title: 4-amino-substituted benzenesulfonamides as inhibitors of human carbonic anhydrases.
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.
authors.affiliation: Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania. kestutis.rutkauskas@ktu.lt.
authors.forename: Kęstutis
authors.initials: K
authors.lastname: Rutkauskas
authors.affiliation: Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania. astzu@ibt.lt.
authors.forename: Asta
authors.initials: A
authors.lastname: Zubrienė
authors.affiliation: Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania. ingrida.tumosiene@ktu.lt.
authors.forename: Ingrida
authors.initials: I
authors.lastname: Tumosienė
authors.affiliation: Department of Physical and Inorganic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania. kristina.kantminiene@ktu.lt.
authors.forename: Kristina
authors.initials: K
authors.lastname: Kantminienė
authors.affiliation: Institute of Biochemistry, Vilnius University, Mokslininkų 12, Vilnius LT-08862, Lithuania. kazemary@gmail.com.
authors.forename: Marytė
authors.initials: M
authors.lastname: Kažemėkaitė
authors.affiliation: Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania. alexeyus1@gmail.com.
authors.forename: Alexey
authors.initials: A
authors.lastname: Smirnov
authors.affiliation: Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania. kazokaite@ibt.lt.
authors.forename: Justina
authors.initials: J
authors.lastname: Kazokaitė
authors.affiliation: Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania. morkunaite@ibt.lt.
authors.forename: Vaida
authors.initials: V
authors.lastname: Morkūnaitė
authors.affiliation: Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania. edita.capkauskaite@chf.stud.vu.lt.
authors.forename: Edita
authors.initials: E
authors.lastname: Čapkauskaitė
authors.affiliation: Department of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, Lithuania. lena@ibt.lt.
authors.forename: Elena
authors.initials: E
authors.lastname: Manakova
authors.affiliation: Department of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, Lithuania. grazulis@ibt.lt.
authors.forename: Saulius
authors.initials: S
authors.lastname: Gražulis
authors.affiliation: Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, Lithuania. zigmuntas.beresnevicius@ktu.lt.
authors.forename: Zigmuntas J
authors.initials: ZJ
authors.lastname: Beresnevičius
authors.affiliation: Department of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, Lithuania. daumantas.matulis@bti.vu.lt.
authors.forename: Daumantas
authors.initials: D
authors.lastname: Matulis
mesh_terms: D002151:Calorimetry / Q000379:methods; D002256:Carbonic Anhydrases / Q000378:metabolism*; D004396:Coloring Agents / Q000737:chemistry; D018360:Crystallography, X-Ray / Q000379:methods; D003979:Diazonium Compounds / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology*; D015091:beta-Alanine / Q000378:metabolism; D000096926:Benzenesulfonamides
chemical_list: D002256:Carbonic Anhydrases; D004396:Coloring Agents; D003979:Diazonium Compounds; D013449:Sulfonamides; D015091:beta-Alanine; D000096926:Benzenesulfonamides; C018908:4-diazobenzenesulfonamide