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  • Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII.

Sulfonamides incorporating boroxazolidone moieties are potent inhibitors of the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII.

Bioorganic & medicinal chemistry letters (2011-04-08)
Marouan Rami, Alfonso Maresca, Fatma-Zhora Smaine, Jean-Louis Montero, Andrea Scozzafava, Jean-Yves Winum, Claudiu T Supuran
ABSTRACT

A new series of sulfonamides was synthesized by the reaction of the boroxazolidone complex of l-lysine with isothiocyanates incorporating sulfamoyl moieties and diverse organic scaffolds. The obtained thioureas have been investigated as inhibitors of four physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII. Inhibition between the low nanomolar to the micromolar range has been observed against them, with several low nanomolar and tumor-CA selective inhibitors detected. These boron-containing compounds might be useful for the management of hypoxic tumors overexpressing hCA IX/XII by means of boron neutron capture therapy, a technique not investigated so far with inhibitors of this enzyme.

MATERIALS
Product Number
Brand
Product Description

Supelco
Sulfanilamide, VETRANAL®, analytical standard
Sigma-Aldrich
Sulfanilamide, ≥98%
Sigma-Aldrich
Sulfanilamide, puriss. p.a., ≥98% (calc. to the dried substance)