetic</span> </div> </a> <ul id="toc-Synthetic-sublist" class="vector-toc-list"> <li id="toc-Non-natural_porphyrin_isomers" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Non-natural_porphyrin_isomers"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.2.1</span> <span>Non-natural porphyrin isomers</span> </div> </a> <ul id="toc-Non-natural_porphyrin_isomers-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Porphyrin</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 37 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-37" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">37 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D9%88%D8%B1%D9%81%D9%8A%D8%B1%D9%8A%D9%86" title="بورفيرين – Arabic" lang="ar" hreflang="ar" data-title="بورفيرين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Porfirin" title="Porfirin – Bosnian" lang="bs" hreflang="bs" data-title="Porfirin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Porfirina" title="Porfirina – Catalan" lang="ca" hreflang="ca" data-title="Porfirina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Porfyriny" title="Porfyriny – Czech" lang="cs" hreflang="cs" data-title="Porfyriny" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Porphyrine" title="Porphyrine – German" lang="de" hreflang="de" data-title="Porphyrine" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Porf%C3%BCriinid" title="Porfüriinid – Estonian" lang="et" hreflang="et" data-title="Porfüriinid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A0%CE%BF%CF%81%CF%86%CF%85%CF%81%CE%AF%CE%BD%CE%B7" title="Πορφυρίνη – Greek" lang="el" hreflang="el" data-title="Πορφυρίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Porfirina" title="Porfirina – Spanish" lang="es" hreflang="es" data-title="Porfirina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Porfirino" title="Porfirino – Esperanto" lang="eo" hreflang="eo" data-title="Porfirino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Porfirina" title="Porfirina – Basque" lang="eu" hreflang="eu" data-title="Porfirina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D9%88%D8%B1%D9%81%DB%8C%D8%B1%DB%8C%D9%86" title="پورفیرین – Persian" lang="fa" hreflang="fa" data-title="پورفیرین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Porphyrine" title="Porphyrine – French" lang="fr" hreflang="fr" data-title="Porphyrine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Porfirina" title="Porfirina – Galician" lang="gl" hreflang="gl" data-title="Porfirina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%8F%AC%EB%A5%B4%ED%94%BC%EB%A6%B0" title="포르피린 – Korean" lang="ko" hreflang="ko" data-title="포르피린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8A%D5%B8%D6%80%D6%86%D5%AB%D6%80%D5%AB%D5%B6" title="Պորֆիրին – Armenian" lang="hy" hreflang="hy" data-title="Պորֆիրին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Porfirin" title="Porfirin – Croatian" lang="hr" hreflang="hr" data-title="Porfirin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Porfirino" title="Porfirino – Ido" lang="io" hreflang="io" data-title="Porfirino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Porfirina" title="Porfirina – Italian" lang="it" hreflang="it" data-title="Porfirina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Porphyrinus" title="Porphyrinus – Latin" lang="la" hreflang="la" data-title="Porphyrinus" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9F%D0%BE%D1%80%D1%84%D0%B8%D1%80%D0%B8%D0%BD" title="Порфирин – Macedonian" lang="mk" hreflang="mk" data-title="Порфирин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Porfirin" title="Porfirin – Malay" lang="ms" hreflang="ms" data-title="Porfirin" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Porfyrine" title="Porfyrine – Dutch" lang="nl" hreflang="nl" data-title="Porfyrine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%9D%E3%83%AB%E3%83%95%E3%82%A3%E3%83%AA%E3%83%B3" title="ポルフィリン – Japanese" lang="ja" hreflang="ja" data-title="ポルフィリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Porfyrin" title="Porfyrin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Porfyrin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Porfyrin" title="Porfyrin – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Porfyrin" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Porfiryny" title="Porfiryny – Polish" lang="pl" hreflang="pl" data-title="Porfiryny" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Porfirina" title="Porfirina – Portuguese" lang="pt" hreflang="pt" data-title="Porfirina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Porfirin%C4%83" title="Porfirină – Romanian" lang="ro" hreflang="ro" data-title="Porfirină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D0%BE%D1%80%D1%84%D0%B8%D1%80%D0%B8%D0%BD%D1%8B" title="Порфирины – Russian" lang="ru" hreflang="ru" data-title="Порфирины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Porfirin" title="Porfirin – Serbian" lang="sr" hreflang="sr" data-title="Porfirin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Porfirin" title="Porfirin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Porfirin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Porfyriinit" title="Porfyriinit – Finnish" lang="fi" hreflang="fi" data-title="Porfyriinit" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Porfyrin" title="Porfyrin – Swedish" lang="sv" hreflang="sv" data-title="Porfyrin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Porfirin" title="Porfirin – Turkish" lang="tr" hreflang="tr" data-title="Porfirin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D0%BE%D1%80%D1%84%D1%96%D1%80%D0%B8%D0%BD%D0%B8" title="Порфірини – Ukrainian" lang="uk" hreflang="uk" data-title="Порфірини" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%8D%9F%E5%95%89" title="卟啉 – Cantonese" lang="yue" hreflang="yue" data-title="卟啉" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%8D%9F%E5%95%89" title="卟啉 – Chinese" lang="zh" hreflang="zh" data-title="卟啉" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q422926#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit 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modified pyrrole subunits</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Perforin" class="mw-redirect" title="Perforin">Perforin</a> or <a href="/wiki/Porphyran" title="Porphyran">Porphyran</a>.</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Porphyrin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Porphyrin.svg/220px-Porphyrin.svg.png" decoding="async" width="220" height="221" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Porphyrin.svg/330px-Porphyrin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Porphyrin.svg/440px-Porphyrin.svg.png 2x" data-file-width="725" data-file-height="727" /></a><figcaption><a href="/wiki/Porphine" title="Porphine">Porphine</a>, the parent porphyrin</figcaption></figure> <p class="mw-empty-elt"> </p><p><b>Porphyrins</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'p' in 'pie'">p</span><span title="/ɔːr/: 'ar' in 'war'">ɔːr</span><span title="'f' in 'find'">f</span><span title="/ər/: 'er' in 'letter'">ər</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span><span title="'s' in 'sigh'">s</span></span>/</a></span></span> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key"><i title="English pronunciation respelling"><span style="font-size:90%">POR</span>-fər-ins</i></a>) are a group of <a href="/wiki/Heterocyclic_compound" title="Heterocyclic compound">heterocyclic</a>, <a href="/wiki/Macrocyclic" class="mw-redirect" title="Macrocyclic">macrocyclic</a>, <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a>, composed of four modified <a href="/wiki/Pyrrole" title="Pyrrole">pyrrole</a> subunits interconnected at their <a href="/wiki/Alpha_and_beta_carbon" class="mw-redirect" title="Alpha and beta carbon">α carbon</a> atoms via <a href="/wiki/Methine" class="mw-redirect" title="Methine">methine</a> bridges (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">=CH−</span>). In <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a>, an essential member of the porphyrin group is <a href="/wiki/Heme" title="Heme">heme</a>, which is a component of <a href="/wiki/Hemoprotein" title="Hemoprotein">hemoproteins</a>, whose functions include carrying <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> in the <a href="/wiki/Circulatory_system" title="Circulatory system">bloodstream</a>. In <a href="/wiki/Plants" class="mw-redirect" title="Plants">plants</a>, an essential porphyrin derivative is <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>, which is involved in <a href="/wiki/Light-harvesting_complex" title="Light-harvesting complex">light harvesting</a> and <a href="/wiki/Electron_transfer" title="Electron transfer">electron transfer</a> in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>. </p><p>The parent of porphyrins is <a href="/wiki/Porphine" title="Porphine">porphine</a>, a rare chemical compound of exclusively theoretical interest. Substituted porphines are called porphyrins.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> With a total of 26 π-electrons, of which 18 π-electrons form a planar, continuous cycle, the porphyrin ring structure is often described as <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> One result of the large <a href="/wiki/Conjugated_system" title="Conjugated system">conjugated system</a> is that porphyrins typically absorb strongly in the visible region of the electromagnetic spectrum, i.e. they are deeply colored. The name "porphyrin" derives from <a href="/wiki/Greek_language" title="Greek language">Greek</a> <i> </i>πορφύρα<i> (porphyra)</i> 'purple'.