Photoinduced intersystem crossing in DNA oxidative lesions and epigenetic intermediates

dc.contributor.affiliationInstituto Universitario Mixto de Tecnología Química
dc.contributor.authorFrancés-Monerris, Antonioes_ES
dc.contributor.authorLineros-Rosa, Mauricioes_ES
dc.contributor.authorMiranda Alonso, Miguel Ángeles_ES
dc.contributor.authorLhiaubet, Virginie Lyria
dc.contributor.authorMonari, Antonioes_ES
dc.contributor.funderEuropean Social Fundes_ES
dc.contributor.funderGeneralitat Valencianaes_ES
dc.contributor.funderUniversité de Lorrainees_ES
dc.contributor.funderUniversitat Politècnica de Valènciaes_ES
dc.contributor.funderCentre National de la Recherche Scientifique, Franciaes_ES
dc.contributor.funderAgencia Estatal de Investigaciónes_ES
dc.date.accessioned2021-04-21T03:31:44Z
dc.date.available2021-04-21T03:31:44Z
dc.date.issued2020-04-25es_ES
dc.description.abstract[EN] The propensity of 5-formyluracil and 5-formylcytosine, i.e. oxidative lesions and epigenetic intermediates, in acting as intrinsic DNA photosensitizers is unraveled by using a combination of molecular modeling, simulation and spectroscopy. Exploration of potential energy surfaces and non-adiabatic dynamics confirm a higher intersystem crossing rate for 5-formyluracil, whereas the kinetic models evidence different equilibria in the excited states for both compounds.en_EN
dc.description.accrualMethodSes_ES
dc.description.bibliographicCitationFrancés-Monerris, A.; Lineros-Rosa, M.; Miranda Alonso, MÁ.; Lhiaubet, VL.; Monari, A. (2020). Photoinduced intersystem crossing in DNA oxidative lesions and epigenetic intermediates. Chemical Communications. 56(32):4404-4407. https://doi.org/10.1039/d0cc01132kes_ES
dc.description.issue32es_ES
dc.description.referencesMadabhushi, R., Pan, L., & Tsai, L.-H. (2014). DNA Damage and Its Links to Neurodegeneration. Neuron, 83(2), 266-282. doi:10.1016/j.neuron.2014.06.034es_ES
dc.description.referencesSage, E. (1993). DISTRIBUTION AND REPAIR OF PHOTOLESIONS IN DNA: GENETIC CONSEQUENCES AND THE ROLE OF SEQUENCE CONTEXT. Photochemistry and Photobiology, 57(1), 163-174. doi:10.1111/j.1751-1097.1993.tb02273.xes_ES
dc.description.referencesCadet, J., Sage, E., & Douki, T. (2005). Ultraviolet radiation-mediated damage to cellular DNA. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 571(1-2), 3-17. doi:10.1016/j.mrfmmm.2004.09.012es_ES
dc.description.referencesG. T. Wondrak , Skin stress response pathways: Environmental factors and molecular opportunities , Springer , 2016es_ES
dc.description.referencesNakamura, J., Mutlu, E., Sharma, V., Collins, L., Bodnar, W., Yu, R., … Swenberg, J. (2014). The endogenous exposome. DNA Repair, 19, 3-13. doi:10.1016/j.dnarep.2014.03.031es_ES
dc.description.referencesEsposito, L., Banyasz, A., Douki, T., Perron, M., Markovitsi, D., & Improta, R. (2014). Effect of C5-Methylation of Cytosine on the Photoreactivity of DNA: A Joint Experimental and Computational Study of TCG Trinucleotides. Journal of the American Chemical Society, 136(31), 10838-10841. doi:10.1021/ja5040478es_ES
dc.description.referencesIkehata, H., Mori, T., Kamei, Y., Douki, T., Cadet, J., & Yamamoto, M. (2019). Wavelength‐ and Tissue‐dependent Variations in the Mutagenicity of Cyclobutane Pyrimidine Dimers in Mouse Skin. Photochemistry and Photobiology, 96(1), 94-104. doi:10.1111/php.13159es_ES
dc.description.referencesCadet, J., & Douki, T. (2018). Formation of UV-induced DNA damage contributing to skin cancer development. Photochemical & Photobiological Sciences, 17(12), 1816-1841. doi:10.1039/c7pp00395aes_ES
