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http://hdl.handle.net/10261/266053
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dc.contributor.author | Rafols, Laia | es_ES |
dc.contributor.author | Josa, Dana | es_ES |
dc.contributor.author | Aguilà, David | es_ES |
dc.contributor.author | Barrios, L. A. | es_ES |
dc.contributor.author | Roubeau, Olivier | es_ES |
dc.contributor.author | Cirera, Jordi | es_ES |
dc.contributor.author | Soto-Cerrato, Vanessa | es_ES |
dc.contributor.author | Pérez-Tomás, Ricardo | es_ES |
dc.contributor.author | Martínez, Manuel | es_ES |
dc.contributor.author | Grabulosa, Arnald | es_ES |
dc.contributor.author | Gamez, Patrick | es_ES |
dc.date.accessioned | 2022-04-01T11:10:54Z | - |
dc.date.available | 2022-04-01T11:10:54Z | - |
dc.date.issued | 2021 | - |
dc.identifier.citation | Inorganic Chemistry 60(11): 7974-7990 (2021) | es_ES |
dc.identifier.uri | http://hdl.handle.net/10261/266053 | - |
dc.description.abstract | We have recently reported a series of piano-stool ruthenium(II) complexes of the general formula [RuCl2(η6-arene)(P(1-pyrenyl)R2R3)] showing excellent cytotoxic activities (particularly when R2 = R3 = methyl). In the present study, new members of this family of compounds have been prepared with the objective to investigate the effect of the steric hindrance of a bulky phosphane ligand, namely diisopropyl(1-pyrenyl)phosphane (L), on exchange reactions involving the coordinated halides (X = Cl, I). Two η6-arene rings were used, i.e. η6-methyl benzoate (mba) and η6-p-cymene (p-cym), and four complexes were synthesized, namely [RuCl2(mba)(L)] (1Cl2iPr), [RuI2(mba)(L)] (1I2iPr), [RuCl2(p-cym)(L)] (2Cl2iPr), and [RuI2(p-cym)(L)] (2I2iPr). Unexpectedly, all of the complexes exhibited poor cytotoxic activities after 24 h of incubation with cells, in contrast to the related compounds previously reported. However, it was observed that aged DMSO solutions of 2I2iPr (from 2 to 7 days) exhibited better activities in comparison to freshly prepared solutions and that the activity improved over “aging” time. Thorough studies were therefore performed to uncover the origin of this lag time in the cytotoxicity efficiency. The data achieved clearly demonstrated that compounds 2I2iPr and 2Cl2iPr were undergoing a series of transformation reactions in DMSO (with higher rates for the iodido complex 2I2iPr), ultimately generating cyclometalated species through a mechanism involving DMSO as a coordinated proton abstractor. The cyclometalated complexes detected in solution were subsequently prepared; hence, pure [RuCl(p-cym)(κ2C-diisopropyl(1-pyrenyl)phosphane)] (3CliPr), [RuI(p-cym)(κ2C-diisopropyl(1-pyrenyl)phosphane)] (3IiPr), and [Ru(p-cym)(κS-dmso)(κ2C-diisopropyl(1-pyrenyl)phosphane)]PF6 (3dmsoiPr) were synthesized and fully characterized. Remarkably, 3CliPr, 3IiPr, and 3dmsoiPr are all very efficient cytotoxic agents, exhibiting slightly better activities in comparison to the chlorido noncyclometalated complexes [RuCl2(η6-arene)(P(1-pyrenyl)R2R3)] described in an earlier report. For comparison purposes, the iodido compounds [RuI2(mba)(dimethyl(1-pyrenyl)phosphane)] (1I2Me) and [RuI2(p-cym)(dimethyl(1-pyrenyl)phosphane)] (2I2Me), bearing the less hindered dimethyl(1-pyrenyl)phosphane ligand, have also been prepared. The cytotoxic and chemical behaviors of 1I2Me and 1I2Me were comparable to those of their chlorido counterparts reported previously. | es_ES |
