Benzotriazole functionalized N-heterocyclic carbene–silver(I) complexes: Synthesis, cytotoxicity, antimicrobial, DNA binding, and molecular docking studies

• Published in: Polyhedron 2018-10, Vol.153, p.31-40
• Main Authors: Onar, Gülnihan, Karataş, Mert Olgun, Balcıoğlu, Sevgi, Tok, Tuğba Taşkın, Gürses, Canbolat, Kılıç-Cıkla, Işın, Özdemir, Namık, Ateş, Burhan, Alıcı, Bülent
• Format: Article
• Language: English
• Subjects: Antimicrobial; Benzotriazole; Cytotoxicity; N-Heterocyclic carbene; Silver(I)
• ISSN: 0277-5387
• DOI: 10.1016/j.poly.2018.06.052

Seven novel benzotriazole functionalized N-heterocyclic carbene–silver(I) complexes were synthesized and characterized. Cytotoxicities of complexes were investigated against human breast (MCF-7) and colorectal (Caco-2) cancer cell lines and non-cancer mouse fibroblast cell lines (L-929). Antimicrobial activities of all compounds were tested against Escherichia coli, Bacillus subtilis and Candida albicans. [Display omitted] 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 1H NMR, 13C 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.