Polymer-conjugated bioactive oligonucleotides

Journal of Bioactive and Compatible Polymers

Volumn 17, Issue 5, 2002, Pages 375-389

  Bonora, Gian Maria ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Anti gene; Antisense; Conjugated; Oligonucleotide; Poly(ethylene glycol)

Indexed keywords

AMINO ACIDS; MOLECULAR WEIGHT; POLYETHYLENE GLYCOLS;

BIOACTIVE MOLECULES;

BIOPOLYMERS;

ANTISENSE OLIGONUCLEOTIDE; MACROGOL; OLIGONUCLEOTIDE; POLYMER;

DRUG ACTIVITY; DRUG CONJUGATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR WEIGHT; NUCLEOTIDE SEQUENCE; REVIEW;

EID: 0036762870     PISSN: 08839115     EISSN: None     Source Type: Journal    
DOI: 10.1177/0883911502017005555     Document Type: Review

References (30)

1. Bennet, C.F., Chiang, M.-Y., Chan, H., Shoemaker, J.E. and Mirabelli, C.K. (1992). Cationic liposomes enhance cellular uptake and activity of phosphorothioate antisense oligonucleotides, Mol. Pharmacol, 41: 1023-1033.
2. Krieg, A.M., Tonkinson, J., Matson, S., Zhao, Q., Saxon, M., Zhang, L.-M., Bhanjia, U., Yakubov, L. and Stein, C.A. (1993). Modification of antisense phosphodiester oligodeoxynucleotides by a 5′-cholesterol moiety increases cellular association and improves efficacy, Proc. Natl. Acad. Sci. USA, 90: 1048-1052.
3. Rait, A., Pirollo, K., Will, D.W., Peyman, A., Rait, V. Uhlmann, E. and Chang, E.H. (2000). 3′-end conjugates of minimally phosphorothioate protected oligonucleotides with 1-O hexadecylglycerol: Synthesis and antiras activity on radiation-resistent cells, Bioconjugate Chem., 11: 153-160.
4. Stetsenko, D.A., Arzumanov, A.A., Khorshun, V.A. and Gait, M.J. (2000). Peptides conjugates of oligonucleotides as enhanced antisense agents: A review, Mol. Biol. (Russ), 34: 852-859.
5. Kabanov, A.V., Vinogradov, S.V. and Alakhov, V.Y. (1995). Water-soluble block polications as carriers for oligonucleotide delivery, Bioconjugate Chem., 6: 639-643.
6. Yoo, H. and Juliano, R.L. (2000). Enhanced delivery of antisense oligonucleotides with fluorophore-conjugate PAMAM dendrimers, Nucleic Acids Res., 28: 4225-4231.
7. Wang, L., Kristensen, J. and Ruffner, D.E. (1998). Delivery of antisense oligonucleotides using HPMA polymer: Synthesis of a thiol polymer and its conjugation to water-soluble molecules, Bioconjugate Chem., 9: 749-757.
8. Jaschke, A., Furste, J.P., Nordhoff, E., Hillenkamp, F., Cech, D. and Erdmann, V.A. (1994). Synthesis and properties of oligodeoxiribonucleotide-poly(ethylene glycol) conjugates, Nucleic Acids Res., 22: 4810-4817.
9. Harris, J.M. (Ed.) (1992). Poly(ethylene glycol) Chemistry: Biotechnical and Biomedical Applications, Plenum Press, New York.
10. Choi, J.H., Choi, J.S., Suh, H. and Park, J.S. (2001). Effect of poly(ethylene glycol) grafting on polyethylenimine as a gene transfer vector in vivo, Bull. of the Khorean Chem. Soc., 22: 46-52.
11. Bonora, G.M., Biancotto, G., Maffini, M. and Scremin, C.L. (1993). Large Scale, liquid phase synthesis of oligonucleotides by the phosphoramidite approach, Nucleic Acids Res., 21: 1213-1217.
12. Bonora, G.M., Ivanova, E., Zarytova, V., Burcovich, B. and Veronese, F.M. (1997). Synthesis and characterization of high-molecular mass poly(ethylene glycol-conjugated oligonucleotides, Bioconjugate Chem., 8: 793-797.
13. Hélène, C. (1991). The antigene strategy: Control of gene expression by triplex-helix forming oligonucleotides, Anticancer Drug Design, 6: -569-584.
14. Ballico, M., Drioli, S., Morvan, F., Xodo, L. and Bonora, G.M. (2001). Triple, MPEG-conjugated, helix forming oligonucleotides (TRIPEGX)s: Liquidphase synthesis of natural and chimeric "all-purine" sequences linked to high-molecular weight polyethylene glycol, Bioconjugate Chem., 12: 719-725.
