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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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    Novel silver(I) complexes bearing mefenamic acid and pyridine derivatives: Synthesis, chemical characterization and in vitro anticancer evaluation
    (Elsevier Science Sa, 2019) Altay, Ahmet; Caglar, Sema; Caglar, Bulent; Sahin, Zarife Sibel
    Two Ag(I) complexes [Ag-2(mu-mef)(2)(2-pymet)(2)]1, [Ag-2(mu-mef)(2)(2-Pyet)(2)](2) containing mefenamic acid, 2-pyridinemethanol and 2-pyridineethanol were synthesized and characterized by using SCXRD, FT-IR, elemental and thermal analysis techniques. The complex 1 was synthesized as a single crystal whereas the complex 2 was obtained as a microcrystalline powder. The complex 1 consists of binuclear structure. The argentophilic interaction occurs among silver(I) ions due to the short Ag center dot center dot center dot Ag distance (2.8710(10) angstrom). Two Ag(I) centers are connected by carboxylato oxygen-bridge to form the binuclear metal core. The FT-IR spectra and thermal analysis studies confirmed that both complexes exhibited similar structures. In vitro antiproliferative activity of both complexes were evaluated against MCF-7, HT-29 and HepG2 cancer cell lines. The apoptotic effects and intracellular ROS generation from both complexes were investigated in MCF-7 cell line by flow cytometry analysis. The XTT and LDH assays revealed that both complexes showed strong antiproliferative activity with higher selectivity towards cancer cells compared to the normal cells. In addition, Annexin V/propidium iodide assay exhibited that apoptotic cell number was increased in MCF-7 cells with increasing concentrations of Ag(I) complexes. Furthermore, both complexes induced the ROS generation considerably in MCF-7 cells suggesting the possible pro-oxidant activity of the novel synthesized Ag(I) complexes. Taken together, these findings provide a notable support for potential utility of Ag(I) complexes as novel anticancer agents against numerous kind of carcinogenesis.
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    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.
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    Synthesis, structural, thermal elucidation and in vitro anticancer activity of novel silver(I) complexes with non-steroidal anti-inflammatory drugs diclofenac and mefenamic acid including picoline derivatives
    (Pergamon-Elsevier Science Ltd, 2018) Altay, Ahmet; Caglar, Sema; Caglar, Bulent; Sahin, Onur
    Six new Ag(I) coordination complexes, namely [Ag-4(mu-dicl)(4)(2-pic)(3)] 1, [Ag-2(mu-mef)(2)(2-pic)(2)] 2, [Ag-2(mu-dicl)(2)(3-pic)(2)] 3, [Ag-2(mu-mef)(2)(3-pic)(2)] 4, [Ag-2(mu-dicl)(2)(4-pic)(2)] 5 and [Ag-2(mu-mef)(2)(4-pic)(2)] 6, were synthesized and characterized by elemental analysis, FT-IR and thermal analysis techniques. The crystal structures of 1, 3, 4 and 5 were determined by X-ray diffraction analysis, whereas 2 and 6 were obtained as microcrystalline powders. X-ray diffraction analysis demonstrated that 1 occurs as a tetranuclear complex, while 3, 4 and 5 have binuclear structures. A short Ag center dot center dot center dot Ag distances of 2.8446 and 2.8823 angstrom for 1, 2.8409 angstrom for 3, 2.8942 angstrom for 4 and 2.8423 angstrom for 5 were found in the complexes, indicating that argentophilic interactions exist between the silver ions. In 1, the dicl ligands act as mu(3)-O,O',O' bridging ligands between three Ag(I) ions. In 3, 4 and 5, the dicl and mef ligands behave as bridging ligands and bind two Ag(I) ions together with the carboxylato oxygen atoms. The simultaneous TG/DTG and DTA techniques were applied to interpret the mass losses, decomposition temperatures and corresponding processes of the thermal behaviours of the complexes. The experimental and calculated mass losses of the proposed structures for complexes 2 and 6 are quite compatible with each other and these complexes have very similar FT-IR spectra to the other complexes, which reflect their same structural geometries and characteristics. The cytotoxic activities of the complexes (16) were tested against three different cancer cell lines, MCF-7, HT-29 and HepG2, and one normal cell line, 3 T3-L1. XTT assay results demonstrated that although all the silver(I) complexes showed good cytotoxic activity, depending on the cell types tested, the complexes with mefanamic acid (2, 4 and 6) were found to predominate over those with diclofenac (1, 3 and 5), as well as the superiority of 3-picoline to 4-picoline and 2-picoline. Moreover, compared with the cytotoxic potential of carboplatin, 4 especially exhibited a significant cancer cell inhibitory rate and lower cytotoxicity toward the normal cell line, with much higher selectivity indexes. (C) 2018 Elsevier Ltd. All rights reserved.