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α-Conotoxin ImI Incorporating Stable Cystathionine Bridges Maintains Full Potency and Identical Three-Dimensional Structure

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Institute for Molecular Bioscience, The University of Queensland, St Lucia 4072, Queensland, Australia
[email protected]
Cite this: J. Am. Chem. Soc. 2011, 133, 40, 15866–15869
Publication Date (Web):September 7, 2011
https://doi.org/10.1021/ja206408q
Copyright © 2011 American Chemical Society
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    Abstract

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    The two disulfide bonds of α-conotoxin ImI, a peptide antagonist of the α7 nicotinic acetylcholine receptor (nAChR), were systematically replaced with isosteric redox-stable cystathionine thioethers. Regioselective thioether formation was accomplished on solid support through substitution of a γ-chlorohomoalanine by an intramolecular cysteine thiol to produce hybrid thioether/disulfide analogues (2 and 3) as well as a dual cystathionine analogue (4) that were found to be structurally homologous to α-conotoxin ImI by 1H NMR. The antagonistic activity at the α7 nAChR of cystathionine analogue 3 (pIC50 = 6.41 ± 0.09) was identical to that of α-conotoxin ImI (1, pIC50 = 6.41 ± 0.09), whereas those of 2 (pIC50 = 5.96 ± 0.09) and 4 (pIC50 = 5.89 ± 0.09) showed a modest decrease. The effect of oxidation of the thioethers to sulfoxides was also investigated, with significant changes in the biological activities observed ranging from a >30-fold reduction (2S═O) to a 3-fold increase (3S═OB) in potencies.

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    Detailed experimental procedures and additional figures (S1 and S2). This material is available free of charge via the Internet at http://pubs.acs.org.

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