Synthesis, characterization and biological activity of novel ionic liquids with bis-imidazole moieties: antitumor, antimicrobial effects and molecular docking studies

• Published in: Organic communications 2024-01, Vol.17 (1), p.23-37
• Main Authors: çelik, Fatih, ünver, Yasemin, Ali, Aydın, Halil Ibrahim Güler, Kadriye Inan Bektaş
• Format: Article
• Language: English
• Subjects: 5-Fluorouracil; Anticancer properties; Antimicrobial activity; Antimicrobial agents; Antitumor activity; Bacteria; Biological activity; Cancer; Carbon 13; Cell proliferation; Chemical synthesis; Cytotoxicity; E coli; Epidermal growth factor receptors; Fourier transforms; Gram-negative bacteria; Gram-positive bacteria; Growth factors; Imidazole; Imines; Ionic liquids; Magnetic resonance spectroscopy; Molecular docking; NMR; NMR spectroscopy; Nuclear magnetic resonance; Protein interaction; Pseudotuberculosis; Receptors; Tumor cell lines; Vascular endothelial growth factor
• ISSN: 1307-6175; 1307-6175
• DOI: 10.25135/acg.oc.163.2401.4014

In this study, bis-Schiff bases with imidazole (2) and bis-imidazolium liquids (3a-g) were synthesized. The new compounds were characterized by Fourier transform infrared (FTIR), proton and carbon-13 nuclear magnetic resonance spectroscopy (1H- and 13C- NMR). The MTT assay was performed by our research group to measure the anticancer effect of the synthesized molecules on cell proliferation (NCI-60 screening method). Accordingly, when molecules 3e, 3g and 3f were compared with other molecules and 5-Fluorouracil (5FU) (positive control), they were found to exhibit potent anticancer activity against all cancer cell lines ((Growth inhibition (GI50): 1.0 - 1.82, total growth inhibition (TGI): 1.09 - 4.79 and lethal concentration (LC50): 2.74 – 59.5 µg/mL), but also a strong cytotoxic effect on normal lung cells Beas2B and normal cartilage cells HC (GI50: 1.0 - 1.28, TGI: 1.03 - 2.61 and LC50: 1.77 - 41.7 µg/mL). The in vitro antimicrobial activity of the synthesized compounds was evaluated against a range of microorganisms, including four Gram-positive bacteria (B. cereus, S. aureus, E. faecalis, B. subtilis,), four Gram-negative bacteria (Y. pseudotuberculosis, P. aeruginosa, E. coli, K. pneumoniae) and two yeast-like fungi (C. albicans, C. tropicalis). Molecular docking calculations were performed to investigate the ligand-protein interactions between the compounds and the Epidermal Growth Factor Receptor (EGFR) and the Vascular Endothelial Growth Factor Receptor (VEGFR1).