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Enhanced Drug Photosafety by Interchromophoric Interaction Due to Intramolecular Charge Separation

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Enhanced Drug Photosafety by Interchromophoric Interaction Due to Intramolecular Charge Separation

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dc.contributor.author Li, Ming-De es_ES
dc.contributor.author Yan, Zhiping es_ES
dc.contributor.author Zhu, Ruixue es_ES
dc.contributor.author Phillips,David Lee es_ES
dc.contributor.author Aparici-Espert, Maria Isabel es_ES
dc.contributor.author Lhiaubet, Virginie Lyria es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2020-05-21T03:02:03Z
dc.date.available 2020-05-21T03:02:03Z
dc.date.issued 2018-05-02 es_ES
dc.identifier.issn 0947-6539 es_ES
dc.identifier.uri http://hdl.handle.net/10251/143880
dc.description.abstract [EN] Imatinib is a synthetic tyrosinase inhibitor that is employed for the treatment of some kinds of human cancer. This drug has a low phototoxicity towards DNA, but its pyridylpyrimidine (1) fragment by itself exhibits significant phototoxicitiy. The intrinsic mechanism that leads to the enhanced photosafety of Imatinib is not yet known. Here, the properties of the excited state and interchromophoric interactions of Imatinib have been explored by using ultrafast laser flash photolysis and agarose electrophoresis studies. An intramolecular charge separation was directly observed for the irradiated Imatinib, which accounts for the relaxation of its excited state. An anionic form of pyridylpyrimidine (1) was deduced from the results of time-resolved resonance Raman spectra and by quenching experimental studies on compound 1 and diaminotoluene. In contrast, compound 1 efficiently transformed into triplet excited states with a long lifetime, which explained the phototoxicity associated with this fragment. This work provides insight into how to design drugs with lower phototoxicitiy or improved photostability by using interchromophoric interactions. es_ES
dc.description.sponsorship This work was supported by Natural Science Foundation of China (21773151) and Shantou University Initial Funding (NTF16010). The Support from the Hong Kong Research Grants Council grants GRF 17307916, AoE/P-03/08, SEG HKU/07, The University of Hong Kong Development Fund 2013-2014 project "New Ultrafast Spectroscopy Experiments for Shared Facilities", the Spanish Government (CTQ2015-70164-P and BES-2013-066566) are also acknowledged. es_ES
dc.language Inglés es_ES
dc.publisher John Wiley & Sons es_ES
dc.relation.ispartof Chemistry - A European Journal es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject Absorption es_ES
dc.subject Charge separation es_ES
dc.subject Chromophores es_ES
dc.subject Electronic structure es_ES
dc.subject Raman spectroscopy es_ES
dc.subject.classification QUIMICA ANALITICA es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Enhanced Drug Photosafety by Interchromophoric Interaction Due to Intramolecular Charge Separation es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1002/chem.201800716 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//BES-2013-066566/ES/BES-2013-066566/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/NSFC//21773151/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/RGC//17307916/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/RGC//AoE%2FP-03%2F08/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/RGC//SEG HKU%2F07/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/STU//NTF16010/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2015-70164-P/ES/LESIONES DEL ADN COMO FOTOSENSIBILIZADORES INTRINSECOS - CONCEPTO DE CABALLO DE TROYA/ 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 Li, M.; Yan, Z.; Zhu, R.; Phillips, DL.; Aparici-Espert, MI.; Lhiaubet, VL.; Miranda Alonso, MÁ. (2018). Enhanced Drug Photosafety by Interchromophoric Interaction Due to Intramolecular Charge Separation. Chemistry - A European Journal. 24(25):6654-6659. https://doi.org/10.1002/chem.201800716 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1002/chem.201800716 es_ES
dc.description.upvformatpinicio 6654 es_ES
dc.description.upvformatpfin 6659 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 24 es_ES
dc.description.issue 25 es_ES
dc.relation.pasarela S\355496 es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
dc.contributor.funder Shantou University es_ES
dc.contributor.funder University of Hong Kong es_ES
dc.contributor.funder Research Grant Council, Hong Kong es_ES
dc.contributor.funder National Natural Science Foundation of China es_ES
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