Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase

Eur J Med Chem. 2010 Mar;45(3):1225-9. doi: 10.1016/j.ejmech.2009.11.052. Epub 2009 Dec 5.

Abstract

Series of perfluoroalkanesulfonamides 1, sodium salt of perfluoroalkanesulfonamides 2 and polyfluoroalkanesulfonamides 3 derivatives were synthesized and characterized by (1)H NMR, (13)C NMR, (19)F NMR, IR and HRMS. Inhibition effects of these compounds on bovine carbonic anhydrase (bCA) and human carbonic anhydrase isoenzyme II (hCA) have been investigated. Comparing IC(50) values of the synthesized molecules 1, 2 and 3, it has been found that compound 2b is a more potent inhibitor than acetazolamide on hCA. Moreover 2b does not present cellular toxicity on sheep red globules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ammonia / chemistry
  • Animals
  • Carbonic Anhydrase II / antagonists & inhibitors*
  • Carbonic Anhydrase Inhibitors / chemistry*
  • Carbonic Anhydrase Inhibitors / pharmacology
  • Carbonic Anhydrases / chemistry*
  • Cattle
  • Enzyme Activation / drug effects
  • Gases
  • Humans
  • Molecular Structure
  • Sheep
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Carbonic Anhydrase Inhibitors
  • Gases
  • Sulfonamides
  • Ammonia
  • Carbonic Anhydrase II
  • Carbonic Anhydrases