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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 hydrophobic moiety to prepare at a gram scale in 3 to 4 steps, cationic amphiphiles 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 thin monolayer at low lateral pressure whereas its thickening occurs at higher pressure with a high percentage of variation of the thickness, thus demonstrating an adaptability to the constraints. 31P NMR 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, the comparison of molecular structures suggests that compounds 5-7 self-organize in inverted hexagonal phase (HII). These cationic amphiphiles, alone or in presence of DOPE, were evaluated for the transfection of three human-derived cell lines (i.e. A549, 16HBE, HeLa). The three compounds demonstrate high transfection efficacies in every cell line tested, 7/DOPE being the most efficient

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Publication details

The article was received on 04 Nov 2019, accepted on 04 Dec 2019 and first published on 04 Dec 2019


Article type: Paper
DOI: 10.1039/C9OB02381J
Org. Biomol. Chem., 2019, Accepted Manuscript

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

    A. Bouraoui, R. Ghanem, M. Berchel, L. Deschamps, V. Vié, G. Paboeuf, T. Le Gall, T. Montier and P. jaffrès, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02381J

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