NDLI: Discrete Cu(i) complexes for azide–alkyne annulations of small molecules inside mammalian cells† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc04643j

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Discrete Cu(i) complexes for azide–alkyne annulations of small molecules inside mammalian cells† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c7sc04643j

Content Provider	Semantic Scholar
Author	Miguel-Ávila, Joan Tomás-Gamasa, María Olmos, Andrea Pérez, Pedro J. Mascareñas, José Luis
Copyright Year	2018
Abstract	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.
Starting Page	1947
Ending Page	1952
Page Count	6
File Format	PDF HTM / HTML
DOI	10.1039/c7sc04643j
PubMed reference number	29675241
Journal	Medline
Volume Number	9
Alternate Webpage(s)	https://minerva.usc.es/xmlui/bitstream/handle/10347/16572/2018_chemscie_miguel_discrete_cu.pdf?isAllowed=y&sequence=1
Alternate Webpage(s)	http://www.rsc.org/suppdata/c7/sc/c7sc04643j/c7sc04643j1.pdf
Alternate Webpage(s)	https://doi.org/10.1039/c7sc04643j
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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