Synthesis, Characterization, DNA Binding, Anticancer, and Molecular Docking Studies of Novel Imidazolium-Based Ionic Liquids with Fluorinated Phenylacetamide Tethers

Nadjet Rezki; Fawzia Faleh Al-Blewi; Salsabeel A Al-Sodies; Asaad Khalid Alnuzha; Mouslim Messali; Imran Ali; Mohamed Reda Aouad

doi:10.1021/acsomega.9b03468

Synthesis, Characterization, DNA Binding, Anticancer, and Molecular Docking Studies of Novel Imidazolium-Based Ionic Liquids with Fluorinated Phenylacetamide Tethers

ACS Omega. 2020 Mar 9;5(10):4807-4815. doi: 10.1021/acsomega.9b03468. eCollection 2020 Mar 17.

Authors

Nadjet Rezki^{1

2}, Fawzia Faleh Al-Blewi¹, Salsabeel A Al-Sodies¹, Asaad Khalid Alnuzha¹, Mouslim Messali¹, Imran Ali^{1

3}, Mohamed Reda Aouad^{1

2}

Affiliations

¹ Department of Chemistry, Faculty of Science, Taibah University, Al-Madinah Al-Munawarah 30002, Saudi Arabia.
² Department of Chemistry, Faculty of Sciences, University of Sciences and Technology Mohamed Boudiaf, Laboratoire de Chimie and Electrochimie des Complexes Metalliques (LCECM) USTO-MB, P.O. Box 1505, El M'nouar, Oran 31000, Algeria.
³ Department of Chemistry, Jamia Millia Islamia (A Central University), New Delhi 110025, India.

Abstract

Newer 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.