dc.description.referencesDumont, E., & Monari, A. (2015). Understanding DNA under oxidative stress and sensitization: the role of molecular modeling. Frontiers in Chemistry, 3. doi:10.3389/fchem.2015.00043es_ES
dc.description.referencesCadet, J., & Wagner, J. R. (2013). DNA Base Damage by Reactive Oxygen Species, Oxidizing Agents, and UV Radiation. Cold Spring Harbor Perspectives in Biology, 5(2), a012559-a012559. doi:10.1101/cshperspect.a012559es_ES
dc.description.referencesBanyasz, A., Douki, T., Improta, R., Gustavsson, T., Onidas, D., Vayá, I., … Markovitsi, D. (2012). Electronic Excited States Responsible for Dimer Formation upon UV Absorption Directly by Thymine Strands: Joint Experimental and Theoretical Study. Journal of the American Chemical Society, 134(36), 14834-14845. doi:10.1021/ja304069fes_ES
dc.description.referencesRauer, C., Nogueira, J. J., Marquetand, P., & González, L. (2016). Cyclobutane Thymine Photodimerization Mechanism Revealed by Nonadiabatic Molecular Dynamics. Journal of the American Chemical Society, 138(49), 15911-15916. doi:10.1021/jacs.6b06701es_ES
dc.description.referencesIKEHATA, H., & ONO, T. (2011). The Mechanisms of UV Mutagenesis. Journal of Radiation Research, 52(2), 115-125. doi:10.1269/jrr.10175es_ES
dc.description.referencesGomez-Mendoza, M., Banyasz, A., Douki, T., Markovitsi, D., & Ravanat, J.-L. (2016). Direct Oxidative Damage of Naked DNA Generated upon Absorption of UV Radiation by Nucleobases. The Journal of Physical Chemistry Letters, 7(19), 3945-3948. doi:10.1021/acs.jpclett.6b01781es_ES
dc.description.referencesBanyasz, A., Martínez-Fernández, L., Balty, C., Perron, M., Douki, T., Improta, R., & Markovitsi, D. (2017). Absorption of Low-Energy UV Radiation by Human Telomere G-Quadruplexes Generates Long-Lived Guanine Radical Cations. Journal of the American Chemical Society, 139(30), 10561-10568. doi:10.1021/jacs.7b05931es_ES
dc.description.referencesEpe, B. (2012). DNA damage spectra induced by photosensitization. Photochem. Photobiol. Sci., 11(1), 98-106. doi:10.1039/c1pp05190ces_ES
dc.description.referencesCuquerella, M. C., Lhiaubet-Vallet, V., Cadet, J., & Miranda, M. A. (2012). Benzophenone Photosensitized DNA Damage. Accounts of Chemical Research, 45(9), 1558-1570. doi:10.1021/ar300054ees_ES
dc.description.referencesCuquerella, M. C., Lhiaubet-Vallet, V., Bosca, F., & Miranda, M. A. (2011). Photosensitised pyrimidine dimerisation in DNA. Chemical Science, 2(7), 1219. doi:10.1039/c1sc00088hes_ES
dc.description.referencesV. Lhiaubet-Vallet and M. A.Miranda , in CRC handbook of organic photochemistry and photobiology , ed. F. Ghetti , A. G. Griesbeck and M. Oelgemöller , CRC Press , 2012 , pp. 1541–1555es_ES
dc.description.referencesCadet, J., Douki, T., & Ravanat, J.-L. (2008). Oxidatively Generated Damage to the Guanine Moiety of DNA: Mechanistic Aspects and Formation in Cells. Accounts of Chemical Research, 41(8), 1075-1083. doi:10.1021/ar700245ees_ES
dc.description.referencesDumont, E., Grüber, R., Bignon, E., Morell, C., Moreau, Y., Monari, A., & Ravanat, J.-L. (2015). Probing the reactivity of singlet oxygen with purines. Nucleic Acids Research, 44(1), 56-62. doi:10.1093/nar/gkv1364es_ES
dc.description.referencesBaptista, M. S., Cadet, J., Di Mascio, P., Ghogare, A. A., Greer, A., Hamblin, M. R., … Yoshimura, T. M. (2017). Type I and Type II Photosensitized Oxidation Reactions: Guidelines and Mechanistic Pathways. Photochemistry and Photobiology, 93(4), 912-919. doi:10.1111/php.12716es_ES
dc.description.referencesDumont, E., Wibowo, M., Roca-Sanjuán, D., Garavelli, M., Assfeld, X., & Monari, A. (2015). Resolving the Benzophenone DNA-Photosensitization Mechanism at QM/MM Level. The Journal of Physical Chemistry Letters, 6(4), 576-580. doi:10.1021/jz502562des_ES
