Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity

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dc.authoridSalva, Emine/0000-0002-1159-5850
dc.authoridŞALVA, EMINE/0000-0002-1159-5850
dc.authoridHalay, Erkan/0000-0002-0084-7709
dc.authorwosidSalva, Emine/ABI-2766-2020
dc.authorwosidAY, EMRİYE/AAW-9002-2020
dc.authorwosidKARAYILDIRIM, Tamer/G-1090-2018
dc.authorwosidŞALVA, EMINE/CAH-3062-2022
dc.authorwosidHalay, Erkan/C-3191-2018
dc.contributor.authorHalay, Erkan
dc.contributor.authorAy, Emriye
dc.contributor.authorSalva, Emine
dc.contributor.authorAy, Kadir
dc.contributor.authorKarayildirim, Tamer
dc.date.accessioned2024-08-04T20:44:24Z
dc.date.available2024-08-04T20:44:24Z
dc.date.issued2018
dc.departmentİnönü Üniversitesien_US
dc.description.abstractCopper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4 center dot 5H(2)O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil-mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 mu M, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.en_US
dc.description.sponsorshipTUBITAK-Research Council of Turkey [114Z757]; TUBITAK-BIDEB [2211A]en_US
dc.description.sponsorshipThis work was supported by TUBITAK-Research Council of Turkey with the project number 114Z757. Author E. Halay also offers his profound thanks to TUBITAK-BIDEB 2211A for their bursary support.en_US
dc.identifier.doi10.1007/s10593-018-2248-4
dc.identifier.endpage166en_US
dc.identifier.issn0009-3122
dc.identifier.issn1573-8353
dc.identifier.issue2en_US
dc.identifier.scopus2-s2.0-85044474058en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.startpage158en_US
dc.identifier.urihttps://doi.org/10.1007/s10593-018-2248-4
dc.identifier.urihttps://hdl.handle.net/11616/98213
dc.identifier.volume54en_US
dc.identifier.wosWOS:000429350900009en_US
dc.identifier.wosqualityQ3en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherSpringeren_US
dc.relation.ispartofChemistry of Heterocyclic Compoundsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectazido sugarsen_US
dc.subjectnucleobasesen_US
dc.subjectnucleosidesen_US
dc.subjecttriazolesen_US
dc.subjectanticancer activityen_US
dc.subjectclick chemistryen_US
dc.titleSynthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicityen_US
dc.typeArticleen_US

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