2-Phenyl substituted Benzimidazole derivatives: Design, synthesis, and evaluation of their antiproliferative and antimicrobial activities

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dc.authoridKUZU, Burak/0000-0002-7305-7177
dc.authoridalagoz, mehmet abdullah/0000-0001-5190-7196
dc.authoridKUZU, Burak/0000-0002-7305-7177;
dc.authorwosidKUZU, Burak/GVS-6838-2022
dc.authorwosidalagoz, mehmet abdullah/W-7847-2018
dc.authorwosidKUZU, Burak/AAE-1597-2022
dc.authorwosidhaj ersan, ronak/GVT-2637-2022
dc.contributor.authorErsan, Ronak Haj
dc.contributor.authorKuzu, Burak
dc.contributor.authorYetkin, Derya
dc.contributor.authorAlagoz, Mehmet Abdullah
dc.contributor.authorDogen, Aylin
dc.contributor.authorBurmaoglu, Serdar
dc.contributor.authorAlgul, Oztekin
dc.date.accessioned2024-08-04T20:51:56Z
dc.date.available2024-08-04T20:51:56Z
dc.date.issued2022
dc.departmentİnönü Üniversitesien_US
dc.description.abstractThe inability to meet the desired outcomes of anticancer treatment and decrease in treatment success of bacterial and fungal infections accelerated research in these areas. Our research group has conducted numerous studies, especially on benzimidazole ring systems' antiproliferative and antimicrobial activities. In this study, the antiproliferative activity of benzimidazole compounds was tested against A549, A498, HeLa, A375, and HepG2 cancer cell lines by MTT assay. All compounds exhibited good to potent antiproliferative activity against all tested cancer cell lines. Compounds 6-chloro-2-(4-fluorobenzyl)-1H-benzo[d] imidazole (30) and 6-chloro-2-phenethyl-1H-benzo[d]imidazole (46) were especially active against HeLa and A375 cancer cell lines with IC50 values in the range of 0.02-0.04 mu M. In contrast, compounds 6-chloro-2-((p-tolyloxy)methyl)-1H-benzo[d] imidazole (67) and 5(6)-chloro-2-((4-hydroxyphenoxy)methyl)-1H-benzimidazole (68) were active against A549 and A498 cancer cell lines with an IC50 value of 0.08 mu M. These compounds (30, 46, 67, and 68) were less toxic to normal human cells than the positive control compound methotrexate, which was screened to determine its toxicity against normal cell lines (HEK293). In the second part of the study, all compounds were tested to demonstrate their antimicrobial properties. All compounds exhibited moderate activity against all tested bacteria and fungi. However, some phenoxy methyl derivatives 5-chloro-2-((4-chlorophenoxy)methyl)-1H-benzo[d]imidazole (69) and 5,6-dichloro-2-((4-chlorophenoxy)methyl)-1H-benzo[d] imidazole and (74) were most active against Candida (<3.90 mu g/mL). Molecular docking studies were carried out against certain proteins in order to identify potential targets of the antiproliferative effects of the synthesized compounds. The docking scores of the compounds were found to be significantly compatible with the antiproliferative activity results. [GRAPHICS] .en_US
dc.description.sponsorshipMersin University [BAP-SBE-2018-1-TP3-2911]en_US
dc.description.sponsorshipWe thank Mersin University for their financial support (BAP-SBE-2018-1-TP3-2911).en_US
dc.identifier.doi10.1007/s00044-022-02900-3
dc.identifier.endpage1208en_US
dc.identifier.issn1054-2523
dc.identifier.issn1554-8120
dc.identifier.issue7en_US
dc.identifier.scopus2-s2.0-85130151295en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage1192en_US
dc.identifier.urihttps://doi.org/10.1007/s00044-022-02900-3
dc.identifier.urihttps://hdl.handle.net/11616/100653
dc.identifier.volume31en_US
dc.identifier.wosWOS:000796337300002en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Birkhauseren_US
dc.relation.ispartofMedicinal Chemistry Researchen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectBenzimidazoleen_US
dc.subjectAntiproliferative activityen_US
dc.subjectAntimicrobial activityen_US
dc.subjectSARen_US
dc.subjectMolecular dockingen_US
dc.subjectADMETen_US
dc.title2-Phenyl substituted Benzimidazole derivatives: Design, synthesis, and evaluation of their antiproliferative and antimicrobial activitiesen_US
dc.typeArticleen_US

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