dc.description.referencesDumont, É., & Monari, A. (2014). Interaction of Palmatine with DNA: An Environmentally Controlled Phototherapy Drug. The Journal of Physical Chemistry B, 119(2), 410-419. doi:10.1021/jp5088515es_ES
dc.description.referencesNogueira, J. J., Oppel, M., & González, L. (2015). Enhancing Intersystem Crossing in Phenotiazinium Dyes by Intercalation into DNA. Angewandte Chemie International Edition, 54(14), 4375-4378. doi:10.1002/anie.201411456es_ES
dc.description.referencesVendrell-Criado, V., Rodríguez-Muñiz, G. M., Cuquerella, M. C., Lhiaubet-Vallet, V., & Miranda, M. A. (2013). Photosensitization of DNA by 5-Methyl-2-Pyrimidone Deoxyribonucleoside: (6-4) Photoproduct as a Possible Trojan Horse. Angewandte Chemie International Edition, 52(25), 6476-6479. doi:10.1002/anie.201302176es_ES
dc.description.referencesVendrell-Criado, V., Rodríguez-Muñiz, G. M., Lhiaubet-Vallet, V., Cuquerella, M. C., & Miranda, M. A. (2016). The (6-4) Dimeric Lesion as a DNA Photosensitizer. ChemPhysChem, 17(13), 1979-1982. doi:10.1002/cphc.201600154es_ES
dc.description.referencesBignon, E., Gattuso, H., Morell, C., Dumont, E., & Monari, A. (2015). DNA Photosensitization by an «Insider»: Photophysics and Triplet Energy Transfer of 5‐Methyl‐2‐pyrimidone Deoxyribonucleoside. Chemistry – A European Journal, 21(32), 11509-11516. doi:10.1002/chem.201501212es_ES
dc.description.referencesFrancés-Monerris, A., Hognon, C., Miranda, M. A., Lhiaubet-Vallet, V., & 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. doi:10.1039/c8cp04866ees_ES
dc.description.referencesLiu, P., Burdzy, A., & Sowers, L. C. (2003). Repair of the mutagenic DNA oxidation product, 5-formyluracil. DNA Repair, 2(2), 199-210. doi:10.1016/s1568-7864(02)00198-2es_ES
dc.description.referencesRogstad, D. K., Heo, J., Vaidehi, N., Goddard, W. A., Burdzy, A., & Sowers, L. C. (2004). 5-Formyluracil-Induced Perturbations of DNA Function. Biochemistry, 43(19), 5688-5697. doi:10.1021/bi030247jes_ES
dc.description.referencesWang, Y., Zhang, X., Zou, G., Peng, S., Liu, C., & Zhou, X. (2019). Detection and Application of 5-Formylcytosine and 5-Formyluracil in DNA. Accounts of Chemical Research, 52(4), 1016-1024. doi:10.1021/acs.accounts.8b00543es_ES
dc.description.referencesXing, J., Ai, Y., Liu, Y., Du, J., Chen, W., Lu, Z., & Wang, X. (2018). Theoretical Studies on the Photophysics and Photochemistry of 5-Formylcytosine and 5-Carboxylcytosine: The Oxidative Products of Epigenetic Modification of Cytosine in DNA. The Journal of Physical Chemistry B, 122(10), 2704-2714. doi:10.1021/acs.jpcb.7b10218es_ES
dc.description.referencesLópez, V., Fernández, A. F., & Fraga, M. F. (2017). The role of 5-hydroxymethylcytosine in development, aging and age-related diseases. Ageing Research Reviews, 37, 28-38. doi:10.1016/j.arr.2017.05.002es_ES
dc.description.referencesBerson, A., Nativio, R., Berger, S. L., & Bonini, N. M. (2018). Epigenetic Regulation in Neurodegenerative Diseases. Trends in Neurosciences, 41(9), 587-598. doi:10.1016/j.tins.2018.05.005es_ES
dc.description.referencesDeans, C., & Maggert, K. A. (2015). What Do You Mean, «Epigenetic»? Genetics, 199(4), 887-896. doi:10.1534/genetics.114.173492es_ES
dc.description.referencesHognon, C., Besancenot, V., Gruez, A., Grandemange, S., & Monari, A. (2019). Cooperative Effects of Cytosine Methylation on DNA Structure and Dynamics. The Journal of Physical Chemistry B, 123(34), 7365-7371. doi:10.1021/acs.jpcb.9b05835es_ES
