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Int. J. Mol. Sci. 2019, 20(4), 820; https://doi.org/10.3390/ijms20040820

Reactivity of Gold(I) Monocarbene Complexes with Protein Targets: A Theoretical Study

Dipartimento di Farmacia, Università degli Studi “G. D’Annunzio” Chieti-Pescara, Via dei Vestini, I-66100 Chieti, Italy
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Received: 15 January 2019 / Revised: 6 February 2019 / Accepted: 12 February 2019 / Published: 14 February 2019
(This article belongs to the Special Issue Interaction between Metal Compounds and Proteins)
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Abstract

Neutral N–heterocyclic carbene gold(I) compounds such as IMeAuCl are widely used both in homogeneous catalysis and, more recently, in medicinal chemistry as promising antitumor agents. In order to shed light on their reactivity with protein side chains, we have carried out density functional theory (DFT) calculations on the thermodynamics and kinetics of their reactions with water and various nucleophiles as a model of plausible protein binding sites such as arginine, aspartic acid, asparagine, cysteine, glutamic acid, glutamine, histidine, lysine, methionine, selenocysteine, and the N-terminal group. In agreement with recent experimental data, our results suggest that IMeAuCl easily interacts with all considered biological targets before being hydrated—unless sterically prevented—and allows the establishment of an order of thermodynamic stability and of kinetic reactivity for its binding to protein residues. View Full-Text
Keywords: anticancer; N-heterocyclic carbenes; gold(I) complexes; DFT calculations; proteins anticancer; N-heterocyclic carbenes; gold(I) complexes; DFT calculations; proteins
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Tolbatov, I.; Coletti, C.; Marrone, A.; Re, N. Reactivity of Gold(I) Monocarbene Complexes with Protein Targets: A Theoretical Study. Int. J. Mol. Sci. 2019, 20, 820.

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