Facile synthesis, X-Ray structure of new multi-substituted aryl imidazole ligand, biological screening and DNA binding of its Cr(III), Fe(III) and Cu(II) coordination compounds as potential antibiotic and anticancer drugs

What is it about?

A simple highly adjustable and effective synthesis of aryl imidazole ligand HL namely (2-(1-butyl-4,5-diphenyl-1H-imidazole-2-yl) (4-bromophenol) was discussed where it was prepared by cyclo condensation of 5-bromo-2-hydroxybenzaldehyde, benzil and butan-1-amine. Three new Cr(III), Fe(III) and Cu(II) coordination compounds of aryl imidazole ligand were synthesized. The multi-substituted aryl imidazole ligand (HL) and its coordination compounds were characterized via a wide range of spectroscopic and analytical tools such as 1H NMR and 13C NMR, infrared (IR) and UV–Vis spectrophotometry, conductivity and magnetic measurements. The crystal and molecular structure of aryl imidazole ligand HL were discussed by using maXus. The structure of the titled aryl imidazole ligand HL and its metal coordination compounds were discussed theoretically by using Gaussian 09 program at the B3LYP/LANL2DZ level of theory. The obtained data showed that the new compounds have 1:1 M ratio (metal: ligand) and non-electrolytes in nature. The newly prepared [Cr(L)Cl2(H2O)2], [Fe(L)(NO3)2(H2O)2] and [Cu(L)Cl(H2O)3] coordination compounds have a distorted-octahedral geometry. Density Functional Theory (DFT) calculations have been carried out to investigate the equilibrium geometry of the ligands and its coordination compound using Gaussian 09 program at the B3LYP/LANL2DZ level. Moreover, the new compounds were tested against the selected species of microorganism namely Staphylococcus aureus (+ve), Pseudomonas aeruginosa (-ve), Escherichia coli (-ve) and also against Candida albicans, Aspergillus flavus and Trichophyton Rubrumin. The result revealed that new compounds showed high efficacy towards the growth inhibition of the selected pathogenic microorganism. Moreover, the interaction of the new coordination compounds with CT-DNA was studied by absorption spectra, gel electrophoresis and viscosity techniques. The result showed that the interaction of the new coordination compounds with CT-DNA is an intercalative binding mode. Furthermore, the growth inhibitory effects of the new compounds were tested against Hep-G2, MCF-7 and HCT-116 cell lines. Moreover, all complexes exhibited stronger cytotoxicity effect on the outgrowth of different types of carcinoma cells, than their corresponding imidazole ligand and follow the order: CuL > CrL > FeL > HL.

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