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Carbonic anhydrase inhibitors: Aliphatic N-phosphorylated sulfamates - A novel zinc-anchoring group leading to nanomolar inhibitors

Bonnac, L, Innocenti, A, Winum, JY, Casini, Angela, Montero, JL, Scozzafava, A, Barragan, V and Supuran, CT 2004. Carbonic anhydrase inhibitors: Aliphatic N-phosphorylated sulfamates - A novel zinc-anchoring group leading to nanomolar inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 19 (3) , pp. 275-278. 10.1080/14756360410001689522

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Abstract

A small library of phosphorylated sulfamates (N-(O-alkylsulfamoyl)-phosphoramidic acids) incorporating long aliphatic chains (C8-C16) has been synthesized and investigated for their interaction with two physiologically relevant carbonic anhydrase (CA) isozymes. These compounds behaved as very potent inhibitors of both isozymes, with inhibition constants in the range of 8.2-16.1nM against isozyme hCA I, and 5.3-11.9nM against isozyme hCA II. Activity was optimal for the n-octyl derivative (similarly with that of the corresponding unsubstituted sulfamates) and gradually decreased for the longer chain derivatives. Some of these compounds are much more effective CA inhibitors as compared to the clinically used derivatives acetazolamide, sulfanilamide or topiramate, which are used as standards for the enzymatic determinations. The phosphorylated sulfamate moiety represents a novel zinc-binding group for the design of effective CA inhibitors.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
R Medicine > RM Therapeutics. Pharmacology
R Medicine > RS Pharmacy and materia medica
Uncontrolled Keywords: Carbonic anhydrase, Isozyme I, II, Sulfamate, N-phosphorylated sulfamate
Publisher: Informa Healthcare
ISSN: 1475-6366
Last Modified: 04 Jun 2017 08:49
URI: http://orca.cf.ac.uk/id/eprint/85531

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