Block polycationic oligonucleotide derivative: Synthesis and inhibition of herpes virus reproduction

Bioconjugate Chemistry

Volumn 7, Issue 1, 1996, Pages 3-6

  Vinogradov, Sergey V ^a,b   Suzdaltseva, Yulia G ^a   Kabanov, Alexander V ^a,c  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^c UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHAINS; ESTERS; VIRUSES;

BUTANEDIOL; CHOLESTERYL GROUPS; DERIVATIVE SYNTHESIS; END GROUPS; H-PHOSPHONATES; HERPES SIMPLEX VIRUS TYPE 1; PHOSPHODIESTERS; POLYCATIONS; SOLID SUPPORTS; SYNTHESISED;

OLIGONUCLEOTIDES;

HERPES; HERPESVIRIDAE; HUMAN HERPESVIRUS 1;

ANTIVIRUS AGENT; CHOLESTEROL; MESSENGER RNA; OLIGODEOXYRIBONUCLEOTIDE;

ANIMAL; ARTICLE; CERCOPITHECUS; COMPARATIVE STUDY; DRUG EFFECT; GENETICS; HERPES SIMPLEX VIRUS 1; IMMEDIATE EARLY GENE; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PHYSIOLOGY; RNA SPLICING; STRUCTURE ACTIVITY RELATION; SYNTHESIS; VERO CELL; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; BASE SEQUENCE; CERCOPITHECUS AETHIOPS; CHOLESTEROL; GENES, IMMEDIATE-EARLY; HERPESVIRUS 1, HUMAN; MOLECULAR SEQUENCE DATA; OLIGODEOXYRIBONUCLEOTIDES; RNA SPLICING; RNA, MESSENGER; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS; VIRUS REPLICATION;

EID: 0029684802     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc9500913     Document Type: Article

References (29)

