{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T00:53:14Z","timestamp":1760316794172,"version":"build-2065373602"},"reference-count":35,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2009,5,21]],"date-time":"2009-05-21T00:00:00Z","timestamp":1242864000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemMedChem"],"published-print":{"date-parts":[[2009,7,6]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p><jats:bold>A mechanism for triflusal\u2010induced photoallergy<\/jats:bold> involving complexation of 2\u2010hydroxy\u20104\u2010trifluoromethylbenzoic acid with site\u2005I of human serum albumin and subsequent formation of a covalent adduct by photoreaction between a metabolite and a neighboring lysine residue is proposed. This is supported by the observed photobinding to poly\u2010<jats:sc>L<\/jats:sc>\u2010lysine. Thereby, a photoantigen is generated, which is a likely trigger of the immune response.<jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" mimetype=\"image\/gif\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic\/mcontent.gif\"><jats:alt-text>magnified image<\/jats:alt-text><\/jats:graphic><\/jats:boxed-text><\/jats:p><jats:p><jats:italic>The goal of the work presented herein is to gain deeper insight into the molecular basis of photoallergy mediated by triflusal through its active metabolite, 2\u2010hydroxy\u20104\u2010trifluoromethylbenzoic acid (HTB). For this purpose, the interaction between HTB and human serum albumin (HSA) was investigated by fluorescence and laser flash photolysis to monitor inclusion into the protein binding sites through variation in the excited\u2010state properties. A remarkable lengthening of HTB triplet lifetime in the presence of HSA was observed. The use of oleic acid as a displacement probe clearly suggests the preference for dark binding in site\u2005I. The mechanism of photobinding was studied by irradiation of HTB in the presence of amino acids, and, in the case of lysine, a photoadduct was detected that arises from nucleophilic attack by the \u03b5\u2010amino group to the trifluoromethyl substituent of HTB. Accordingly, photobinding of the metabolite to poly\u2010<jats:sc>L<\/jats:sc>\u2010lysine was also observed. Overall, these results are consistent with a mechanism for triflusal photoallergy involving complexation of HTB to site\u2005I of HSA and subsequent formation of a covalent photoadduct with one neighboring lysine residue.<\/jats:italic><\/jats:p>","DOI":"10.1002\/cmdc.200900066","type":"journal-article","created":{"date-parts":[[2009,5,21]],"date-time":"2009-05-21T05:28:32Z","timestamp":1242883712000},"page":"1196-1202","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Photonucleophilic Addition of the \u03b5\u2010Amino Group of Lysine to a Triflusal Metabolite as a Mechanistic Key to Photoallergy Mediated by the Parent Drug"],"prefix":"10.1002","volume":"4","author":[{"given":"Sara","family":"Montanaro","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Virginie","family":"Lhiaubet\u2010Vallet","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"M.\u2005Consuelo","family":"Jim\u00e9nez","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miguel","family":"Blanca","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miguel\u2005Angel","family":"Miranda","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2009,6,29]]},"reference":[{"key":"e_1_2_6_1_2","first-page":"263","volume":"13","author":"Messa G. 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