4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases
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 result...
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| Format: | Article |
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MDPI AG
2014-10-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/11/17356 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Kęstutis Rutkauskas |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-22T08:34:30Z |
| format | Article |
| id | doaj.art-801ba8f6972c46bd9927207905c7355b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T08:34:30Z |
| publishDate | 2014-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-801ba8f6972c46bd9927207905c7355b2022-12-21T18:32:24ZengMDPI AGMolecules1420-30492014-10-011911173561738010.3390/molecules191117356molecules1911173564-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic AnhydrasesKęstutis Rutkauskas0Asta Zubrienė1Ingrida Tumosienė2Kristina Kantminienė3Marytė Kažemėkaitė4Alexey Smirnov5Justina Kazokaitė6Vaida Morkūnaitė7Edita Čapkauskaitė8Elena Manakova9Saulius Gražulis10Zigmuntas J. Beresnevičius11Daumantas Matulis12Department of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, LithuaniaDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, LithuaniaDepartment of Physical and Inorganic Chemistry, Kaunas University of Technology, Kaunas LT-50254, LithuaniaInstitute of Biochemistry, Vilnius University, Mokslininkų 12, Vilnius LT-08862, LithuaniaDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Protein-DNA Interactions, Vilnius University Institute of Biotechnology, Graičiūno 8, Vilnius LT-02241, LithuaniaDepartment of Organic Chemistry, Kaunas University of Technology, Kaunas LT-50254, LithuaniaDepartment of Biothermodynamics and Drug Design, Institute of Biotechnology, Vilnius University, Graičiūno 8, Vilnius LT-02241, LithuaniaA 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.http://www.mdpi.com/1420-3049/19/11/17356benzenesulfonamidehydrazidehydrazoneazoletriazenecarbonic anhydrasefluorescent thermal shift assayThermoFluor®isothermal titration calorimetry |
| spellingShingle | 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 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases Molecules benzenesulfonamide hydrazide hydrazone azole triazene carbonic anhydrase fluorescent thermal shift assay ThermoFluor® isothermal titration calorimetry |
| title | 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases |
| title_full | 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases |
| title_fullStr | 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases |
| title_full_unstemmed | 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases |
| title_short | 4-Amino-substituted Benzenesulfonamides as Inhibitors of Human Carbonic Anhydrases |
| title_sort | 4 amino substituted benzenesulfonamides as inhibitors of human carbonic anhydrases |
| topic | benzenesulfonamide hydrazide hydrazone azole triazene carbonic anhydrase fluorescent thermal shift assay ThermoFluor® isothermal titration calorimetry |
| url | http://www.mdpi.com/1420-3049/19/11/17356 |
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