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In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II.

Bioorganic & medicinal chemistry (2008-09-30)
Esra Bayram, Murat Senturk, O Irfan Kufrevioglu, Claudiu T Supuran
ABSTRACT

The inhibition of two human cytosolic carbonic anhydrase (hCA, EC 4.2.1.1) isozymes, hCA I and II, with a series of salicylic acid derivatives was investigated by using the esterase method with 4-nitrophenyl acetate as substrate. IC(50) values for sulfasalazine, diflunisal, 5-chlorosalicylic acid, dinitrosalicylic acid, 4-aminosalicylic acid, 4-sulfosalicylic acid, 5-sulfosalicylic acid, salicylic acid, acetylsalicylic acid (aspirin) and 3-metylsalicylic acid were of 3.04 microM, 3.38 microM, 4.07 microM, 7.64 microM, 0.13 mM, 0.29 mM, 0.42 mM, 0.56 mM, 2.71 mM and 3.07 mM for hCA I and of 4.49 microM, 2.70 microM, 0.72 microM, 2.80 microM, 0.75 mM, 0.72 mM, 0.29 mM, 0.68 mM, 1.16 mM and 4.70 mM for hCA II, respectively. Lineweaver-Burk plots were also used for the determination of the inhibition mechanism of these substituted phenols, most of which were noncompetitive inhibitors with this substrate. Some salicylic acid derivatives investigated here showed effective hCA I and II inhibitory activity, and might be used as leads for generating enzyme inhibitors eventually targeting other isoforms which have not been assayed yet for their interactions with such agents.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Salicylic acid, ACS reagent, ≥99.0%
Sigma-Aldrich
Acetylsalicylic acid, ≥99.0%
Sigma-Aldrich
Aspirin, meets USP testing specifications
Sigma-Aldrich
Salicylic acid, suitable for plant cell culture
Sigma-Aldrich
Salicylic acid, ≥99%, FG
Sigma-Aldrich
Salicylic acid, puriss. p.a., ≥99.0% (T)
Sigma-Aldrich
Salicylic acid, BioXtra, ≥99.0%
Sigma-Aldrich
Acetylsalicylic acid, analytical standard
Sigma-Aldrich
Salicylic acid, meets analytical specification of Ph. Eur., BP, USP, 99.5-100.5% (calc. to the dried substance)
Sigma-Aldrich
Salicylic acid, ReagentPlus®, ≥99%
Sigma-Aldrich
5-Chlorosalicylic acid, 98%
Sigma-Aldrich
3-Methylsalicylic acid, 96.0%
Supelco
Salicylic acid, certified reference material, TraceCERT®