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Characterization of Locally Excited and Charge-Transfer States of the Anticancer Drug Lapatinib by Ultrafast Spectroscopy and Computational Studies

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Characterization of Locally Excited and Charge-Transfer States of the Anticancer Drug Lapatinib by Ultrafast Spectroscopy and Computational Studies

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dc.contributor.author Vayá Pérez, Ignacio es_ES
dc.contributor.author Andreu Ros, María Inmaculada es_ES
dc.contributor.author Lence, Emilio es_ES
dc.contributor.author González-Bello, Concepción es_ES
dc.contributor.author Cuquerella Alabort, Maria Consuelo es_ES
dc.contributor.author Navarrete-Miguel, Miriam es_ES
dc.contributor.author Roca-Sanjuán, Daniel es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2021-05-14T12:41:21Z
dc.date.available 2021-05-14T12:41:21Z
dc.date.issued 2020-12-04 es_ES
dc.identifier.issn 0947-6539 es_ES
dc.identifier.uri http://hdl.handle.net/10251/166376
dc.description This is the peer reviewed version of the following article: I. Vayá, I. Andreu, E. Lence, C. González-Bello, M. Consuelo Cuquerella, M. Navarrete-Miguel, D. Roca-Sanjuán, M. A. Miranda, Chem. Eur. J. 2020, 26, 15922, which has been published in final form at https://doi.org/10.1002/chem.202001336. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving. es_ES
dc.description.abstract [EN] Lapatinib (LAP) is an anticancer drug, which is metabolized to theN- and O-dealkylated products (N-LAP andO-LAP, respectively). In view of the photosensitizing potential of related drugs, a complete experimental and theoretical study has been performed on LAP,N-LAP andO-LAP, both in solution and upon complexation with human serum albumin (HSA). In organic solvents, coplanar locally excited (LE) emissive states are generated; they rapidly evolve towards twisted intramolecular charge-transfer (ICT) states. By contrast, within HSA only LE states are detected. Accordingly, femtosecond transient absorption reveals a very fast switching (ca. 2 ps) from LE (lambda(max)=550 nm) to ICT states (lambda(max)=480 nm) in solution, whereas within HSA the LE species become stabilized and live much longer (up to the ns scale). Interestingly, molecular dynamics simulation studies confirm that the coplanar orientation is preferred for LAP (or to a lesser extentN-LAP) within HSA, explaining the experimental results. es_ES
dc.description.sponsorship Financial support from the Spanish Government (RYC-2015-17737, CTQ2017-89416-R, ISCIII grants RD16/0006/0004, PI16/01877 and CPII16/00052, SAF2016-75638-R, RYC-2015-19234, CTQ2017-87054-C2-2-P, and MDM-2015-0538), Conselleria d'Educacio Cultura i Esport (PROMETEO/2017/075), the Xunta de Galicia [ED431B 2018/04 and Centro singular de investigacion de Galicia accreditation 2019-2022 (ED431G 2019/03)] and the European Regional Development Fund is gratefully acknowledged. We thank the Centro de Supercomputacion de Galicia (CESGA) for use of the Finis Terrae computer. es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation ISCIII/RD16/0006/0004 es_ES
dc.relation MINISTERIO DE ECONOMIA Y EMPRESA/RYC-2015-17737 es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Anticancer drugs es_ES
dc.subject Femtosecond transient absorption es_ES
dc.subject Fluorescence es_ES
dc.subject Lapatinib es_ES
dc.subject Molecular dynamics simulations es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Characterization of Locally Excited and Charge-Transfer States of the Anticancer Drug Lapatinib by Ultrafast Spectroscopy and Computational Studies es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/chem.202001336 es_ES
dc.relation.projectID info: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.projectID info:eu-repo/grantAgreement/MINECO//SAF2016-75638-R/ES/DESARROLLO DE NUEVOS FARMACOS PARA EL TRATAMIENTO DE LAS INFECCIONES BACTERIANAS MULTIRESISTENTES: APROXIMACIONES QUE INCIDEN SOBRE VIABILIDAD, RESISTENCIA Y VIRULENCIA/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//MDM-2015-0538/ES/INSTITUTO DE CIENCIA MOLECULAR/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//RYC-2015-19234/ES/RYC-2015-19234/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Xunta de Galicia//ED431B 2018%2F04/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/ISCIII//CP1116%2F00052/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/Xunta de Galicia//ED431G 2019%2F03/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//PI16%2F01877/ES/Estrategia integrada de fotodiagnóstico combinando evaluación clínica, ensayos biológicos y estudios mecanísticos/ 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/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. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.description.bibliographicCitation Vayá Pérez, I.; Andreu Ros, MI.; Lence, E.; González-Bello, C.; Cuquerella Alabort, MC.; Navarrete-Miguel, M.; Roca-Sanjuán, D.... (2020). Characterization of Locally Excited and Charge-Transfer States of the Anticancer Drug Lapatinib by Ultrafast Spectroscopy and Computational Studies. Chemistry - A European Journal. 26(68):15922-15930. https://doi.org/10.1002/chem.202001336 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/chem.202001336 es_ES
dc.description.upvformatpinicio 15922 es_ES
dc.description.upvformatpfin 15930 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 26 es_ES
dc.description.issue 68 es_ES
dc.identifier.pmid 32585059 es_ES
dc.relation.pasarela S\426409 es_ES
dc.contributor.funder Xunta de Galicia es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Instituto de Salud Carlos III es_ES
dc.contributor.funder Agencia Estatal de Investigación es_ES
dc.contributor.funder European Regional Development Fund es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Ministerio de Ciencia, Innovación y Universidades es_ES
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