Novel coumarin-chalcone derivatives: Synthesis, characterization, antioxidant, cyclic voltammetry, molecular modelling and biological evaluation studies as acetylcholinesterase, ?-glycosidase, and carbonic anhydrase inhibitors

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dc.contributor.authorOnar, Hulya Celik
dc.contributor.authorOzden, Eda Mehtap
dc.contributor.authorTaslak, Hava Dudu
dc.contributor.authorGulcin, Ilhami
dc.contributor.authorEce, Abdulilah
dc.contributor.authorErcag, Erol
dc.date.accessioned2024-10-29T17:58:23Z
dc.date.available2024-10-29T17:58:23Z
dc.date.issued2023
dc.departmentTekirdağ Namık Kemal Üniversitesi
dc.description.abstractIn this study, a total of 12 coumarin-chalcone derivatives, 6 of which are original were synthesized. The structures of the newly synthesized compounds were elucidated by H-1 NMR, C-13 NMR, IR, and elemental analysis methods (7g-7l). The antioxidant potencies measured by using CUPRAC method (Trolox equivalent total anti-oxidant capacity) were as follows: 7j > 7i > 7c > 7d > 7k > 7l > 7f > 7h > 7e > 7g > 7a > 7b. Furthermore, the compounds were evaluated against human carbonic anhydrases I, II, acetylcholinesterase and alpha-glycosidase enzymes. Compounds 7c, 7e, 7g, 7i, 7j and 7l showed promising human carbonic anhydrase I inhibition compared to the standard Acetazolamide (K-i: 16.64 +/- 4.72-49.82 +/- 5.82 nM vs K-i: 57.64 +/- 5.41 nM). In addition, all compounds exhibited strong inhibition against acetylcholinesterase and a-glycosidase. K-i values were between 2.39 +/- 0.97-9.35 +/- 3.95 nM (Tacrine K-i: 13.78 +/- 4.36 nM) for acetylcholinesterase, and 14.49 +/- 8.51-75.67 +/- 26.38 nM (Acarbose K-i: 12600 +/- 78.00 nM) for a-glycosidase. Binding of 7g was predicted using molecular docking and stability of the complex was confirmed with molecular dynamics simulations which shed a light on the observed activity against acetylcholinesterase. Finally, cyclic voltammetry was also used for the electrochemical characterization of the synthesized compounds.
dc.description.sponsorshipIstanbul University-Cerrahpasa Research Fund [FYL-2018-30372]
dc.description.sponsorshipSynthesis and characterization of the structures of the compounds used in this study was supported by the Istanbul University-Cerrahpasa Research Fund as Hava Dudu Taslak's master's thesis (Project number: FYL-2018-30372).
dc.identifier.doi10.1016/j.cbi.2023.110655
dc.identifier.issn0009-2797
dc.identifier.issn1872-7786
dc.identifier.pmid37573926
dc.identifier.scopus2-s2.0-85168009966
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.cbi.2023.110655
dc.identifier.urihttps://hdl.handle.net/20.500.11776/14278
dc.identifier.volume383
dc.identifier.wosWOS:001065161600001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherElsevier Ireland Ltd
dc.relation.ispartofChemico-Biological Interactions
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccess
dc.subjectCoumarin-chalcone
dc.subjectMolecular modelling
dc.subjectEnzyme inhibition
dc.subjectAntioxidant activity
dc.subjectCyclic voltammetry
dc.titleNovel coumarin-chalcone derivatives: Synthesis, characterization, antioxidant, cyclic voltammetry, molecular modelling and biological evaluation studies as acetylcholinesterase, ?-glycosidase, and carbonic anhydrase inhibitors
dc.typeArticle

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