Structural characterization, cytotoxic and enzyme inhibitory profile of a novel triazole-linked ferrocene hybrid of 18?-glycyrrhetinic acid

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dc.authorid0000-0002-2882-6811
dc.authorid0000-0003-3276-1413
dc.authorid0009-0001-4597-4007
dc.contributor.authorOzturk, Zehra
dc.contributor.authorYildiz, Yaren
dc.contributor.authorAbul, Nurgul
dc.contributor.authorErtik, Onur
dc.contributor.authorAri, Ferda
dc.contributor.authorGulcin, Ilhami
dc.contributor.authorKoz, Gamze
dc.date.accessioned2026-02-08T15:15:24Z
dc.date.available2026-02-08T15:15:24Z
dc.date.issued2025
dc.departmentBursa Teknik Üniversitesi
dc.description.abstract18 beta-Glycyrrhetinic acid (GA) is a pentacyclic triterpene which was obtained from the roots of Glycyrrhiza glabra known for its diverse pharmaceutical applications. The primary aim of this study is to enhance the pharmaceutical properties of GA by modifying it with a 1,2,3-triazole-functionalized ferrocene moiety. The hybrid compound 3 was synthesized by amide functionalization of GA at the C-30 position with ferrocene, linked via a 1,4-disubstituted 1,2,3-triazole bridge. Additionally, the C-3 hydroxyl group of GA was converted into an acetyl ester. The hybrid compound 3 was characterized using FT-IR, NMR (1H and 13C) and HR-MS. The aim of the modification was to enhance the cytotoxic and enzyme inhibitory effects of GA. 1,2,3,-Triazole substituted ferrocene (1), C-3 acetylated GA and the hybrid compound 3 were tested on A549, MCF-7, HCT-116, and PC-3 cancer cell lines. MCF-7 and HCT-116 cells showed the highest sensitivity to the compounds. Compound 3 showed more cytotoxicity than both GA and compound 1 with IC50 values of 23.97 and 50 mu M in MCF-7 and HCT-116 cells, respectively. Morphological analysis indicated that compound 3 induced apoptotic cell death. In addition, the inhibitory effect of compounds on carbonic anhydrase I-II isoenzymes (hCAI-II), acetylcholinesterase/butyrylcholinesterase (AChE/BChE) enzymes, and alpha-glucosidase was tested. According to the results, compound 3, exhibited the strongest inhibitory properties for all enzymes tested with IC50 values of 0.0323, 0.3058, 0.0078, 0.0090 and 0.0120 mu M, respectively. Molecular docking studies were performed to investigate the ligand-target protein interactions. Incorporating an organometallic sandwich-like compound ferrocene into GA via a 1,2,3-triazole bridge appears to be an effective strategy for modifying and enhancing its bioactivity.
dc.description.sponsorshipScientific and Technological Research Council of Turkey [TUBITAK 2209-A]
dc.description.sponsorshipThe Scientific and Technological Research Council of Turkey (TUBITAK 2209-A) is gratefully acknowledged.
dc.identifier.doi10.1016/j.poly.2025.117620
dc.identifier.issn0277-5387
dc.identifier.issn1873-3719
dc.identifier.scopus2-s2.0-105007135153
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.poly.2025.117620
dc.identifier.urihttps://hdl.handle.net/20.500.12885/5765
dc.identifier.volume279
dc.identifier.wosWOS:001510085200001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofPolyhedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzWOS_KA_20260207
dc.subject18 beta-Glycyrrhetinic acid
dc.subjectFerrocene
dc.subject1,2,3-Triazole
dc.subjectCytotoxicity
dc.subjectEnzyme inhibition
dc.titleStructural characterization, cytotoxic and enzyme inhibitory profile of a novel triazole-linked ferrocene hybrid of 18?-glycyrrhetinic acid
dc.typeArticle

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