Bis-Thioether-Containing Lipid Chains in Cationic Amphiphiles: Physicochemical Properties and Applications in Gene Delivery

Amal Bouraoui (1) , Rosy Ghanem (2, 3) , Mathieu Berchel (1) , Véronique Vié (4, 5) , Yann Le Guen (3, 2) , Gilles Paboeuf (4, 5) , Laure Burel-Deschamps (1) , Tony Le Gall (3, 2) , Tristan Montier (3, 2) , Paul-Alain Jaffres (1)

1 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique
2 IBSAM - Institut Brestois Santé Agro Matière
3 GGB - Génétique, génomique fonctionnelle et biotechnologies (UMR 1078)
4 IPR - Institut de Physique de Rennes
5 ScanMAT - Synthèse Caractérisation Analyse de la Matière

Cationic amphiphiles featuring two thioether functions in each lipid chain of bicatenar cationic amphiphiles are reported here for the first time. The physicochemical properties and transfection abilities of these new amphiphiles were compared with those of already reported analogues featuring either (i) saturated, (ii) unsaturated or (iii) mono-thioether containing lipid chains. The homogeneity of the series of new compounds allowed to clearly underscore the effect of bis-thioether containing lipid chains. This study shows that besides previous strategies based on unsaturation or ramification, the incorporation of two thioether functions per lipid chain constitutes an original complementary alternative to tune the supramolecular properties of amphiphilic compounds. The potential of this strategy was evaluated in the context of gene delivery and report that two cationic amphiphiles (i. e. 4 a and 4 b) can be proposed as new efficient transfection reagents.

Mots clés: transfection; thioether; lipids; supramolecular chemistry; cationic amphiphiles

Domaines: Physique [physics]

Amal Bouraoui, Rosy Ghanem, Mathieu Berchel, Véronique Vié, Yann Le Guen, et al.. Bis-Thioether-Containing Lipid Chains in Cationic Amphiphiles: Physicochemical Properties and Applications in Gene Delivery. ChemPhysChem, 2019, 20 (17), pp.2187-2194. ⟨10.1002/cphc.201900626⟩. ⟨hal-02278044⟩