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Porphyrin_complexes" class="mw-redirect" title="Porphyrin complexes">Porphyrin complexes</a> consist of a square planar MN<sub>4</sub> core. The periphery of the porphyrins, consisting of sp<sup>2</sup>-hybridized carbons, generally display small deviations from planarity. "Ruffled" or saddle-shaped porphyrins is attributed to interactions of the system with its environment.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Additionally, the metal is often not centered in the N<sub>4</sub> plane.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> For free porphyrins, the two pyrrole protons are mutually trans and project out of the N<sub>4</sub> plane.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> These nonplanar distortions are associated with altered chemical and physical properties. <a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophyll</a>-rings are more distinctly nonplanar, but they are more saturated than porphyrins.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Complexes_of_porphyrins">Complexes of porphyrins</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=2" title="Edit section: Complexes of porphyrins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Transition_metal_porphyrin_complexes" title="Transition metal porphyrin complexes">Transition metal porphyrin complexes</a></div> <p>Concomitant with the displacement of two N-<i>H</i> protons, porphyrins bind metal ions in the N4 "pocket". The metal <a href="/wiki/Ion" title="Ion">ion</a> usually has a charge of 2+ or 3+. A schematic equation for these syntheses is shown, where M = metal ion and L = a <a href="/wiki/Ligand" title="Ligand">ligand</a>: </p> <dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>porphyrin + [ML<sub class="template-chem2-sub"><i>n</i></sub>]<sup>2+</sup> → M(porphyrinate)L<sub class="template-chem2-sub"><i>n</i>−4</sub> + 4 L + 2 H<sup class="template-chem2-sup">+</sup></span></dd></dl> <p><br /> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerycaption">Representative porphyrins and derivatives</li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 170px;"><span typeof="mw:File"><a href="/wiki/File:PPIXtransH.png" class="mw-file-description" title="Derivatives of protoporphyrin IX are common in nature, the precursor to hemes."><img alt="Derivatives of protoporphyrin IX are common in nature, the precursor to hemes." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/PPIXtransH.png/105px-PPIXtransH.png" decoding="async" width="105" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/PPIXtransH.png/158px-PPIXtransH.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/PPIXtransH.png/211px-PPIXtransH.png 2x" data-file-width="1216" data-file-height="1616" /></a></span></div> <div class="gallerytext">Derivatives of <a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">protoporphyrin IX</a> are common in nature, the precursor to <a href="/wiki/Heme" title="Heme">hemes</a>.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 170px;"><span typeof="mw:File"><a href="/wiki/File:H2octaethylporphyrin.png" class="mw-file-description" title="Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical."><img alt="Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP2− is highly symmetrical." src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/H2octaethylporphyrin.png/140px-H2octaethylporphyrin.png" decoding="async" width="140" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/H2octaethylporphyrin.png/210px-H2octaethylporphyrin.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/H2octaethylporphyrin.png/280px-H2octaethylporphyrin.png 2x" data-file-width="1623" data-file-height="1619" /></a></span></div> <div class="gallerytext"><a href="/wiki/Octaethylporphyrin" title="Octaethylporphyrin">Octaethylporphyrin</a> (H<sub>2</sub>OEP) is a synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, OEP<sup>2−</sup> is highly symmetrical.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 170px;"><span typeof="mw:File"><a href="/wiki/File:H2TPP.png" class="mw-file-description" title="Tetraphenylporphyrin (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methyne centers are occupied by phenyl groups."><img alt="Tetraphenylporphyrin (H2TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP2− is highly symmetrical. Another difference is that its methyne centers are occupied by phenyl groups." src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/H2TPP.png/140px-H2TPP.png" decoding="async" width="140" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/H2TPP.png/210px-H2TPP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/H2TPP.png/280px-H2TPP.png 2x" data-file-width="436" data-file-height="435" /></a></span></div> <div class="gallerytext"><a href="/wiki/Tetraphenylporphyrin" title="Tetraphenylporphyrin">Tetraphenylporphyrin</a> (H<sub>2</sub>TPP)is another synthetic analogue of protoporphyrin IX. Unlike the natural porphyrin ligands, TPP<sup>2−</sup> is highly symmetrical. Another difference is that its methyne centers are occupied by phenyl groups.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 170px;"><span typeof="mw:File"><a href="/wiki/File:Heme_B.svg" class="mw-file-description" title="Simplified view of heme, a complex of a protoporphyrin IX."><img alt="Simplified view of heme, a complex of a protoporphyrin IX." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Heme_B.svg/120px-Heme_B.svg.png" decoding="async" width="120" height="140" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Heme_B.svg/181px-Heme_B.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Heme_B.svg/241px-Heme_B.svg.png 2x" data-file-width="512" data-file-height="595" /></a></span></div> <div class="gallerytext">Simplified view of <a href="/wiki/Heme" title="Heme">heme</a>, a complex of a protoporphyrin IX.</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 170px;"><span typeof="mw:File"><a href="/wiki/File:CP40model.png" class="mw-file-description" title="A macrocycle of 40 porphyrin molecules, model"><img alt="A macrocycle of 40 porphyrin molecules, model" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/CP40model.png/140px-CP40model.png" decoding="async" width="140" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/CP40model.png/210px-CP40model.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/CP40model.png/280px-CP40model.png 2x" data-file-width="826" data-file-height="810" /></a></span></div> <div class="gallerytext">A macrocycle of 40 porphyrin molecules, model</div> </li> <li class="gallerybox" style="width: 175px"> <div class="thumb" style="width: 170px; height: 170px;"><span typeof="mw:File"><a href="/wiki/File:CP40-STM.png" class="mw-file-description" title="A macrocycle of 40 porphyrin molecules, STM image"><img alt="A macrocycle of 40 porphyrin molecules, STM image" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/CP40-STM.png/140px-CP40-STM.png" decoding="async" width="140" height="138" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/CP40-STM.png/210px-CP40-STM.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/CP40-STM.png/280px-CP40-STM.png 2x" data-file-width="548" data-file-height="540" /></a></span></div> <div class="gallerytext">A macrocycle of 40 porphyrin molecules, <a href="/wiki/Scanning_tunneling_microscope" title="Scanning tunneling microscope">STM image</a></div> </li> </ul> <div class="mw-heading mw-heading2"><h2 id="Ancient_porphyrins">Ancient porphyrins</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=3" title="Edit section: Ancient porphyrins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A geoporphyrin, also known as a petroporphyrin, is a porphyrin of geologic origin.<sup id="cite_ref-handbook_9-0" class="reference"><a href="#cite_note-handbook-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> They can occur in <a href="/wiki/Crude_oil" class="mw-redirect" title="Crude oil">crude oil</a>, <a href="/wiki/Oil_shale" title="Oil shale">oil shale</a>, coal, or sedimentary rocks.<sup id="cite_ref-handbook_9-1" class="reference"><a href="#cite_note-handbook-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Abelsonite" title="Abelsonite">Abelsonite</a> is possibly the only geoporphyrin mineral, as it is rare for porphyrins to occur in isolation and form crystals.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>The field of <a href="/wiki/Organic_geochemistry" title="Organic geochemistry">organic geochemistry</a> had its origins in the isolation of porphyrins from petroleum.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2020)">citation needed</span></a></i>]</sup> This finding helped establish the biological origins of petroleum. Petroleum is sometimes "fingerprinted" by analysis of trace amounts of nickel and <a href="/wiki/Vanadyl" class="mw-redirect" title="Vanadyl">vanadyl</a> porphyrins.