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Photochemical and photophysical properties of dibenzoylmethane derivatives within protein

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Photochemical and photophysical properties of dibenzoylmethane derivatives within protein

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dc.contributor.author Marín Melchor, Mireia es_ES
dc.contributor.author Lhiaubet, Virginie Lyria es_ES
dc.contributor.author PARIS, CECILIA GERTRUDIS es_ES
dc.contributor.author Yamaji, Minoru es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel
dc.date.accessioned 2013-09-04T11:32:03Z
dc.date.available 2013-09-04T11:32:03Z
dc.date.issued 2011
dc.identifier.issn 1474-905X
dc.identifier.uri http://hdl.handle.net/10251/31764
dc.description.abstract In the present work, three dibenzoylmethane derivatives in their beta-diketo form have been selected to investigate their photophysical and photochemical behavior upon interaction with human serum albumin (HSA). In organic solvents, absorption and phosphorescence emission spectra of the a-bromo derivative of avobenzone (BrAB) were similar to those of the a-methylated and a-propyl analogs (MeAB and PrAB). However, laser flash photolysis experiments revealed a different transient species centered at 350 nm, assigned to the radical obtained from a singlet excited state dehalogenation process. Interestingly, the transient absorption spectrum of BrAB within HSA showed the typical features of the beta-diketone triplet excited state. In the case of MeAB and PrAB derivatives, binding to HSA was associated with a significant increase of their triplet lifetimes as compared to acetonitrile. Finally, the Norrish type II process has been considered as a model to evaluate the influence of the protein microenvironment on the photoreactivity. In this context, photodegradation of PrAB in aerated solutions, to give avobenzone (AB), has been monitored by UV spectroscopy. Interestingly, the quantum yields of AB formation were markedly dependent on the reaction medium (1.4 10(-2) in acetonitrile and 3.9 10(-2) within albumin medium); by contrast, chemical yields of ca. 50% were obtained in both cases. es_ES
dc.description.sponsorship Spanish Government (CTQ2009-13699 project, Ramon y Cajal contract to V. L.-V. and JAE pre-doc contract to M. M.), Generalitat Valenciana (Prometeo Program 2008/090 and GV/2009/051 projects) and Universidad Politecnica de Valencia (PAID 06-08 project) are gratefully acknowledged for financial support. M. Y. is grateful for a financial support, Grant-in-Aid for Scientific Research (KAKENHI) from JSPS. 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 HUMAN SERUM-ALBUMIN es_ES
dc.subject LASER FLASH-PHOTOLYSIS es_ES
dc.subject SUPRAMOLECULAR PHOTOCHIROGENESIS es_ES
dc.subject EXCITED-STATES es_ES
dc.subject FRIES REACTION es_ES
dc.subject 2-ANTHRACENECARBOXYLATE es_ES
dc.subject PHOTOCYCLODIMERIZATION es_ES
dc.subject WATER es_ES
dc.subject PHOTOSTABILITY es_ES
dc.subject CYCLIZATION es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Photochemical and photophysical properties of dibenzoylmethane derivatives within protein es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c1pp05072a
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CTQ2009-13699/ES/MECANISMOS FOTOQUIMICOS DEL DAÑO AL ADN Y SU REPARACION. FOTOSENSIBILIZACION FRENTE A FOTOPROTECCION/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Generalitat Valenciana//GV%2F2009%2F051/ES/Las albuminas como fotobiocatalizadores supramoleculares/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/UPV//PAID-06-08/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Generalitat Valenciana//GV%2F2008%2F090/ES/ es_ES
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Marín Melchor, M.; Lhiaubet, VL.; Paris, CG.; Yamaji, M.; Miranda Alonso, MÁ. (2011). Photochemical and photophysical properties of dibenzoylmethane derivatives within protein. Photochemical & Photobiological Sciences Photochemical and Photobiological Sciences. 10(9):1474-1479. https://doi.org/10.1039/c1pp05072a es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c1pp05072a es_ES
dc.description.upvformatpinicio 1474 es_ES
dc.description.upvformatpfin 1479 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 10 es_ES
dc.description.issue 9 es_ES
dc.relation.senia 197867
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Ciencia e Innovación es_ES
dc.contributor.funder Universitat Politècnica de València es_ES
dc.contributor.funder Japan Society for the Promotion of Science es_ES
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