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Synthesis, DFT, electrochemical, biological and DNA-interaction studies of a novel copper(II) complex of salicylic acid and N-tosyl substituted benzimidazole

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journal contribution
posted on 2020-01-20, 12:22 authored by Naghmana Rashid, Almas Kiran, Iqbal Ahmad, Zaman Ashraf, Bohari Mohd. Yamin, Muhammad Rafiq

Sulfonylbenzimidazoles and their copper complexes have tremendous applications in drug development. In the present work, bis(2-hydroxylbenzoato-κ2O,O′)bis(2-methyl-1-(toluene-4-sulfonyl)-1H-benzimidazole) copper(II) complex [Cu(L1)(L2)] has been synthesized and structurally characterized by Fourier-transformed infrared spectroscopy (FTIR) and single-crystal X-ray diffraction (XRD). The complex formed a distorted octahedral geometry with the benzimidazole ligands occupying the axial position and the hydroxylbenzoato ligands in the equatorial positions. The latter ligands coordinated in an isobidentate manner with a Cu–Odeprotenated bond length of 1.955(18) Å and a long range Cu–Ocarbonyl of 2.574(2) Å. An excellent correlation was found between bond lengths and bond angles obtained experimentally from single-crystal XRD analysis and that obtained from density functional theory. Electrochemical behavior of [Cu(L1)(L2)] has been probed by cyclic voltammetry (CV). CV studies revealed that it undergoes one-electron reduction followed by one-electron oxidation process. In vitro tyrosinase inhibitory activity of the complex was evaluated and it was observed that it exhibited good inhibitory potential with IC50 value 56.8 ± 11.4 μM. Complex-DNA-interaction studies were performed by CV, electronic and florescence spectroscopic titrations and it has been inferred that the [Cu(L1)(L2)] binds with DNA through intercalation and the value of binding constant was 3.6 × 104 M−1.

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