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2020)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In non-photosynthetic <a href="/wiki/Eukaryotes" class="mw-redirect" title="Eukaryotes">eukaryotes</a> such as animals, insects, fungi, and <a href="/wiki/Protozoa" title="Protozoa">protozoa</a>, as well as the α-proteobacteria group of bacteria, the <a href="/wiki/Committed_step" title="Committed step">committed step</a> for porphyrin <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> is the formation of <a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">δ-aminolevulinic acid</a> (δ-ALA, 5-ALA or dALA) by the reaction of the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> <a href="/wiki/Glycine" title="Glycine">glycine</a> with <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a> from the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. In <a href="/wiki/Plants" class="mw-redirect" title="Plants">plants</a>, <a href="/wiki/Algae" title="Algae">algae</a>, <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> (except for the α-proteobacteria group) and <a href="/wiki/Archaea" title="Archaea">archaea</a>, it is produced from <a href="/wiki/Glutamic_acid" title="Glutamic acid">glutamic acid</a> via glutamyl-tRNA and <a href="/wiki/Glutamate-1-semialdehyde" title="Glutamate-1-semialdehyde">glutamate-1-semialdehyde</a>. The enzymes involved in this pathway are <a href="/wiki/Aminoacyl_tRNA_synthetases,_class_I" title="Aminoacyl tRNA synthetases, class I">glutamyl-tRNA synthetase</a>, <a href="/wiki/Glutamyl-tRNA_reductase" title="Glutamyl-tRNA reductase">glutamyl-tRNA reductase</a>, and <a href="/wiki/Glutamate-1-semialdehyde_2,1-aminomutase" title="Glutamate-1-semialdehyde 2,1-aminomutase">glutamate-1-semialdehyde 2,1-aminomutase</a>. This pathway is known as the C5 or Beale pathway. </p><p>Two molecules of dALA are then combined by <a href="/wiki/Porphobilinogen_synthase" class="mw-redirect" title="Porphobilinogen synthase">porphobilinogen synthase</a> to give <a href="/wiki/Porphobilinogen" title="Porphobilinogen">porphobilinogen</a> (PBG), which contains a pyrrole ring. Four PBGs are then combined through <a href="/wiki/Deamination" title="Deamination">deamination</a> into <a href="/wiki/Hydroxymethyl_bilane" class="mw-redirect" title="Hydroxymethyl bilane">hydroxymethyl bilane</a> (HMB), which is <a href="/wiki/Hydrolysation" class="mw-redirect" title="Hydrolysation">hydrolysed</a> to form the circular tetrapyrrole <a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">uroporphyrinogen III</a>. This molecule undergoes a number of further modifications. Intermediates are used in different species to form particular substances, but, in humans, the main end-product <a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">protoporphyrin IX</a> is combined with iron to form heme. Bile pigments are the breakdown products of heme. </p><p>The following scheme summarizes the biosynthesis of porphyrins, with references by EC number and the <a href="/wiki/OMIM" class="mw-redirect" title="OMIM">OMIM</a> database. The <a href="/wiki/Porphyria" title="Porphyria">porphyria</a> associated with the deficiency of each enzyme is also shown: </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Heme-Synthesis-Chemical-Details-Mirror.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Heme-Synthesis-Chemical-Details-Mirror.svg/600px-Heme-Synthesis-Chemical-Details-Mirror.svg.png" decoding="async" width="600" height="424" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Heme-Synthesis-Chemical-Details-Mirror.svg/900px-Heme-Synthesis-Chemical-Details-Mirror.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Heme-Synthesis-Chemical-Details-Mirror.svg/1200px-Heme-Synthesis-Chemical-Details-Mirror.svg.png 2x" data-file-width="1052" data-file-height="744" /></a><figcaption>Heme B biosynthesis pathway and its modulators. Major enzyme deficiences are also shown.</figcaption></figure> <table class="wikitable"> <tbody><tr> <th><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a> </th> <th>Location </th> <th><a href="/wiki/Substrate_(biochemistry)" class="mw-redirect" title="Substrate (biochemistry)">Substrate</a> </th> <th>Product </th> <th><a href="/wiki/Chromosome" title="Chromosome">Chromosome</a> </th> <th><a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> </th> <th><a href="/wiki/OMIM" class="mw-redirect" title="OMIM">OMIM</a> </th> <th><a href="/wiki/Disorder_(medicine)" class="mw-redirect" title="Disorder (medicine)">Disorder</a> </th></tr> <tr> <td><a href="/wiki/ALA_synthase" class="mw-redirect" title="ALA synthase">ALA synthase</a> </td> <td>Mitochondrion </td> <td><a href="/wiki/Glycine" title="Glycine">Glycine</a>, <a href="/wiki/Succinyl_CoA" class="mw-redirect" title="Succinyl CoA">succinyl CoA</a> </td> <td>δ-Aminolevulinic acid </td> <td>3p21.1 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?2.3.1.37">2.3.1.37</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=125290">125290</a> </td> <td>X-linked dominant protoporphyria, X-linked <a href="/wiki/Sideroblastic_anemia" title="Sideroblastic anemia">sideroblastic anemia</a> </td></tr> <tr> <td><a href="/wiki/ALA_dehydratase" class="mw-redirect" title="ALA dehydratase">ALA dehydratase</a> </td> <td>Cytosol </td> <td><a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">δ-Aminolevulinic acid</a> </td> <td>Porphobilinogen </td> <td>9q34 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?4.2.1.24">4.2.1.24</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=125270">125270</a> </td> <td><a href="/wiki/Aminolevulinic_acid_dehydratase_deficiency_porphyria" title="Aminolevulinic acid dehydratase deficiency porphyria">aminolevulinic acid dehydratase deficiency porphyria</a> </td></tr> <tr> <td><a href="/wiki/Porphobilinogen_deaminase" title="Porphobilinogen deaminase">PBG deaminase</a> </td> <td>Cytosol </td> <td><a href="/wiki/Porphobilinogen" title="Porphobilinogen">Porphobilinogen</a> </td> <td>Hydroxymethyl bilane </td> <td>11q23.3 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?2.5.1.61">2.5.1.61</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=176000">176000</a> </td> <td><a href="/wiki/Acute_intermittent_porphyria" title="Acute intermittent porphyria">acute intermittent porphyria</a> </td></tr> <tr> <td><a href="/wiki/Uroporphyrinogen_III_synthase" title="Uroporphyrinogen III synthase">Uroporphyrinogen III synthase</a> </td> <td>Cytosol </td> <td><a href="/wiki/Hydroxymethyl_bilane" class="mw-redirect" title="Hydroxymethyl bilane">Hydroxymethyl bilane</a> </td> <td>Uroporphyrinogen III </td> <td>10q25.2-q26.3 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?4.2.1.75">4.2.1.75</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=606938">606938</a> </td> <td><a href="/wiki/Congenital_erythropoietic_porphyria" class="mw-redirect" title="Congenital erythropoietic porphyria">congenital erythropoietic porphyria</a> </td></tr> <tr> <td><a href="/wiki/Uroporphyrinogen_III_decarboxylase" title="Uroporphyrinogen III decarboxylase">Uroporphyrinogen III decarboxylase</a> </td> <td>Cytosol </td> <td><a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">Uroporphyrinogen III</a> </td> <td>Coproporphyrinogen III </td> <td>1p34 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?4.1.1.37">4.1.1.37</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=176100">176100</a> </td> <td><a href="/wiki/Porphyria_cutanea_tarda" title="Porphyria cutanea tarda">porphyria cutanea tarda</a>, <a href="/wiki/Hepatoerythropoietic_porphyria" title="Hepatoerythropoietic porphyria">hepatoerythropoietic porphyria</a> </td></tr> <tr> <td><a href="/wiki/Coproporphyrinogen_III_oxidase" title="Coproporphyrinogen III oxidase">Coproporphyrinogen III oxidase</a> </td> <td>Mitochondrion </td> <td><a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">Coproporphyrinogen III</a> </td> <td>Protoporphyrinogen IX </td> <td>3q12 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?1.3.3.3">1.3.3.3</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=121300">121300</a> </td> <td><a href="/wiki/Hereditary_coproporphyria" title="Hereditary coproporphyria">hereditary coproporphyria</a> </td></tr> <tr> <td><a href="/wiki/Protoporphyrinogen_oxidase" title="Protoporphyrinogen oxidase">Protoporphyrinogen oxidase</a> </td> <td>Mitochondrion </td> <td><a href="/wiki/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a> </td> <td>Protoporphyrin IX </td> <td>1q22 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?1.3.3.4">1.3.3.4</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=600923">600923</a> </td> <td><a href="/wiki/Variegate_porphyria" title="Variegate porphyria">variegate porphyria</a> </td></tr> <tr> <td><a href="/wiki/Ferrochelatase" title="Ferrochelatase">Ferrochelatase</a> </td> <td>Mitochondrion </td> <td><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a> </td> <td>Heme </td> <td>18q21.3 </td> <td><a rel="nofollow" class="external text" href="http://www.expasy.org/cgi-bin/nicezyme.pl?4.99.1.1">4.99.1.1</a> </td> <td><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=177000">177000</a> </td> <td><a href="/wiki/Erythropoietic_protoporphyria" title="Erythropoietic protoporphyria">erythropoietic protoporphyria</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Laboratory_synthesis">Laboratory synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=5" title="Edit section: Laboratory synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Rothemund_reaction" title="Rothemund reaction">Rothemund reaction</a></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Tetratolylporphyrin.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tetratolylporphyrin.jpg/220px-Tetratolylporphyrin.jpg" decoding="async" width="220" height="268" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tetratolylporphyrin.jpg/330px-Tetratolylporphyrin.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Tetratolylporphyrin.jpg/440px-Tetratolylporphyrin.jpg 2x" data-file-width="1026" data-file-height="1249" /></a><figcaption>Brilliant crystals of <i>meso</i>-tetratolylporphyrin, prepared from <a href="/wiki/4-methylbenzaldehyde" class="mw-redirect" title="4-methylbenzaldehyde">4-methylbenzaldehyde</a> and pyrrole in refluxing <a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a></figcaption></figure> <p>A common synthesis for porphyrins is the <a href="/wiki/Rothemund_reaction" title="Rothemund reaction">Rothemund reaction</a>, first reported in 1936,<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> which is also the basis for more recent methods described by Adler and Longo.