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Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols.

Abstract：

:Inhibition of the newest isoform of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1), CA XV, with a series of phenols was investigated. Murine CA XV showed an inhibition profile by phenols distinct of those of the cytosolic human isoforms CA I and II. Phenol and some of its 2-, 3-, and 4-substituted derivatives incorporating hydroxy, fluoro, carboxy, and acetamido moieties were effective CA XV inhibitors, with inhibition constants in the range of 7.20-11.30 microM, whereas compounds incorporating 4-amino-, 4-cyano, or 3-hydroxy groups were less effective (K(I)s of 335-434 microM). The best phenol inhibitor was clioquinol (K(I) of 2.33 microM). Phenols show a different inhibition mechanism as compared to sulfonamides and their isosteres, and may lead to the design of compounds with selectivity for inhibiting different CA isozymes with medicinal chemistry applications.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Innocenti A,Hilvo M,Scozzafava A,Parkkila S,Supuran CT

doi

10.1016/j.bmcl.2008.04.077

subject

Has Abstract

pub_date

2008-06-15 00:00:00

pages

3593-6

issue

12

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(08)00481-2

journal_volume

18

pub_type

杂志文章

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