Ionic liquids with thioether motifs as synthetic cationic lipids for gene delivery

Chem Commun (Camb). 2017 Jul 20;53(59):8328-8331. doi: 10.1039/c7cc03235h.

Abstract

This study introduces a novel class of imidazolium- and ammonium-based ionic liquids possessing two C12 and C14 tails and thioether linkers designed for lipoplex-mediated DNA delivery. Imidazolium-based ionic liquids displayed efficient gene delivery properties with low toxicity. Thiol-yne click chemistry was employed for the facile and robust synthesis of these thioether-based cationic lipioids with enhanced lipophilicity and low fluidity.

MeSH terms

  • Ammonium Compounds / chemistry
  • Ammonium Compounds / pharmacology
  • Cations / chemical synthesis
  • Cations / chemistry
  • Cations / pharmacology
  • Cell Survival / drug effects
  • Click Chemistry
  • DNA / genetics*
  • Dose-Response Relationship, Drug
  • Gene Transfer Techniques*
  • HEK293 Cells
  • HeLa Cells
  • Humans
  • Hydrophobic and Hydrophilic Interactions
  • Imidazoles / chemistry
  • Imidazoles / pharmacology
  • Ionic Liquids / chemistry*
  • Ionic Liquids / pharmacology
  • Lipids / chemistry*
  • Lipids / pharmacology
  • Molecular Structure
  • Plasmids
  • Quantum Theory
  • Structure-Activity Relationship
  • Sulfides / chemistry*
  • Sulfides / pharmacology

Substances

  • Ammonium Compounds
  • Cations
  • Imidazoles
  • Ionic Liquids
  • Lipids
  • Sulfides
  • DNA