Synthesis and Characterization of 8-Amino-6-Methoxy Quinolinium 2,4-Dinitrophenolate: DFT, Molecular Docking, Antimicrobial, and In Vitro Cytotoxicity Evaluation Studies

Abstract

Quinoline and its derivatives are well recognized for their anticancer activities and pharmacological properties. In this work, the compound 8-Amino-6-methoxyquinolinium 2,4-dinitrophenolate (8A6MQDNP) was synthesized and characterized using FT-IR, FT-Raman, and UV–Vis spectroscopic techniques. The optimized molecular structure, structural properties, and harmonic vibrational frequencies of the molecule were calculated using the DFT/B3LYP method with a cc-pVTZ basis set using the Gaussian 09 software. The observed and calculated vibrational wavenumbers were assigned and correlated well each other. The UV–Vis spectral analysis reveals the π to π* and n to π* electronic transitions of the molecule. The title molecule’s bioactivity is confirmed by frontier molecular orbital (FMOs) analysis; also the intramolecular charge transfer occurred from the quinoline ring to the dinitrophenol. Molecular electrostatic potential surface analysis verifies the FMOs results. The bioactivity of the molecule was confirmed by the natural bond orbital analysis. The Mulliken atomic charge distribution indicates the molecule’s chemical reactivity. Furthermore, the antibacterial results show that the 8A6MQDNP compound can inhibit the development of the tested bacterial strains, most notably the staphylococcus aureus bacterial strain. In vitro cytotoxicity test demonstrates that the 8A6MQDNP compound suppresses the development of A549 cancer cell lines more than HeLa cancer cell lines. Molecular docking investigation confirms that the title molecule inhibits the function of the epidermal growth factor receptor, which has been associated with lung cancer. As a result, the current study paves the way for the development of novel drugs for the treatment of lung cancer.