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The general scheme is a <a href="/wiki/Condensation_reaction" title="Condensation reaction">condensation</a> and <a href="/wiki/Organic_oxidation_reaction" class="mw-redirect" title="Organic oxidation reaction">oxidation</a> process starting with pyrrole and an <a href="/wiki/Aldehyde" title="Aldehyde">aldehyde</a>. </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:H2TPPsyn.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/H2TPPsyn.png/400px-H2TPPsyn.png" decoding="async" width="400" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5b/H2TPPsyn.png/600px-H2TPPsyn.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5b/H2TPPsyn.png/800px-H2TPPsyn.png 2x" data-file-width="1141" data-file-height="435" /></a></span></dd></dl> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Potential_applications">Potential applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=6" title="Edit section: Potential applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Photodynamic_therapy">Photodynamic therapy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=7" title="Edit section: Photodynamic therapy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Porphyrins have been evaluated in the context of <a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">photodynamic therapy</a> (PDT) since they strongly absorb light, which is then converted to heat in the illuminated areas.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> This technique has been applied in <a href="/wiki/Macular_degeneration" title="Macular degeneration">macular degeneration</a> using <a href="/wiki/Verteporfin" title="Verteporfin">verteporfin</a>.<sup id="cite_ref-pmid17636693_16-0" class="reference"><a href="#cite_note-pmid17636693-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>PDT is considered a noninvasive cancer treatment, involving the interaction between light of a determined frequency, a photo-sensitizer, and oxygen. This interaction produces the formation of a highly reactive oxygen species (ROS), usually singlet oxygen, as well as superoxide anion, free hydroxyl radical, or hydrogen peroxide.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> These high reactive oxygen species react with susceptible cellular organic biomolecules such as; lipids, aromatic amino acids, and nucleic acid heterocyclic bases, to produce oxidative radicals that damage the cell, possibly inducing apoptosis or even necrosis.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Molecular_electronics_and_sensors">Molecular electronics and sensors</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=8" title="Edit section: Molecular electronics and sensors"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Porphyrin-based compounds are of interest as possible components of <a href="/wiki/Molecular_electronics" title="Molecular electronics">molecular electronics</a> and photonics.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Synthetic porphyrin dyes have been incorporated in prototype <a href="/wiki/Dye-sensitized_solar_cells" class="mw-redirect" title="Dye-sensitized solar cells">dye-sensitized solar cells</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Biological_applications">Biological applications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=9" title="Edit section: Biological applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Porphyrins have been investigated as possible anti-inflammatory agents<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> and evaluated on their anti-cancer and anti-oxidant activity.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Several porphyrin-peptide conjugates were found to have antiviral activity against HIV <i>in vitro</i>.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicology">Toxicology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=10" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Heme biosynthesis is used as <a href="/wiki/Biomarker" title="Biomarker">biomarker</a> in environmental toxicology studies. While excess production of porphyrins indicate <a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">organochlorine</a> exposure, <a href="/wiki/Lead" title="Lead">lead</a> inhibits <a href="/wiki/ALA_dehydratase" class="mw-redirect" title="ALA dehydratase">ALA dehydratase</a> enzyme.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Gallery">Gallery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=11" title="Edit section: Gallery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:H2TPP.png" class="mw-file-description" title="Lewis structure for meso-tetraphenylporphyrin"><img alt="Lewis structure for meso-tetraphenylporphyrin" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/H2TPP.png/120px-H2TPP.png" decoding="async" width="120" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/H2TPP.png/180px-H2TPP.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/H2TPP.png/240px-H2TPP.png 2x" data-file-width="436" data-file-height="435" /></a></span></div> <div class="gallerytext">Lewis structure for <i>meso</i>-tetraphenylporphyrin</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Meso-tetraphenylporphyrin_UV-vis.JPG" class="mw-file-description" title="UV–vis readout for meso-tetraphenylporphyrin"><img alt="UV–vis readout for meso-tetraphenylporphyrin" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Meso-tetraphenylporphyrin_UV-vis.JPG/120px-Meso-tetraphenylporphyrin_UV-vis.JPG" decoding="async" width="120" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Meso-tetraphenylporphyrin_UV-vis.JPG/180px-Meso-tetraphenylporphyrin_UV-vis.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0a/Meso-tetraphenylporphyrin_UV-vis.JPG/240px-Meso-tetraphenylporphyrin_UV-vis.JPG 2x" data-file-width="627" data-file-height="546" /></a></span></div> <div class="gallerytext"><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV–vis</a> readout for <i>meso</i>-tetraphenylporphyrin</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Porfirina_activada_con_la_luz.svg" class="mw-file-description" title="Light-activated porphyrin. Monatomic oxygen. Cellular aging"><img alt="Light-activated porphyrin. Monatomic oxygen. Cellular aging" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Porfirina_activada_con_la_luz.svg/120px-Porfirina_activada_con_la_luz.svg.png" decoding="async" width="120" height="59" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Porfirina_activada_con_la_luz.svg/180px-Porfirina_activada_con_la_luz.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fc/Porfirina_activada_con_la_luz.svg/240px-Porfirina_activada_con_la_luz.svg.png 2x" data-file-width="590" data-file-height="290" /></a></span></div> <div class="gallerytext">Light-activated porphyrin. Monatomic oxygen. Cellular aging</div> </li> </ul> <div style="clear:both;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Related_species">Related species</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=12" title="Edit section: Related species"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="In_nature">In nature</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=13" title="Edit section: In nature"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Several heterocycles related to porphyrins are found in nature, almost always bound to metal ions. These include </p> <table class="wikitable"> <tbody><tr> <th>N4-macrocycle</th> <th>Cofactor name</th> <th>metal</th> <th>comment </th></tr> <tr> <td><a href="/wiki/Chlorin" title="Chlorin">chlorin</a></td> <td>chlorophyll</td> <td>magnesium</td> <td>several versions of chlorophyll exist (sidechain; exception being <a href="/wiki/Chlorophyll_c" title="Chlorophyll c">chlorophyll c</a>) </td></tr> <tr> <td>bacteriochlorin</td> <td><a href="/wiki/Bacteriochlorophyll" title="Bacteriochlorophyll">bacteriochlorophyll</a> (in part)</td> <td>magnesium</td> <td>several versions of bacteriochlorophyll exist (sidechain; some use a usual chlorin ring) </td></tr> <tr> <td rowspan="2"><a href="/wiki/Sirohydrochlorin" title="Sirohydrochlorin">sirohydrochlorin</a> (an isobacteriochlorin)</td> <td><a href="/wiki/Siroheme" title="Siroheme">siroheme</a></td> <td>iron</td> <td>Important cofactor in sulfur assimilation </td></tr> <tr> <td> </td> <td> </td> <td>biosynthetic intermediate en route to cofactor F430 and B12 </td></tr> <tr> <td><a href="/wiki/Corrin" title="Corrin">corrin</a></td> <td>vitamin B12</td> <td>cobalt</td> <td>several variants of B12 exist (sidechain) </td></tr> <tr> <td>corphin</td> <td><a href="/wiki/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></td> <td>nickel</td> <td>highly reduced macrocycle </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Synthetic">Synthetic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=14" title="Edit section: Synthetic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A <b>benzoporphyrin</b> is a porphyrin with a benzene ring fused to one of the pyrrole units. e.g. <a href="/wiki/Verteporfin" title="Verteporfin">verteporfin</a> is a benzoporphyrin derivative.<sup id="cite_ref-Scott2000_26-0" class="reference"><a href="#cite_note-Scott2000-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Non-natural_porphyrin_isomers">Non-natural porphyrin isomers</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=15" title="Edit section: Non-natural porphyrin isomers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:First_Porphycene_synthesis.