Retarded photooxidation of cyamemazine in biomimetic microenvironments

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...

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Detalles Bibliográficos
Autores: Limones Herrero, Daniel, Pérez Ruiz, Raúl, Miranda Alonso, Miguel Ángel, Jiménez, M Consuelo|||0000-0002-8057-4316
Tipo de recurso: artículo
Fecha de publicación:2014
País:España
Institución:Universitat Politècnica de València (UPV)
Repositorio:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
Idioma:inglés
OAI Identifier:oai:riunet.upv.es:10251/60806
Acceso en línea:https://riunet.upv.es/handle/10251/60806
Access Level:acceso abierto
Palabra clave:3 PHENOTHIAZINE-DERIVATIVES
LASER FLASH-PHOTOLYSIS
ALPHA-1-ACID GLYCOPROTEIN
ALPHA(1)-ACID GLYCOPROTEIN
NEUROLEPTICS
DRUGS
CHLORPROMAZINE
CYCLODEXTRIN
FLUORESCENCE
MECHANISMS
QUIMICA ORGANICA
QUIMICA ANALITICA
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spelling Retarded photooxidation of cyamemazine in biomimetic microenvironmentsLimones Herrero, DanielPérez Ruiz, RaúlMiranda Alonso, Miguel ÁngelJiménez, M Consuelo|||0000-0002-8057-43163 PHENOTHIAZINE-DERIVATIVESLASER FLASH-PHOTOLYSISALPHA-1-ACID GLYCOPROTEINALPHA(1)-ACID GLYCOPROTEINNEUROLEPTICSDRUGSCHLORPROMAZINECYCLODEXTRINFLUORESCENCEMECHANISMSQUIMICA ORGANICAQUIMICA ANALITICACyamemazine (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.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.WileyDepartamento de QuímicaEscuela Técnica Superior de Ingeniería IndustrialGrupo de estudio de estados excitados: detección, dinámica, transformaciones y campos de aplicaciónMinisterio de Ciencia e InnovaciónGeneralitat ValencianaRepositorio Institucional de la Universitat Politècnica de València Riunet20142014-10-01journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfapplication/pdfhttps://riunet.upv.es/handle/10251/60806reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valénciainstname:Universitat Politècnica de València (UPV)InglésengMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 CTQ2010-14882 DIADAS FOTOACTIVAS COMO SONDAS PARA LA GENERACION DE ESPECIES TRANSITORIAS EN SISTEMAS MICROHETEROGENEOS DE TIPO BIOMIMETICOGeneralitat Valenciana https://doi.org/10.13039/501100003359 PROMETEOII%2F2013%2F005 ESPECIES FOTOACTIVAS Y SU INTERACCION CON BIOMOLECULASMinisterio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 JCI-2010-06204 JCI-2010-06204Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 BES-2011-043706 BES-2011-043706open accesshttp://purl.org/coar/access_right/c_abf2Reserva de todos los derechoshttp://rightsstatements.org/vocab/InC/1.0/info:eu-repo/semantics/openAccessoai:riunet.upv.es:10251/608062026-06-13T07:49:27Z
dc.title.none.fl_str_mv Retarded photooxidation of cyamemazine in biomimetic microenvironments
title Retarded photooxidation of cyamemazine in biomimetic microenvironments
spellingShingle Retarded photooxidation of cyamemazine in biomimetic microenvironments
Limones Herrero, Daniel
3 PHENOTHIAZINE-DERIVATIVES
LASER FLASH-PHOTOLYSIS
ALPHA-1-ACID GLYCOPROTEIN
ALPHA(1)-ACID GLYCOPROTEIN
NEUROLEPTICS
DRUGS
CHLORPROMAZINE
CYCLODEXTRIN
FLUORESCENCE
MECHANISMS
QUIMICA ORGANICA
QUIMICA ANALITICA
title_short Retarded photooxidation of cyamemazine in biomimetic microenvironments
title_full Retarded photooxidation of cyamemazine in biomimetic microenvironments
title_fullStr Retarded photooxidation of cyamemazine in biomimetic microenvironments
title_full_unstemmed Retarded photooxidation of cyamemazine in biomimetic microenvironments
title_sort Retarded photooxidation of cyamemazine in biomimetic microenvironments
dc.creator.none.fl_str_mv Limones Herrero, Daniel
Pérez Ruiz, Raúl
Miranda Alonso, Miguel Ángel
Jiménez, M Consuelo|||0000-0002-8057-4316
author Limones Herrero, Daniel
author_facet Limones Herrero, Daniel
Pérez Ruiz, Raúl
Miranda Alonso, Miguel Ángel
Jiménez, M Consuelo|||0000-0002-8057-4316
author_role author
author2 Pérez Ruiz, Raúl
Miranda Alonso, Miguel Ángel
Jiménez, M Consuelo|||0000-0002-8057-4316
author2_role author
author
author
dc.contributor.none.fl_str_mv Departamento de Química
Escuela Técnica Superior de Ingeniería Industrial
Grupo de estudio de estados excitados: detección, dinámica, transformaciones y campos de aplicación
Ministerio de Ciencia e Innovación
Generalitat Valenciana
Repositorio Institucional de la Universitat Politècnica de València Riunet
dc.subject.none.fl_str_mv 3 PHENOTHIAZINE-DERIVATIVES
LASER FLASH-PHOTOLYSIS
ALPHA-1-ACID GLYCOPROTEIN
ALPHA(1)-ACID GLYCOPROTEIN
NEUROLEPTICS
DRUGS
CHLORPROMAZINE
CYCLODEXTRIN
FLUORESCENCE
MECHANISMS
QUIMICA ORGANICA
QUIMICA ANALITICA
topic 3 PHENOTHIAZINE-DERIVATIVES
LASER FLASH-PHOTOLYSIS
ALPHA-1-ACID GLYCOPROTEIN
ALPHA(1)-ACID GLYCOPROTEIN
NEUROLEPTICS
DRUGS
CHLORPROMAZINE
CYCLODEXTRIN
FLUORESCENCE
MECHANISMS
QUIMICA ORGANICA
QUIMICA ANALITICA
description 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.
publishDate 2014
dc.date.none.fl_str_mv 2014
2014-10-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://riunet.upv.es/handle/10251/60806
url https://riunet.upv.es/handle/10251/60806
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 CTQ2010-14882 DIADAS FOTOACTIVAS COMO SONDAS PARA LA GENERACION DE ESPECIES TRANSITORIAS EN SISTEMAS MICROHETEROGENEOS DE TIPO BIOMIMETICO
Generalitat Valenciana https://doi.org/10.13039/501100003359 PROMETEOII%2F2013%2F005 ESPECIES FOTOACTIVAS Y SU INTERACCION CON BIOMOLECULAS
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 JCI-2010-06204 JCI-2010-06204
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 BES-2011-043706 BES-2011-043706
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Reserva de todos los derechos
http://rightsstatements.org/vocab/InC/1.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
instname:Universitat Politècnica de València (UPV)
instname_str Universitat Politècnica de València (UPV)
reponame_str RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
collection RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.301603

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