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Photooxygenation mechanisms in naproxen-amino acid linked systems

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Photooxygenation mechanisms in naproxen-amino acid linked systems

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dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.contributor.author Andreu Ros, María Inmaculada es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2015-06-11T12:08:21Z
dc.date.available 2015-06-11T12:08:21Z
dc.date.issued 2014
dc.identifier.issn 1474-905X
dc.identifier.uri http://hdl.handle.net/10251/51552
dc.description.abstract The photooxygenation of model compounds containing the two enantiomers of naproxen (NPX) covalently linked to histidine (His), tryptophan (Trp) and tyrosine (Tyr) has been investigated by steady state irradiation, fluorescence spectroscopy and laser flash photolysis. The NPX–His systems presented the highest oxygen-mediated photoreactivity. Their fluorescence spectra matched that of isolated NPX and showed a clear quenching by oxygen, leading to a diminished production of the NPX triplet excited state ( 3 NPX*–His). Analysis of the NPX–His and NPX–Trp photolysates by UPLC-MS–MS revealed in both cases the formation of two photoproducts, arising from the reaction of singlet oxygen (1 O2) with the amino acid moiety. The most remarkable feature of NPX–Trp systems was a fast and stereoselective intramolecular fluorescence quenching, which prevented the efficient formation of 3 NPX*–Trp, thus explaining their lower reactivity towards photooxygenation. Finally, the NPX–Tyr systems were nearly unreactive and exhibited photophysical properties essentially coincident with those of the parent NPX. Overall, these results point to a type II photooxygenation mechanism, triggered by generation of 1 O2 from the 3 NPX* chromophore es_ES
dc.description.sponsorship Financial support from the Spanish Government (CTQ2010-14882, JCI-2011-09926, Miguel Servet CP11/00154), from the EU (PCIG12-GA-2012-334257), from the Universitat Politecnica de Valencia (SP20120757) and from the Conselleria de Educacio, cultura i Esport (PROMETEOII/2013/005, GV/2013/051) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Photochemical & Photobiological Sciences Photochemical and Photobiological Sciences es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Amino acid es_ES
dc.subject Naproxen es_ES
dc.subject Oxygen es_ES
dc.subject Absorption es_ES
dc.subject Chemical structure es_ES
dc.subject Chemistry es_ES
dc.subject Conformation es_ES
dc.subject Photolysis es_ES
dc.subject Molecular Conformation es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Photooxygenation mechanisms in naproxen-amino acid linked systems es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c3pp50252j
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CTQ2010-14882/ES/DIADAS FOTOACTIVAS COMO SONDAS PARA LA GENERACION DE ESPECIES TRANSITORIAS EN SISTEMAS MICROHETEROGENEOS DE TIPO BIOMIMETICO/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//GV%2F2013%2F051/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/FP7/334257/EU/EXCITED STATES AS PROBES TO INVESTIGATE DRUG-DNA AND DRUG-PROTEIN INTERACTIONS. PHOTOSENSITIZED PROCESSES LEADING TO DAMAGE TO BIOMOLECULES/
dc.relation.projectID info:eu-repo/grantAgreement/UPV//SP20120757/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//PROMETEOII%2F2013%2F005/ES/ESPECIES FOTOACTIVAS Y SU INTERACCION CON BIOMOLECULAS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//JCI-2011-09926/ES/JCI-2011-09926/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CP11%2F00154/ES/CP11%2F00154/ / es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Vayá Pérez, I.; Andreu Ros, MI.; Jiménez Molero, MC.; Miranda Alonso, MÁ. (2014). Photooxygenation mechanisms in naproxen-amino acid linked systems. Photochemical & Photobiological Sciences Photochemical and Photobiological Sciences. 13:224-230. https://doi.org/10.1039/c3pp50252j es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c3pp50252j es_ES
dc.description.upvformatpinicio 224 es_ES
dc.description.upvformatpfin 230 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 13 es_ES
dc.relation.senia 254956
dc.identifier.eissn 1474-9092
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Universitat Politècnica de València es_ES
dc.contributor.funder European Commission
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