Issue 18, 2009
From the journal:

Organic & Biomolecular Chemistry

Poly-6-cationic amphiphilic cyclodextrins designed for gene delivery

Colin Byrne,a   Florence Sallas,a   Dilip K. Rai,a   Julien Ogiera  and  Raphael Darcy*a  

* Corresponding authors

a Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, Ollscoil na hEireann, University College Dublin, Belfield, Dublin 4, Ireland
E-mail: raphael.darcy@ucd.ie

Abstract

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 C1–C16 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.

Graphical abstract: Poly-6-cationic amphiphilic cyclodextrins designed for gene delivery

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Article information

DOI
https://doi.org/10.1039/B907232B
Article type
Paper
Submitted
30 Apr 2009
Accepted
27 May 2009
First published
14 Jul 2009

Org. Biomol. Chem., 2009,7, 3763-3771

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Poly-6-cationic amphiphilic cyclodextrins designed for gene delivery

C. Byrne, F. Sallas, D. K. Rai, J. Ogier and R. Darcy, Org. Biomol. Chem., 2009, 7, 3763 DOI: 10.1039/B907232B

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