ao9b03468_si_001.pdf (4.4 MB)
Synthesis, Characterization, DNA Binding, Anticancer, and Molecular Docking Studies of Novel Imidazolium-Based Ionic Liquids with Fluorinated Phenylacetamide Tethers
journal contribution
posted on 2020-03-09, 17:44 authored by Nadjet Rezki, Fawzia Faleh Al-blewi, Salsabeel A. Al-Sodies, Asaad Khalid Alnuzha, Mouslim Messali, Imran Ali, Mohamed Reda AouadNewer imidazolium ionic liquid (IL)
halides 4a–f appending variety of fluorinated
phenylacetamide side chains were designed and synthesized through
quaternization of 1-methyl and/or 1,2-dimethylimidazole with appropriate
2-chloro-N-(fluorinatedphenyl)acetamides. The resulting
ILs were converted to their respective ionic liquid analogues carrying
fluorinated counteranions (PF6–, BF4–, and/or CF3COO–) 5a–r. All newly synthesized ILs were fully
characterized using several spectroscopic experiments such as 1H, 13C, 11B, 19F, 31P NMR, and mass analysis. The synthesized ionic liquids were investigated
for their DNA binding and anticancer activities. The obtained DNA
binding constants ranged from 1.444 × 105 to 3.518
× 105, indicating a reasonably good binding affinity.
The percentage of anticancer activities ranged from 48 to 59 with
H-1229 cell line, showing quite good anticancer potential. The modeling
studies indicated the interactions of the reported molecules with
DNA via hydrogen bonds. These were in agreement with
those of DNA binding and anticancer results. Briefly, the designed
ionic liquids may be used as good anticancer candidates for treating
human cancer.