Sulfonamide inhibition studies of the δ-carbonic anhydrase from the diatom Thalassiosira weissflogii

被引：53
作者：
Vullo, Daniela [1 ]
Del Prete, Sonia [2 ]
Osman, Sameh M. [3 ]
De Luca, Viviana [2 ]
Scozzafava, Andrea [1 ]
AlOthman, Zeid [3 ]
Supuran, Claudiu T. [1 ,3 ,4 ]
Capasso, Clemente [2 ]
机构：
[1] Univ Florence, Lab Chim Bioinorgan, I-50019 Florence, Italy
[2] CNR, Ist Biochim Prot, I-80131 Naples, Italy
[3] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
[4] Univ Florence, Dipartimento NEIROFABA, Sez Sci Farm & Nutraceut, Polo Sci, I-50019 Florence, Italy
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2014年 / 24卷 / 01期
关键词：
Carbonic anhydrase; delta-Class enzyme; Sulfonamide; Enzyme inhibitor; Thalassiosira weissflogii; TRYPANOSOMA-CRUZI; CAUSATIVE AGENT; CLASS ENZYME; BETA; CLONING; PATENT; ANTICANCER; PARASITE; CADMIUM;
D O I：
10.1016/j.bmcl.2013.11.021
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The delta-carbonic anhydrase (CA, EC 4.2.1.1) TweCA from the marine diatom Thalassiosira weissflogii has recently been cloned, purified and its activity/inhibition with anions investigated. Here we report the first sulfonamide/sulfamate inhibition study of a delta-class CA. Among the 40 such compounds investigated so far, 3-bromosulfanilamide, acetazolamide, ethoxzolamide, dorzolamide and brinzolamide were the most effective TweCA inhibitors detected, with K(I)s of 49.6-118 nM. Many simple aromatic sulfonamides as well as dichlorophenamide, benzolamide, topiramate, zonisamide, indisulam and valdecoxib were medium potency inhibitors, (K(I)s of 375-897 nM). Saccharin and hydrochlorothiazide were ineffective inhibitors of the delta-class enzyme, with K(I)s of 4.27-9.20 mu M. The inhibition profile of the delta-CA is very different from that of alpha-, beta- and gamma-CAs from different organisms. Although no X-ray crystal structure of this enzyme is available, we hypothesize that as for other CA classes, the sulfonamides inhibit the enzymatic activity by binding to the Zn(II) ion from the delta-CA active site. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：275 / 279
页数：5
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