Synthesis and characterization of new functionalized ionic liquids: Anticancer, cheminformatics and modeling studies

Abstract

Twelve new functionalized imidazolium-based ionic liquids (ILs) were synthesized under both conventional and eco-friendly ultrasound procedures. The yields were better with eco-friendly and green ultrasound procedures (6.10-11.11% greater). Newly synthesized ILs were well-characterized with FT-IR, ¹H NMR, ¹³C NMR, ¹¹B, ¹⁹F, ³¹P, and elemental analyses. All ILs (5–16) were screened for their in vitro antitumor activities for four cancer cell lines. The results revealed that most of the ILs exhibited excellent anti-tumor activities against both colon and breast cancer cells. However, ILs 9 and 10 appear to be the most active against the selected cell lines with IC₅₀ values in the range of 0.11±4 to 0.14±10 and 0.11±9 to 0.88±4. The anticancer mechanism was developed by docking study with DNA. The binding affinities were in the range of -4.1 to -4.5 kcal/mol; confirming strong interactions with DNA. The reported ILs showed significant anticancer activities which may be future anti-cancer drugs. In silico data followed Lipinski’s rule for selection as drug candidates. Toxicity data have also shown that all compounds have a non-toxic profile and observed in vivo IC₅₀ in accepted criteria (2.61-2.75 mol). Therefore, the reported ILs may be the future safe anticancer medicines.