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Triplet photosensitization mechanism of thymine by an oxidized nucleobase: from a dimeric model to DNA environment

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Triplet photosensitization mechanism of thymine by an oxidized nucleobase: from a dimeric model to DNA environment

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dc.contributor.author Francés-Monerris, Antonio es_ES
dc.contributor.author Hognon, Cécilia es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Lhiaubet, Virginie Lyria es_ES
dc.contributor.author Monari, Antonio es_ES
dc.date.accessioned 2020-06-03T05:53:24Z
dc.date.available 2020-06-03T05:53:24Z
dc.date.issued 2018-10-28 es_ES
dc.identifier.issn 1463-9076 es_ES
dc.identifier.uri http://hdl.handle.net/10251/145122
dc.description.abstract [EN] Nucleic acids are constantly exposed to external agents that can induce chemical and photochemical damage. In spite of the great advances achieved in the last years, some molecular mechanisms of DNA damage are not completely understood yet. A recent experimental report (I. Aparici-Espert et al., ACS Chem. Biol. 2018, 13, 542) proved the ability of 5-formyluracil (ForU), a common oxidatively generated product of thymine, to act as an intrinsic sensitizer of nucleic acids, causing single strand breaks and cyclobutane pyrimidine dimers in plasmid DNA. In the present contribution, we use theoretical methodologies to study the triplet photosensitization mechanism of thymine exerted by ForU in a model dimer and in DNA environment. The photochemical pathways in the former system are described combining the CASPT2 and TD-DFT methods, whereas molecular dynamics simulations and QM/MM calculations are employed for the DNA duplex. It is unambiguously shown that the (1)n,* state localised in ForU mediates the population of the triplet manifold, most likely the (3),* state centred in ForU, whereas the (3),* state localized in thymine can be populated via triplet-triplet energy transfer given the small energy barrier of <0.23 eV determined for this pathway. es_ES
dc.description.sponsorship A. F. M. is grateful to Région Grand Est government (France) for the financial support. Spanish government (CTQ2015-70164P and CTQ2017-87054-C2-2-P projects) and Regional government (Prometeo/2017/075) are also acknowledged. es_ES
dc.language Inglés es_ES
dc.publisher The Royal Society of Chemistry es_ES
dc.relation MICINN/CTQ2017-87054-C2-2-P es_ES
dc.relation MINECO/CTQ2015-70164-P es_ES
dc.relation GENERALITAT VALENCIANA/PROMETEO/2017/075 es_ES
dc.relation.ispartof Physical Chemistry Chemical Physics es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Cyclobutane Pyrimidine dimers es_ES
dc.subject UV-Irradiated DNA es_ES
dc.subject Molecular-Dynamics es_ES
dc.subject Nucleic-Acids es_ES
dc.subject 5-Methyl-2-Pyrimidone Deoxyribonucleoside es_ES
dc.subject Biological consequences es_ES
dc.subject Photodynamic therapy es_ES
dc.subject Charge-Transfer es_ES
dc.subject Singlet oxygen es_ES
dc.subject Cellular-DNA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Triplet photosensitization mechanism of thymine by an oxidized nucleobase: from a dimeric model to DNA environment es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c8cp04866e 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 Francés-Monerris, A.; Hognon, C.; Miranda Alonso, MÁ.; Lhiaubet, VL.; Monari, A. (2018). Triplet photosensitization mechanism of thymine by an oxidized nucleobase: from a dimeric model to DNA environment. Physical Chemistry Chemical Physics. 20(40):25666-25675. https://doi.org/10.1039/c8cp04866e es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion http://doi.org/10.1039/c8cp04866e es_ES
dc.description.upvformatpinicio 25666 es_ES
dc.description.upvformatpfin 25675 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 20 es_ES
dc.description.issue 40 es_ES
dc.identifier.pmid 30298156 es_ES
dc.relation.pasarela S\379638 es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Conseil Régional Grand Est, Francia es_ES
dc.contributor.funder Ministerio de Ciencia, Innovación y Universidades es_ES


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