Sterol modified oligonucleotide duplexes having anticancer activ

Details Sterol modified oligonucleotide duplexes having anticancer activ Sterol modified oligonucleotide duplexes having anticancer activ

1994-02-28

1997-07-08

Elliott, George C.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

435 6, 536 221, 536 231, 536 243, 536 245, A61K 4800, C12Q 168, C07H 2102, C07H 2104

Patent

active

056461267

ABSTRACT:
Oligonucleotides having approximately 8 to 18 nucleotide units and a 3'-tail which includes asteroid structure attached to the 3'-end through the A ring of the steroid skeleton and which form substantially stable duplexes at physiological temperature, have selective cytotoxic activity against certain tumor cell lines.

REFERENCES:
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Gryaznov et al, "Modulation of oligonucleotide duplex and triplex stability via hydrophobic interactions", Nucleic Acids Res. 21(25):5909-5915 1993.
Ma et al, "Design and synthesis of RNA miniduplexes via a synthetic linker approach. 2. Generation of covalently closed, double stranded cyclic HIV-1 TAR RNA analogs with high Tat binding affinity", Nucleic Acids Res. 21(11):2585-2589 1993.
Ma et al, "Design and synthesis of RNA miniduplexes via a synthetic linker approach", Biochemistry 32:1751-1758 1993.
Bielinska et al, "Regulation of gene expression with double-stranded phosphorothioate oligonucleotides", Science 250:997-1000 Nov. 1990.
MacKellar et al, "Synthesis and physical properties of anti-HIV antisense oligonucleotides bearing terminal lipophilic groups", Nucleic Acids Res. 20(13):3411-3417 1992.
Zhou et al, "Discovery of short, 3' cholesterol modified DNA duplexes with unique antittumor cell activity", Cancer Res. 54:5783-5787 Nov. 1994.
Stanfield et al., "Synthesis of protected amino alcohols: a comparative study", J. Org. Chem., 46:4799 (1981).
Gamper, H. B. et al., "Facile preparation and exonuclease stability of 3' modified oligodeoxynucleotides", Nucleic Acids Res., 21, 145-150 (1993).
Reed, M. W. et al., "Arcidine and cholesterol-derivatized solid supports for improved synthesis of 3'-modified oligonucleotides", Bioconjugate Chem., 2, 217-225 (1993).
Atkinson, T. and Michael S., "Solid-phase synthesis of oligodeoxyribonecleotides by the phosphitetriester method", Oligonucleotide Synthesis: A Practical Approach, M. J. Gait, ed., IRL Press, pp. 35-81 (1984).

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