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Nucleic Acids Research, 1992, Vol. 20, No. 3 533-538
© 1992

CHEMISTRY

Effective incorporation of 2'-O-methyl-oligoribonuclectides into liposomes and enhanced cell association through modification with thiocholesterol

Berndt Oberhauser and Ernst Wagner

Institute of Molecular Pathology Dr. Bohr Gasse 7, A-1030 Vienna, Austria

Received October 3, 1991. Revised December 30, 1991. Accepted December 30, 1991.

Cholesterol was linked to 2'-O-methyI-oligoriboin)uclleotides (2'-OMe-RNA) via a disulfide bond by reacting the 3'-(pyridyldithio)-moditfied 2'-OMe-RNA with thiochoIesteroD on dichloromethane-metfaoTioll solution. This ligation reaction was made possible by a novel strategy on which the highly charged oligonucleotide was rendered soluble in nonaqueous solvent through conversion to a lipophilic amidinium salt. The biodegradable lipophilic modification of 2'-OMe-RNA resulted in a large increase in incorporation of such oligonucleotides into liposomes prepared by reverse-phase evaporation. Furthermore, association of these modified oligonucleotides with celltured TIB 73 cells was 100-fold higher than that seen with unmodified 2'-OMe-RNA in serum-free medium and about 10 to 30-fold higher on the presence of 10% calf serum. During incubation with cells, release of the internalized oligonucleotide from the thiocholesteryD moiety can be demonstrated.


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