Benzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and ?-glycosidase

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dc.authoridAygün, Muhittin/0000-0001-9670-9062
dc.authoridTezcan, Burcu/0000-0001-5630-5522
dc.authoridAktaş, Aydın/0000-0001-8496-6782
dc.authoridGulcin, ilhami/0000-0001-5993-1668
dc.authoridTASKIN-TOK, Tugba/0000-0002-0064-8400
dc.authorwosidAygün, Muhittin/P-3605-2019
dc.authorwosidGök, Yetkin/AAA-5669-2021
dc.authorwosidTezcan, Burcu/GSN-1194-2022
dc.authorwosidAktaş, Aydın/J-6194-2019
dc.authorwosidGüzel, Bilgehan/D-1464-2018
dc.authorwosidTaslimi, Parham/AAL-2788-2020
dc.authorwosidGulcin, ilhami/F-1428-2014
dc.contributor.authorTezcan, Burcu
dc.contributor.authorGok, Yetkin
dc.contributor.authorSevincek, Resul
dc.contributor.authorTaslimi, Parham
dc.contributor.authorTaskin-Tok, Tugba
dc.contributor.authorAktas, Aydin
dc.contributor.authorGuzel, Bilgehan
dc.date.accessioned2024-08-04T20:51:44Z
dc.date.available2024-08-04T20:51:44Z
dc.date.issued2022
dc.departmentİnönü Üniversitesien_US
dc.description.abstractHere, we report the synthesis, characterization, and biological activities of a series of benzimidazolium salts bearing the trifluoromethylbenzyl group. All benzimidazolium salts were characterized by using nuclear magnetic resonance (NMR) (H-1 NMR and C-13 NMR), Fourier transform-infrared spectroscopy, and elemental analysis techniques. The crystal structures of some of these compounds were obtained by the single-crystal X-ray diffraction method. Furthermore, the acetylcholinesterase (AChE) and alpha-glycosidase (alpha-Gly) enzyme inhibition activities of these compounds were investigated. The obtained results revealed that 2e, with K-i value of 1.36 +/- 0.34 mu M against AChE and 3d with K-i value of 91.37 +/- 10.38 mu M against alpha-Gly, were the most potent compounds against both assigned enzymes. It should be noted that most of the synthesized compounds were more potent than standard inhibitor tacrine (TAC) against AChE. In silico studies, we focused on compound 2e, 3d, 3e, and 3f as potent inhibitors of AChE and alpha-Gly, the compound 2e showed good binding energy (-10.23 kcal/mol), among the three selected compounds and positive control (-10.18, -10.08, and -7.37 kcal/mol for 3d, 3f, and TAC, respectively). Likewise, as a result of the same compounds against the alpha-Gly enzyme, the compound 3d had the highest binding affinity (-8.39 kcal/mol) between the four selected compounds and the positive control (-8.27, -8.10, -8.06, and -7.53 kcal/mol for 3f, 3e, 2e, and acarbose, respectively). From the absorption, distribution, metabolism, excretion, and toxicity analyses, it can be concluded that the compounds under consideration exhibited more drug-likeness properties in the prediction studies compared to positive controls.en_US
dc.description.sponsorshipDokuz Eylul University for the use of the Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University) [2010.KB.FEN.13]en_US
dc.description.sponsorshipThe authors acknowledge Dokuz Eylul University for the use of the Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13).en_US
dc.identifier.doi10.1002/jbt.23001
dc.identifier.issn1095-6670
dc.identifier.issn1099-0461
dc.identifier.issue4en_US
dc.identifier.pmid35225413en_US
dc.identifier.scopus2-s2.0-85125423704en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.urihttps://doi.org/10.1002/jbt.23001
dc.identifier.urihttps://hdl.handle.net/11616/100506
dc.identifier.volume36en_US
dc.identifier.wosWOS:000761655800001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherWileyen_US
dc.relation.ispartofJournal of Biochemical and Molecular Toxicologyen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectacetylcholinesteraseen_US
dc.subjectbenzimidazolium salten_US
dc.subjectin silico studyen_US
dc.subjecttrifluoromethylen_US
dc.subjectalpha-glycosidaseen_US
dc.titleBenzimidazolium salts bearing the trifluoromethyl group as organofluorine compounds: Synthesis, characterization, crystal structure, in silico study, and inhibitory profiles against acetylcholinesterase and ?-glycosidaseen_US
dc.typeArticleen_US

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