A thiabendazole sulfonamide shows potent inhibitory activity against mammalian and nematode α-carbonic anhydrases

被引：23

作者：

Crocetti, Letizia ^{[1
]}

Maresca, Alfonso ^{[1
]}

Temperini, Claudia ^{[1
]}

Hall, Rebecca A. ^{[2
]}

Scozzafava, Andrea ^{[1
]}

Muehlschlegel, Fritz A. ^{[2
]}

Supuran, Claudiu T. ^{[1
]}

机构：

[1] Univ Florence, Lab Chim Bioinorgan, I-50019 Florence, Italy

[2] Univ Kent, Dept Biosci, Canterbury CT2 7NJ, Kent, England

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 05期

关键词：

Carbonic anhydrase; alpha-Isoforms; Sulfonamide; Thiabendazole; Caenorhabditis elegans; Antihelmintics; TRANSMEMBRANE ISOZYME-XIV; X-RAY; THERAPEUTIC APPLICATIONS; DESIGN; DIURETICS; ANTITUMOR; ISOFORMS; TARGET; EMATE; IX;

D O I：

10.1016/j.bmcl.2009.01.038

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A sulfonamide derivative of the antihelmintic drug thiabendazole was prepared and investigated for inhibition of the zinc enzyme carbonic anhydrase CA (EC 4.2.1.1). Mammalian isoforms CA I-XIV and the nematode enzyme of Caenorhabditis elegans CAH-4b were included in this study. Thiabendazole-5-sulfonamide was a very effective inhibitor of CAH-4b and CA IX (K(I)s of 6.4-9.5 nm) and also inhibited effectively isozymes CA I, II, IV-VII, and XII, with KIs in the range of 17.8-73.2 nM. The high resolution X-ray crystal structure of its adduct with isozyme II evidenced the structural elements responsible for this potent inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1371 / 1375

页数：5

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