15. Xodo, L.E., Rathinavelan, T., Quadrifoglio, F., Manzini, G. and Yathindra, N. (2001). Targeting neighboring poly(purine-pyrimidine) sequences located in the human bcr promoter by triplex-forming oligonucleotides, Eur. J. Biochem., 268: 1-10.
16. Deininger, M.W.N., Goldman, J.M. and Melo, J.V. (2000). The molecular biology of chronic myeloid leukemia, Blood, 96: 3343-3356.
17. Skorski, T., Nieborowska-Skorska, M., Nicolaides, N.C., Szczylik, C., Iversen, P., Iozzo, R.V., Zon, G. and Calabretta, B. (1994). Suppression of Philadelphia 1 leukemia cell growth in mice by bcr-abl antisense oligodeoxynucleotide, Proc. Natl. Acad. Sci. USA, 91: 4504-4508.
18. Cogoi, S., Rapozzi, V., Quadrifoglio, F. and Xodo, L. (2001). Antigene effect in live cells of AG motif triplex-forming oligonucleotides containing an increasing number of phosphorothioate linkages, Biochemistry, 409: 1135-1143.
19. Agrawal, S., Iodarola, P.L. and Temsamani, J. (1996). Effect of G-Rich sequences on the synthesis, purification, hybridization, cell uptake, and haemolytic activity of oligonucleotides, Bioorg. Med. Chem. Lett., 6: 2219-2224.
20. Rapozzi, V., Cogoi, S., Spessotto, P., Risso, A., Bonora, G.M., Quadrifoglio, F. and Xodo, L.E. (2002). Anti-gene effect in K562 cell of a PEG-conjugated triplex-forming oligonucleotide targeted to the bcr/abl oncogene, Biochemistry, 41: 502-510.
21. Meyer, O., Kirpotin, D., Hong, K., Sternberg, B., Park, J.W., Woodlwe, M.C. and Papahadjopoulos, D. (1998). Cationic liposomes coated with polyethylene glycol as carriers for ODNs, J. Biol. Chem., 273: 15621-15627.
22. Burcovich, B., Veronese, F.M., Zarytova, V. and Bonora, G.M. (1998). Branched polyethylene glycol (bPEG) conjugated antisense oligonucleotides, Nucleosides and Nucleotides, 17: 1567-1570.
23. Bonora, G.M., Ivanova, E., Komarova, N., Pishniyi, D., Vorobjev, P., Zarytova, V., Zaramella, S. and Veronese, F.M. (1999). Biological properties of antisense oligonucleotides conjugated to different high-molecular mass poly(ethylene glycols), Nucleosides and Nucleotides, 18: 1723-1725.
24. Walder, R.Y. and Walder, J.A. (1988). Role of Rnase H in hybrid-arrested translation by antisense oligonucleotides, Proc. Natl. Acad. Sci. USA, 85: 5011-5015.
25. Vorobjev, P.E., Zarytova V.F. and Bonora G.M. (1999). Oligonucleotide conjugated to linear and branched high molecular weight polyethylene glycol as substrates for Rnase H, Nucleosides and Nucleotides, 18: 2735-2750.
26. Bonora, G.M., Baldan, A., Schiavon, O., Ferruti, P., Veronese, F.M. (1996). Poly(N-acryloylmorpholine) as a New soluble support for the liquid-phase synthesis of oligonucleotides, Tetrahedron Lett., 37: 4761-4764.
27. Svinarchuk, F.P., Konevetz, O.A., Pliasunova, O.A., Pokrovsky, A.G. and Vlassov, V.V. (1993). Inhibition of HIV proliferation in MT-4 cells by antisense oligonucleotide conjugated to lipophylic groups, Biochimie, 75: 49-54.
28. Eritjia, R., Pons, A., Escarceller, M., Giralt, E. and Albericio, F. (1991). Synthesis of defined peptide-oligonucleotide hybrids containing a nuclear transport signal sequence, Tetrahedron, 47: 4113-4120.
29. Ljungstrom, T., Knudsen, H. and Nielsen, P.E. (1999). Cellular uptake of adamantyl conjugated peptide nucleic acids, Bioconjugate Chem., 10: 965-972.
30. Drioli, S., Benedetti, F. and Bonora, G.M. (2001). Pure, homo-bifunctional poly(ethylene glycol) orthogonally protected: Synthesis and characterisation, Reactive and Functional Polymers, 48: 119-128.