Synthesis, self-assembling and gene delivery potential of a novel highly unsaturated, conjugated cationic phospholipid

• A new highly unsaturated cationic phospholipid is synthesized.
• Its aggregation behavior, aggregate size and morphology are determined.
• The lipid aggregate (liposome) forms with pDNA lipoplexes.
• The lipoplexe formulated with DOPE and protamine shows in vitro transfection comparable to the standard reference Lipofectamine 2000.

The synthesis and self-assembling properties of a model compound in a new class of cationic phospholipids with a highly unsaturated conjugated fatty acid are described. In addition, the potential of this new lipid as a nucleic acid carrier was evaluated through lipoplex formulations employing 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) as helper lipid with and without the polycationic peptide protamine, together with a plasmid DNA (pDNA). Lipoplexes composed of this novel unsaturated lipid exhibited pDNA binding and protection from DNase I degradation when formulated with protamine. The new cationic lipid revealed transfection efficiency comparable to the commercial reference 1,2-dimyristoyl-sn-glycero-3-ethylphophocholine (EPC) in Chinese hamster ovary-K1 (CHO-K1) cells and performed equally to the standard reference Lipofectamine 2000 when the formulation included protamine.

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