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Novel Biodegradable Pyridinium Amphiphiles for Gene Delivery
Author(s) -
Pijper Dirk,
Bulten Erna,
Šmisterová Jarmila,
Wagenaar Anno,
Hoekstra Dick,
Engberts Jan B. F. N.,
Hulst Ron
Publication year - 2003
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.200300361
Subject(s) - chemistry , amphiphile , pyridinium , cationic polymerization , vesicle , differential scanning calorimetry , gene delivery , transfection , hydrolysis , nuclear magnetic resonance spectroscopy , organic chemistry , polymer chemistry , combinatorial chemistry , copolymer , membrane , biochemistry , polymer , gene , physics , thermodynamics
Biodegradable synthetic cationic pyridinium‐based amphiphiles (SAINTs) prove to be promising non‐viral carrier systems for delivery of DNA into eukaryotic cells. Six novel SAINTs were synthesised from 3,5‐pyridinedicarboxylic acid as starting material, with two ester groups as linkers between the cationic headgroup and the hydrophobic tails. The vesicle‐forming properties of the amphiphiles were studied by differential scanning calorimetry and transmission electron microscopy, whereas the hydrolysis of the diesters in water was investigated by NMR spectroscopy. Finally, the transfection potential and cytotoxicity were determined on COS‐7 and HepG‐2 cells in culture. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)