N-glycosyl-N-hydroxysulfamides as potent inhibitors of Brucella suis carbonic anhydrases

Journal of Enzyme Inhibition and Medicinal Chemistry
Joanna OmboumaJean-Yves Winum

Abstract

We investigated a series of N-hydroxysulfamides obtained by Ferrier sulfamidoglycosylation for the inhibition of two bacterial carbonic anhydrases (CAs, EC 4.2.1.1) present in the pathogen Brucella suis. bsCA I was moderately inhibited by these compounds with inhibition constants ranging between 522 and 958 nM and no notable differences of activity between the acetylated or the corresponding deacetylated derivatives. The compounds incorporating two trans-acetates and the corresponding deprotected ones were the most effective inhibitors in the series. bsCA II was better inhibited, with inhibition constants ranging between 59.8 and 799 nM. The acetylated derivatives were generally better bsCA II inhibitors compared to the corresponding deacetylated compounds. Although these compounds were not highly isoform-selective CA inhibitors (CAIs) for the bacterial over the human CA isoforms, some of them possess inhibition profiles that make them interesting leads for obtaining better and more isoform-selective CAIs targeting bacterial enzymes.

References

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Jan 17, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Sonia Del PreteClemente Capasso
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Mar 7, 2013·Expert Opinion on Therapeutic Patents·Claudiu T Supuran
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May 1, 2013·Journal of Enzyme Inhibition and Medicinal Chemistry·Clemente Capasso, Claudiu T Supuran
Apr 29, 2014·Journal of Enzyme Inhibition and Medicinal Chemistry·Clemente Capasso, Claudiu T Supuran

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Citations

Sep 13, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Sonia Del PreteClemente Capasso
Mar 10, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Stephan KöhlerJean-Yves Winum
May 19, 2017·Organic & Biomolecular Chemistry·Nuno M XavierM Conceição Oliveira
Aug 19, 2020·Expert Opinion on Therapeutic Patents·Claudiu T Supuran, Clemente Capasso

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