{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T16:57:45Z","timestamp":1791824265503,"version":"4.3.4"},"reference-count":42,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2023,12,15]],"date-time":"2023-12-15T00:00:00Z","timestamp":1702598400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"NSERC Discovery","award":["06919"],"award-info":[{"award-number":["06919"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Mesalamine, also called 5-ASA (5-aminosalicylic acid), is a largely used anti-inflammatory agent and is a main choice to treat Ulcerative Colitis. This report is aimed to investigate enzymatic processes involved in the oxidation of mesalamine to better understand some of its side-effects. Oxidation with oxygen (catalyzed by ceruloplasmin) or with hydrogen peroxide (catalyzed by peroxidase or hemoglobin) showed that these oxidases, despite their different mechanisms of oxidation, could recognize mesalamine as a substrate and trigger its oxidation to a corresponding quinone-imine. These enzymes were chosen because they may recognize hydroquinone (a p-diphenol) as substrate and oxidize it to p-benzoquinone and that mesalamine, as a p-aminophenol, presents some similarities with hydroquinone. The UV-Vis kinetics, FTIR and 1H NMR supported the hypothesis of oxidizing mesalamine. Furthermore, mass spectrometry suggested the quinone\u2013imine as reaction product. Without enzymes, the oxidation process was very slow (days and weeks), but it was markedly accelerated with the oxidases, particularly with peroxidase. Cyclic voltammetry supported the hypothesis of the oxidative process and allowed a ranking of susceptibility to oxidizing mesalamine in comparison with other oxidizable drug molecules with related structures. The susceptibility to oxidation was higher for mesalamine, in comparison with Tylenol (acetaminophen) and with aspirin (salicylic acid).<\/jats:p>","DOI":"10.3390\/molecules28248105","type":"journal-article","created":{"date-parts":[[2023,12,15]],"date-time":"2023-12-15T11:26:52Z","timestamp":1702639612000},"page":"8105","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Oxidation of Mesalamine under Phenoloxidase- or Peroxidase-like Enzyme Catalysis"],"prefix":"10.3390","volume":"28","author":[{"given":"Rimaz","family":"El Zein","sequence":"first","affiliation":[{"name":"Department of Chemistry and Center CERMO-FC, Universit\u00e9 du Qu\u00e9bec \u00e0 Montr\u00e9al, Downtown Branch, P.O. Box 8888, Montr\u00e9al, QC H3C 3P8, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7878-9804","authenticated-orcid":false,"given":"Pompilia","family":"Ispas-Szabo","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center CERMO-FC, Universit\u00e9 du Qu\u00e9bec \u00e0 Montr\u00e9al, Downtown Branch, P.O. Box 8888, Montr\u00e9al, QC H3C 3P8, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3165-781X","authenticated-orcid":false,"given":"Maziar","family":"Jafari","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center CERMO-FC, Universit\u00e9 du Qu\u00e9bec \u00e0 Montr\u00e9al, Downtown Branch, P.O. Box 8888, Montr\u00e9al, QC H3C 3P8, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0499-4260","authenticated-orcid":false,"given":"Mohamed","family":"Siaj","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center CERMO-FC, Universit\u00e9 du Qu\u00e9bec \u00e0 Montr\u00e9al, Downtown Branch, P.O. Box 8888, Montr\u00e9al, QC H3C 3P8, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5922-4701","authenticated-orcid":false,"given":"Mircea Alexandru","family":"Mateescu","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Center CERMO-FC, Universit\u00e9 du Qu\u00e9bec \u00e0 Montr\u00e9al, Downtown Branch, P.O. Box 8888, Montr\u00e9al, QC H3C 3P8, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,15]]},"reference":[{"key":"ref_1","first-page":"216","article-title":"Crohn\u2019s disease and colorectal carcinoma: Rectal cancer complicating longstanding active perianal disease","volume":"90","author":"Nikias","year":"1995","journal-title":"Am. J. Gastroenterol."},{"key":"ref_2","first-page":"306","article-title":"5-Aminosalyclic acid (5-ASA): A unique anti-inflammatory salicylate","volume":"6","year":"2016","journal-title":"Med. Chem."},{"key":"ref_3","unstructured":"(2023, October 19). Mesalazine European Pharmacopoeia (EP) Reference Standard. Y0000297. 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