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Synthesis, <i>in vitro</i> enzyme activity and molecular docking studies of new benzylamine-sulfonamide derivatives as selective MAO-B inhibitors

Begüm Nurpelin Sağlık, Derya Osmani̇ye, Ulviye Acar Çevik, Serkan Levent, Betül Kaya Çavuşoğlu, Özlem Atlı Eklioğlu, Yusuf Özkay, Ali Savaş Koparal, Zafer Asım Kaplancıklı

2020Journal of Enzyme Inhibition and Medicinal Chemistry13 citationsDOIOpen Access PDF

Abstract

Many studies have been conducted on the selective inhibition of human monoamine oxidase B (hMAO-B) enzyme using benzylamine-sulphonamide derivatives. Using various chemical modifications on BB-4h, which was reported previously by our team and showed a significant level of MAO-B inhibition, novel benzylamine-sulphonamide derivatives were designed, synthesised, and their MAO inhibition potentials were evaluated. Among the tested derivatives, compounds 4i and 4t achieved IC50 values of 0.041 ± 0.001 µM and 0.065 ± 0.002 µM, respectively. The mechanism of hMAO-B inhibition by compounds 4i and 4t was studied using Lineweaver–Burk plot. The nature of inhibition was also determined to be non-competitive. Cytotoxicity tests were conducted and compounds 4i and 4t were found to be non-toxic. Molecular docking studies were also carried out for compound 4i, which was found as the most potent agent, within hMAO-B catalytic site.

Topics & Concepts

BenzylamineChemistryDocking (animal)SulfonamideIC50Monoamine oxidaseEnzymeStereochemistryNon-competitive inhibitionMonoamine oxidase BCytotoxicityIn vitroCombinatorial chemistryPharmacologyMedicinal chemistryBiochemistryBiologyMedicineNursingCholinesterase and Neurodegenerative DiseasesChemical synthesis and alkaloidsEnzyme Catalysis and Immobilization
Synthesis, <i>in vitro</i> enzyme activity and molecular docking studies of new benzylamine-sulfonamide derivatives as selective MAO-B inhibitors | Litcius