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    Binuclear silver(I) complexes with the non-steroidal anti-inflammatory drug tolfenamic acid: Synthesis, characterization, cytotoxic activity and evaluation of cellular mechanism of action
    (Pergamon-Elsevier Science Ltd, 2021) Harurluoglu, Betul; Altay, Ahmet; Caglar, Sema; Yeniceri, Esma Kubra Kagan; Caglar, Bulent; Sahin, Zarife Sibel
    In this study, two new binuclear silver(I)-tolfenamic acid complexes including picoline derivative ligands, [Ag-2(mu-tolf)(2)(2-pic)(2)] 1 and [Ag-2(mu-tolf)(2)(4-pic)(2)] 2, were synthesized and identified by elemental analysis, FT-IR, 1H NMR and thermal analysis techniques. The in vitro cytotoxicity of the complexes was investigated against human breast cancer cell lines by XTT, flow cytometry, enzyme activity and western blot studies. The structures of 1 and 2 were clarified by single-crystal X-ray diffraction determination. The data clearly indicated that the Ag(I) ion is coordinated to one auxiliary ligand (2-pic or 4-pic), two tolfenamato ligands and another Ag(I) ion, demonstrating a distorted tetrahedral geometry. The tolfenamato ligands act as a bridging bidentate ligands. The chains are stabilized by intramolecular Ag(I)...pi and pi....pi interactions. The H-1 NMR and thermal analyses displayed the presence of picoline and tolfenamato ligands in the coordination sphere and the purity of the complexes. Both complexes exhibited potent cytotoxicity against cancer cell lines with higher selectivity than carboplatin. Flow cytometry and enzyme activity studies indicated that both complexes caused an increase in apoptosis, ROS and NO levels, cell cycle arrest, mitochondrial membrane damage and caspase activity, as well as inhibiting PI3K/Akt phosphorylation and modulating the oxidant/antioxidant balance system. Western blot analyses revealed the up-regulation of bax, caspase-3, caspase-9 and p53 proteins, but the down-regulation of bcl-2. These results demonstrate the vigorous apoptotic potential of the novel Ag(I) complexes in human breast cancer MDA-MB-453 cells. (C) 2021 Elsevier Ltd. All rights reserved.
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    Öğe
    Synthesis, structural characterization and evaluation of anticancer activity of polymeric silver(I) complexes based on niflumic acid/naproxen and picoline derivatives
    (Taylor & Francis Ltd, 2022) Caglar, Sema; Altay, Ahmet; Harurluoglu, Betul; Yeniceri, Esma K. K.; Caglar, Bulent; Sahin, Onur
    Two polymeric mixed-ligand silver(I) complexes, [Ag(mu-nif)(4-pic)](n) (1) and [Ag-4(mu-nap)(4)(2-pic)(2)](n) (2), where Hnif: niflumic acid, Hnap: naproxen, 4-pic: 4-picoline and 2-pic: 2-picoline, were synthesized and characterized by single-crystal X-ray diffraction, FT-IR and H-1 NMR spectroscopies, elemental and thermal analysis techniques. In 1, nif ligand behaves as a mu(3)-N,O,O' bridge connecting three silver(I) ions and each silver(I) ion exhibits a seesaw geometry. In 2, nap ligands act as a mu-carboxylato-(O,O') bridge between two silver(I) ions and mu(3)-carboxylato-(O,O,O') bridge linking three silver(I) ions. Each silver(I) ion occurs in trigonal geometry. To uncover the anticancer properties of the complexes, first, their cytotoxic abilities were tested against three cancer cell lines, HT-29 (human colorectal adenocarcinoma), A-549 (human lung carcinoma), and MDA-MB-453 (human breast adenocarcinoma), and normal 3T3-L1 (mouse fibroblast) cell line by XTT tests. Afterwards, the anticancer mechanism of the complexes was tried to be elucidated through the flow cytometry analyzes. XTT assay results showed that the complexes exhibited the highest cytotoxic activity and selectivity on HT-29 cells among all the cell lines. Flow cytometry analyses revealed that both complexes induced the apoptosis through the mitochondrial membrane depolarization and activation of the caspase cascade in HT-29 cells.