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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5892125/ https://www.ncbi.nlm.nih.gov/pubmed/29675241 http://dx.doi.org/10.1039/c7sc04643j |
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author | Miguel-Ávila, Joan Tomás-Gamasa, María Olmos, Andrea Pérez, Pedro J. Mascareñas, José L. |
author_facet | Miguel-Ávila, Joan Tomás-Gamasa, María Olmos, Andrea Pérez, Pedro J. Mascareñas, José L. |
author_sort | Miguel-Ávila, Joan |
collection | PubMed |
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. |
format | Online Article Text |
id | pubmed-5892125 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-58921252018-04-19 Discrete Cu(i) complexes for azide–alkyne annulations of small molecules inside mammalian cells Miguel-Ávila, Joan Tomás-Gamasa, María Olmos, Andrea Pérez, Pedro J. Mascareñas, José L. Chem Sci Chemistry 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. Royal Society of Chemistry 2018-01-15 /pmc/articles/PMC5892125/ /pubmed/29675241 http://dx.doi.org/10.1039/c7sc04643j Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Miguel-Ávila, Joan Tomás-Gamasa, María Olmos, Andrea Pérez, Pedro J. Mascareñas, José L. 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
|
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_short | 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 |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5892125/ https://www.ncbi.nlm.nih.gov/pubmed/29675241 http://dx.doi.org/10.1039/c7sc04643j |
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