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/First_Porphycene_synthesis.tif/lossy-page1-220px-First_Porphycene_synthesis.tif.jpg" decoding="async" width="220" height="68" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5e/First_Porphycene_synthesis.tif/lossy-page1-330px-First_Porphycene_synthesis.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5e/First_Porphycene_synthesis.tif/lossy-page1-440px-First_Porphycene_synthesis.tif.jpg 2x" data-file-width="1315" data-file-height="409" /></a><figcaption>Porphycene, first porphyrin isomer, synthesised from bipyrrole dialdehyde through <a href="/wiki/McMurry_reaction" title="McMurry reaction">McMurry coupling reaction</a></figcaption></figure> <p>The first synthetic porphyrin <a href="/wiki/Isomer" title="Isomer">isomer</a> was reported by Emanual Vogel and coworkers in 1986.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> This isomer [18]porphyrin-(2.0.2.0) is named as <b>porphycene</b>, and the central N<sub>4</sub> Cavity forms a <a href="/wiki/Rectangle" title="Rectangle">rectangle</a> shape as shown in figure.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Porphycenes showed interesting <a href="/wiki/Photochemistry" title="Photochemistry">photophysical</a> behavior and found versatile compound towards the <a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">photodynamic therapy</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> This inspired Vogel and <a href="/wiki/Jonathan_Sessler" title="Jonathan Sessler">Sessler</a> to took up the challenge of preparing [18]porphyrin-(2.1.0.1) and named it as <b>corrphycene</b> or <b>porphycerin</b>.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> The third porphyrin that is [18]porphyrin-(2.1.1.0), was reported by Callot and Vogel-Sessler. Vogel and coworkers reported successful isolation of [18]porphyrin-(3.0.1.0) or <b>isoporphycene</b>.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> The Japanese scientist Furuta<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> and Polish scientist Latos-Grażyński<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> almost simultaneously reported the <b>N-confused porphyrins</b>. The inversion of one of the pyrrolic subunits in the macrocyclic ring resulted in one of the nitrogen atoms facing outwards from the core of the macrocycle. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Isomers_of_porphyrins_soman.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Isomers_of_porphyrins_soman.jpg/500px-Isomers_of_porphyrins_soman.jpg" decoding="async" width="500" height="320" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Isomers_of_porphyrins_soman.jpg/750px-Isomers_of_porphyrins_soman.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Isomers_of_porphyrins_soman.jpg/1000px-Isomers_of_porphyrins_soman.jpg 2x" data-file-width="8851" data-file-height="5664" /></a><figcaption>Various reported Isomers of porphyrin</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=16" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>A porphyrin-related disease: <a href="/wiki/Porphyria" title="Porphyria">porphyria</a></li> <li>Porphyrin coordinated to iron: <a href="/wiki/Heme" title="Heme">heme</a></li> <li>A heme-containing group of enzymes: <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">Cytochrome P450</a></li> <li>Porphyrin coordinated to magnesium: <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a></li> <li>The one-carbon-shorter analogues: <a href="/wiki/Corrole" title="Corrole">corroles</a>, including <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a>, which is coordinated to a cobalt</li> <li>Corphins, the highly reduced porphyrin coordinated to nickel that binds the <a href="/wiki/Cofactor_F430" title="Cofactor F430">Cofactor F430</a> active site in <a href="/wiki/Methyl_coenzyme_M_reductase" class="mw-redirect" title="Methyl coenzyme M reductase">methyl coenzyme M reductase</a> (MCR)</li> <li>Nitrogen-substituted porphyrins: <a href="/wiki/Phthalocyanine" title="Phthalocyanine">phthalocyanine</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Porphyrin&action=edit&section=17" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFRayatiMalekmohammadi2016" class="citation journal cs1">Rayati S, Malekmohammadi S (2016). <a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F17458080.2016.1179802">"Catalytic activity of multi-wall carbon nanotube supported manganese (III) porphyrin: an efficient, selective and reusable catalyst for oxidation of alkenes and alkanes with urea–hydrogen peroxide"</a>. <i>Journal of Experimental Nanoscience</i>. <b>11</b> (11): 872. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2016JENan..11..872R">2016JENan..11..872R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F17458080.2016.1179802">10.1080/17458080.2016.1179802</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Experimental+Nanoscience&rft.atitle=Catalytic+activity+of+multi-wall+carbon+nanotube+supported+manganese+%28III%29+porphyrin%3A+an+efficient%2C+selective+and+reusable+catalyst+for+oxidation+of+alkenes+and+alkanes+with+urea%E2%80%93hydrogen+peroxide&rft.volume=11&rft.issue=11&rft.pages=872&rft.date=2016&rft_id=info%3Adoi%2F10.1080%2F17458080.2016.1179802&rft_id=info%3Abibcode%2F2016JENan..11..872R&rft.aulast=Rayati&rft.aufirst=S&rft.au=Malekmohammadi%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1080%252F17458080.2016.1179802&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIvanovBoldyrev2014" class="citation journal cs1">Ivanov AS, Boldyrev AI (August 2014). "Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning". <i>Organic & Biomolecular Chemistry</i>. <b>12</b> (32): 6145–6150. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC4OB01018C">10.1039/C4OB01018C</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25002069">25002069</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+%26+Biomolecular+Chemistry&rft.atitle=Deciphering+aromaticity+in+porphyrinoids+via+adaptive+natural+density+partitioning&rft.volume=12&rft.issue=32&rft.pages=6145-6150&rft.date=2014-08&rft_id=info%3Adoi%2F10.1039%2FC4OB01018C&rft_id=info%3Apmid%2F25002069&rft.aulast=Ivanov&rft.aufirst=AS&rft.au=Boldyrev%2C+AI&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLash2011" class="citation journal cs1"><a href="/wiki/Timothy_D._Lash" title="Timothy D. Lash">Lash TD</a> (2011). "Origin of aromatic character in porphyrinoid systems". <i>Journal of Porphyrins and Phthalocyanines</i>. <b>15</b> (11n12): 1093–1115. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1142%2FS1088424611004063">10.1142/S1088424611004063</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Porphyrins+and+Phthalocyanines&rft.atitle=Origin+of+aromatic+character+in+porphyrinoid+systems&rft.volume=15&rft.issue=11n12&rft.pages=1093-1115&rft.date=2011&rft_id=info%3Adoi%2F10.1142%2FS1088424611004063&rft.aulast=Lash&rft.aufirst=TD&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarperBuglione" class="citation web cs1">Harper D, Buglione DC. <a rel="nofollow" class="external text" href="http://www.etymonline.com/index.php?allowed_in_frame=0&search=porphyrin&searchmode=none">"porphyria (n.)"</a>. <i>The Online Etymology Dictionary</i><span class="reference-accessdate">. Retrieved <span class="nowrap">14 September</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=The+Online+Etymology+Dictionary&rft.atitle=porphyria+%28n.%29&rft.aulast=Harper&rft.aufirst=D&rft.au=Buglione%2C+DC&rft_id=http%3A%2F%2Fwww.etymonline.com%2Findex.php%3Fallowed_in_frame%3D0%26search%3Dporphyrin%26searchmode%3Dnone&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSengeMacGowanO'Brien2015" class="citation journal cs1">Senge MO, MacGowan SA, O'Brien JM (December 2015). "Conformational control of cofactors in nature - the influence of protein-induced macrocycle distortion on the biological function of tetrapyrroles". <i>Chemical Communications</i>. <b>51</b> (96): 17031–17063. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2FC5CC06254C">10.1039/C5CC06254C</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2262%2F75305">2262/75305</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26482230">26482230</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=Conformational+control+of+cofactors+in+nature+-+the+influence+of+protein-induced+macrocycle+distortion+on+the+biological+function+of+tetrapyrroles&rft.volume=51&rft.issue=96&rft.pages=17031-17063&rft.date=2015-12&rft_id=info%3Ahdl%2F2262%2F75305&rft_id=info%3Apmid%2F26482230&rft_id=info%3Adoi%2F10.1039%2FC5CC06254C&rft.aulast=Senge&rft.aufirst=MO&rft.au=MacGowan%2C+SA&rft.au=O%27Brien%2C+JM&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWalkerSimonis2011" class="citation book cs1">Walker FA, Simonis U (2011). "Iron Porphyrin Chemistry". <i>Encyclopedia of Inorganic and Bioinorganic Chemistry</i>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9781119951438.eibc0104">10.1002/9781119951438.eibc0104</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781119951438" title="Special:BookSources/9781119951438"><bdi>9781119951438</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Iron+Porphyrin+Chemistry&rft.btitle=Encyclopedia+of+Inorganic+and+Bioinorganic+Chemistry&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F9781119951438.eibc0104&rft.isbn=9781119951438&rft.aulast=Walker&rft.aufirst=FA&rft.au=Simonis%2C+U&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJentzenMaShelnutt1998" class="citation journal cs1">Jentzen W, Ma JG, Shelnutt JA (February 1998). