Elsevier

Tetrahedron Letters

Volume 53, Issue 2, 11 January 2012, Pages 232-234
Tetrahedron Letters

Oxidation of thiols promoted by PhSeZnCl

https://doi.org/10.1016/j.tetlet.2011.11.025Get rights and content

Abstract

The ability of PhSeZnCl 1 to catalyze the oxidation of thiols to disulfides has been evaluated and correlated to a catalytic GPx-like activity. The first evidence that vinyl phenylselenides can promote the oxidation of thiols reducing hydrogen peroxide through the formation of a selenoxide intermediate is also reported.

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Acknowledgments

Financial support from Fondazione Cassa di Risparmio di Perugia, Ricerca di Base 2010 – progetto 2010.011.0415, M.I.U.R. (Ministero Italiano Università e Ricerca), National Projects PRIN2007 (Progetto di Ricerca d’Interesse Nazionale), Consorzio CINMPIS, Bari (Consorzio Interuniversitario Nazionale di Metodologie e Processi Innovativi di Sintesi) are gratefully acknowledged.

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    At the same time, not all cellular thiols are the same level of importance in making a cancer cell susceptible of the cytotoxic activity of Se compounds. Several laboratories have assessed the GPx-mimetic (thiol peroxidase) activity of Se compounds and in some studies the correlation of this activity with the impact on cellular thiols and the apoptotic signaling of different cancer cell models has been demonstrated (Bartolini, Piroddi, et al., 2015; Tidei, Piroddi, Galli, & Santi, 2012; references therein). In our recent studies we also explored the role of GST, one of the main protein thiols of several cancer cells, in the response to highly reactive Se-compounds.

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