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Dinuclear rectangular-shaped assemblies of bis-benzimidazolydine salt coordinated to Ag(I) and Cu(I) N-heterocyclic carbene complexes and their biological applications

A. G. Bharathi Dileepan, A. Ganesh Kumar, R. Mathumidha, R. Rajaram, and Shameela Rajam

Bishop Heber College, Tiruchirappalli, India

 

E-mail: shameelarajam@gmail.com

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)].

Keywords: N-Heterocyclic carbene ; Silver(I) ; Copper(I) ; Antimicrobial activity ; Antioxidant 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-0538-z

 

Chemical Papers 72 (12) 3017–3031 (2018)

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