Synthesis, structural characterization, molecular docking and biological evaluation studies on 6-methoxy-8-nitroquinolinium 2,4-dinitrophenolate: a potent lung cancer drug

Quinoline and its derivatives have long been known for their anticancer and pharmacological characteristics. The compound 6-Methoxy-8-Nitroquinolinium 2,4-dinitrophenolate was synthesized and characterized using FT-IR, FT-Raman, and UV-Visible spectroscopic techniques. The molecule’s optimized molecular structure, structural parameters, and harmonic vibrational frequencies were calculated using the Gaussian 09 program. The calculated and observed vibrational wavenumbers were assigned and interpreted. Moreover, PXRD confirmed the formation of a new crystalline phase of 6M8NDNP, distinct from the starting materials, while ESI-MS analysis revealed a dominant molecular ion at m/z 312.14 and characteristic fragmentation peaks at m/z 211.13 and 181.21, validating the proposed structure. UV-Vis spectral analysis reveals the molecule’s π to π* and n to π* electronic transitions. Frontier molecular orbitals study confirms the bioactivity of the title molecule; moreover, intramolecular charge transfer occurred from the dinitrophenol to the quinoline ring. Further, Frontier molecular orbitals analysis results are validated by molecular electrostatic potential surface analysis. The Mulliken atomic charge distribution reveals the chemical reactivity of a molecule. Furthermore, the antibacterial results reveal that the title compound can suppress the growth of the tested bacterial strains, most notably <i>Klebsiella pneumonia.</i> In vitro cytotoxicity tests show that the title compound inhibits the growth of A549 cancer cell lines more than HeLa cancer cell lines. Molecular docking analysis shows the title molecule suppresses the action of the epidermal growth factor receptor, which is associated with lung cancer. As a result, the present study paves the way for developing novel drugs to treat lung cancer.