{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T00:23:01Z","timestamp":1760660581542,"version":"build-2065373602"},"reference-count":19,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2014,1,3]],"date-time":"2014-01-03T00:00:00Z","timestamp":1388707200000},"content-version":"vor","delay-in-days":2,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Mass Spectrom."],"published-print":{"date-parts":[[2014,1]]},"abstract":"<jats:p>Isocoproporphyrin and its derivatives are commonly used as biomarkers of porphyria cutanea tarda, heavy metal toxicity and hexachlorobenzene (HCB) intoxication in humans and animals. However, most are isobaric with other porphyrins and reference materials are unavailable commercially. The structural characterisation of these porphyrins is important but very little data is available. We report here the separation and characterisation of isocoproporphyrin, deethylisocoproporphyrin, hydroxyisocoproporphyrin and ketoisocoproporphyrin, isolated in the faeces of rats fed with a diet containing HCB, by ultra high performance liquid chromatography\u2010exact mass tandem mass spectrometry (UHPLC\u2010MS\/MS). Furthermore, we report the identification and characterisation of a previously unreported porphyrin metabolite, isocoproporphyrin sulfonic acid isolated in the rat faeces. The measured mass\u2010to\u2010charge ratio (<jats:italic>m\/z<\/jats:italic>) of the precursor ion was <jats:italic>m\/z<\/jats:italic> 735.2338, corresponding to a molecular formula of C<jats:sub>36<\/jats:sub>H<jats:sub>39<\/jats:sub>N<jats:sub>4<\/jats:sub>O<jats:sub>11<\/jats:sub>S with an error of 0.3\u2009ppm from the calculated <jats:italic>m\/z<\/jats:italic> 735.2336. The MS\/MS data was consistent with an isocoproporphyrin sulfonic acid structure, derived from dehydroisocoproporphyrinogen by sulfonation of the vinyl group. The metabolite was present in a greater abundance than other isocoproporphyrin derivatives and may be a more useful biomarker for HCB intoxication. Copyright \u00a9 2014 John Wiley &amp; Sons, Ltd.<\/jats:p>","DOI":"10.1002\/jms.3307","type":"journal-article","created":{"date-parts":[[2014,1,7]],"date-time":"2014-01-07T00:38:52Z","timestamp":1389055132000},"page":"80-85","source":"Crossref","is-referenced-by-count":2,"title":["Separation and fragmentation study of isocoproporphyrin derivatives by UHPLC\u2010ESI\u2010exact mass MS\/MS and identification of a new isocoproporphyrin sulfonic acid metabolite"],"prefix":"10.1002","volume":"49","author":[{"given":"Christopher M.","family":"Benton","sequence":"first","affiliation":[{"name":"Clinical Biochemistry King's College Hospital  Denmark Hill London SE5 9RS UK"},{"name":"Cancer Studies and Molecular Medicine, RKCSB University of Leicester  Leicester LE2 7LX UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chang Kee","family":"Lim","sequence":"additional","affiliation":[{"name":"Clinical Biochemistry King's College Hospital  Denmark Hill London SE5 9RS UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Caje","family":"Moniz","sequence":"additional","affiliation":[{"name":"Clinical Biochemistry King's College Hospital  Denmark Hill London SE5 9RS UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sin\u00e9ad L.","family":"Baxter","sequence":"additional","affiliation":[{"name":"Clinical Biochemistry King's College Hospital  Denmark Hill London SE5 9RS UK"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Donald J. L.","family":"Jones","sequence":"additional","affiliation":[{"name":"Cancer Studies and Molecular Medicine, RKCSB University of Leicester  Leicester LE2 7LX UK"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2014,1,3]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(09)61925-5"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-1007142"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10534-010-9387-0"},{"key":"e_1_2_6_5_1","doi-asserted-by":"crossref","unstructured":"C. K.Lim.High\u2010performance liquid chromatography and mass spectrometry of porphyrins chlorophylls and bilins. 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Available at:http:\/\/www.greatplainslaboratory.com\/Porphyrin_gpllabcorp_vs_auguste_philippe%20_2_.pdf"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/bmc.2772"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/bmc.656"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1093\/clinchem\/31.7.1163"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1080\/10915810802657002"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.768"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1124\/dmd.31.8.983"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf980516q"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M802026200"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00351821"}],"container-title":["Journal of Mass Spectrometry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjms.3307","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jms.3307","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T14:26:19Z","timestamp":1760624779000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jms.3307"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,1]]},"references-count":19,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2014,1]]}},"alternative-id":["10.1002\/jms.3307"],"URL":"https:\/\/doi.org\/10.1002\/jms.3307","archive":["Portico"],"relation":{},"ISSN":["1076-5174","1096-9888"],"issn-type":[{"type":"print","value":"1076-5174"},{"type":"electronic","value":"1096-9888"}],"subject":[],"published":{"date-parts":[[2014,1]]}}}