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Retarded photooxidation of cyamemazine in biomimetic microenvironments

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Retarded photooxidation of cyamemazine in biomimetic microenvironments

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dc.contributor.author Limones Herrero, Daniel es_ES
dc.contributor.author Pérez Ruiz, Raúl es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2016-02-11T13:00:30Z
dc.date.available 2016-02-11T13:00:30Z
dc.date.issued 2014-10
dc.identifier.issn 0031-8655
dc.identifier.uri http://hdl.handle.net/10251/60806
dc.description.abstract Cyamemazine (CMZ) is a neuroleptic drug that mediates cutaneous phototoxicity in humans. Here, the photobehavior of CMZ has been examined within (1)-acid glycoproteins, - and -cyclodextrins and SDS micelles. In all these microenvironments, CMZ emission was enhanced and blue-shifted, and its lifetime was longer. Irradiation of the entrapped drug at 355nm, under air; led to the N,S-dioxide. Within glycoproteins or SDS micelles the reaction was clearly slower than in phosphate buffered solution (PBS); protection by cyclodextrins was less marked. Transient absorption spectroscopy in PBS revealed formation of the triplet state ((3)CMZ*) and the radical cation (CMZ(+center dot)). Upon addition of glycoprotein, the contribution of CMZ(+center dot) became negligible, whereas (3)CMZ* dominated the spectra; in addition, the triplet lifetime became considerably longer. In cyclodextrins, this occurred to a lower extent. In all microheterogeneous systems, quenching by oxygen was slower than in solution; this was most remarkable inside glycoproteins. The highest protection from photooxidation was achieved inside SDS micelles. The results are consistent with photooxidation of CMZ through photoionization and subsequent trapping of the resulting radical cation by oxygen. This reaction is extremely sensitive to the medium and constitutes an appropriate probe for localization of the drug within a variety of biological compartments. es_ES
dc.description.sponsorship Financial support from the Spanish Government (CTQ2010-14882, BES-2011-043706, JCI-2010-06204) and from the Generalitat Valenciana (PROMETEOII/2013/005) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Wiley es_ES
dc.relation Spanish Government CTQ2010-14882 BES-2011-043706 JCI-2010-06204 es_ES
dc.relation Generalitat Valenciana PROMETEOII/2013/005 es_ES
dc.relation.ispartof Photochemistry and Photobiology es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject 3 PHENOTHIAZINE-DERIVATIVES es_ES
dc.subject LASER FLASH-PHOTOLYSIS es_ES
dc.subject ALPHA-1-ACID GLYCOPROTEIN es_ES
dc.subject ALPHA(1)-ACID GLYCOPROTEIN es_ES
dc.subject NEUROLEPTICS es_ES
dc.subject DRUGS es_ES
dc.subject CHLORPROMAZINE es_ES
dc.subject CYCLODEXTRIN es_ES
dc.subject FLUORESCENCE es_ES
dc.subject MECHANISMS es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Retarded photooxidation of cyamemazine in biomimetic microenvironments es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1111/php.12303 es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Limones Herrero, D.; Pérez Ruiz, R.; Jiménez Molero, MC.; Miranda Alonso, MÁ. (2014). Retarded photooxidation of cyamemazine in biomimetic microenvironments. Photochemistry and Photobiology. 90(5):1012-1016. doi:10.1111/php.12303 es_ES
dc.description.accrualMethod Senia es_ES
dc.relation.publisherversion http://dx.doi.org/10.1111/php.12303 es_ES
dc.description.upvformatpinicio 1012 es_ES
dc.description.upvformatpfin 1016 es_ES
dc.type.version info:eu repo/semantics/publishedVersion es_ES
dc.description.volume 90 es_ES
dc.description.issue 5 es_ES
dc.relation.senia 269625 es_ES
dc.identifier.eissn 1751-1097


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