Novel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities

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dc.authoridOkten, Salih/0000-0001-9656-1803
dc.authoridAYDIN, Ali/0000-0002-4931-9843
dc.contributor.authorMisir, Busra A.
dc.contributor.authorDerin, Yavuz
dc.contributor.authorOkten, Salih
dc.contributor.authorAydin, Ali
dc.contributor.authorKocyigit, Umit M.
dc.contributor.authorSahin, Hatice
dc.contributor.authorTutar, Ahmet
dc.date.accessioned2025-01-21T16:42:56Z
dc.date.available2025-01-21T16:42:56Z
dc.date.issued2024
dc.departmentKırıkkale Üniversitesi
dc.description.abstractIn this study, our goal was to synthesize novel aryl tacrine derivatives and assess their potential as anticancer, antibacterial agents, and enzyme inhibitors. We adopted a two-step approach, initiating with the synthesis of dibromotacrine derivatives 3 and 4 through the Friedlander reaction. These intermediates underwent further transformation into diarylated tacrine derivatives 3a-e and 4a-e using a Suzuki-Miyaura cross-coupling reaction. Thorough characterization of these novel diarylated tacrines was achieved using various spectroscopic techniques. Our findings highlighted the potent anticancer effects of these innovative compounds across a range of cancer cell lines, including lung, gynecologic, bone, colon, and breast cancers, while demonstrating low cytotoxicity against normal cells. Notably, these compounds surpassed the control drug, 5-Fluorouracil, in terms of antiproliferative activity in numerous cancer cell lines. Moreover, our investigation included an analysis of the inhibitory properties of these novel compounds against various microorganisms and cytosolic carbonic anhydrase enzymes. The results suggest their potential for further exploration as cancer-specific, enzyme inhibitory, and antibacterial therapeutic agents. Notably, four compounds, namely, 5,7-bis(4-(methylthio)phenyl)tacrine (3d), 5,7-bis(4-(trifluoromethoxy)phenyl)tacrine (3e), 2,4-bis(4-(trifluoromethoxy)phenyl)-7,8,9,10-tetrahydro-6H-cyclohepta[b]quinolin-11-amine (4e), and 6,8-dibromotacrine (3), emerged as the most promising candidates for preclinical studies. The novel aryl substituted tacrine were efficiently synthesized and their anticancer potentials were highlighted in this study. Their inducing apoptosis, cell migration, and mitochondrial membrane potentials were screened. image
dc.description.sponsorshipTurkish Health Institutes [24138]; TUBITAK 2209-A Program [1919B012106356]; Council of Higher Education (CoHE) of Turkey; [100/2000]
dc.description.sponsorshipTurkish Health Institutes, Grant/Award Number: TUSEB A-Project No 24138; TUBITAK 2209-A Program,Grant/Award Number: 1919B012106356; Council of Higher Education (CoHE) of Turkey,Grant/Award Number: 100/2000
dc.identifier.doi10.1002/jbt.23706
dc.identifier.issn1095-6670
dc.identifier.issn1099-0461
dc.identifier.issue4
dc.identifier.pmid38591869
dc.identifier.scopus2-s2.0-85190123135
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1002/jbt.23706
dc.identifier.urihttps://hdl.handle.net/20.500.12587/25170
dc.identifier.volume38
dc.identifier.wosWOS:001198676500001
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherWiley
dc.relation.ispartofJournal of Biochemical and Molecular Toxicology
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_20241229
dc.subjectantibacterial agents; anticancer agents; cytotoxicity; diarylated tacrine; enzyme inhibition; inducing apoptosis; Suzuki coupling
dc.titleNovel diarylated tacrine derivatives: Synthesis, characterization, anticancer, antiepileptic, antibacterial, and antifungal activities
dc.typeArticle

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