Poly-6-cationic amphiphilic cyclodextrins designed for gene delivery.
A new series of amphiphilic cyclodextrins containing cationic groups at the 6-positions and alkyl or biolabile ester groups at the 2-positions has been synthesised. Selective 2-O-allylation followed by photochemical addition of lipophilic thiols made it possible to control lipophilicity in these mesomolecules and allow solubility and self-assembly in water. The cationic groups are cysteamine-derived, while the alkyl and ester groups are C(1)-C(16) and benzyl ester groups. This is a new general synthetic route to a potentially wide range of polycationic cyclodextrins capable of acting as gene delivery vectors by condensing DNA and forming liquid crystalline complexes with oligonucleotides.
Byrne
Colin
C
Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, Ollscoil na hEireann, University College Dublin, Belfield, Dublin 4, Ireland.
Sallas
Florence
F
Rai
Dilip K
DK
Ogier
Julien
J
Darcy
Raphael
R
D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D015195:Drug Design; D004952:Esters / Q000737:chemistry; D018014:Gene Transfer Techniques; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism
D003505:Cyclodextrins; D004952:Esters; D013440:Sulfides; D047392:beta-Cyclodextrins; C569426:heptakis(6-(2-aminoethylthio)-6-deoxy-2-O-octyloxycarbonylethylsulfanylpropyl)-beta-cyclodextrin