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.

Comparative reactivity of medicinal gold(i) compounds with the cyclic peptide vasopressin and its diselenide analogue / Lamarche J.; Alcoceba Alvarez E.; Cordeau E.; Enjalbal C.; Massai L.; Messori L.; Lobinski R.; Ronga L.. - In: DALTON TRANSACTIONS. - ISSN 1477-9226. - ELETTRONICO. - 50:(2021), pp. 17487-17490. [10.1039/d1dt03470g]

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

Messori L.;
2021

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.
2021
50
17487
17490
Lamarche J.; Alcoceba Alvarez E.; Cordeau E.; Enjalbal C.; Massai L.; Messori L.; Lobinski R.; Ronga L.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1259275
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