Structural, Spectroscopic and Anti-cancer Properties of Hydroxy- and Sulfonamide-Azobenzene Platinum (II) Complexes: DFT and Molecular Docking Studies
Journal Title: Cumhuriyet Science journal - Year 2018, Vol 39, Issue 4
Abstract
The three platinum (II) complexes ([Pt(L1)(DMSO)Cl], [Pt(L2)(DMSO)Cl] and [Pt(L2)2]) bearing the bidentate ligands sulphonamide-((E)-2-(4-methylphenylsulfonamido)-2′,6′-difluoroazobenzene, HL1) and hydroxy-azo-2,6-difluorobenzene ((E)-2-((2,6-difluorophenyl)diazenyl)phenol, HL2) were optimized with the optimum levels of B3LYP/6-31+G(d) and B3LYP/LANL2DZ/6-31+G(d) level. The structural parameters (bond lengths and ligand angles), IR and 1H, 13C and 19F-NMR spectra obtained from the optimized structures were compared with the experimental data and the results were found to be consistent with the experimental results. Experimental inhibition activities against A2780 and A2780CP70 cancer cells were compared with quantum chemical parameters such as HOMO energy (EHOMO), LUMO energy (ELUMO), LUMO-HOMO energy vacancy (DE), hardness (h), softness (s), electronegativity (c) and chemical potential (m). The relationship between the molecular structure with the biological activity was examined and ELUMO order was found to be compatible with the experimental inhibition efficiency ranking. Molecular electrostatic potential (MEP) maps were studied of ligands and complexes exhibiting anti-cancer properties and for ligands and complexes, regions of attachment to cancer cells were determined. In addition, electrostatic potential (ESP) charges obtained from MEP maps of ligands and complexes were ranked according to their ease of binding to the cancer cell. The obtained ranking was found to be in accordance with the experimental inhibition efficiency order. For studied ligands and complexes, molecular docking studies were carried out with the Hex.8.0.0 program. The target proteins (PDB ID: 4M5W and 5FI4, respectively) corresponding to the A2780 and A2780CP70 cell lines were selected in the literature. The interaction energies of 4M5W and 5FI4 target proteins with HL1 and HL2 ligands were calculated to be -300.02, -240.80 and -336.64, -247.04 kJ/mol, respectively. The binding energies between the complexes and 4M5W and 5FI4 target proteins were calculated to be -387.52, -285.44, -364.88 and -399.63, -297.8, -385.323 kJ/mol. According to these results, the experimental and calculated inhibition efficiency order was found to be compatible.
Authors and Affiliations
Sultan ERKAN
Keywords
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- EP ID EP488407
- DOI 10.17776/csj.421027
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