Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes

Polyamine amides are useful in gene delivery as synthetic (non-viral) vectors or mimics of polycationic histones. The application of a homologation strategy, based upon reductive alkylation, allows unsymmetrical polyamine amides to be prepared in good yield. The interaction of this polyamine amide w...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 5; pp. 443 - 446
Main Authors Geall, Andrew J., Blagbrough, Ian S.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 29.01.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EFFICIENT GENE-TRANSFER
CELLS
DNA-BINDING PROPERTIES
AGENTS
COMPLEXES
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Summary:Polyamine amides are useful in gene delivery as synthetic (non-viral) vectors or mimics of polycationic histones. The application of a homologation strategy, based upon reductive alkylation, allows unsymmetrical polyamine amides to be prepared in good yield. The interaction of this polyamine amide with calf thymus DNA was demonstrated in an ethidium bromide fluorescence quenching assay. Using trifluoroacetyl as a protecting group and a reductive alkylation homologation strategy allows the gram scale synthesis of unsymmetrical polyamine amides including lipo-spermine which is more efficient than poly-L-lysine interacting with DNA (ethidium bromide fluorescence quenching assay) and therefore has potential in gene delivery.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(97)10543-3