Grinberg, S. Linder, C. Kolot, V. Waner, T. Wiesman, Z. Shaubi, E. Heldman, E. Novel Cationic Amphiphilic Derivatives from Vernonia Oil:  Synthesis and Self-Aggregation into Bilayer Vesicles, Nanoparticles, and DNA Complexants Self-assembling nanostructures were prepared from novel cationic amphiphilic compounds synthesized from vernonia oil, a natural epoxydized triglyceride. The presence of a 12,13-epoxy group on the C18 unsaturated fatty acid, vernolic acid, which is the main constituent of vernonia oil, permitted the synthesis of novel amphiphilic derivatives with a hydrogen-bonding hydroxyl and a cationic headgroup moiety on adjacent carbon atoms. The amphiphiles were prepared in a two-stage synthesis that comprised opening of the epoxy groups with a haloacetic acid, followed by quaternization of the halo group with a tertiary amine containing a C12 aliphatic chain. Intact vernonia oil as the starting material gave a triple-headed cationic amphiphile, containing three vernolic acid derived moieties connected through a glycerol backbone. A single-headed amphiphile with two alkyl chains and a single quaternary ammonium headgroup was synthesized from the methyl ester of vernolic acid as the starting material. The triple-headed derivative could form nonencapsulating structures. Cholesterol was required in the formulation (1:1) to make spherical vesicles that could encapsulate a water-soluble marker. The single-headed derivative, however, formed spherical encapsulating vesicles without cholesterol. TEM, NMR, and FT-IR were used to characterize the vesicles, and molecular structure vs morphology relationships were postulated on the basis of these data. The triple-headed amphiphile also formed a DNA complex that was highly resistant to hydrolysis by DNase. This amphiphile−DNA complex was used as vector for gene transfer in cell culture demonstrating efficient DNA transfection. quaternary ammonium headgroup;vernolic acid;material;cationic headgroup moiety;novel amphiphilic derivatives;structure vs morphology relationships;vernonia oil;amphiphile;novel cationic amphiphilic compounds;C 12 aliphatic chain;TEM;synthesis;DNA;vesicle;Intact vernonia oil;NMR;Novel Cationic Amphiphilic Derivatives 2005-08-16
    https://acs.figshare.com/articles/journal_contribution/Novel_Cationic_Amphiphilic_Derivatives_from_Vernonia_Oil_Synthesis_and_Self_Aggregation_into_Bilayer_Vesicles_Nanoparticles_and_DNA_Complexants/3272848
10.1021/la050091j.s001