Abstract
A benzimidazolydine-based novel ligand L2 was prepared from 1,2-bis(benzimidazol-1-yl)ethane (L1) and synthesis of metallocycle complexes such as Ag(I)–N-Heterocyclic Carbene abbreviated as Ag–NHC and Cu(I)–N-Heterocyclic Carbene complex as Cu–NHC were synthesized and then estimated for antimicrobial and antioxidant properties. Synthesis of Ag–NHC and Cu–NHC metallocycle complexes was described. The benzimidazolydine ligand precursor and its Ag–NHC and Cu–NHC were successfully characterized by FT-IR, FT-Raman, 1D and 2D NMR, HR-ESI mass spectra, and cyclic voltammetric studies. In the present work, antimicrobial study discloses that ligand (L1 and L2) do not show inhibitory activity against various pathogens; however, it was gradually increased, when they were coordinated to metals like Ag and Cu. Among the four compounds, the Ag–NHC strongly hampers the growth of fungal strains. The minimal inhibitory concentration (MIC) ranged between 46 and 750 μg mL−1. A distinctive cell growth reduction was observed in C. albicans when treated with minimum concentration of Ag–NHC complex. Ag–NHC exhibited the ability to prevent the growth of C. albicans by causing severe membrane damage and accumulation of intracellular reactive oxygen species (ROS), which were revealed by fluorescence spectroscopic studies. The tested (L1, L2, Ag–NHC and Cu–NHC) compounds demonstrated significant activity with IC50 values range (0.20–30 μM) for DPPH, OH and NO antioxidant activity. Ascorbic acid was used as standard drug. The radical scavenging potencies of the compounds were explored by employing DPPH, OH and NO assays, in which Ag–NHC exhibited highest inhibitory effect on the radicals [IC50 = 57.3 μM (DPPH), 57.7 μM (OH), 52.3 μM (NO)].
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Acknowledgements
The authors thank Dr. Ramanathan, NMR Laboratory, Indian Institute of Science, Bangalore for recording complete set of NMR analysis. Additionally, we are thankful to SAIF, Indian Institute of Technology Madras, Chennai for recording ESI–MS and HRMS analysis. The authors thank Bharathidasan University for recording antimicrobial and antioxidant activity. The authors also thank Research Scholar, Department of Chemistry, Bishop Heber College, Trichy for their kind support.
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Dileepan, A.G.B., Ganesh Kumar, A., Mathumidha, R. et al. Dinuclear rectangular-shaped assemblies of bis-benzimidazolydine salt coordinated to Ag(I) and Cu(I) N-heterocyclic carbene complexes and their biological applications. Chem. Pap. 72, 3017–3031 (2018). https://doi.org/10.1007/s11696-018-0538-z
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DOI: https://doi.org/10.1007/s11696-018-0538-z