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
Affiliations
Kęstutis Rutkauskas
Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania
Asta Zubrienė
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
Ingrida Tumosienė
Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania
Kristina Kantminienė
Department of Physical and Inorganic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania
Marytė Kažemėkaitė
Institute of Biochemistry, Vilnius University, Mokslininkų 12, Vilnius LT-08862, Lithuania
Alexey Smirnov
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
Justina Kazokaitė
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
Vaida Morkūnaitė
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
Edita Čapkauskaitė
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
Elena Manakova
Department of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, Lithuania
Saulius Gražulis
Department of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, Lithuania
Zigmuntas J. Beresnevičius
Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania
Daumantas Matulis
Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania
DOI
https://doi.org/10.3390/molecules191117356
Journal volume & issue
Vol. 19,
no. 11
pp.
17356
– 17380
Abstract
Read online
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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