Dealkylation of Organotin Compounds by Biological Dithiols: Toward the Chemistry of Organotin Toxicity

Bethany Buck, Alessandro Mascioni, Lawrence Que, Gianluigi Veglia

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

In this Communication, we report evidence for the dealkylation of trialkyltin compounds by a short linear peptide extracted from a small membrane protein (stannin) involved in cellular apoptosis and containing a CXC motif. We show that (a) organotin binding induces the formation of a β-turn in the linear peptide, (b) both cysteines are necessary for the dealkylation reaction, and (c) stable 1:1 complexes are formed between the peptide and diorganotins that can be observed by ESI-MS. Organotin degradation by biological dithiols may be responsible for both the delayed activity of these toxins in humans and the organotin resistance mechanisms in bacteria.

Original languageEnglish (US)
Pages (from-to)13316-13317
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number44
DOIs
StatePublished - Nov 5 2003

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