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Molecules 2014, 19(11), 17356-17380; doi:10.3390/molecules191117356

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

1
Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania
2
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
3
Department of Physical and Inorganic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania
4
Institute of Biochemistry, Vilnius University, Mokslininkų 12, Vilnius LT-08862, Lithuania
5
Department of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, Lithuania
*
Author to whom correspondence should be addressed.
Received: 18 September 2014 / Revised: 14 October 2014 / Accepted: 21 October 2014 / Published: 28 October 2014
(This article belongs to the Section Medicinal Chemistry)
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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. View Full-Text
Keywords: benzenesulfonamide; hydrazide; hydrazone; azole; triazene; carbonic anhydrase; fluorescent thermal shift assay; ThermoFluor®; isothermal titration calorimetry benzenesulfonamide; hydrazide; hydrazone; azole; triazene; carbonic anhydrase; fluorescent thermal shift assay; ThermoFluor®; isothermal titration calorimetry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Rutkauskas, K.; Zubrienė, A.; Tumosienė, I.; Kantminienė, K.; Kažemėkaitė, M.; Smirnov, A.; Kazokaitė, J.; Morkūnaitė, V.; Čapkauskaitė, E.; Manakova, E.; Gražulis, S.; Beresnevičius, Z.J.; Matulis, D. 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases. Molecules 2014, 19, 17356-17380.

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