Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells

The 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 interio...

Descripción completa

Detalles Bibliográficos
Autores: Miguel Ávila, Joan, Tomás Gamasa, María, Olmos Verge, Andrea, Pérez Romero, Pedro José, Mascareñas, José L.
Tipo de recurso: artículo
Fecha de publicación:2018
País:España
Institución:Universidad de Huelva (UHU)
Repositorio:Arias Montano. Repositorio Institucional de la Universidad de Huelva
Idioma:inglés
OAI Identifier:oai:ariasmontano.uhu.es:10272/15917
Acceso en línea:http://hdl.handle.net/10272/15917
Access Level:acceso abierto
Palabra clave:Click chemistry
Cycloaddition
id ES_ee2bbce558d39fa644f9b6d452e09e47
oai_identifier_str oai:ariasmontano.uhu.es:10272/15917
network_acronym_str ES
network_name_str España
repository_id_str
spelling Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cellsMiguel Ávila, JoanTomás Gamasa, MaríaOlmos Verge, AndreaPérez Romero, Pedro JoséMascareñas, José L.Click chemistryCycloadditionThe 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.Royal Society of Chemistry20182018-01-0120182018-01-01journal articlehttp://purl.org/coar/resource_type/c_6501info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10272/15917reponame:Arias Montano. Repositorio Institucional de la Universidad de Huelvainstname:Universidad de Huelva (UHU)InglésengMinisterio de Economia y Competitividad [IJCI-2015-23210]info:eu-repo grantAgreement MINECO [SAF2013-41943-R, SAF2016-76689-R, CTQ2014-52769-C03-01, CTQ2015-73693-JIN, Orfeo-cinqa CTQ2016-81797-REDC]open accesshttp://purl.org/coar/access_right/c_abf2Atribución-NoComercial-SinDerivadas 3.0 Españahttp://creativecommons.org/licenses/by-nc-nd/3.0/es/info:eu-repo/semantics/openAccessoai:ariasmontano.uhu.es:10272/159172026-06-02T14:58:11Z
dc.title.none.fl_str_mv Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
title Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
spellingShingle Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
Miguel Ávila, Joan
Click chemistry
Cycloaddition
title_short Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
title_full Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
title_fullStr Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
title_full_unstemmed Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
title_sort Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells
dc.creator.none.fl_str_mv Miguel Ávila, Joan
Tomás Gamasa, María
Olmos Verge, Andrea
Pérez Romero, Pedro José
Mascareñas, José L.
author Miguel Ávila, Joan
author_facet Miguel Ávila, Joan
Tomás Gamasa, María
Olmos Verge, Andrea
Pérez Romero, Pedro José
Mascareñas, José L.
author_role author
author2 Tomás Gamasa, María
Olmos Verge, Andrea
Pérez Romero, Pedro José
Mascareñas, José L.
author2_role author
author
author
author
dc.contributor.none.fl_str_mv
dc.subject.none.fl_str_mv Click chemistry
Cycloaddition
topic Click chemistry
Cycloaddition
description The 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.
publishDate 2018
dc.date.none.fl_str_mv 2018
2018-01-01
2018
2018-01-01
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10272/15917
url http://hdl.handle.net/10272/15917
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Ministerio de Economia y Competitividad [IJCI-2015-23210]info:eu-repo grantAgreement MINECO [SAF2013-41943-R, SAF2016-76689-R, CTQ2014-52769-C03-01, CTQ2015-73693-JIN, Orfeo-cinqa CTQ2016-81797-REDC]
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución-NoComercial-SinDerivadas 3.0 España
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Atribución-NoComercial-SinDerivadas 3.0 España
http://creativecommons.org/licenses/by-nc-nd/3.0/es/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:Arias Montano. Repositorio Institucional de la Universidad de Huelva
instname:Universidad de Huelva (UHU)
instname_str Universidad de Huelva (UHU)
reponame_str Arias Montano. Repositorio Institucional de la Universidad de Huelva
collection Arias Montano. Repositorio Institucional de la Universidad de Huelva
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869423620657250304
score 15,812455

Similares en LA Referencia