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1302556">"Conservation of the conformation of the porphyrin macrocycle in hemoproteins"</a>. <i>Biophysical Journal</i>. <b>74</b> (2 Pt 1): 753–763. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1998BpJ....74..753J">1998BpJ....74..753J</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0006-3495%2898%2974000-7">10.1016/S0006-3495(98)74000-7</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1302556">1302556</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9533688">9533688</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biophysical+Journal&rft.atitle=Conservation+of+the+conformation+of+the+porphyrin+macrocycle+in+hemoproteins&rft.volume=74&rft.issue=2+Pt+1&rft.pages=753-763&rft.date=1998-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1302556%23id-name%3DPMC&rft_id=info%3Apmid%2F9533688&rft_id=info%3Adoi%2F10.1016%2FS0006-3495%2898%2974000-7&rft_id=info%3Abibcode%2F1998BpJ....74..753J&rft.aulast=Jentzen&rft.aufirst=W&rft.au=Ma%2C+JG&rft.au=Shelnutt%2C+JA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1302556&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSengeRyanLetchfordMacGowan2014" class="citation journal cs1">Senge MO, Ryan AA, Letchford KA, MacGowan SA, Mielke T (2014). <a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fsym6030781">"Chlorophylls, Symmetry, Chirality, and Photosynthesis"</a>. <i>Symmetry</i>. <b>6</b> (3): 781–843. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2014Symm....6..781S">2014Symm....6..781S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fsym6030781">10.3390/sym6030781</a></span>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2262%2F73843">2262/73843</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Symmetry&rft.atitle=Chlorophylls%2C+Symmetry%2C+Chirality%2C+and+Photosynthesis&rft.volume=6&rft.issue=3&rft.pages=781-843&rft.date=2014&rft_id=info%3Ahdl%2F2262%2F73843&rft_id=info%3Adoi%2F10.3390%2Fsym6030781&rft_id=info%3Abibcode%2F2014Symm....6..781S&rft.aulast=Senge&rft.aufirst=MO&rft.au=Ryan%2C+AA&rft.au=Letchford%2C+KA&rft.au=MacGowan%2C+SA&rft.au=Mielke%2C+T&rft_id=https%3A%2F%2Fdoi.org%2F10.3390%252Fsym6030781&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-handbook-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-handbook_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-handbook_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKadish1999" class="citation book cs1">Kadish KM, ed. (1999). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Ci7rIe0Ohn8C&pg=PA381"><i>The Porphyrin Handbook</i></a>. <a href="/wiki/Elsevier" title="Elsevier">Elsevier</a>. p. 381. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780123932006" title="Special:BookSources/9780123932006"><bdi>9780123932006</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Porphyrin+Handbook&rft.pages=381&rft.pub=Elsevier&rft.date=1999&rft.isbn=9780123932006&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCi7rIe0Ohn8C%26pg%3DPA381&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZhangLash2003" class="citation journal cs1">Zhang B, Lash TD (September 2003). "Total synthesis of the porphyrin mineral abelsonite and related petroporphyrins with five-membered exocyclic rings". <i>Tetrahedron Letters</i>. <b>44</b> (39): 7253. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.tetlet.2003.08.007">10.1016/j.tetlet.2003.08.007</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tetrahedron+Letters&rft.atitle=Total+synthesis+of+the+porphyrin+mineral+abelsonite+and+related+petroporphyrins+with+five-membered+exocyclic+rings&rft.volume=44&rft.issue=39&rft.pages=7253&rft.date=2003-09&rft_id=info%3Adoi%2F10.1016%2Fj.tetlet.2003.08.007&rft.aulast=Zhang&rft.aufirst=B&rft.au=Lash%2C+TD&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMasonTrudellBranthaver1989" class="citation journal cs1">Mason GM, Trudell LG, Branthaver JF (1989). "Review of the stratigraphic distribution and diagenetic history of abelsonite". <i>Organic Geochemistry</i>. <b>14</b> (6): 585. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1989OrGeo..14..585M">1989OrGeo..14..585M</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0146-6380%2889%2990038-7">10.1016/0146-6380(89)90038-7</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Organic+Geochemistry&rft.atitle=Review+of+the+stratigraphic+distribution+and+diagenetic+history+of+abelsonite&rft.volume=14&rft.issue=6&rft.pages=585&rft.date=1989&rft_id=info%3Adoi%2F10.1016%2F0146-6380%2889%2990038-7&rft_id=info%3Abibcode%2F1989OrGeo..14..585M&rft.aulast=Mason&rft.aufirst=GM&rft.au=Trudell%2C+LG&rft.au=Branthaver%2C+JF&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRothemund1936" class="citation journal cs1">Rothemund P (1936). "A New Porphyrin Synthesis. The Synthesis of Porphin". <i><a href="/wiki/J._Am._Chem._Soc." class="mw-redirect" title="J. Am. Chem. Soc.">J. Am. Chem. Soc.</a></i> <b>58</b> (4): 625–627. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01295a027">10.1021/ja01295a027</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=A+New+Porphyrin+Synthesis.+The+Synthesis+of+Porphin&rft.volume=58&rft.issue=4&rft.pages=625-627&rft.date=1936&rft_id=info%3Adoi%2F10.1021%2Fja01295a027&rft.aulast=Rothemund&rft.aufirst=P&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRothemund1935" class="citation journal cs1">Rothemund P (1935). "Formation of Porphyrins from Pyrrole and Aldehydes". <i>J. Am. Chem. Soc</i>. <b>57</b> (10): 2010–2011. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja01313a510">10.1021/ja01313a510</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=Formation+of+Porphyrins+from+Pyrrole+and+Aldehydes&rft.volume=57&rft.issue=10&rft.pages=2010-2011&rft.date=1935&rft_id=info%3Adoi%2F10.1021%2Fja01313a510&rft.aulast=Rothemund&rft.aufirst=P&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAdlerLongoFinarelliGoldmacher1967" class="citation journal cs1">Adler AD, Longo FR, Finarelli JD, Goldmacher J, Assour J, Korsakoff L (1967). "A simplified synthesis for <i>meso</i>-tetraphenylporphine". <i><a href="/wiki/J._Org._Chem." class="mw-redirect" title="J. Org. Chem.">J. Org. Chem.</a></i> <b>32</b> (2): 476. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjo01288a053">10.1021/jo01288a053</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Org.+Chem.&rft.atitle=A+simplified+synthesis+for+meso-tetraphenylporphine&rft.volume=32&rft.issue=2&rft.pages=476&rft.date=1967&rft_id=info%3Adoi%2F10.1021%2Fjo01288a053&rft.aulast=Adler&rft.aufirst=AD&rft.au=Longo%2C+FR&rft.au=Finarelli%2C+JD&rft.au=Goldmacher%2C+J&rft.au=Assour%2C+J&rft.au=Korsakoff%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGiuntiniBoyleSibrian-VazquezVicente2014" class="citation encyclopaedia cs1">Giuntini F, Boyle R, Sibrian-Vazquez M, Vicente MG (2014). "Porphyrin conjugates for cancer therapy". In Kadish KM, Smith KM, Guilard R (eds.). <i>Handbook of Porphyrin Science</i>. Vol. 27. pp. 303–416.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Porphyrin+conjugates+for+cancer+therapy&rft.btitle=Handbook+of+Porphyrin+Science&rft.pages=303-416&rft.date=2014&rft.aulast=Giuntini&rft.aufirst=F&rft.au=Boyle%2C+R&rft.au=Sibrian-Vazquez%2C+M&rft.au=Vicente%2C+MG&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-pmid17636693-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17636693_16-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWormaldEvansSmeethHenshaw2007" class="citation journal cs1">Wormald R, Evans J, Smeeth L, Henshaw K (July 2007). <a rel="nofollow" class="external text" href="https://researchonline.lshtm.ac.uk/id/eprint/6367/1/Wormald_et_al-2007-The_Cochrane_library.pdf">"Photodynamic therapy for neovascular age-related macular degeneration"</a> <span class="cs1-format">(PDF)</span>. <i>The Cochrane Database of Systematic Reviews</i> (3): CD002030. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14651858.CD002030.pub3">10.1002/14651858.CD002030.pub3</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17636693">17636693</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=Photodynamic+therapy+for+neovascular+age-related+macular+degeneration&rft.issue=3&rft.pages=CD002030&rft.date=2007-07&rft_id=info%3Adoi%2F10.1002%2F14651858.CD002030.pub3&rft_id=info%3Apmid%2F17636693&rft.aulast=Wormald&rft.aufirst=R&rft.au=Evans%2C+J&rft.au=Smeeth%2C+L&rft.au=Henshaw%2C+K&rft_id=https%3A%2F%2Fresearchonline.lshtm.ac.uk%2Fid%2Feprint%2F6367%2F1%2FWormald_et_al-2007-The_Cochrane_library.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPriceTerleckyKessel2009" class="citation journal cs1">Price M, Terlecky SR, Kessel D (2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2783742">"A role for hydrogen peroxide in the pro-apoptotic effects of photodynamic therapy"</a>. <i>Photochemistry and Photobiology</i>. <b>85</b> (6): 1491–1496. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1751-1097.2009.00589.x">10.1111/j.1751-1097.2009.00589.x</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2783742">2783742</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19659920">19659920</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Photochemistry+and+Photobiology&rft.atitle=A+role+for+hydrogen+peroxide+in+the+pro-apoptotic+effects+of+photodynamic+therapy&rft.volume=85&rft.issue=6&rft.pages=1491-1496&rft.date=2009&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2783742%23id-name%3DPMC&rft_id=info%3Apmid%2F19659920&rft_id=info%3Adoi%2F10.1111%2Fj.1751-1097.2009.00589.x&rft.aulast=Price&rft.aufirst=M&rft.au=Terlecky%2C+SR&rft.au=Kessel%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2783742&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-18">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSinghAggarwalBhupathirajuArianna2015" class="citation journal cs1">Singh S, Aggarwal A, Bhupathiraju NV, Arianna G, Tiwari K, Drain CM (September 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6011754">"Glycosylated Porphyrins, Phthalocyanines, and Other Porphyrinoids for Diagnostics and Therapeutics"</a>. <i>Chemical Reviews</i>. <b>115</b> (18): 10261–10306. