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. 2023 Jan 17;16(3):897.
doi: 10.3390/ma16030897.

Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation

Mohamed Ali Ibrahim Al-Gaber  1 , Hany M Abd El-Lateef  1   2 , Mai M Khalaf  1   2 , Saad Shaaban  1   3 , Mohamed Shawky  4 , Gehad G Mohamed  4   5 , Aly Abdou  2 , Mohamed Gouda  1 , Ahmed M Abu-Dief  2   6
Affiliations

Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation

Mohamed Ali Ibrahim Al-Gaber et al. Materials (Basel). .

Abstract

A new heterocyclic azo dye ligand (L) was synthesized by the combination of 4-amino antipyrine with 4-aminophenol. The new Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), and Cd(II) complexes were synthesized in excellent yields. The metal chelate structures were elucidated using elemental analyses, FT-IR, 1H-NMR, mass, magnetic moment, diffused reflectance spectral and thermal analysis (TG-DTG), and molar conductivity measurement. According to the FT-IR study, the azo dye ligand exhibited neutral tri-dentate behavior, binding to the metal ions with the azo N, carbonyl O, and protonated phenolic OH. The 1H-NMR spectral study of the Zn(II) complex supported the coordination of the zo dye ligand without proton displacement of the phenolic OH. Diffused reflectance and magnetic moment studies revealed the octahedral geometry of the complexes, as well as their good electrolytic nature, excepting the Zn(II) and Cd(II) complexes, which were nonelectrolytes, as deduced from the molar conductivity study. The theoretical calculations of optimized HOMO-LUMO energies, geometrical parameters, electronic spectra, natural atomic charges, 3D-plots of MEP, and vibrational wavenumbers were computed and elucidated using LANL2DZ and 6-311G (d, p) basis sets of density functional theory (DFT) with the approach of B3LYP DFT and TD-DFT methods. The ligand and complexes have been assayed for their antimicrobial activity and compared with the standard drugs. Most of the complexes have manifested excellent antimicrobial activity against various microbial strains. A molecular docking investigation was also performed, to acquire more information about the binding mode and energy of the ligand and its metal complexes to the Escherichia coli receptor using molecular docking. Altogether, the newly created ligand and complexes showed positive antibacterial effects and are worth future study.

Keywords: antimicrobial activities; azo dye; complexes; docking; molecular geometries.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
The proposed structure of azo dye ligand (L).
Figure 2
Figure 2
Mass spectra of (a) azo dye ligand (L), (b) Cd L complex.
Figure 3
Figure 3
The structure of the L-metal complexes.
Figure 4
Figure 4
Optimized geometry of the studied compounds.
Figure 5
Figure 5
The HOMO and LUMO of the L, CrL, MnL, FeL, Co, NiL, Cu, ZnL, and CdL compounds.
Figure 5
Figure 5
The HOMO and LUMO of the L, CrL, MnL, FeL, Co, NiL, Cu, ZnL, and CdL compounds.
Figure 6
Figure 6
MEP of the studied compounds.
Figure 7
Figure 7
Biological activity of azo dye ligand (L) and its complexes.
Figure 8
Figure 8
Interaction between the active site of 3t88 with synthesized complexes.
Figure 8
Figure 8
Interaction between the active site of 3t88 with synthesized complexes.
Figure 8
Figure 8
Interaction between the active site of 3t88 with synthesized complexes.
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