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Branched lipid chains to prepare cationic amphiphiles producing hexagonal aggregates: supramolecular behavior and application to gene delivery

Abstract : A ramified lipid alcohol, 2-hexyldecanol, was used as a hydrophobic moiety to prepare cationic amphiphiles on a gram scale in 3 to 4 steps, featuring either a trimethylammonium 5, dimethylhydroxyethylammonium 6 or N-methylimidazolium 7 polar head group. Compression isotherms at the air-water interface reveal that all these cationic amphiphiles collapse at a relatively low pressure indicating a weak stabilization of the monolayer via hydrophobic interactions. Ellipsometry measurements point out the presence of a thin monolayer at low lateral pressure whereas thickening of the monolayer occurs at higher pressure with a high percentage of variation of the thickness, thus demonstrating an adaptability to the constraints. P-31 NMR spectroscopy of the hydrated cationic amphiphiles clearly shows that these cationic amphiphiles self-assemble in water to form hexagonal phases, irrespective of the nature of their polar head group. Furthermore, a comparison of molecular structures suggests that compounds 5-7 self-organize into an inverted hexagonal phase (H-II). These cationic amphiphiles, alone or in the presence of DOPE, were evaluated for the transfection of three human-derived cell lines (i.e. A549, 16HBE and HeLa). The three compounds demonstrated high transfection efficacies in every cell line tested, 7/DOPE being the most efficient.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-02469674
Contributor : Laurent Jonchère <>
Submitted on : Thursday, February 6, 2020 - 4:36:12 PM
Last modification on : Friday, February 7, 2020 - 3:17:37 PM

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Amal Bouraoui, Rosy Ghanem, Mathieu Berchel, Laure Deschamps, Véronique Vié, et al.. Branched lipid chains to prepare cationic amphiphiles producing hexagonal aggregates: supramolecular behavior and application to gene delivery. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2020, 18 (2), pp.337-345. ⟨10.1039/c9ob02381j⟩. ⟨hal-02469674⟩

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