dc.description.referencesTang, Y., Zheng, S.-J., Qi, C.-B., Feng, Y.-Q., & Yuan, B.-F. (2015). Sensitive and Simultaneous Determination of 5-Methylcytosine and Its Oxidation Products in Genomic DNA by Chemical Derivatization Coupled with Liquid Chromatography-Tandem Mass Spectrometry Analysis. Analytical Chemistry, 87(6), 3445-3452. doi:10.1021/ac504786res_ES
dc.description.referencesBachman, M., Uribe-Lewis, S., Yang, X., Burgess, H. E., Iurlaro, M., Reik, W., … Balasubramanian, S. (2015). 5-Formylcytosine can be a stable DNA modification in mammals. Nature Chemical Biology, 11(8), 555-557. doi:10.1038/nchembio.1848es_ES
dc.description.referencesIurlaro, M., Ficz, G., Oxley, D., Raiber, E.-A., Bachman, M., Booth, M. J., … Reik, W. (2013). A screen for hydroxymethylcytosine and formylcytosine binding proteins suggests functions in transcription and chromatin regulation. Genome Biology, 14(10), R119. doi:10.1186/gb-2013-14-10-r119es_ES
dc.description.referencesEtienne, T., Assfeld, X., & Monari, A. (2014). Toward a Quantitative Assessment of Electronic Transitions’ Charge-Transfer Character. Journal of Chemical Theory and Computation, 10(9), 3896-3905. doi:10.1021/ct5003994es_ES
dc.description.referencesCrespo-Otero, R., & Barbatti, M. (2018). Recent Advances and Perspectives on Nonadiabatic Mixed Quantum–Classical Dynamics. Chemical Reviews, 118(15), 7026-7068. doi:10.1021/acs.chemrev.7b00577es_ES
dc.description.referencesMai, S., Marquetand, P., & González, L. (2015). A general method to describe intersystem crossing dynamics in trajectory surface hopping. International Journal of Quantum Chemistry, 115(18), 1215-1231. doi:10.1002/qua.24891es_ES
dc.description.referencesMartin, R. L. (2003). Natural transition orbitals. The Journal of Chemical Physics, 118(11), 4775-4777. doi:10.1063/1.1558471es_ES
dc.description.referencesJanicki, M. J., Szabla, R., Šponer, J., & Góra, R. W. (2018). Solvation effects alter the photochemistry of 2-thiocytosine. Chemical Physics, 515, 502-508. doi:10.1016/j.chemphys.2018.06.016es_ES
dc.description.referencesMai, S., Pollum, M., Martínez-Fernández, L., Dunn, N., Marquetand, P., Corral, I., … González, L. (2016). The origin of efficient triplet state population in sulfur-substituted nucleobases. Nature Communications, 7(1). doi:10.1038/ncomms13077es_ES
dc.description.referencesMarazzi, M., Mai, S., Roca-Sanjuán, D., Delcey, M. G., Lindh, R., González, L., & Monari, A. (2016). Benzophenone Ultrafast Triplet Population: Revisiting the Kinetic Model by Surface-Hopping Dynamics. The Journal of Physical Chemistry Letters, 7(4), 622-626. doi:10.1021/acs.jpclett.5b02792es_ES
dc.description.sponsorshipSupport from the Universite de Lorraine, CNRS and Spanish Government (PGC2018-096684-B-I00) is kindly acknowledged. A. F.-M. is grateful to Generalitat Valenciana (CTQ2017-87054-C2-2-P) and the European Social Fund for a postdoctoral contract (APOSTD/2019/149), M. L.-R. acknowledges the Universitat Politecnica de Valencia for the FPI grant. Calculations have been performed on the local LPCT computer center and on the Explor regional center in the framework of the project "Dancing under the light''.es_ES
dc.description.upvformatpfin4407es_ES
dc.description.upvformatpinicio4404es_ES
dc.description.volume56es_ES
dc.identifier.doi10.1039/d0cc01132kes_ES
dc.identifier.issn1359-7345es_ES
dc.identifier.pmid32239074es_ES
dc.identifier.urihttps://riunet.upv.es/handle/10251/165411
dc.languageIngléses_ES
dc.publisherThe Royal Society of Chemistryes_ES
dc.relation.ispartofChemical Communicationses_ES
dc.relation.pasarelaS\425469es_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-87054-C2-2-P/ES/FOTOFISICA DE SISTEMAS ORGANICOS DE TRANSFERENCIA DE CARGA INNOVADORES/es_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-096684-B-I00/ES/REPARACION DEL ADN POR PROCESOS MULTIFOTONICOS/es_ES
