RT Journal Article
T1 Discrete Cu(I) complexes for azide-alkyne annulations of small molecules inside mammalian cells
A1 Miguel Ávila, Joan
A1 Tomás Gamasa, María
A1 Olmos, Andrea
A1 Pérez, Pedro J.
A1 Mascareñas Cid, José Luis
AB 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
PB Royal Society of Chemistry
YR 2018
FD 2018-01-15
LK http://hdl.handle.net/10347/16572
UL http://hdl.handle.net/10347/16572
LA eng
NO Miguel-Ávila, J., Tomás-Gamasa, M., Olmos, A., Pérez, P., & Mascareñas, J. (2018). Discrete Cu(i) complexes for azide–alkyne annulations of small molecules inside mammalian cells. Chemical Science, 9(7), 1947-1952. http://dx.doi.org/10.1039/c7sc04643j
NO This work has received financial support from the MINECO (SAF2013-41943-R, SAF2016-76689-R, CTQ2014-52769-C03-01 and CTQ2015-73693-JIN and Orfeo-cinqa CTQ2016-81797-REDC), the Xunta de Galicia (2015-CP082, ED431C 2017/19 and Centro singular de investigación de Galicia accreditation 2016– 2019, ED431G/09) and the European Union (European Regional Development Fund – ERDF), and the European Research Council (Advanced Grant No. 340055). M. T.-G. thanks the Ministerio de Economía y Competitividad for the Juan de la Cierva-Incorporación fellowship (IJCI-2015-23210)
DS Minerva
RD 28 abr 2026