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Chemical tuning for potential antitumor fluoroquinolones

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Chemical tuning for potential antitumor fluoroquinolones

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dc.contributor.author Anaya-González, Cristina es_ES
dc.contributor.author Soldevila Serrano, Sonia es_ES
dc.contributor.author García-Laínez, Guillermo es_ES
dc.contributor.author Bosca Mayans, Francisco es_ES
dc.contributor.author Andreu Ros, María Inmaculada es_ES
dc.date.accessioned 2021-05-20T03:34:12Z
dc.date.available 2021-05-20T03:34:12Z
dc.date.issued 2019-09 es_ES
dc.identifier.issn 0891-5849 es_ES
dc.identifier.uri http://hdl.handle.net/10251/166533
dc.description.abstract [EN] Phototoxic effects of 6,8 dihalogenated quinolones confers to this type of molecules a potential property as photochemotherapeutic agents. Two photodehalogenation processes seem to be involved in the remarkable photoinduced cellular damage. In this context, a new 6,8 dihalogenated quinolone 1 (1-methyl-6,8-difluoro-4-oxo-7-aminodimethy1-1,4-dihydroquinoline-3-carboxylic acid) was synthesized looking for improving the phototoxic properties of fluoroquinolones (FQ) and to determine the role of the photodegradation pathways in the FQ phototoxicity. With this purpose, fluorescence emissions, laser flash photolysis experiments and photodegradation studies were performed with compound 1 using 1-ethyl-6,8-difluoro-4-oxo-7-aminodimethy1-1,4-dihidroquinoline-3-carboxylic acid (2) and lomefloxacin (LFX) as reference compounds. The shortening of alkyl chain of the N(1) of the quinolone ring revealed a lifetime increase of the reactive aryl cation generated from photolysis of the three FQ and a significant reduction of the FQ photodegradation quantum yield. The fact that these differences were smaller when the same study was done using a hydrogen donor solvent (ethanol-aqueous buffer, 50/50 v/v) evidenced the highest ability of the reactive intermediate arising from 1 to produce intermolecular alkylations. These results were correlated with in vitro 3T3 NRU phototoxicity test. Thus, when PhotoIrritation-Factor (PIF) was determined for 1, 2 and LFX using cytotoxicity profiles of BALB/c 3T3 fibroblasts treated with each compound in the presence and absence of UVA light, a PIF more higher than 30 was obtained for 1 while the values for 2 and LFX were only higher than 8 and 10, respectively. Thereby, the present study illustrates an approach to modulate the photosensitizing properties of FQ with the purpose to improve the chemotherapeutic properties of antitumor quinolones. Moreover, the results obtained in this study also evidence that the key pathway responsible for the phototoxic properties associated with dihalogenated quinolones is the aryl cation generation. es_ES
dc.description.sponsorship Financial support from Spanish government (MINECO grant CTQ2014-54729-C2-2-P and Severo Ochoa fellowship for C. A., Carlos III Institute of Health grant PI16/01877), and the Generalitat Valenciana (PROMETEO program, 2017-075). We thank M.P. Marin of IIS La Fe Microscopy Unit for confocal microscopy. es_ES
dc.language Inglés es_ES
dc.publisher Elsevier es_ES
dc.relation.ispartof Free Radical Biology and Medicine es_ES
dc.rights Reconocimiento - No comercial - Sin obra derivada (by-nc-nd) es_ES
dc.subject Excited states es_ES
dc.subject Fluorescence emission es_ES
dc.subject Laser flash photolysis es_ES
dc.subject Photodehalogenation process es_ES
dc.subject Phototoxicity test es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Chemical tuning for potential antitumor fluoroquinolones es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1016/j.freeradbiomed.2019.06.010 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MINECO//CTQ2014-54729-C2-2-P/ES/DISEÑO DE NUEVAS PRODROGAS ANTICANCERIGENAS FOTOACTIVABLES/ 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//PI16%2F01877/ES/Estrategia integrada de fotodiagnóstico combinando evaluación clínica, ensayos biológicos y estudios mecanísticos/ es_ES
dc.rights.accessRights Abierto 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 Anaya-González, C.; Soldevila Serrano, S.; García-Laínez, G.; Bosca Mayans, F.; Andreu Ros, MI. (2019). Chemical tuning for potential antitumor fluoroquinolones. Free Radical Biology and Medicine. 141:150-158. https://doi.org/10.1016/j.freeradbiomed.2019.06.010 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1016/j.freeradbiomed.2019.06.010 es_ES
dc.description.upvformatpinicio 150 es_ES
dc.description.upvformatpfin 158 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 141 es_ES
dc.identifier.pmid 31195085 es_ES
dc.relation.pasarela S\404701 es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Economía y Competitividad es_ES
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