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.chemrev.5b00244">10.1021/acs.chemrev.5b00244</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6011754">6011754</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/26317756">26317756</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Reviews&rft.atitle=Glycosylated+Porphyrins%2C+Phthalocyanines%2C+and+Other+Porphyrinoids+for+Diagnostics+and+Therapeutics&rft.volume=115&rft.issue=18&rft.pages=10261-10306&rft.date=2015-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6011754%23id-name%3DPMC&rft_id=info%3Apmid%2F26317756&rft_id=info%3Adoi%2F10.1021%2Facs.chemrev.5b00244&rft.aulast=Singh&rft.aufirst=S&rft.au=Aggarwal%2C+A&rft.au=Bhupathiraju%2C+NV&rft.au=Arianna%2C+G&rft.au=Tiwari%2C+K&rft.au=Drain%2C+CM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6011754&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLewtakGryko2012" class="citation journal cs1">Lewtak JP, Gryko DT (October 2012). "Synthesis of π-extended porphyrins via intramolecular oxidative coupling". <i>Chemical Communications</i>. <b>48</b> (81): 10069–10086. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2Fc2cc31279d">10.1039/c2cc31279d</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22649792">22649792</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Communications&rft.atitle=Synthesis+of+%CF%80-extended+porphyrins+via+intramolecular+oxidative+coupling&rft.volume=48&rft.issue=81&rft.pages=10069-10086&rft.date=2012-10&rft_id=info%3Adoi%2F10.1039%2Fc2cc31279d&rft_id=info%3Apmid%2F22649792&rft.aulast=Lewtak&rft.aufirst=JP&rft.au=Gryko%2C+DT&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWalterRudineWamser2010" class="citation journal cs1">Walter MG, Rudine AB, Wamser CC (2010). "Porphyrins and phthalocyanines in solar photovoltaic cells". <i><a href="/wiki/Journal_of_Porphyrins_and_Phthalocyanines" title="Journal of Porphyrins and Phthalocyanines">Journal of Porphyrins and Phthalocyanines</a></i>. <b>14</b> (9): 759–792. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1142%2FS1088424610002689">10.1142/S1088424610002689</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Porphyrins+and+Phthalocyanines&rft.atitle=Porphyrins+and+phthalocyanines+in+solar+photovoltaic+cells&rft.volume=14&rft.issue=9&rft.pages=759-792&rft.date=2010&rft_id=info%3Adoi%2F10.1142%2FS1088424610002689&rft.aulast=Walter&rft.aufirst=MG&rft.au=Rudine%2C+AB&rft.au=Wamser%2C+CC&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFYellaLeeTsaoYi2011" class="citation journal cs1">Yella A, Lee HW, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, et al. (November 2011). "Porphyrin-sensitized solar cells with cobalt (II/III)-based redox electrolyte exceed 12 percent efficiency". <i>Science</i>. <b>334</b> (6056): 629–634. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2011Sci...334..629Y">2011Sci...334..629Y</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1209688">10.1126/science.1209688</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/22053043">22053043</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:28058582">28058582</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Porphyrin-sensitized+solar+cells+with+cobalt+%28II%2FIII%29-based+redox+electrolyte+exceed+12+percent+efficiency&rft.volume=334&rft.issue=6056&rft.pages=629-634&rft.date=2011-11&rft_id=info%3Adoi%2F10.1126%2Fscience.1209688&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28058582%23id-name%3DS2CID&rft_id=info%3Apmid%2F22053043&rft_id=info%3Abibcode%2F2011Sci...334..629Y&rft.aulast=Yella&rft.aufirst=A&rft.au=Lee%2C+HW&rft.au=Tsao%2C+HN&rft.au=Yi%2C+C&rft.au=Chandiran%2C+AK&rft.au=Nazeeruddin%2C+MK&rft.au=Diau%2C+EW&rft.au=Yeh%2C+CY&rft.au=Zakeeruddin%2C+SM&rft.au=Gr%C3%A4tzel%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlonso-CastroZapata-MoralesHernández-MuniveCampos-Xolalpa2015" class="citation journal cs1">Alonso-Castro AJ, Zapata-Morales JR, Hernández-Munive A, Campos-Xolalpa N, Pérez-Gutiérrez S, Pérez-González C (May 2015). "Synthesis, antinociceptive and anti-inflammatory effects of porphyrins". <i>Bioorganic & Medicinal Chemistry</i>. <b>23</b> (10): 2529–2537. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bmc.2015.03.043">10.1016/j.bmc.2015.03.043</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25863493">25863493</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry&rft.atitle=Synthesis%2C+antinociceptive+and+anti-inflammatory+effects+of+porphyrins&rft.volume=23&rft.issue=10&rft.pages=2529-2537&rft.date=2015-05&rft_id=info%3Adoi%2F10.1016%2Fj.bmc.2015.03.043&rft_id=info%3Apmid%2F25863493&rft.aulast=Alonso-Castro&rft.aufirst=AJ&rft.au=Zapata-Morales%2C+JR&rft.au=Hern%C3%A1ndez-Munive%2C+A&rft.au=Campos-Xolalpa%2C+N&rft.au=P%C3%A9rez-Guti%C3%A9rrez%2C+S&rft.au=P%C3%A9rez-Gonz%C3%A1lez%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBajjuAhmedDevi2019" class="citation journal cs1">Bajju GD, Ahmed A, Devi G (December 2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6661832">"Synthesis and bioactivity of oxovanadium(IV)tetra(4-methoxyphenyl)porphyrinsalicylates"</a>. <i>BMC Chemistry</i>. <b>13</b> (1): 15. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1186%2Fs13065-019-0523-9">10.1186/s13065-019-0523-9</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6661832">6661832</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31384764">31384764</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMC+Chemistry&rft.atitle=Synthesis+and+bioactivity+of+oxovanadium%28IV%29tetra%284-methoxyphenyl%29porphyrinsalicylates&rft.volume=13&rft.issue=1&rft.pages=15&rft.date=2019-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6661832%23id-name%3DPMC&rft_id=info%3Apmid%2F31384764&rft_id=info%3Adoi%2F10.1186%2Fs13065-019-0523-9&rft.aulast=Bajju&rft.aufirst=GD&rft.au=Ahmed%2C+A&rft.au=Devi%2C+G&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6661832&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMendonçaBakkerCruz-OliveiraNeves2021" class="citation journal cs1">Mendonça DA, Bakker M, Cruz-Oliveira C, Neves V, Jiménez MA, Defaus S, et al. (June 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8485325">"Penetrating the Blood-Brain Barrier with New Peptide-Porphyrin Conjugates Having anti-HIV Activity"</a>. <i>Bioconjugate Chemistry</i>. <b>32</b> (6): 1067–1077. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.bioconjchem.1c00123">10.1021/acs.bioconjchem.1c00123</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8485325">8485325</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/34033716">34033716</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioconjugate+Chemistry&rft.atitle=Penetrating+the+Blood-Brain+Barrier+with+New+Peptide-Porphyrin+Conjugates+Having+anti-HIV+Activity&rft.volume=32&rft.issue=6&rft.pages=1067-1077&rft.date=2021-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8485325%23id-name%3DPMC&rft_id=info%3Apmid%2F34033716&rft_id=info%3Adoi%2F10.1021%2Facs.bioconjchem.1c00123&rft.aulast=Mendon%C3%A7a&rft.aufirst=DA&rft.au=Bakker%2C+M&rft.au=Cruz-Oliveira%2C+C&rft.au=Neves%2C+V&rft.au=Jim%C3%A9nez%2C+MA&rft.au=Defaus%2C+S&rft.au=Cavaco%2C+M&rft.au=Veiga%2C+AS&rft.au=Cadima-Couto%2C+I&rft.au=Castanho%2C+MA&rft.au=Andreu%2C+D&rft.au=Todorovski%2C+T&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8485325&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWalkerSilbyHopkinPeakall2012" class="citation book cs1">Walker CH, Silby RM, Hopkin SP, Peakall DB (2012). <i>Principles of Ecotoxicology</i>. Boca Raton, FL: CRC Press. p. 182. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4665-0260-4" title="Special:BookSources/978-1-4665-0260-4"><bdi>978-1-4665-0260-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+of+Ecotoxicology&rft.place=Boca+Raton%2C+FL&rft.pages=182&rft.pub=CRC+Press&rft.date=2012&rft.isbn=978-1-4665-0260-4&rft.aulast=Walker&rft.aufirst=CH&rft.au=Silby%2C+RM&rft.au=Hopkin%2C+SP&rft.au=Peakall%2C+DB&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-Scott2000-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-Scott2000_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScottGoa2000" class="citation journal cs1">Scott LJ, Goa KL (February 2000). "Verteporfin". <i>Drugs & Aging</i>. <b>16</b> (2): 139–146, discussion 146–8. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00002512-200016020-00005">10.2165/00002512-200016020-00005</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10755329">10755329</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:260491296">260491296</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs+%26+Aging&rft.atitle=Verteporfin&rft.volume=16&rft.issue=2&rft.pages=139-146%2C+discussion+146-8&rft.date=2000-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A260491296%23id-name%3DS2CID&rft_id=info%3Apmid%2F10755329&rft_id=info%3Adoi%2F10.2165%2F00002512-200016020-00005&rft.aulast=Scott&rft.aufirst=LJ&rft.au=Goa%2C+KL&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVogelKöcher1986" class="citation journal cs1">Vogel E, Köcher M (March 1986). "Porphycene—a Novel Porphin Isomer". <i>Angewandte Chemie</i>. <b>25</b> (3): 257. