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Solving the Challenging Synthesis of Highly Cytotoxic Silver Complexes Bearing Sterically Hindered NHC Ligands with Mechanochemistry

preprint
submitted on 17.01.2020 and posted on 20.01.2020 by Audrey Beillard, François Quintin, jeremie gatignol, Pascal Retailleau, Jean-Luc Renaud, Sylvain Gaillard, Thomas-Xavier Métro, Frédéric Lamaty, Xavier Bantreil

The use of ball-mills enabled the straightforward synthesis of a variety of silver(I) complexes featuring challenging NHC ligands. Sterically hindered including electron-poor or with very low solubility imidazolium salts were grinded with silver(I) oxide to furnish heteroleptic or homoleptic complexes in high yield and short reaction times. The synthesis of heteroleptic bis-NHC silver(I) complexes was also performed for the first time in a ball-mill. The efficiency and rapidity of the mechanochemical approach enabled the generation of a library of unprecedented NHC silver complexes, which cytotoxicity on HCT116 colorectal cancer cell line was evaluated providing a rare example of medicinal mechanochemistry. The cationic silver complexes were found more potent than the neutral analogues, with IC50 values down to 21 nM, 256 times more potent than cisplatin.

Funding

ANR-16-CE07-0009-01

History

Email Address of Submitting Author

xavier.bantreil@umontpellier.fr

Institution

University of Montpellier

Country

France

ORCID For Submitting Author

0000-0002-2676-6851

Declaration of Conflict of Interest

no conflict of interest

Version Notes

Version 1.0

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