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  • Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines.

Ureido-substituted sulfamates show potent carbonic anhydrase IX inhibitory and antiproliferative activities against breast cancer cell lines.

Bioorganic & medicinal chemistry letters (2012-06-23)
Jean-Yves Winum, Fabrizio Carta, Carol Ward, Peter Mullen, David Harrison, Simon P Langdon, Alessandro Cecchi, Andrea Scozzafava, Ian Kunkler, Claudiu T Supuran
ABSTRACT

A series of 50 sulfamates were obtained by reacting 4-aminophenol with isocyanates followed by sulfamoylation. Most of the new compounds were nanomolar inhibitors of the tumor-associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms IX and XII, whereas they inhibited less cytosolic offtarget isoforms CA I and II. Some of these sulfamates showed significant antiproliferative activity in several breast cancer cell lines, such as SKBR3, MCF10A, ZR75/1, MDA-MB-361 and MCF7, constituting interesting anticancer leads.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sulfamic acid, 99.999% trace metals basis
Supelco
Sulfamic acid, analytical standard (for acidimetry), ACS reagent
Sigma-Aldrich
Sulfamic acid, reagent grade, 98%
Sigma-Aldrich
S4, ≥98% (HPLC)
Sigma-Aldrich
Ammonium sulfamate, BioXtra, ≥98.0%
Sigma-Aldrich
Ammonium sulfamate, ACS reagent, ≥98.0%
Sigma-Aldrich
Sulfamic acid, ACS reagent, 99.3%
Sigma-Aldrich
Sulfamic acid, ReagentPlus®, ≥99%