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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

Novel polyamine-dialkyl phosphate conjugates for gene carriers. Facile synthetic route via an unprecedented dialkyl phosphate.

To develop a novel nonviral gene carrier, three types of polyamine-dialkyl phosphates conjugates were synthesized via an unprecedented synthetic intermediate, dimerized dicetyl phosphate (DCP) anhydride, and the transfection efficiency and the complexation properties of the conjugate-DNA were evaluated. Condensation of DCP by 1,3,5-triisopropylbenzenesulfonyl chloride, TPSCl, gives the dimerized anhydride, which is stable enough to isolate by column chromatography in approximately 90% yield. The anhydride is reactive with various amines, i.e., spermidine, spermine, and polyethylenimine (PEI(1800)), providing corresponding polyamine-DCP conjugates via phosphoramidate linkage. The polyamine-DCP conjugates exhibited moderate transfection efficacy evaluated by beta-galactosidase assay. The conjugate-DNA complex was observed by using an atomic force microscope (AFM), revealing that the PEI(1800)-DCP conjugate, which showed the most efficient transfection, enables the formation of the more compact complex with DNA.[1]

References

  1. Novel polyamine-dialkyl phosphate conjugates for gene carriers. Facile synthetic route via an unprecedented dialkyl phosphate. Dewa, T., Ieda, Y., Morita, K., Wang, L., MacDonald, R.C., Iida, K., Yamashita, K., Oku, N., Nango, M. Bioconjug. Chem. (2004) [Pubmed]
 
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