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Issue 7, 2018
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Discrete Cu(I) complexes for azide–alkyne annulations of small molecules inside mammalian cells

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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

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Publication details

The article was received on 26 Oct 2017, accepted on 15 Jan 2018 and first published on 15 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04643J
Citation: Chem. Sci., 2018,9, 1947-1952
  • Open access: Creative Commons BY license
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    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

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