Design of New Schiff-Base Copper(II) Complexes: Synthesis, Crystal Structures, DFT Study, and Binding Potency toward Cytochrome P450 3A4

Abstract

We report the synthesis and crystal structures of three new copper­(II) Schiff-base complexes. The complexes have been characterized by elemental analysis and Fourier transform infrared (FT-IR) and UV–visible spectroscopies. The X-ray diffraction (XRD) analysis reveals that complexes 1 and 3 crystallize in a monoclinic space group C2/c and 2 in a triclinic space group P1̅, each adopting a square planar geometry around the metal center. We use a density functional theory method to explore the quantum chemical properties of these complexes. The calculation proceeds with the three-dimensional (3D) crystal structure characterization of the complexes in which the calculated IR and UV–vis values are comparable to the experimental results. Charge distribution and molecular orbital analyses enabled quantum chemical property prediction of these complexes. We study the drug-likeness properties and binding potentials of the synthesized complexes. The in silico outcome showed that they could serve as permeability-glycoprotein (P-gp) and different cytochrome P450 substrates. Our calculations showed that the complexes significantly bind to cytochrome P450 3A4.

Efficient Catalytic Reduction of 4-Nitrophenol Using Copper(II) Complexes with N,O-Chelating Schiff Base Ligands

“…A similar shift was also seen in the signals of ν(C−O) between the ligands and complexes, indicating the coordination of phenol oxygen to the copper. These observations were consistent with other published works involving copper complexes [ 19 , 23 , 24 , 25 , 26 ]. The signals observed around 460 and 410 cm −1 in the spectra were assigned to the stretching frequencies of the copper-donor atom-chelating ligand, ν(Cu−O) and ν(Cu−N), respectively.…”

The effect of structural configuration on the DNA binding andin vitroantioxidant properties of new copper(ii) N2O2Schiff base complexes

“…The bond lengths of each of these complexes 1-3 are within the range. 23,26 For molecular packing in complex 1, the structure is held together by CHÁ Á Áp (3.717 Å) and halogen bonding interaction between ClÁ Á ÁCH (3.202 Å) from the neighbouring independent molecules.…”

“…20 Several ways in which antioxidants inhibit oxidizing chain reactions are direct quenching of reactive oxygen species, chelating of metal ions (Fe 2+ , Cu 2+ ), and inhibition of enzymes. 21 In continuing our work on Schiff base metal complexes and their biological activities, [22][23][24][25][26] we synthesized and characterized three new Cu(II) complexes derived from three analogous Schiff bases with varying substituents with the hope of analyzing the effect of the different functional group on the ligand moiety and the antioxidant properties and DNA binding studies. Furthermore, the pharmacokinetic properties of these new complexes are also reported.…”

Anti-Corrosion potential of the Ortho and Para-Substituted Schiff Bases of 2- Methoxybenzaldehyde on Fe (110) surface in acid medium: Synthesis, DFT and Molecular Dynamics Studies

“…The Schiff base ligands (E)-2-((2-methoxybenzylidene)amino)phenol L1 and (E)-2-((4methoxybenzylidene)amino)phenol L2 were obtained in excellent yields (97 -98 %) by solvent-free grinding using a mortar and pestle (Scheme 1) according to commonly described protocol in literature 14,15 . The resultant products were dried in vacuo to completely remove the water and characterized spectroscopically using IR, NMR and UV-Vis.…”

“…The electronic absorption spectra of the ligands obtained in dichloromethane are shown in Figure1. Due to intra-ligand charge transfer observed between 238 and 274 nm, absorption bands were assigned to π → π* while the band around 350 nm was assigned to n → π* transition14 .…”