Molecules (Oct 2014)

4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases

  • Kęstutis Rutkauskas,
  • Asta Zubrienė,
  • Ingrida Tumosienė,
  • Kristina Kantminienė,
  • Marytė Kažemėkaitė,
  • Alexey Smirnov,
  • Justina Kazokaitė,
  • Vaida Morkūnaitė,
  • Edita Čapkauskaitė,
  • Elena Manakova,
  • Saulius Gražulis,
  • Zigmuntas J. Beresnevičius,
  • Daumantas Matulis

DOI
https://doi.org/10.3390/molecules191117356
Journal volume & issue
Vol. 19, no. 11
pp. 17356 – 17380

Abstract

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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.

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