Issue 7, 2018

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

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.

Graphical abstract: Discrete Cu(i) complexes for azide–alkyne annulations of small molecules inside mammalian cells

Supplementary files

Article information

Article type
Edge Article
Submitted
26 Okt. 2017
Accepted
15 Janv. 2018
First published
15 Janv. 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 1947-1952

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

J. Miguel-Ávila, M. Tomás-Gamasa, A. Olmos, P. J. Pérez and J. L. Mascareñas, Chem. Sci., 2018, 9, 1947 DOI: 10.1039/C7SC04643J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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