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dc.contributor.authorMiguel Ávila, Joan
dc.contributor.authorTomás Gamasa, María
dc.contributor.authorOlmos, Andrea
dc.contributor.authorPérez, Pedro J.
dc.contributor.authorMascareñas Cid, José Luis
dc.date.accessioned2018-03-14T08:17:18Z
dc.date.available2018-03-14T08:17:18Z
dc.date.issued2018-01-15
dc.identifier.citationMiguel-Ávila, J., Tomás-Gamasa, M., Olmos, A., Pérez, P., & Mascareñas, J. (2018). Discrete Cu(i) complexes for azide–alkyne annulations of small molecules inside mammalian cells. Chemical Science, 9(7), 1947-1952. http://dx.doi.org/10.1039/c7sc04643j
dc.identifier.urihttp://hdl.handle.net/10347/16572
dc.description.abstractThe archetype reaction of “click” chemistry, namely, the copper-promoted azide–alkyne cycloaddition (CuAAC), has found an impressive number of applications in biological chemistry. However, methods for promoting intermolecular annulations of exogenous, small azides and alkynes in the complex interior of mammalian cells, are essentially unknown. Herein we demonstrate that isolated, well-defined copper(I)– tris(triazolyl) complexes featuring designed ligands can readily enter mammalian cells and promote intracellular CuAAC annulations of small, freely diffusible molecules. In addition to simplifying protocols and avoiding the addition of “non-innocent” reductants, the use of these premade copper complexes leads to more efficient processes than with the alternative, in situ made copper species prepared from Cu(II) sources, tris(triazole) ligands and sodium ascorbate. Under the reaction conditions, the well-defined copper complexes exhibit very good cell penetration properties, and do not present significant toxicities
dc.description.sponsorshipThis work has received financial support from the MINECO (SAF2013-41943-R, SAF2016-76689-R, CTQ2014-52769-C03-01 and CTQ2015-73693-JIN and Orfeo-cinqa CTQ2016-81797-REDC), the Xunta de Galicia (2015-CP082, ED431C 2017/19 and Centro singular de investigación de Galicia accreditation 2016– 2019, ED431G/09) and the European Union (European Regional Development Fund – ERDF), and the European Research Council (Advanced Grant No. 340055). M. T.-G. thanks the Ministerio de Economía y Competitividad for the Juan de la Cierva-Incorporación fellowship (IJCI-2015-23210)
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.relationinfo:eu-repo/grantAgreement/EC/H2020/340055
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797/ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2016-76689-R/ES
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/SAF2013-41943-R/ES/HERRAMIENTAS SINTETICAS EN QUIMICA BIOLOGICA. NUEVAS ESTRATEGIAS MOLECULARES PARA EL TRATAMIENTO Y DIAGNOSTICO DE CANCERES
dc.relationinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-73693-JIN/ES/FROM NATURAL GAS TO CHEMICAL SYNTHESIS
dc.rightsThis article is licensed under a Creative Commons Attribution 3.0 Unported Licence
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/
dc.titleDiscrete Cu(I) complexes for azide-alkyne annulations of small molecules inside mammalian cells
dc.typeinfo:eu-repo/semantics/article
dc.identifier.DOI10.1039/C7SC04643J
dc.relation.publisherversionhttps://doi.org/10.1039/C7SC04643J
dc.type.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.e-issn2041-6539
dc.rights.accessrightsinfo:eu-repo/semantics/openAccess
dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.description.peerreviewedSI


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