DFT study on molecular structure, spectroscopic properties, Hirshfeld surface and molecular docking reveals the potential of flavones based on experimental and theoretical investigations

Abstract

Abstract In the present investigation, theoretical study on molecular geometry, vibrational, pharmaceutical and electronic properties of 3,4,5,7-tetrahydroxyflavone (7THDFN) and 3,4,7,8-tetrahydroxyflavone (8THDFN) were carried out using various functional levels at 6-311 + + G(d,p) as basis set. The results of the optimized geometrical parameters are presented and compared with the experimental values. The harmonic vibrational frequencies were calculated and the computed FT-IR and FT-Raman spectra have been compared with the experimental data. The 1H and 13C NMR chemical shifts were calculated using Gauge Independent Atomic Orbital (GIAO) approach. As an outcome, we found a good agreement between the experimental and computational structural values for FT-IR, FT-Raman, and NMR spectra. The molecular frontier orbital analysis was used to determine the charge transfer interaction, chemical reactivity, and non-linear optical properties of the designed molecules at the PBEPBE level theory. In addition, the molecular electrostatic potential surface maps were plotted to determine the chemical reactivity and the intermolecular interactions of the bioactive molecules. All these theoretical and experimental calculations will help us to characterize the chemical or biological properties of the designed drug molecules. The molecular modeling programs were also performed to estimate the pharmaceutical activities of the flavone compounds against human breast cancer. Finally, the in vitro cytotoxicity of bioactive molecules against human MCF-7 cell lines measured in MTT assays.