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Comparative reactivity of medicinal gold( i ) compounds with the cyclic peptide vasopressin and its diselenide analogue

Abstract : The reactions of the medicinal gold(i) compound auranofin and its close analogues with vasopressin and the diselenide analogue were comparatively investigated by LC-electrospray MS/MS. Evidence is gained of the possible cleavage of the S-S and Se-Se bridges induced by Au(i). Notably, we found that, in the absence of reducing agents, the sulfur and selenium atoms are metallated only at high temperature (70 °C) with the preferential binding of gold to selenium. The reaction with the S-S bridge can take place at physiological temperature (37 °C) under reducing conditions. The implications of these results are discussed in the general frame of the reactivity of biologically relevant soft Lewis acids with peptides and proteins.
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Submitted on : Friday, January 7, 2022 - 10:10:46 AM
Last modification on : Friday, April 1, 2022 - 3:56:26 AM

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Jeremy Lamarche, Enrique Alcoceba Álvarez, Emmanuelle Cordeau, Christine Enjalbal, Lara Massai, et al.. Comparative reactivity of medicinal gold( i ) compounds with the cyclic peptide vasopressin and its diselenide analogue. Dalton Transactions, Royal Society of Chemistry, 2021, 50 (47), pp.17487-17490. ⟨10.1039/d1dt03470g⟩. ⟨hal-03516255⟩

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