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    Antimicrobial activity, inhibition of biofilm formation, and molecular docking study of novel Ag-NHC complexes
    (Elsevier Science Sa, 2021) Sahin, Neslihan; Ustun, Elvan; Tutar, Ugur; Celik, Cem; Gurbuz, Nevin; Ozdemir, Ismail
    In this study, we reported the synthesis of a new series of Silver(I)-N-heterocyclic carbene complexes which were obtained from the corresponding new N-heterocyclic carbene (NHC) precursors. All new compounds were characterized by elemental analysis, FT-IR, LC-MS, H-1 NMR, and C-13{H-1} NMR spectroscopy. These new N-heterocyclic carbene precursors and Ag(I)-NHC complexes were evaluated for their antibacterial, antifungal, and antibiofilm activities. The biological activities of synthesized products were compared with standard drugs. All compounds have moderate antibacterial and antibiofilm activities. In particular, while compound 2a was found to be the best inhibitor of E. coli biofilms, while compound 2d inhibited C. albicans biofilm at the highest rate. All the compounds were also analyzed by molecular docking methods with the certain target molecules. (C) 2021 Elsevier B.V. All rights reserved.
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    Benzimidazol-2-ylidene Silver Complexes: Synthesis, Characterization, Antimicrobial and Antibiofilm Activities, Molecular Docking and Theoretical Investigations
    (Mdpi, 2023) Tutar, Ugur; Celik, Cem; Ustuen, Elvan; Ozdemir, Namik; Sahin, Neslihan; Semeril, David; Gurbuz, Nevin
    Five silver(I) complexes, namely chloro[1-methallyl-3-benzyl)benzimidazol-2-ylidene] silver (6), chloro[1-methallyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazol-2-ylidene]silver (7), chloro[1-methallyl-3-(3,4,5-trimethoxylbenzyl)benzimidazol-2-ylidene]silver (8), chloro[1-methallyl- 3-(naphthylmethyl)benzimidazol-2-ylidene]silver (9), and chloro [1-methallyl-3-(anthracen-9-yl- methyl)benzimidazol-2-ylidene]silver (10), were prepared starting from their corresponding benzimidazolium salts and silver oxide in 71-81% yields. A single-crystal X-ray structure of 7 was determined. These five Ag-NHC complexes were evaluated for their antimicrobial and biofilm formation inhibition properties. Complex 10 exhibited high antimicrobial activities comparable to those obtained with standard drugs such as Fluconazole in contact with Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Acinetobacter baumannii, and Candida albicans. The latter complex has been shown to be very efficient in antibiofilm activity, with 92.9% biofilm inhibition at 1.9 mu g/mL on Escherichia coli. Additionally, the molecules were optimized with DFT-based computational methods for obtaining insight into the structure/reactivity relations through the relative energies of the frontier orbitals. The optimized molecules were also analyzed by molecular docking method against DNA gyrase of Escherichia coli and CYP51 from Candida albicans.
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    Synthesis, characterization, antimicrobial and antibiofilm activity, and molecular docking analysis of NHC precursors and their Ag-NHC complexes
    (Royal Soc Chemistry, 2021) Ustun, Elvan; Sahin, Neslihan; Celik, Cem; Tutar, Ugur; Ozdemir, Namik; Gurbuz, Nevin; Ozdemir, Ismail
    Microorganisms attach to surfaces and interfaces and form biofilms which create a sheltered area for host cell response. Therefore, biofilms provide troubles in fields such as medicine, food, and pharmaceuticals. Inhibition of formation of biofilms through hindering of quorum sensing could be a method for the production of new generation antibiotics. In this study, four new benzimidazole type NHC precursors (1-allyl-3-benzyl-5,6-dimethylbenzimidazolium chloride, 1-allyl-3-(2,4,6-trimethylbenzyl)-5,6-dimethylbenzimidazolium chloride, 1-allyl-3-(2,3,5,6-tetramethylbenzyl)-5,6-dimethylbenzimidazolium chloride, and 1-allyl-3-(2,3,4,5,6-pentamethylbenzyl)-5,6-dimethylbenzimidazolium chloride and Ag-NHC complexes of these molecules were synthesized and characterized by elemental analysis, FT-IR spectroscopy, H-1, and C-13{H-1} NMR spectroscopy, LC-MS, and single crystal crystallography. Antimicrobial and biofilm formation inhibition activities of the molecules were evaluated. In addition, the activities of the molecules were examined in detail by molecular docking analysis. According to the results obtained, higher activity was achieved with the complex molecules when compared with the benzimidazole derivative ligands.