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    Benzotriazole functionalized N-heterocyclic carbene-silver(I) complexes: Synthesis, cytotoxicity, antimicrobial, DNA binding, and molecular docking studies
    (Pergamon-Elsevier Science Ltd, 2018) Onar, Gulnihan; Karatas, Mert Olgun; Balcioglu, Sevgi; Tok, Tugba Taskin; Gurses, Canbolat; Kilic-Cikla, Isin; Ozdemir, Namik
    In this study, six [Ag(NHC)(2)](+)[AgCl2](-) type silver complexes were synthesized by the reaction of corresponding carbene precursor and Ag2O. One [Ag(NHC)(2)]+NO3- type complex was synthesized by the anion exchange reaction of corresponding silver-NHC and NaNO3. The synthesized complexes were characterized by H-1 NMR, C-13 NMR and IR spectroscopic methods, and elemental analysis. X-ray crystal structure of 5a was also reported. Cytotoxicities of all compounds were evaluated against human breast (MCF-7) and colorectal (Caco-2) cancer cell lines and non-cancer mouse fibroblast (L-929) cell lines. All complexes performed stronger activity against both cancer cell lines than standard compound cisplatin while complex 3b performed nearly equal cytotoxicity to cisplatin against non-cancer L-929. Antimicrobial effects of all compounds were evaluated against Escherichia coli, Bacillus subtilis and Candida albicans and good activities were observed. The docking results indicated that complex 3b might be classified as druggable molecule in drug design. DNA binding study also demonstrates that 3b complex has an interaction ability to DNA. Combination of experimental and molecular docking results revealed that reported complexes are promising structures and deserve further research as anticancer drugs. (C) 2018 Elsevier Ltd. All rights reserved.
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    Microwave-Assisted Synthesis of Novel Perimidinium Salts as N-Heterocyclic Carbene Precursors: Involvement in Palladium-Catalyzed Cross-Coupling Reactions
    (Springer, 2015) Onar, Gulnihan; Karatas, Mert Olgun; Alici, Bulent; Cetinkaya, Engin
    In the current study, five novel perimidinium chlorides were synthesized in good yields by reaction of 1-(3-methylbenzyl)perimidine with five different alkyl chlorides under microwave irradiation in 30 minutes. Synthesized compounds were characterized by IR, H-1, C-13 NMR spectroscopic methods and elemental analyses. Performance of in situ formed catalytic system which consist of the perimidinium salts and Pd(OAc)(2) was investigated for Heck and Suzuki reactions in aqueous media, and desired products were obtained in good yields.
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    Palladium(II) and ruthenium(II) complexes of benzotriazole functionalized N-heterocyclic carbenes: Cytotoxicity, antimicrobial, and DNA interaction studies
    (Elsevier Science Sa, 2019) Onar, Gulnihan; Gurses, Canbolat; Karatas, Mert Olgun; Balcioglu, Sevgi; Akbay, Nuriye; Ozdemir, Namik; Ates, Burhan
    In the present study, four palladium and four ruthenium complexes were synthesized with benzotriazole substituted N-heterocyclic carbene ligands. The structures of complexes were established by appropriate spectroscopic methods and elemental analyses. In addition, the crystal structure of a Pd-NHC complex (1c) was reported. Anticancer, antimicrobial and DNA interaction properties of the complexes were examined. Antimicrobial effects of the complexes were tested against two bacteria strains and one fungi strain. Cytotoxic effects of the complexes were tested against human breast (MCF-7) and colorectal (Caco-2) cancer cell lines and non-cancer mouse fibroblast (L-929) cell lines. Ruthenium complexes were found as more cytotoxic than palladium complexes against cancer cell lines. Especially, benzyl containing, benzimidazole-based ruthenium complexes (3c and 3d) were found as non-cytotoxic against non-cancer L-929 cell lines while performing comparable cytotoxicity against Caco-2 cancer cell lines with cisplatin. In addition, DNA interaction studies were performed with pBR322 plasmid DNA and ctDNA and results showed that both palladium and ruthenium complexes have weaker ability to interact with DNA than cisplatin. The results from this study showed that although the cytotoxic properties of the complexes are not stronger than cisplatin, selectivity of benzyl containing benzimidazole-based ruthenium-NHC complexes against Caco-2 cell lines provides them an advantage, and they deserve further research in the treatment of human colorectal cancer. (c) 2019 Elsevier B.V. All rights reserved.