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Influence of the linking bridge on the photoreactivity of benzophenone-thymine conjugates

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Influence of the linking bridge on the photoreactivity of benzophenone-thymine conjugates

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dc.contributor.author Blasco-Brusola, Alejandro es_ES
dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2021-04-01T03:31:53Z
dc.date.available 2021-04-01T03:31:53Z
dc.date.issued 2020-11-06 es_ES
dc.identifier.issn 0022-3263 es_ES
dc.identifier.uri http://hdl.handle.net/10251/164825
dc.description.abstract [EN] Benzophenone (BP) is present in a variety of bioactive molecules. This chromophore is able to photosensitize DNA damage, where one of the most relevant BP/ DNA interactions occurs with thymine (Thy). In view of the complex photoreactivity previously observed for dyads containing BP covalently linked to thymidine, the aim of this work is to investigate whether appropriate changes in the nature of the spacer could modulate the intramolecular BP/Thy photoreactivity, resulting in an enhanced selectivity. Accordingly, the photobehavior of a series of dyads derived from BP and Thy, separated by linear linkers of different length, has been investigated by steady-state photolysis, as well as femtosecond and nanosecond transient absorption spectroscopy. Irradiation of the dyads led to photoproducts arising from formal hydrogen abstraction or Paterno-Buchi (PB) photoreaction, with a chemoselectivity that was clearly dependent on the nature of the linking bridge; moreover, the PB process occurred with complete regio- and stereoselectivity. The overall photoreactivity increased with the length of the spacer and correlated well with the rate constants estimated from the BP triplet lifetimes. A reaction mechanism explaining these results is proposed, where the key features are the strain associated with the reactive conformations and the participation of triplet exciplexes. es_ES
dc.description.sponsorship Financial support from the Spanish Government (RYC-2015-17737 and CTQ2017-89416-R) and from the Conselleria d'Educació Cultura i Esport (PROMETEO/2017/075 and GRISOLIAP/2017/005) is gratefully acknowledged. The authors would like to thank the use of RIAIDT-USC analytical facilities for the X-ray crystallography analysis. es_ES
dc.language Inglés es_ES
dc.publisher American Chemical Society es_ES
dc.relation.ispartof The Journal of Organic Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Excited-State interactions es_ES
dc.subject Laser flash-photolysis es_ES
dc.subject DNA-Damage es_ES
dc.subject 6-4 Photoproduct es_ES
dc.subject Naphthalene es_ES
dc.subject Repair es_ES
dc.subject Ketoprofen es_ES
dc.subject Drugs es_ES
dc.subject Light es_ES
dc.subject Photosensitization es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Influence of the linking bridge on the photoreactivity of benzophenone-thymine conjugates es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1021/acs.joc.0c02088 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//GRISOLIAP%2F2017%2F005/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/GVA//PROMETEO%2F2017%2F075/ES/Reacciones fotoquímicas de biomoléculas/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RYC-2015-17737/ES/RYC-2015-17737/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-89416-R/ES/FUNCIONALIZACION DE NANOPARTICULAS DE ORO CON MARCADORES BIOLOGICOS Y SENSIBILIZADORES DE OXIGENO SINGLETE PARA SU USO EN BIOMEDICINA/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Blasco-Brusola, A.; Vayá Pérez, I.; Miranda Alonso, MÁ. (2020). Influence of the linking bridge on the photoreactivity of benzophenone-thymine conjugates. The Journal of Organic Chemistry. 85(21):14068-14076. https://doi.org/10.1021/acs.joc.0c02088 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1021/acs.joc.0c02088 es_ES
dc.description.upvformatpinicio 14068 es_ES
dc.description.upvformatpfin 14076 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 85 es_ES
dc.description.issue 21 es_ES
dc.identifier.pmid 33108203 es_ES
dc.relation.pasarela S\422472 es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
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