共 43 条
Synthesis and transfection efficiencies of new lipophilic polyamines
被引:30
作者:

Gardner, Richard Andrew
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机构: Univ Cent Florida, Dept Chem, Orlando, FL 32816 USA

Belting, Mattias
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机构: Univ Cent Florida, Dept Chem, Orlando, FL 32816 USA

Svensson, Katrin
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机构: Univ Cent Florida, Dept Chem, Orlando, FL 32816 USA

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机构:
[1] Univ Cent Florida, Dept Chem, Orlando, FL 32816 USA
[2] Lund Univ, Dept Oncol, S-22185 Lund, Sweden
关键词:
D O I:
10.1021/jm0607101
中图分类号:
R914 [药物化学];
学科分类号:
100701 ;
摘要:
A homologous series of lipophilic polyamines was synthesized and evaluated for DNA delivery and transfection efficiency. The series contained 1,4-butanediamine, 1,8-octanediamine, 2-[2-(2-amino-ethoxy)-ethoxy]-ethylamine, homospermidine, and homospermine covalently attached via their N-1 terminus to a 3,4-bis(oleyloxy)-benzyl motif. In addition, homospermidine and homospermine were also attached via amide linkers. The homospermidine derivatives (i.e., benzyl tether 25 and benzamide tether 27) showed a 3-fold and 4-fold respective enhancement in delivery of AlexaFluor-488-labeled DNA over the butanediamine analogue 22. Homospermine derivative 26 was shown to inhibit C-14-spermine uptake (IC50 similar to 10 mu M), which implied that 26 is able to compete effectively for polyamine recognition sites on the cell surface. This study demonstrated that the number and position of the positive charges along the polyamine scaffold plays a key role in DNA delivery and in determining the transfection efficiency.
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页码:308 / 318
页数:11
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