1. Helene, C. (1991) Rational design of sequence-specific oncogene inhibitors based on antisense and antigene oligonucleotides. Eur. J. Cancer 27, 1466-1471.
2. Crooke, R. M. (1991) In vitro toxicology and pharmacokinetics of antisense oligonucleotides. Anti-Cancer Drug Des. 6, 609-646.
3. Stein, C. A., and Cheng, Y.-C. (1993) Antisense oligonucleotides as therapeutic agents - is the bullet really magical? Science 261, 1004-1012.
4. Letsinger, R. L., Zhang, X., Sun, D. K., Ikeuchi, T., and Sarin, P. S. (1989) Cholesteryl-conjugated oligonucleotides: synthesis, properties and activity as inhibitors of replication of human immunodeficiencey virus in cell culture. Proc. Natl. Acad. Sci. U.S.A. 86, 6553-6556.
5. Kabanov, A. V., Vinogradov, S. V., Ovcharenko, A. V., Krivonos, A. V., Melik-Nubarov, N. S., Kiselev, V. I., and Severin, E. S. (1990) A new class of antivirals: antisense oligonucleotides combined with a hydrophobic substituent effectively inhibit influenza virus reproduction and synthesis of virus-specific proteins in MDCK cells. FEBS Lett. 259, 327-330.
6. Shea, R. G., Marsters, J. C., and Bischofberger, N. (1990) Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucleotide conjugates. Nucleic Acids Res. 18, 3777-3783.
7. Miller, P. S. (1989) Non-ionic antisense oligonucleotides. In Antisense Inhibitors of Gene Expression (J. Cohen, Ed.) CRC Press, Boca Raton, FL.
8. Fathi, R., Huang, Q., Coppola, G., Delaney, W., Teasdale, R., Krieg, A. M., and Cook, A. F. (1994) Oligonucleotides with novel, cationic backbone substituents: aminoethylphosphonates. Nucleic Acids Res. 22, 5416-5424.
9. Leonetti, J.-P., Degols, G., and Lebleu, B. (1990) Biological Activity of Oligonucleotide-Poly(L-Lysine) Conjugates: Mechanism of Cell Uptake. Bioconjugate Chem. 1, 149-153.
10. Wei, Z., Tung, C. H., Zhu, T., Stein, S. (1994) Synthesis of Oligoarginine-Oligonucleotide Conjugates and Oligoarginine-Bridged Oligonucleotide Pairs. Bioconjugate Chem. 5, 468-474.
11. Kabanov, A. V., and Kabanov, V. A. (1995) DNA Complexes with Polycations for Delivery of Genetic Material into Cells. Bioconjugate Chem. 6, 7-20.
12. Kabanov, A. V., Astafieva, I. V., Maksimova, I. V., Lukanidin, E. M., Georgiev, G. P., and Kabanov, V. A. (1993) Efficient Transformation of Mammalian Cells Using DNA Interpolyelectrolyte Complexes with Carbon Chain Polycations. Bioconjugate Chem. 4, 448-454.
13. Kabanov, A. V., Astafieva, I. V., Chikindas, M. L., Rosenblat, G. F., Kiselev, V. I., Severin, E. S., and Kabanov, V. A. (1991) DNA interpolyelectrolyte complexes as a tool for efficient cell transformation. Biopolymers 31, 1437-1443.
14. Kulka, M., Smith, C. C., Aurelian, L., Fishelevich, R., Meade, K., Miller, P., and Tso, P. O. P. (1989) Site specificity of the inhibitory effects of oligo(nucleoside methylphosphonate)s complementary to the acceptor splice junction of herpes simplex virus type 1 immediate early mRNA 4. Proc. Natl. Acad. Sci. U.S.A. 86, 6868-6872.
15. Kulka, M., Smith, C. C., Levis, J., Fishelevich, R., Hunter, J. C. R., Cushman, C. D., Miller, P. S., Ts'o, P. O. P., and Aurelian, L. (1994) Synergistic antiviral activities of oligonucleotide methylphosphonates complementary to herpes simplex virus type 1 immediate-early mRNAs 4.5 and 1. Antimicrob. Agents Chemother. 38, 675-680.
16. Vinogradov, S. V., Suzdaltseva, Yu., Alakhov, V. Yu., and Kabanov, A. V. (1994) Inhibition of Herpes simplex virus 1 reproduction with hydrophobized antisense oligonucleotides. Biochem. Biophys. Res. Commun. 203, 959-966.
17. Kabanov, A. V., Vinogradov, S. V., Suzdaltseva, Yu. G., and Alakhov, V. Yu. (1995) Water-Soluble Block Polycations as Carriers for Oligonucleotide Delivery. Btoconjugate Chem. 6, 639-643.
18. Agrawal, S. (1994) Functionalization of oligonucleotides with amino groups and attachment of amino specific reporter groups. In Protocols for Oligonucleotide Conjugates (S. Agrawal, Ed.) pp 93-120, Humana Press, Totowa, NJ.
19. Atkinson, T., and Smith, M. (1984) Solid-phase synthesis of oligodeoxyribonucleotides by the phosphite-triester method. In Oligonucleotide Synthesis. A Practical Approach (M. J. Gait, Ed.) pp 35-82, IRL Press, Oxford, Washington, DC.
20. Friser, H. (1975) An improved 2,4,6-trinitrobenzenesulfonic acid method for the determination of amines. Anal. Biochem. 64, 284-288.
21. Freshney, R. I. (1994) Culture of Animal Cells, 3rd ed., John Willey & Sons, Inc., New York.
22. Bailey, C. A., Miller, D. K., and Lenard, J. (1984) Effects of DEAE-dextran on infection and homolysis by VSV. Evidence that nonspecific electrostatic interactions mediate effective binding of VSV to cells. Virology 133, 111-118.
23. Prakash, J., and Foxe, M. J. (1985) Optimization of conditions for infection of isolated potato protoplasts with potato virus X. Arch. Virol. 85, 269-279.
24. Rousculp, M. D., Goldsmith, K. T., and Garver, R. I. (1992) Quantative evaluation of retroviral gene transduction efficiency in human lung cancer cells. Hum. Gene Ther. 3, 471-477.
25. Langeland, N., Moore, L. J., Holmsen, H., and Haarr, L. (1988) Interaction of polylysine with the cellular receptor for herpes simplex virus type 1. J. Gen. Virol. 69, 1137-1145.
26. Jasachke, A., Furste, J. P., Nordorf, E., Hillenkapm, F., Cech, D., and Erdmann, V. A. (1994) Synthesis and properties of oligodeoxyribonucleotide-polyethylene glycol conjugates. Nucleic Acids Res. 22, 4810-4817.
27. Jones, D. S., Hachmann, J. P., Osgood, S. A., Hayag, M. S., Barstad, P. A., Iversen, G. M., and Couttus, S. M. (1994) Conjugates of Double-Stranded Oligonucleotides with Poly-(ethylene glycol) and Keyhole Limpet Hemocyanin: A Model for Treating Systemic Lupus Erythematosus. Bioconjugate Chem. 5, 390-399.
28. Soukchareun, S., Tregear, G. W., and Haralambidis, J. (1995) Preparation and Characterization of Antisense Oligonucleotide-Peptide Hybrids Containing Viral Fusion Peptides. Bioconjugate Chem. 6, 43-53.
29. α-(Bromoacetyl) peptides. Bioconjugate Chem. 6, 573-577.