Thiosemicarbazone-benzenesulfonamide Derivatives as Human Carbonic Anhydrases Inhibitors: Synthesis, Characterization, and In silico Studies


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Abstract

Introduction:Carbonic anhydrases (CAs) are widespread metalloenzymes with the core function of catalyzing the interconversion of CO2 and HCO3-. Targeting these enzymes using selective inhibitors has emerged as a promising approach for the development of novel therapeutic agents against multiple diseases.

Methods:A series of novel thiosemicarbazones-containing derivatives were synthesized, characterized, and tested for their inhibitory activity against pharmaceutically important human CA I (hCA I), II (hCA II), IX (hCA IX), and XII (hCA XII) using the single tail approach.

Results:The compounds generally inhibited the isoenzymes at low nanomolar concentrations, with compound 6b having Ki values of 7.16, 0.31, 92.5, and 375 nM against hCA I, II, IX and XII, respectively. Compound 6e exhibited Ki values of 27.6, 0.34, 872, and 94.5 nM against hCA I, II, IX and XII, respectively.

Conclusion:To rationalize the inhibition data, molecular docking studies were conducted, providing insight into the binding mechanisms, molecular interactions, and selectivity of the compounds towards the isoenzymes.

About the authors

Muhammed Trawally

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University

Email: info@benthamscience.net

Kübra Demir-Yazıcı

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University

Email: info@benthamscience.net

Andrea Angeli

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence

Author for correspondence.
Email: info@benthamscience.net

Kerem Kaya

Department of Chemistry, Istanbul Technical University

Email: info@benthamscience.net

Atilla Akdemir

Department of Pharmacology, Faculty of Pharmacy, Istinye University

Email: info@benthamscience.net

Claudiu Supuran

Department of NEUROFARBA, Section of Pharmaceutical and Nutraceutical Sciences, University of Florence

Email: info@benthamscience.net

Özlen Güzel-Akdemir

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University

Author for correspondence.
Email: info@benthamscience.net

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