dc.description.sponsorship | Financial support from the Spanish Ministerio de Ciencia Innovación, y Universidades (Project Nos. CTQ2015-65040-P, RED2018-102471-T, PID2019-107006GB-C21, PGC2018-098630-B-I00, and CTQ2017-88446-R AEI/FEDER, UE) and from the Instituto de Salud Carlos III (ISCIIIFIS PI18/00441, FEDER) is acknowledged. A.G. thanks the Royal Society of Chemistry for financial support (RSC Research Fund grant RF19-7147). J.C. thanks the Spanish MICINN for a Ramoń y Cajal research contract (RYC2018-024692-I) and the Spanish Structures of Excellence María de Maeztu program (MDM-2017-0767). P.G. acknowledges the Institució Catalana de Recerca i Estudis Avançats (ICREA). | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO//CTQ2015-65040-P/ES/COMPUESTOS ORGANOMETALICOS: APLICACIONES COMO METALOFARMACOS Y EN CATALISIS ASIMETRICA/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI//RED2018-102471-T | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-107006GB-C21/ES/ESTUDIOS CINETICO-MECANISTICOS DE LA REACTIVIDAD DE COMPUESTOS DE COORDINACION EN DISOLUCION: LA IMPORTANCIA DE LAS VARIABLES INOCENTES EN LOS PARAMETROS DE ACTIVACION/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-098630-B-I00/ES/DISEÑO Y NANOESTRUCTURACION DE MOLECULAS MULTIFUNCIONALES PARA EL AVANCE DE LA ESPINTRONICA/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-88446-R/ES/NANOTRANSPORTADORES PARA LA ADMINISTRACION DE FARMACOS MEDIANTE LIBERACION TERMICA/ | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI//RYC2018-024692-I | es_ES |
dc.relation.isversionof | Publisher's version | es_ES |
dc.rights | openAccess | es_ES |
dc.title | Piano-stool ruthenium(II) complexes with delayed cytotoxic activity: Origin of the lag time | es_ES |
dc.type | artículo | es_ES |
dc.identifier.doi | 10.1021/acs.inorgchem.1c00507 | - |
dc.description.peerreviewed | Peer reviewed | es_ES |
dc.relation.publisherversion | https://doi.org/10.1021/acs.inorgchem.1c00507 | es_ES |
dc.identifier.e-issn | 1520-510X | - |
dc.rights.license | https://creativecommons.org/licenses/by/4.0/ | es_ES |
dc.contributor.funder | Ministerio de Ciencia, Innovación y Universidades (España) | es_ES |
dc.contributor.funder | Agencia Estatal de Investigación (España) | es_ES |
dc.contributor.funder | Ministerio de Economía y Competitividad (España) | es_ES |
dc.contributor.funder | European Commission | es_ES |
dc.contributor.funder | Instituto de Salud Carlos III | es_ES |
dc.contributor.funder | Royal Society of Chemistry (UK) | es_ES |
dc.contributor.funder | Institución Catalana de Investigación y Estudios Avanzados | es_ES |
dc.relation.csic | Sí | es_ES |
oprm.item.hasRevision | no ko 0 false | * |
dc.identifier.funder | http://dx.doi.org/10.13039/501100000780 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100003741 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100004587 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100003329 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100000704 | es_ES |
dc.identifier.funder | http://dx.doi.org/10.13039/501100011033 | es_ES |
dc.type.coar | http://purl.org/coar/resource_type/c_6501 | es_ES |
item.grantfulltext | open | - |
item.openairecristype | http://purl.org/coar/resource_type/c_18cf | - |
item.fulltext | With Fulltext | - |
item.cerifentitytype | Publications | - |
item.languageiso639-1 | en | - |
item.openairetype | artículo | - |
Aparece en las colecciones: | (INMA) Artículos (CIN2) Artículos (ICMA) Artículos |
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