Benzoselenoates: A novel class of carbonic anhydrase inhibitors

被引：3

作者：

Tanini, Damiano ^{[1
]}

Capperucci, Antonella ^{[1
]}

Locuoco, Maria ^{[1
]}

Ferraroni, Marta ^{[1
]}

Costantino, Gabriele ^{[2
]}

Angeli, Andrea ^{[2
,3
]}

Supuran, Claudiu T. ^{[3
]}

机构：

[1] Univ Florence, Dept Chem Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, Italy

[2] Univ Parma, Dept Food & Drug, Parco Area Sci 27-A, I-43124 Parma, Italy

[3] Univ Florence, NEUROFARBA Dept, Sez Sci Farmaceut, Via Ugo Schiff 6, I-50019 Florence, Italy

来源：

BIOORGANIC CHEMISTRY | 2022年 / 122卷

关键词：

POTASSIUM SELENOCARBOXYLATES;

D O I：

10.1016/j.bioorg.2022.105751

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of benzoselenoates has been prepared and their inhibitory properties against the most relevant human Carbonic Anhydrases (CAs) isoforms, among which hCA I, II, IV, VII, IX, and XII were investigated. These inhibitors were designed considering the carboxylates and mono-/dithiocarbamates as lead and led to the observation that the COSe- is a new zinc-binding group (ZBG) for metalloenzymes possessing zinc ions at their active site. The substitution pattern on aromatic ring of the benzoselenoates is the crucial structural element influencing selectivity towards various isoforms. We elucidated the binding mode of benzoselenoates to hCA I and hCA II by using X-ray crystallography. The negatively charged selenium atom from the new ZBG was observed coordinated to the zinc ion from the CA active site at a distance of 2.30-2.40 angstrom from it. Overall, these data might be useful for the development of new inhibitors with higher selectivity and efficacy for various hCAs.

引用

页数：8

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