Spectroscopic, DFT and molecular docking studies of novel diosgenin NSAID conjugates and their in vitro evaluation as potential anti-cancer agents against SiHa cells
•An approach to synthesize conjugates of NSAIDs and a steroid molecule has been done for enhanced biological activity.•Synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, UV-VIS spectroscopy and mass spectrometry.•The compounds exhibited good cervical anti-cancer activity against SiH...
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Veröffentlicht in: | Journal of molecular structure 2025-02, Vol.1321, p.140086, Article 140086 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | •An approach to synthesize conjugates of NSAIDs and a steroid molecule has been done for enhanced biological activity.•Synthesized compounds were characterized by 1H NMR, 13C NMR, FT-IR, UV-VIS spectroscopy and mass spectrometry.•The compounds exhibited good cervical anti-cancer activity against SiHa cells.•Molecular docking studies of the synthesized molecules demonstrated good binding energy with the studied receptor protein molecules as compared to the parent molecule.•Static first hyperpolarizability result showed that the studied compounds may be used in non-linear optics.
In the current study, diosgenin-etodolac and diosgenin-naproxen conjugates have been synthesized using Steglich reaction. The synthesized compound 2 and 3 were purified using column chromatography and characterized with the help of modern spectroscopic techniques like 1H, 13C NMR, FT-IR, UV-Visible spectroscopy and mass spectrometry. The geometries of both the compounds were optimized in the ground state by density function theory at the B3LYP/6-31G(d,p) level. These synthesized compounds were evaluated in vitro for their anti-cancer activity against SiHa cells which demonstrated an increased apoptotic activity in comparison to the parent compound i.e. diosgenin. Molecular docking studies were carried out to investigate the inhibitory action of steroidal derivatives against the HPV16 E7 (PDBID- 2B9D) and HPV18 E2 (PDBID- 1F9F) proteins. The result of molecular docking revealed good interactions between compound 2 and 3 with the selected proteins. The computational analysis data and experimental data were in conformation with each other. Molecular simulation was performed for 50ns to access the conformational stability and fluctuation of protein ligand complexes during the simulation.
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ISSN: | 0022-2860 |
DOI: | 10.1016/j.molstruc.2024.140086 |