Spectroscopic, electronic properties analysis for 2, 6-Bis (phenylamino)-4-(iminophenyl) benzoquinone molecule and molecular docking clarification for its anticancer activity detected by strong inhibition of NQO1 enzyme

Abstract

Quinone compounds have been the subject of extensive research due to their remarkable efficiency and prospective use as drugs and in a variety of fields. In this study, we report the spectroscopic characterization, electronic structure, ADMET evaluation, and molecular docking assessment of 2,6-Bis(phenylamino)-4-(iminophenyl)benzoquinone as an anticancer drug. By using DFT investigations, the vibrational wavenumbers were calculated and utilized to assign vibrational bands, which were found to be in good accordance with the experimentally observed data. The analysis of the UV-Vis spectra revealing an absorption peak from electronic transitions HOMO→LUMO at 547 nm is found to be in good conformity with its experimental value. The HOMO and LUMO frontier molecular orbitals and their associated energies highlighted the mechanism of charge transfer within the molecule and revealed a small energy gap. The chemically reactive sites identified by the MEP surface helped predict the spots of the molecule's biological activity. According to NBO analysis, the π C9-C10 → π* C11-C12 interaction has the maximum energy stability with 23.74 Kcal/mol., due to π electron delocalization within the ring. At the same level of theory, third-order NLO polarizability was found to be 4-fold stronger than the third-order of P-NA (a prototype NLO molecule). The potential for a safe oral bioavailability drug was identified by computing ADMET parameters and evaluating drug-likeness based on Lipinski's rule of five. The molecular docking study found that the molecule binding to NQO1 receptor protein with superior binding energy -8.69 kcal/mol than previously studied Quinone derivatives. Additionally, molecular dynamics simulations were performed to test the dynamic behavior of the ligand-NQO1 complex. The complex was stable in the binding pocket of the receptor proteins, according to the analysis of the simulation outcomes such as RMSD and RMSF. These results suggests using this molecule as a potential anticancer drug due to its high capability to inhibit the NQO1 enzyme.