Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation
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...
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| author | Mohamed Ali Ibrahim Al-Gaber Hany M. Abd El-Lateef Mai M. Khalaf Saad Shaaban Mohamed Shawky Gehad G. Mohamed Aly Abdou Mohamed Gouda Ahmed M. Abu-Dief |
| author_facet | Mohamed Ali Ibrahim Al-Gaber Hany M. Abd El-Lateef Mai M. Khalaf Saad Shaaban Mohamed Shawky Gehad G. Mohamed Aly Abdou Mohamed Gouda Ahmed M. Abu-Dief |
| author_sort | Mohamed Ali Ibrahim Al-Gaber |
| collection | DOAJ |
| description | 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, <sup>1</sup>H-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 <sup>1</sup>H-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 <i>Escherichia coli</i> receptor using molecular docking. Altogether, the newly created ligand and complexes showed positive antibacterial effects and are worth future study. |
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| issn | 1996-1944 |
| language | English |
| last_indexed | 2024-03-11T09:36:24Z |
| publishDate | 2023-01-01 |
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| spelling | doaj.art-501fdbf1315e4a05906fa576369f56da2023-11-16T17:14:12ZengMDPI AGMaterials1996-19442023-01-0116389710.3390/ma16030897Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological EvaluationMohamed Ali Ibrahim Al-Gaber0Hany M. Abd El-Lateef1Mai M. Khalaf2Saad Shaaban3Mohamed Shawky4Gehad G. Mohamed5Aly Abdou6Mohamed Gouda7Ahmed M. Abu-Dief8Department of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi ArabiaChemistry Department, Faculty of Science, Cairo University, Giza 12613, EgyptChemistry Department, Faculty of Science, Cairo University, Giza 12613, EgyptDepartment of Chemistry, Faculty of Science, Sohag University, Sohag 82534, EgyptDepartment of Chemistry, College of Science, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Sohag University, Sohag 82534, EgyptA 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, <sup>1</sup>H-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 <sup>1</sup>H-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 <i>Escherichia coli</i> receptor using molecular docking. Altogether, the newly created ligand and complexes showed positive antibacterial effects and are worth future study.https://www.mdpi.com/1996-1944/16/3/897azo dyecomplexesantimicrobial activitiesdockingmolecular geometries |
| spellingShingle | Mohamed Ali Ibrahim Al-Gaber Hany M. Abd El-Lateef Mai M. Khalaf Saad Shaaban Mohamed Shawky Gehad G. Mohamed Aly Abdou Mohamed Gouda Ahmed M. Abu-Dief Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation Materials azo dye complexes antimicrobial activities docking molecular geometries |
| title | Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation |
| title_full | Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation |
| title_fullStr | Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation |
| title_full_unstemmed | Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation |
| title_short | Design, Synthesis, Spectroscopic Inspection, DFT and Molecular Docking Study of Metal Chelates Incorporating Azo Dye Ligand for Biological Evaluation |
| title_sort | design synthesis spectroscopic inspection dft and molecular docking study of metal chelates incorporating azo dye ligand for biological evaluation |
| topic | azo dye complexes antimicrobial activities docking molecular geometries |
| url | https://www.mdpi.com/1996-1944/16/3/897 |
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