4-amino-substituted benzenesulfonamides as inhibitors of human carbonic anhydrases

Molecules. 2014 Oct 28;19(11):17356-80. doi: 10.3390/molecules191117356.

Abstract

A series of N-aryl-β-alanine derivatives and diazobenzenesulfonamides containing aliphatic rings were designed, synthesized, and their binding to carbonic anhydrases (CA) I, II, VI, VII, XII, and XIII was studied by the fluorescent thermal shift assay and isothermal titration calorimetry. The results showed that 4-substituted diazobenzenesulfonamides were more potent CA binders than N-aryl-β-alanine derivatives. Most of the N-aryl-β-alanine derivatives showed better affinity for CA II while diazobenzenesulfonamides possessed nanomolar affinities towards CA I isozyme. X-ray crystallographic structures showed the modes of binding of both compound groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calorimetry / methods
  • Carbonic Anhydrases / metabolism*
  • Coloring Agents / chemistry
  • Crystallography, X-Ray / methods
  • Diazonium Compounds / chemistry*
  • Diazonium Compounds / pharmacology*
  • Humans
  • Sulfonamides / chemistry*
  • Sulfonamides / pharmacology*
  • beta-Alanine / metabolism

Substances

  • Coloring Agents
  • Diazonium Compounds
  • Sulfonamides
  • beta-Alanine
  • 4-diazobenzenesulfonamide
  • benzenesulfonamide
  • Carbonic Anhydrases