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Probing lipid peroxidatin by using linoleic acid and benzophenone

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Probing lipid peroxidatin by using linoleic acid and benzophenone

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dc.contributor.author Andreu Ros, María Inmaculada es_ES
dc.contributor.author Neshchadin, Dmytro es_ES
dc.contributor.author Rico Inglada, Enrique es_ES
dc.contributor.author Griesser, Markus es_ES
dc.contributor.author Samadi, Abdelouahid es_ES
dc.contributor.author Morera Bertomeu, Isabel María es_ES
dc.contributor.author Gescheidt, Georg es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel
dc.date.accessioned 2013-11-11T13:45:01Z
dc.date.issued 2011-07-26
dc.identifier.issn 0947-6539
dc.identifier.uri http://hdl.handle.net/10251/33427
dc.description.abstract A thorough mechanistic study has been performed on the reaction between benzophenone (BZP) and a series of 1,4-dienes, including 1,4-cyclohexadiene (CHD), 1,4-dihydro-2-methylbenzoic acid (MBA), 1,4-dihydro-1,2-dimethylbenzoic acid (DMBA) and linoleic acid (LA). A combination of steady-state photolysis, laser flash photolysis (LFP), and photochemically induced dynamic nuclear polarization (photo-CIDNP) have been used. Irradiation of BZP and CHD led to a cross-coupled sensitizer¿diene product, together with 6, 7, and 8. With MBA and DMBA as hydrogen donors, photoproducts arising from cross-coupling of sensitizer and diene radicals were found; compound 7 was also obtained, but 6 and o-toluic acid were only isolated in the irradiation of BZP with MBA. Triplet lifetimes were determined in the absence and in the presence of several diene concentrations. All three model compounds showed similar reactivity (kq¿108¿m¿1¿s¿1) towards triplet excited BZP. Partly reversible hydrogen abstraction of the allylic hydrogen atoms of CHD, MBA, and DMBA was also detected by photo-CIDNP on different timescales. Polarizations of the diamagnetic products were in full agreement with the results derived from LFP. Finally, LA also underwent partly reversible hydrogen abstraction during photoreaction with BZP. Subsequent hydrogen transfer between primary radicals led to conjugated derivatives of LA. The unpaired electron spin population in linoleyl radical (LA.) was predominantly found on H(1-5) protons. To date, LA-related radicals were only reported upon hydrogen transfer from highly substituted model compounds by steady-state EPR spectroscopy. Herein, we have experimentally established the formation of LA. and shown that it converts into two dominating conjugated isomers on the millisecond timescale. Such processes are at the basis of alterations of membrane structures caused by oxidative stress. es_ES
dc.description.sponsorship Financial support from the MICINN (grants CTQ2009-13699 and CTQ2010-14882), from the Generalitat Valenciana (GV/2009/104) and from Carlos III Institute of Health (grant RIRAAF, RETICS program) is gratefully acknowledged. We thank also COST project CM603 for facilitating our collaboration. en_EN
dc.format.extent 8 es_ES
dc.language Inglés es_ES
dc.publisher Wiley-VCH Verlag es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Dienes es_ES
dc.subject Hydrogen abstraction es_ES
dc.subject Photochemistry es_ES
dc.subject Photolysis es_ES
dc.subject Transient absorption spectroscopy es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Probing lipid peroxidatin by using linoleic acid and benzophenone es_ES
dc.type Artículo es_ES
dc.embargo.lift 10000-01-01
dc.embargo.terms forever es_ES
dc.identifier.doi 10.1002/chem.201100983
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/COST//CM0603/EU/Free Radicals in Chemical Biology (CHEMBIORADICAL)/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Generalitat Valenciana//GV%2F2009%2F104/ES/Estudio de la Fotoperoxidación de Lípidos de Membrana por Fármacos/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MICINN//CTQ2009-13699/ES/CTQ2009-13699/ es_ES
dc.rights.accessRights Cerrado 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 Andreu Ros, MI.; Neshchadin, D.; Rico Inglada, E.; Griesser, M.; Samadi, A.; Morera Bertomeu, IM.; Gescheidt, G.... (2011). Probing lipid peroxidatin by using linoleic acid and benzophenone. Chemistry - A European Journal. 17(36):10089-10096. https://doi.org/10.1002/chem.201100983 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://onlinelibrary.wiley.com/doi/10.1002/chem.201100983/full es_ES
dc.description.upvformatpinicio 10089 es_ES
dc.description.upvformatpfin 10096 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 17 es_ES
dc.description.issue 36 es_ES
dc.relation.senia 197850
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder European Cooperation in Science and Technology es_ES
dc.contributor.funder Instituto de Salud Carlos III es_ES
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