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J Enzyme Inhib Med Chem. 2014 Aug;29(4):495-9. doi: 10.3109/14756366.2013.806497. Epub 2013 Jul 1.

Carbonic anhydrase inhibitors. Phenols incorporating 2- or 3-pyridyl-ethenylcarbonyl and tertiary amine moieties strongly inhibit Saccharomyces cerevisiae β-carbonic anhydrase.

Author information

1
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University , Erzurum , Turkey .

Abstract

A series of phenols incorporating tertiary amine and trans-pyridylethenyl-carbonyl moieties were assayed as inhibitors of the β-carbonic anhydrase (CA, EC 4.2.1.1) from Saccharomyces cerevisiae, ScCA. One of these compounds was a low nanomolar ScCA inhibitor, whereas the remaining ones inhibited the enzyme with KIs in the range of 23.5-95.4 nM. The off-target human (h) isoforms hCA I and hCA II were much less inhibited by these phenols, with KIs in the range of 0.78-23.5 µM (hCA I) and 10.8-52.4 µM (hCA II). The model organism S. cerevisiae and this particular enzyme may be useful for detecting antifungals with a novel mechanism of action compared to the classical azole drugs to which significant drug resistance emerged.

KEYWORDS:

Antifungalscarbonic anhydrase; Saccharomyces cerevisiae; phenols; pyridylethenyl-carbonyl

PMID:
23808805
DOI:
10.3109/14756366.2013.806497
[Indexed for MEDLINE]

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