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Bis‐Thioether‐Containing Lipid Chains in Cationic Amphiphiles: Physicochemical Properties and Applications in Gene Delivery
Author(s) -
Bouraoui Amal,
Ghanem Rosy,
Berchel Mathieu,
Vié Véronique,
Le Guen Yann,
Paboeuf Gilles,
Deschamps Laure,
Le Gall Tony,
Montier Tristan,
Jaffrès PaulAlain
Publication year - 2019
Publication title -
chemphyschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.016
H-Index - 140
eISSN - 1439-7641
pISSN - 1439-4235
DOI - 10.1002/cphc.201900626
Subject(s) - thioether , amphiphile , cationic polymerization , chemistry , gene delivery , degree of unsaturation , supramolecular chemistry , organic chemistry , combinatorial chemistry , context (archaeology) , transfection , phospholipid , stereochemistry , biochemistry , membrane , copolymer , polymer , molecule , biology , paleontology , gene
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.