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Carbonic anhydrase inhibitors. Inhibition of human erythrocyte isozymes I and II with a series of antioxidant phenols.

Bioorganic & medicinal chemistry (2009-02-24)
Murat Sentürk, Ilhami Gülçin, Arif Daştan, O Irfan Küfrevioğlu, Claudiu T Supuran
ABSTRACT

The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes I and II, with a series of phenol derivatives was investigated by using the esterase assay, with 4-nitrophenyl acetate as substrate. 2,6-Dimethylphenol, 2,6-diisopropylphenol (propofol), 2,6-di-t-butylphenol, butylated hydroxytoluene, butylated hydroxyanisole, vanillin, guaiacol, di(2,6-dimethylphenol), di(2,6-diisopropylphenol), di(2,6-di-t-butylphenol), and acetazolamide showed K(I) values in the range of 37.5-274.5 microM for hCA I and of 0.29-113.5 microM against hCA II, respectively. All these phenols were non-competitive inhibitors with 4-nitrophenylacetate as substrate. Some antioxidant phenol derivatives investigated here showed effective hCA II inhibitory effects, in the same range as the clinically used sulfonamide acetazolamide, and might be used as leads for generating enzyme inhibitors possibly targeting other CA isoforms which have not been yet assayed for their interactions with such agents.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
2,6-Di-tert-butyl-4-methylphenol, ≥99.0% (GC), powder
Supelco
2,6-Dimethylphenol, PESTANAL®, analytical standard
Sigma-Aldrich
2,6-Di-tert-butylphenol, 99%
Sigma-Aldrich
2,6-Dimethylphenol, ≥99.5%
Sigma-Aldrich
2,6-Di-tert-butyl-4-methoxyphenol, 97%
Sigma-Aldrich
2,6-Diisopropylphenol, 97%
Sigma-Aldrich
2,6-Dimethylphenol, 99%
Supelco
3,5-Di-tert-4-butylhydroxytoluene (BHT), analytical standard
Sigma-Aldrich
2,6-Di-tert-butyl-4-methylphenol, tested according to Ph. Eur.
Sigma-Aldrich
2,6-Di-tert-butyl-4-methylphenol, purum, ≥99.0% (GC)
Sigma-Aldrich
Guaiacol, oxidation indicator
Sigma-Aldrich
2,6-Xylenol, ≥99%, FG
Sigma-Aldrich
Butylated hydroxytoluene, ≥99%, FCC, FG
Sigma-Aldrich
Guaiacol, natural, ≥99%, FG