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.198602571">10.1002/anie.198602571</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie&rft.atitle=Porphycene%E2%80%94a+Novel+Porphin+Isomer&rft.volume=25&rft.issue=3&rft.pages=257&rft.date=1986-03&rft_id=info%3Adoi%2F10.1002%2Fanie.198602571&rft.aulast=Vogel&rft.aufirst=E&rft.au=K%C3%B6cher%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNagamaiahDuttaPatiSahoo2022" class="citation journal cs1">Nagamaiah J, Dutta A, Pati NN, Sahoo S, Soman R, Panda PK (March 2022). "3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation". <i>The Journal of Organic Chemistry</i>. <b>87</b> (5): 2721–2729. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.joc.1c02652">10.1021/acs.joc.1c02652</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35061396">35061396</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:246165814">246165814</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Organic+Chemistry&rft.atitle=3%2C6%2C13%2C16-Tetrapropylporphycene%3A+Rational+Synthesis%2C+Complexation%2C+and+Halogenation&rft.volume=87&rft.issue=5&rft.pages=2721-2729&rft.date=2022-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A246165814%23id-name%3DS2CID&rft_id=info%3Apmid%2F35061396&rft_id=info%3Adoi%2F10.1021%2Facs.joc.1c02652&rft.aulast=Nagamaiah&rft.aufirst=J&rft.au=Dutta%2C+A&rft.au=Pati%2C+NN&rft.au=Sahoo%2C+S&rft.au=Soman%2C+R&rft.au=Panda%2C+PK&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDougherty2001" class="citation journal cs1">Dougherty TJ (2001). "Basic principles of photodynamic therapy". <i>Journal of Porphyrins and Phthalocyanines</i>. <b>5</b> (2): 105. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjpp.328">10.1002/jpp.328</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Porphyrins+and+Phthalocyanines&rft.atitle=Basic+principles+of+photodynamic+therapy&rft.volume=5&rft.issue=2&rft.pages=105&rft.date=2001&rft_id=info%3Adoi%2F10.1002%2Fjpp.328&rft.aulast=Dougherty&rft.aufirst=TJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVogelGuilard1993" class="citation journal cs1">Vogel E, Guilard R (November 1993). "New Porphycene Ligands: Octaethyl‐ and Etioporphycene (OEPc and EtioPc)—Tetra‐ and Pentacoordinated Zinc Complexes of OEPc". <i>Angewandte Chemie International Edition</i>. <b>32</b> (11): 1600. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.199316001">10.1002/anie.199316001</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=New+Porphycene+Ligands%3A+Octaethyl%E2%80%90+and+Etioporphycene+%28OEPc+and+EtioPc%29%E2%80%94Tetra%E2%80%90+and+Pentacoordinated+Zinc+Complexes+of+OEPc&rft.volume=32&rft.issue=11&rft.pages=1600&rft.date=1993-11&rft_id=info%3Adoi%2F10.1002%2Fanie.199316001&rft.aulast=Vogel&rft.aufirst=E&rft.au=Guilard%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVogelScholzDemuthErben1999" class="citation journal cs1">Vogel E, Scholz P, Demuth R, Erben C, Bröring M, Schmickler H, et al. (October 1999). "Isoporphycene: The Fourth Constitutional Isomer of Porphyrin with an N(4) Core-Occurrence of E/Z Isomerism". <i>Angewandte Chemie</i>. <b>38</b> (19): 2919–2923. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F%28SICI%291521-3773%2819991004%2938%3A19%3C2919%3A%3AAID-ANIE2919%3E3.0.CO%3B2-W">10.1002/(SICI)1521-3773(19991004)38:19<2919::AID-ANIE2919>3.0.CO;2-W</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10540393">10540393</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie&rft.atitle=Isoporphycene%3A+The+Fourth+Constitutional+Isomer+of+Porphyrin+with+an+N%284%29+Core-Occurrence+of+E%2FZ+Isomerism&rft.volume=38&rft.issue=19&rft.pages=2919-2923&rft.date=1999-10&rft_id=info%3Adoi%2F10.1002%2F%28SICI%291521-3773%2819991004%2938%3A19%3C2919%3A%3AAID-ANIE2919%3E3.0.CO%3B2-W&rft_id=info%3Apmid%2F10540393&rft.aulast=Vogel&rft.aufirst=E&rft.au=Scholz%2C+P&rft.au=Demuth%2C+R&rft.au=Erben%2C+C&rft.au=Br%C3%B6ring%2C+M&rft.au=Schmickler%2C+H&rft.au=Lex%2C+J&rft.au=Hohlneicher%2C+G&rft.au=Bremm%2C+D&rft.au=Wu%2C+YD&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHiroyuki1994" class="citation journal cs1">Hiroyuki F (1994). "<span class="cs1-kern-left"></span>"N-Confused Porphyrin": A New Isomer of Tetraphenylporphyrin". <i>J. Am. Chem. Soc</i>. <b>116</b> (2): 767. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fja00081a047">10.1021/ja00081a047</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Am.+Chem.+Soc.&rft.atitle=%22N-Confused+Porphyrin%22%3A+A+New+Isomer+of+Tetraphenylporphyrin&rft.volume=116&rft.issue=2&rft.pages=767&rft.date=1994&rft_id=info%3Adoi%2F10.1021%2Fja00081a047&rft.aulast=Hiroyuki&rft.aufirst=F&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> <li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChmielewskiLatos-GrażyńskiRachlewiczGlowiak1994" class="citation journal cs1">Chmielewski PJ, Latos-Grażyński L, Rachlewicz K, Glowiak T (18 April 1994). "Tetra‐p‐tolylporphyrin with an Inverted Pyrrole Ring: A Novel Isomer of Porphyrin". <i>Angewandte Chemie International Edition</i>. <b>33</b> (7): 779. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fanie.199407791">10.1002/anie.199407791</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie+International+Edition&rft.atitle=Tetra%E2%80%90p%E2%80%90tolylporphyrin+with+an+Inverted+Pyrrole+Ring%3A+A+Novel+Isomer+of+Porphyrin&rft.volume=33&rft.issue=7&rft.pages=779&rft.date=1994-04-18&rft_id=info%3Adoi%2F10.1002%2Fanie.199407791&rft.aulast=Chmielewski&rft.aufirst=PJ&rft.au=Latos-Gra%C5%BCy%C5%84ski%2C+L&rft.au=Rachlewicz%2C+K&rft.au=Glowiak%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3APorphyrin" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 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href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li> <li><a href="/wiki/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytobilin&action=edit&redlink=1" class="new" title="Phytobilin (page does not exist)">Phytobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytochromobilin" class="mw-redirect" title="Phytochromobilin">Phytochromobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phycobilin" title="Phycobilin">Phycobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phycoerythrobilin" title="Phycoerythrobilin">Phycoerythrobilin</a></li> <li><a href="/wiki/Phycocyanobilin" title="Phycocyanobilin">Phycocyanobilin</a></li> <li><a href="/wiki/Phycourobilin" title="Phycourobilin">Phycourobilin</a></li> <li><a href="/w/index.php?title=Phycoviolobilin&action=edit&redlink=1" class="new" title="Phycoviolobilin (page does not exist)">Phycoviolobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Macrocycle" title="Macrocycle">Macrocycle</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corrinoid" title="Corrinoid">Corrinoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">Porphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Protoporphyrin" class="mw-redirect" title="Protoporphyrin">Protoporphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heme" title="Heme">Heme</a> (<a href="/wiki/Heme_b" class="mw-redirect" title="Heme b"><i>b</i></a>, <a href="/wiki/Heme_c" class="mw-redirect" title="Heme c"><i>c</i></a>, <a href="/wiki/Heme_a" class="mw-redirect" title="Heme a"><i>a</i></a>, <a href="/wiki/Heme_o" class="mw-redirect" title="Heme o"><i>o</i></a>)</li> <li><a href="/w/index.php?title=Magnesium_protoporphyrin&action=edit&redlink=1" class="new" title="Magnesium protoporphyrin (page does not exist)">Magnesium protoporphyrin</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a></li> <li><a href="/wiki/Pterobilin" title="Pterobilin">Pterobilin</a></li> <li><a href="/wiki/Zinc_protoporphyrin" title="Zinc protoporphyrin">Zinc protoporphyrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytoporphyrin&action=edit&redlink=1" class="new" title="Phytoporphyrin (page does 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title="Uroporphyrinogen">Uroporphyrinogen</a> (<a href="/wiki/Uroporphyrinogen_I" title="Uroporphyrinogen I">I</a>, <a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">III</a>)</li> <li><a href="/wiki/Coproporphyrinogens" title="Coproporphyrinogens">Coproporphyrinogen</a> (<a href="/wiki/Coproporphyrinogen_I" title="Coproporphyrinogen I">I</a>, <a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">III</a>)</li> <li><a href="/wiki/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chlorin" title="Chlorin">Chlorins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorophyllide" title="Chlorophyllide">Chlorophyllide</a> (<a href="/wiki/Chlorophyllide_a" class="mw-redirect" title="Chlorophyllide a"><i>a</i></a>, <a href="/wiki/Chlorophyllide_b" class="mw-redirect" title="Chlorophyllide b"><i>b</i></a>)</li> <li><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophyll</a> (<a href="/wiki/Chlorophyll_a" title="Chlorophyll a"><i>a</i></a>, <a href="/wiki/Chlorophyll_b" title="Chlorophyll b"><i>b</i></a>)</li> <li><a href="/wiki/Pheophytin" title="Pheophytin">Pheophytin</a> (<a href="/wiki/Pheophytin_a" class="mw-redirect" title="Pheophytin a"><i>a</i></a>, <a href="/w/index.php?title=Pheophytin_b&action=edit&redlink=1" class="new" title="Pheophytin b (page does not exist)"><i>b</i></a>)</li> <li><a href="/wiki/Bacteriochlorophyll_c" class="mw-redirect" title="Bacteriochlorophyll c">Bacteriochlorophyll <i>c</i></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacteriochlorin" class="mw-redirect" title="Bacteriochlorin">Bacteriochlorins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div 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