In a seminal 1987 paper, Felgner and co-workers described the self-assembly in water of lipidic amphiphiles ('liposomes') that �interact with DNA spontaneously, fuse with tissue culture cells, and facilitate the delivery of functional DNA into the eukaryotic cell.� Describing this transfection process as �simple, highly reproducible, and more efficient than some other, commonly-used procedures,� it has since been extended to the delivery of therapeutic payloads such as siRNA and small-molecule drugs. Enabling this now standard technology are commercially available cationic lipids such as DOTMA (1,2-di-O-octadecenyl-3-trimethylammonium propane�chloride), DOTAP (1,2-dioleoyl-3-trimethylammonium propane�chloride), and other closely related salts.In this study, complimentary family of lipidic ionic liquids were synthesized by using commercially available cationic lipids (liposomes) derived from DOTMA and related species which collapsed into macroscopically hydrophobic phases by replacing their standard Cl- anions with (CF3SO2)2N-.  DSC shows that the resulting salts have Tm values ranging from -47 oC to 65 oC, making each an ionic liquid.  Significantly, clear and explainable relationships between these Tm values and the nature of each cation are manifestly apparent, providing key insights into structural features that are consistent with ILs that are simultaneously lipophilic and low-melting.

Cationic lipids (transfection) as design tutors: insights into structure-property relationships in lipidic ionic liquids

243rd National Meeting (2012)

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