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Issue 35, 2016
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Mycobacterial carbonic anhydrase inhibition with phenolic acids and esters: kinetic and computational investigations

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Abstract

A series of phenolic acids and some of their esters, derivatives of caffeic, ferulic, and p-coumaric acid, was investigated for the inhibition of three β-carbonic anhydrases (CAs, EC 4.2.1.1) from the pathogenic bacterium Mycobacterium tuberculosis, Rv1248, Rv3588 and Rv3273 β-CAs. Some of these compounds were low micromolar inhibitors of the pathogenic enzymes and they did not show inhibitory activity against the human widespread cytosolic isoforms CA I and II. The binding mode of these inhibitors to two of the bacterial enzymes was investigated by computational approaches. We propose that the inhibitors anchor to the zinc-coordinated water molecule from the CA active site interfering with the nucleophilic attack of the zinc hydroxide on the substrate CO2. These compounds may be considered as interesting anti-mycobacterial lead compounds.

Graphical abstract: Mycobacterial carbonic anhydrase inhibition with phenolic acids and esters: kinetic and computational investigations

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Publication details

The article was received on 12 Jul 2016, accepted on 09 Aug 2016 and first published on 09 Aug 2016


Article type: Paper
DOI: 10.1039/C6OB01477A
Org. Biomol. Chem., 2016,14, 8322-8330

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    Mycobacterial carbonic anhydrase inhibition with phenolic acids and esters: kinetic and computational investigations

    Y. Cau, M. Mori, C. T. Supuran and M. Botta, Org. Biomol. Chem., 2016, 14, 8322
    DOI: 10.1039/C6OB01477A

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