Imidazolium salts carrying two positive charges: design, synthesis, characterization, molecular docking, antibacterial and enzyme inhibitory activities

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dc.contributor.authorDemirhan, Ilter
dc.contributor.authorNecip, Adem
dc.contributor.authorOner, Erkan
dc.contributor.authorGumuscu, Nalin
dc.contributor.authorDemirci, Ozlem
dc.contributor.authorGok, Yetkin
dc.contributor.authorDoni, Nebiye Yentur
dc.date.accessioned2026-04-04T13:31:18Z
dc.date.available2026-04-04T13:31:18Z
dc.date.issued2025
dc.departmentİnönü Üniversitesi
dc.description.abstractIntroduction The discovery of alternative drugs has gained importance due to the many side effects of these drugs used for treatment.Methods Herein, the synthesis of a series of unsymmetrical imidazolium salts containing 4-acetylphenyl/4-formylphenyl and bioactive heterocyclic groups such as morpholine, piperidine, pyrrole or pyridine was reported. 4-(1-H-imidazol-1-yl)acetophenone and 4-(1-H-imidazol-1-yl)benzaldehyde were used as salt precursors. Alkyl halides containing heterocyclic groups such as 2-morpholinoethyl hydrochloride, 2-pyrrolidinoethyl hydrochloride, 2-piperidinoethyl hydrochloride and pyridin-2-ylmethyl bromide hydrobromide were used. Thus, there are two positively charged nitrogens in the structure of these salts synthesized by the quaternization method. The structures of all salts were fully characterized by 1H, 13C NMR, FTIR spectroscopic and elemental analysis methods. the a series of imidazolium salts (1a-d and 2a-d) were designed, synthesized and fully characterized by spectroscopic methods.Results The inhibitory effect against AChE of the series compounds was evaluated as in vitro and in silico studies. The results indicated that the compounds showed remarkably potent inhibitory effects on AChE with K I values ranging from 0.63 +/- 0.04 mu M to 11.23 +/- 1.05 mu M and IC50 values spanning from 0.82 +/- 0.06 mu M to 14.75 +/- 0.82 mu M. The antimicrobial activities of the synthesized compounds were measured by inhibition of bacterial growth expressed as minimum inhibitory concentration (MIC) values. It was observed that the synthesized compounds exhibited antimicrobial activity especially against Gram negative bacteria. In addition, the results of molecular docking studies of bacteria supported our antimicrobial results.Conclusions The results suggested that the synthesized compounds showed the potential to be antimicrobial and acetylcholinesterase inhibitors.
dc.description.sponsorshipHarran University Research Fund [D7-21306]
dc.description.sponsorshipThe author(s) declare that financial support was received for the research and/or publication of this article. This study was financially supported by Harran University Research Fund (Project Code: D7-21306).
dc.identifier.doi10.3389/fcimb.2025.1579916
dc.identifier.issn2235-2988
dc.identifier.orcid0000-0002-6332-6484
dc.identifier.orcid0000-0002-0383-4970
dc.identifier.orcid0000-0002-4677-8104
dc.identifier.orcid0000-0002-0044-4758
dc.identifier.pmid40756032
dc.identifier.scopus2-s2.0-105012392667
dc.identifier.scopusqualityN/A
dc.identifier.urihttps://doi.org/10.3389/fcimb.2025.1579916
dc.identifier.urihttps://hdl.handle.net/11616/108711
dc.identifier.volume15
dc.identifier.wosWOS:001541280500001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherFrontiers Media Sa
dc.relation.ispartofFrontiers in Cellular and Infection Microbiology
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250329
dc.subjectN-heterocyclic carbene
dc.subjectimidazolium salt
dc.subjectacetylcholinesterase
dc.subjectantimicrobial
dc.subjectanti-Alzheimer
dc.titleImidazolium salts carrying two positive charges: design, synthesis, characterization, molecular docking, antibacterial and enzyme inhibitory activities
dc.typeArticle

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