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Excited state interactions between flurbiprofen and tryptophan in drug-protein complexes and in model dyads. Fluorescence studies from the femtosecond to the nanosecond time domains

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Excited state interactions between flurbiprofen and tryptophan in drug-protein complexes and in model dyads. Fluorescence studies from the femtosecond to the nanosecond time domains

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dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.contributor.author Bonancía Roca, Paula es_ES
dc.contributor.author Jiménez Molero, María Consuelo es_ES
dc.contributor.author Markovitsi, Dimitra es_ES
dc.contributor.author Gustavsson, Thomas es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2016-02-23T11:06:34Z
dc.date.available 2016-02-23T11:06:34Z
dc.date.issued 2013
dc.identifier.issn 1463-9076
dc.identifier.uri http://hdl.handle.net/10251/61116
dc.description.abstract We report here on the interaction dynamics between flurbiprofen (FBP) and tryptophan (Trp) covalently linked in model dyads and in a complex of FBP with human serum albumin (HSA) probed by time-resolved fluorescence spectroscopy from the femto- to the nano-second timescales. In the dyads, a rapid (k > 10(10) s(-1)) dynamic quenching of the (FBP star)-F-1 fluorescence is followed by a slower (k > 10(9) s(-1)) quenching of the remaining (1)Trp(star) fluorescence. Both processes display a clear stereoselectivity; the rates are 2-3 times higher for the (R,S)-dyad. In addition, a red-shifted exciplex emission is observed, rising in the range of 100-200 ps. A similar two-step dynamic fluorescence quenching is also observed in the FBP-HSA complex, although the kinetics of the involved processes are slower. The characteristic reorientational times determined for the two enantiomeric forms of FBP in the protein show that the interaction is stronger for the (R)-form. This is, to our knowledge, the first observation of stereo-selective flurbiprofen-tryptophan interaction dynamics with femtosecond time resolution. es_ES
dc.description.sponsorship Financial support from the Spanish Government (Grants CTQ2010-14882 and CTQ2009-13699, JCI-2011-09926, BES-2008-003314 and PR2011-0581), the Generalitat Valenciana (Prometeo 2008/090) and from the Universitat Politecnica de Valencia (PAID 05-11, Ref 2766) is gratefully acknowledged. en_EN
dc.language Inglés es_ES
dc.publisher Royal Society of Chemistry es_ES
dc.relation.ispartof Physical Chemistry Chemical Physics es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject HUMAN SERUM-ALBUMIN es_ES
dc.subject NONSTEROIDAL ANTIINFLAMMATORY DRUGS es_ES
dc.subject BIOLOGICAL NANOCAVITIES es_ES
dc.subject SPECTROSCOPIC ANALYSIS es_ES
dc.subject OCHRATOXIN-A es_ES
dc.subject BINDING es_ES
dc.subject DYNAMICS es_ES
dc.subject SOLVATION es_ES
dc.subject RESONANCE es_ES
dc.subject PHOSPHORESCENCE es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.title Excited state interactions between flurbiprofen and tryptophan in drug-protein complexes and in model dyads. Fluorescence studies from the femtosecond to the nanosecond time domains es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c3cp43847c
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//PROMETEO08%2F2008%2F090/ES/Especies fotoactivas como sondas para proteínas/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/UPV//PAID-05-11-2766/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//BES-2008-003314/ES/BES-2008-003314/ 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//CTQ2009-13699/ES/CTQ2009-13699/ 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.; Bonancía Roca, P.; Jiménez Molero, MC.; Markovitsi, D.; Gustavsson, T.; Miranda Alonso, MÁ. (2013). Excited state interactions between flurbiprofen and tryptophan in drug-protein complexes and in model dyads. Fluorescence studies from the femtosecond to the nanosecond time domains. Physical Chemistry Chemical Physics. 15(13):4727-4734. https://doi.org/10.1039/c3cp43847c es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://dx.doi.org/10.1039/c3cp43847c es_ES
dc.description.upvformatpinicio 4727 es_ES
dc.description.upvformatpfin 4734 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 15 es_ES
dc.description.issue 13 es_ES
dc.relation.senia 234593 es_ES
dc.identifier.eissn 1463-9084
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Universitat Politècnica de València es_ES
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