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Substitution of unsaturated lipid chains by thioether containing lipid chains in cationic amphiphiles: physico-chemical consequences and application for gene delivery

Abstract

The hydrophobic moiety of cationic amphiphiles plays an important role in the transfection process because its structure has an impact on both the type of the supramolecular assembly and the dynamic properties of these assemblies. These latter have to exhibit a compromise between stability and lability to efficiently compact then deliver DNA into target cells. In the present work, we report the synthesis of new cationic amphiphiles featuring a thioether function at different positions of two 18-atoms length lipid chains and we study their physicochemical properties (anisotropy of fluorescence, compression isotherms) with analogues possessing either oleyl (C18:1) or stearyl (C18:0) chains. We show that the fluidity of cationic lipids featuring a thioether function located close to the middle of each lipid chain is intermediate with that of oleyl- and stearyl-containing analogues. These properties are also supported by the compression isotherms assays. When used as carriers to deliver a plasmid DNA, thioether-containing cationic amphiphiles demonstrate a good ability to tranfect human-derived cell lines, those incorporating such a moiety in the middle of the chain being the most efficient. This work supports the use of a thioether function as a possible alternative to unsaturation in aliphatic lipid chains of cationic amphiphiles to modulate physicochemical behaviours and in turn biological activities such as gene delivery ability

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Publication details

The article was accepted on 14 Mar 2019 and first published on 14 Mar 2019


Article type: Paper
DOI: 10.1039/C9OB00473D
Citation: Org. Biomol. Chem., 2019, Accepted Manuscript

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    Substitution of unsaturated lipid chains by thioether containing lipid chains in cationic amphiphiles: physico-chemical consequences and application for gene delivery

    A. Bouraoui, M. Berchel, R. Ghanem, V. Vié, G. Paboeuf, L. Deschamps, O. Lozach, T. Le Gall, T. Montier and P. Jaffres, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB00473D

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