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Sunfish Amphiphiles: Conceptually New Carriers for DNA Delivery
Author(s) -
Hulst Ron,
Muizebelt Inouk,
Oosting Peter,
van der Pol Cornelia,
Wagenaar Anno,
Šmisterová Jarmila,
Bulten Erna,
Driessen Cecile,
Hoekstra Dick,
Engberts Jan B. F. N.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300524
Subject(s) - amphiphile , chemistry , cationic polymerization , transfection , biophysics , dna , gene delivery , nanotechnology , combinatorial chemistry , biochemistry , gene , organic chemistry , copolymer , biology , materials science , polymer
A conceptually new class of cationic amphiphiles, Sunfish amphiphiles, designed for the delivery of genes into cells is introduced. Sunfish amphiphiles have two hydrophobic tails, connected at the 4‐ and the N ‐position to the cationic pyridinium headgroup. Two extreme morphologies visualised by backfolding and combining of both tails at one site (matching situation) or unfolding of the tails at distinct interaction sites at biological membranes will lead to considerable differences in morphological behaviour. The underlying rationale allows controlled release by using this morphological alteration of the Sunfish/helper‐lipid/DNA complex (lipoplex). The often‐excellent transfection efficiencies are probably related to these morphological changes. In addition, the Sunfish amphiphiles possess low toxicities, resulting in high cell survival after internalisation. The underlying rationale, design, synthesis and in vitro transfection potential are discussed in detail. Moreover, some physico‐chemical characteristics of the Sunfish amphiphiles have been studied. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)