Carbonic anhydrase inhibitors: Inhibition of human, bacterial, and archaeal isozymes with benzene-1,3-disulfonamides - Solution and crystallographic studies

被引：39

作者：

Alterio, Vincenzo

De Simone, Giuseppina

Monti, Simona Maria

Scozzafava, Andrea

Supuran, Claudiu T.

机构：

[1] CNR, Ist Biostrutture & Bioimmagini, I-80134 Naples, Italy

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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2007年 / 17卷 / 15期

关键词：

carbonic anhydrase; isozymes; benzene-1,3-disulfonamide; dichlorophenamide; x-ray crystallography; drug design;

D O I：

10.1016/j.bmcl.2007.05.045

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Three benzene-1,3-disulfonamide derivatives were investigated for their interaction with 12 mammalian alpha-carbonic anhydrases (CAs, EC 4.2.1.1), and three bacterial/archaeal CAs belonging to the alpha-, beta-, and gamma-CA class, respectively. X-ray crystal structure of the three inhibitors in complex with the dominant human isozyme CA II revealed a particular binding mode within the cavity. The sulfonamide group in meta-position to the Zn2+-coordinated SO2NH2 moiety was oriented toward the hydrophilic side of the active site cleft, establishing hydrogen bonds with His64, Asn67, Gln92, and Thr200. The plane of the phenyl moiety of the inhibitors was rotated by 45 degrees and tilted by 10 degrees with respect to its most recurrent orientation in other CA II-sulfonamide complexes. (c) 2007 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4201 / 4207

页数：7

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