dc.relation.projectIDinfo:eu-repo/grantAgreement/GVA//APOSTD%2F2019%2F149/es_ES
dc.relation.publisherversionhttps://doi.org/10.1039/d0cc01132kes_ES
dc.relation.references10.1016/j.neuron.2014.06.034es_ES
dc.relation.references10.1111/j.1751-1097.1993.tb02273.xes_ES
dc.relation.references10.1016/j.mrfmmm.2004.09.012es_ES
dc.relation.references10.1007/978-3-319-43157-4es_ES
dc.relation.references10.1016/j.dnarep.2014.03.031es_ES
dc.relation.references10.1021/ja5040478es_ES
dc.relation.references10.1111/php.13159es_ES
dc.relation.references10.1039/C7PP00395Aes_ES
dc.relation.references10.3389/fchem.2015.00043es_ES
dc.relation.references10.1101/cshperspect.a012559es_ES
dc.relation.references10.1021/ja304069fes_ES
dc.relation.references10.1021/jacs.6b06701es_ES
dc.relation.references10.1269/jrr.10175es_ES
dc.relation.references10.1021/acs.jpclett.6b01781es_ES
dc.relation.references10.1021/jacs.7b05931es_ES
dc.relation.references10.1039/C1PP05190Ces_ES
dc.relation.references10.1021/ar300054ees_ES
dc.relation.references10.1039/c1sc00088hes_ES
dc.relation.references10.1021/ar700245ees_ES
dc.relation.references10.1093/nar/gkv1364es_ES
dc.relation.references10.1111/php.12716es_ES
dc.relation.references10.1021/jz502562des_ES
dc.relation.references10.1021/jp5088515es_ES
dc.relation.references10.1002/anie.201411456es_ES
dc.relation.references10.1002/anie.201302176es_ES
dc.relation.references10.1002/cphc.201600154es_ES
dc.relation.references10.1002/chem.201501212es_ES
dc.relation.references10.1039/C8CP04866Ees_ES
dc.relation.references10.1021/acschembio.7b01097es_ES
dc.relation.references10.1016/S1568-7864(02)00198-2es_ES
dc.relation.references10.1021/bi030247jes_ES
dc.relation.references10.1021/acs.accounts.8b00543es_ES
dc.relation.references10.1021/acs.jpcb.7b10218es_ES
dc.relation.references10.1016/j.arr.2017.05.002es_ES
dc.relation.references10.1016/j.tins.2018.05.005es_ES
dc.relation.references10.1534/genetics.114.173492es_ES
dc.relation.references10.1021/acs.jpcb.9b05835es_ES
dc.relation.references10.1021/ac504786res_ES
dc.relation.references10.1038/nchembio.1848es_ES
dc.relation.references10.1186/gb-2013-14-10-r119es_ES
dc.relation.references10.1021/ct5003994es_ES
dc.relation.references10.1021/acs.chemrev.7b00577es_ES
dc.relation.references10.1002/qua.24891es_ES
dc.relation.references10.1063/1.1558471es_ES
dc.relation.references10.1016/j.chemphys.2018.06.016es_ES
dc.relation.references10.1038/ncomms13077es_ES
dc.relation.references10.1021/acs.jpclett.5b02792es_ES
dc.rightsReconocimiento (by)es_ES
dc.rights.accessRightsAbiertoes_ES
dc.subject.classificationQUIMICA ORGANICAes_ES
dc.titlePhotoinduced intersystem crossing in DNA oxidative lesions and epigenetic intermediateses_ES
dc.typeArtículoes_ES
dc.type.versioninfo:eu-repo/semantics/publishedVersiones_ES
dspace.entity.typePublication
person.identifier262233
person.identifier.orcid0000-0002-8205-8892
relation.isAuthorOfPublicationa49adf87-a055-4c4f-9f19-6acea9beef4f
relation.isAuthorOfPublication.latestForDiscoverya49adf87-a055-4c4f-9f19-6acea9beef4f
relation.isOrgUnitOfPublicationb97c2806-5147-442a-a1a8-a2c75cc2a941
relation.isOrgUnitOfPublication.latestForDiscoveryb97c2806-5147-442a-a1a8-a2c75cc2a941
upv.uuid8bf20b07-313f-4e7d-ac65-80de037fb5cees_ES

Archivos

Bloque original

Mostrando 1 - 1 de 1
Cargando...
Miniatura
Nombre:
Francés-Monerrs;Lneros-Rosa;Mranda - Photonducedntersystem crossngn DNA oxdatve lesons and epgene....pdf
Tamaño:
3.03 MB
Formato:
Adobe Portable Document Format
Descripción:
Versión editorial