期刊
CHEMICAL SCIENCE
卷 9, 期 7, 页码 1947-1952出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc04643j
关键词
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资金
- MINECO [SAF2013-41943-R, SAF2016-76689-R, CTQ2014-52769-C03-01, CTQ2015-73693-JIN, Orfeo-cinqa CTQ2016-81797-REDC]
- Xunta de Galicia [2015-CP082, ED431C 2017/19]
- European Union (European Regional Development Fund - ERDF)
- Xunta de Galicia (Centro singular de investigacion de Galicia accreditation) [20162019, ED431G/09]
- European Research Council [340055]
- Ministerio de Economia y Competitividad [IJCI-2015-23210]
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.
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