Water-soluble N-heterocyclic carbene precursors bearing benzimidazole core: synthesis, characterization, in vitro antioxidant and anticancer studies

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dc.authoridDOGAN ULU, OZNUR/0000-0002-5561-227X
dc.contributor.authorUlu, Oznur Dogan
dc.contributor.authorKurucay, Ali
dc.contributor.authorOzdemir, Ismail
dc.date.accessioned2024-08-04T20:53:31Z
dc.date.available2024-08-04T20:53:31Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractBenzimidazole is an important member of the nitrogen-containing heterocyclic ring system since it confers surprisingly good biological properties in medicinal chemistry such as anticancer drug applications. Keeping this in mind, a new series of asymmetrical 1,3-disubstituted benzimidazolium salts were designed and reported. The compounds were synthesized by the reaction of 1-alkylbenzimidazoles with 2-(2-bromoethyl)-1,3-dioxane. The structures of all the compounds were determined using FT-IR, H-1 and C-13 NMR spectroscopy, LC-MS, and elemental analysis. The compounds were used for their antioxidant capacity by commercial kit assay. Further, these were screened for their cytotoxic effect against cell lines including MCF-7, A-549, and L929 using cisplatin as a reference drug. It resulted that the total antioxidant capacity values of the compounds were found to be quite low compared to the trolox equivalent. On the other side, most importantly, two compounds showed remarkable anticancer activity against MCF-7 and A-549 with IC50 values of 18.06 and 20.44 mu g/cm(3), respectively, in comparison with cisplatin (IC50 = 83.11 and 87.80 mu g/cm(3)). Furthermore, most of the compounds were found to be safe on normal L929 fibroblast cells compared to cancer cells (IC50 values for healthy fibroblasts were 142.70-268.37 mu g/cm(3)). Taken together, the newly synthesized compounds containing benzimidazole core can be readily constructed and used as an attractive class of anticancer agents.{graphical abstracts}en_US
dc.identifier.doi10.1007/s00706-023-03041-y
dc.identifier.endpage440en_US
dc.identifier.issn0026-9247
dc.identifier.issn1434-4475
dc.identifier.issue3-4en_US
dc.identifier.scopus2-s2.0-85150239933en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage429en_US
dc.identifier.urihttps://doi.org/10.1007/s00706-023-03041-y
dc.identifier.urihttps://hdl.handle.net/11616/101227
dc.identifier.volume154en_US
dc.identifier.wosWOS:000953806500001en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringer Wienen_US
dc.relation.ispartofMonatshefte Fur Chemieen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectN-Heterocyclic carbineen_US
dc.subjectBenzimidazolium salten_US
dc.subject1en_US
dc.subject3-Dioxaneen_US
dc.subjectAntioxidant activityen_US
dc.subjectAnticancer activityen_US
dc.titleWater-soluble N-heterocyclic carbene precursors bearing benzimidazole core: synthesis, characterization, in vitro antioxidant and anticancer studiesen_US
dc.typeArticleen_US

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