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.
journal_name
J Enzyme Inhib Med Chemjournal_title
Journal of enzyme inhibition and medicinal chemistryauthors
Bonnac L,Innocenti A,Winum JY,Casini A,Montero JL,Scozzafava A,Barragan V,Supuran CTdoi
10.1080/14756360410001689522keywords:
subject
Has Abstractpub_date
2004-06-01 00:00:00pages
275-8issue
3eissn
1475-6366issn
1475-6374journal_volume
19pub_type
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