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Solid-Phase Synthesis of Dimerizable Cationic Detergents for Gene Delivery
N. Guilloteau, L. Le Gourriérec, K. Fabio, C. Di Giorgio, J. Greiner, P. Vierling*
Université de Nice-Sophia Antipolis, Nice, France
23 March 2009 (online)
Solid-phase synthesis of perfluoroalkylated dimerizable cationic detergents 1 and 2 for gene delivery was described. Thus, 1-(N-Boc)-3,6-dioxa-8-octaneamine a and N,N′,N′′-tri-Boc-spermine b reacted with Fmoc-Cys(SASRINTM-®)-OH resin 3 in the presence of DMAP and HBTU to give 4a and 4b, respectively. Deprotection of the N-Fmoc group was performed in a 20% piperidine-DMF solution; resulting 5a,b reacted with perfluoroalkylated acid, HBTU and DIPEA to give 6a and 6b. Treatment of 6 with TFA-CH2Cl2 (afforded perfluoroalkylated dimerizable cationic detergents 1 and 2 (as TFA salts) in quantitative yield.