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  • Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of the tumor-associated isoforms IX and XII.

Carbonic anhydrase inhibitors: copper(II) complexes of polyamino-polycarboxylamido aromatic/heterocyclic sulfonamides are very potent inhibitors of the tumor-associated isoforms IX and XII.

Bioorganic & medicinal chemistry letters (2007-11-29)
Marouan Rami, Jean-Yves Winum, Alessio Innocenti, Jean-Louis Montero, Andrea Scozzafava, Claudiu T Supuran
ABSTRACT

Reaction of EDTA/DTPA dianhydride with aromatic/heterocyclic sulfonamides afforded a series of derivatives incorporating polyaminopolycarboxylate tails and benzenesulfonamide or 1,3,4-thiadiazole-2-sulfonamide heads. These compounds have been used as ligands to prepare Cu(II) complexes. Both parent sulfonamides as well as their copper complexes behaved as potent inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the cytosolic CA I and II, and transmembrane CA IX and XII. Some Cu(II) complexes showed subnanomolar affinities and some selectivity for the inhibition of the tumor-associated isoforms IX and XII and might be used as PET hypoxia markers of tumors.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Saccharin, ≥99%
Supelco
Sulfanilamide, VETRANAL®, analytical standard
Sigma-Aldrich
Sulfanilamide, ≥98%
Sigma-Aldrich
Saccharin, ≥98%
Sigma-Aldrich
Sulfanilamide, puriss. p.a., ≥98% (calc. to the dried substance)