Benzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesterase

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dc.authoridAktaş, Aydın/0000-0001-8496-6782
dc.authoridDemir, Yeliz/0000-0003-3216-1098
dc.authoridONER, Erkan/0000-0002-6332-6484
dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authoridTASKIN TOK, Tugba/0000-0002-0064-8400
dc.authorwosidYalın, Serap/L-7402-2017
dc.authorwosidAktaş, Aydın/J-6194-2019
dc.authorwosidDemir, Yeliz/ABI-5719-2020
dc.authorwosidONER, Erkan/JCN-8212-2023
dc.authorwosidGulcin, ilhami/F-1428-2014
dc.authorwosidTASKIN TOK, Tugba/A-8885-2016
dc.contributor.authorOner, Erkan
dc.contributor.authorGok, Yetkin
dc.contributor.authorDemir, Yeliz
dc.contributor.authorTaskin-Tok, Tugba
dc.contributor.authorAktas, Aydin
dc.contributor.authorGulcin, Ilhami
dc.contributor.authorYalin, Serap
dc.date.accessioned2024-08-04T20:54:51Z
dc.date.available2024-08-04T20:54:51Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractThis report presents the synthesis and characterization of a range of benzimidazolium salts featuring 3-cyanopropyl groups on the 1st nitrogen atom and varied alkyl groups on the 3rd nitrogen atom within the benzimidazole structure. Benzimidazolium salts were synthesized by N-alkylation of 1-alkyl benzimidazole with 3-cyanopropyl-bromide. The new salts were characterized by 1H and 13C-NMR, FT-IR spectroscopic and elemental analysis techniques. In this study, the enzyme inhibition abilities of seven nitrile substituted benzimidazolium salts were investigated against acetylcholinesterase (AChE) and carbonic anhydrase isoenzymes I and II (hCA I and hCA II). They showed a highly potent inhibition effect on AChE, hCA I and hCA II (Ki values are in the range of 26.71-119.09 nM for AChE, 19.77 to 133.68 nM for hCA I and 13.09 to 266.38 nM for hCA II). Reflecting the binding mode of the synthesized cyanopropyl series, the importance of the 2,3,5,6-tetramethylbenzyl, 3-methylbenzyl and 3-benzyl groups for optimal interactions with target proteins, evaluated by molecular docking studies. At the same time, the docking findings support the inhibition constants (Ki) values of the related compounds in this study. Potential compounds were also evaluated by their pharmacokinetic properties were predicted. imageen_US
dc.description.sponsorshipThe authors thank Esin Akimath; Yalcin and the research group for technical assistance. The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). This study [2021-1-TP3-4244]; Research Fund of Mersin University in Turkeyen_US
dc.description.sponsorshipThe authors thank Esin Ak & imath; Yalcin and the research group for technical assistance. The numerical calculations reported in this paper were partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources). This study was financially supported by the Research Fund of Mersin University in Turkey with Project Number: 2021-1-TP3-4244.en_US
dc.identifier.doi10.1002/cbdv.202301362
dc.identifier.issn1612-1872
dc.identifier.issn1612-1880
dc.identifier.issue12en_US
dc.identifier.pmid37953698en_US
dc.identifier.scopus2-s2.0-85177439889en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1002/cbdv.202301362
dc.identifier.urihttps://hdl.handle.net/11616/101681
dc.identifier.volume20en_US
dc.identifier.wosWOS:001104368200001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherWiley-V C H Verlag Gmbhen_US
dc.relation.ispartofChemistry & Biodiversityen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectacetylcholinesteraseen_US
dc.subjectbenzimidazoleen_US
dc.subjectcarbonic anhydraseen_US
dc.subjectdrug likenessen_US
dc.subjectmolecular dockingen_US
dc.subjectnitrileen_US
dc.titleBenzimidazolium Salts Bearing Nitrile Moieties: Synthesis, Enzyme Inhibition Profiling, and Molecular Docking Analysis for Carbonic Anhydrase and Acetylcholinesteraseen_US
dc.typeArticleen_US

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