Preparation of conjugates of oligodeoxynucleotides and lipid structures and their interaction with low-density lipoprotein

Bioconjugate Chemistry

Volumn 9, Issue 3, 1998, Pages 341-349

  Rump, Erik T ^a   De Vrueh, Remco L A ^a   Sliedregt, Leo A J M ^a   Biessen, Erik A L ^a   Van Berkel, Theo J C ^a   Bijsterbosch, Martin K ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGODEOXYNUCLEOTIDE; ELECTROPHORESIS; LITHOCHOLIC ACID; LOW DENSITY LIPOPROTEIN; OLEIC ACID; OLIGONUCLEOTIDE; PENTAFLUOROPHENYL ESTER;

CHOLESTEROL; CONTROLLED DRUG DELIVERY; ELECTROPHORESIS; ESTERS; LIPOPROTEINS; TARGETED DRUG DELIVERY;

ANTISENSE OLIGODEOXYNUCLEOTIDES; BILE ACID; EXPRESSION LEVELS; LIPID STRUCTURES; LIPOPHILICITY; LITHOCHOLIC ACIDS; LOW DENSITY LIPOPROTEINS; OLIGODEOXYNUCLEOTIDES; SYNTHESISED; TUMOUR CELLS;

OLEIC ACID;

EID: 0032080246     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc970176z     Document Type: Article

References (44)

1. Wagner, R. W., and Flanagan, W. M. (1997) Antisense technology and prospects for therapy of viral infections and cancer. Mol. Med. Today 3 (1), 31-38.
2. Szymkowski, D. E. (1996) Developing antisense oligonucleotides from the laboratory to clinical trials. Drug Discovery Today 1 (10), 415-428.
3. Boutorine, A. S., and Kostina, E. V. (1993) Reversible Covalent Attachment of Cholesterol to Oligodeoxyribonucleotides for Studies of the Mechanisms of Their Penetration into Eucaryotic Cells. Biochimie 75 (1-2), 35-41.
4. Boutorine, A. S., Gus'kova, L. V., Ivanova, E. M., Kobetz, N. D., Zarytova, V. F., Ryte, A. S., Yurchenko, L. V., and Vlassov, V. V. (1989) Synthesis of alkylating oligonucleotide derivatives containing cholesterol or phenazinium residues at their 3′-terminus and their interaction with DNA within mammalian cells. FEBS Lett. 254, 129-132.
5. Vu, H., Singh, P., Lewis, L., Zendegui, J. G., and Jayaraman, K. (1993) Synthesis of cholesteryl supports and phosphoramidate for automated DNA synthesis of triple-helix forming oligonucleotides (TFOs). Nucleosides Nucleotides 12, 853-864.
6. Shea, R. G., Marsters, J. C., and Bischofberger, N. (1990) Synthesis, hybridization properties and antiviral activity of lipid-oligonucleotide conjugates. Nucleic Acids Res. 18, 3777-3783.
7. Alahari, S. K., Dean, N. M., Fisher, M. H., Delong, R., Manoharan, M., Tivel, K. L., and Juliano, R. L. (1996) Inhibition of expression of the multidrug resistance-associated P-glycoprotein by phosphorothioate and 5′ cholesterol-conjugated phosphorothioate antisense oligonucleotides. Mol. Pharmacol. 50 (4), 808-819.
8. Svinarchuk, F. P., Konevetz, D. 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 Lipophilic Groups. Biochimie 75 (1-2), 49-54.
9. Desjardins, J., Mata, J., Brown, T., Graham, D., Zon, G., and Iversen, P. (1995) Cholesteryl-conjugated phosphorothioate oligodeoxynucleotides modulate CYP2B1 expression in vivo. J. Drug Targeting 2 (6), 477-485.
10. Krieg, A. M., Tonkinson, J., Matson, S., Zhao, Q., Saxon, M., Zhang, L.-M., Bhanja, U., Yakubov, L., and Stein, C. A. (1993) Modification of antisense phosphodiester oligodeoxynucleotides by a 5′ cholesteryl moiety increases cellular association and improves efficacy. Proc. Natl. Acad. Sci. U.S.A. 90, 1048-1052.
11. Farooqui, F., Sarin, P. S., Sun, D., and Letsinger, R. L. (1991) Effect of structural variations in cholesteryl-conjugated oligonucleotides in inhibitory activity toward HIV-1. Bioconjugate Chem. 2, 422-426.
12. Brown, M. S., and Goldstein, J. L. (1986) A receptor-mediated pathway for cholesterol homeostasis. Science 232, 34-47.
13. Firestone, R. A., Pisano, J. M., Falck, J. R., McPaul, M. M., and Krieger, M. (1984) Selective delivery of cytotoxic compounds to cells by the LDL pathway. J. Med. Chem. 27, 1037-1043.
14. Dubowchik, G. M., and Firestone, R. A. (1995) Improved cytotoxicity of antitumor compounds deliverable by the LDL pathway. Bioconjugate Chem. 6, 427-439.
15. Firestone, R. A. (1994) Low-density lipoprotein as a vehicle for targeting antitumor compounds to cancer cells. Bioconjugate Chem. 5 (2), 105-113.
16. Shaw, J. M., Shaw, K. V., Yanovich, S., Jwanik, M., Futch, W. S., Rosowsky, A., and Schook, L. B. (1987) Delivery of lipophilic drugs using lipoproteins. Ann. N. Y. Acad. Sci. 507, 252-271.
17. Rojanasakul, Y., Weissman, D. N., Shi, X. L., Castranova V., Ma, J. K. H., and Liang, W. W. (1997) Antisense inhibition of silica-induced tumor necrosis factor in alveolar macroph ages. J. Biol. Chem. 272 (7), 3910-3914.
18. Rojanasakul, Y. Y. (1996) Antisense oligonucleotide therapeutics: Drug delivery and targeting. Adv. Drug Delivery Rev. 18 (2), 115-131.
19. De Smidt, P. C., Le Doan, T., De Falco, S., and van Berkel, Th. J. C. (1991) Association of antisense oligonucleotides with lipoproteins prolongs the plasma half-life and modifies the tissue distribution. Nucleic Acids Res. 19, 4695-4700.
20. Mishra, R. K., Moreau, C., Ramazeilles, C., Moreau, S., Bonnet, J., and Toulmé, J.-J. (1995) Improved leishmanicidal effect of phosphorothioate antisense oligonucleotides by LDL-mediated delivery. Biochim. Biophys. Acta 1264, 229-237
21. Ferrari, S., Torelli, U., Selleri, L., Donelli, A., Venturelli, D., Narni, F., Moretti, L., and Torelli, G. (1985) Study of the levels of expression of two oncogenes, c-myc and c-myb, in acute and chronic leukemias of both lymphoid and myeloid lineage. Leuk. Res. 9, 833-842.
22. Gopal, V., Hulette, B., Li, Y. Q., Kuvelkar, R., Raza, A., Larson, R., Goldberg, J., Tricot, G., Bennett, J., and Preisler, H. (1992) C-myc and c-myb expression in acute myelogenous leukemia. Leuk. Res. 16, 1003-1011.
23. Ratajczak, M. Z., and Kant, J. A. (1992) In vivo treatment of human leukemia in a seid mouse model with c-myb antisense oligodeoxynucleotides. Proc. Natl. Acad. Sci. U.S.A. 89, 11823-11827.
24. Hijiya, N., Zhang, J., Ratajczak, M. Z., Kant, J. A., Deriel, K., Herlyn, M., Zon, G., and Gewirtz, A. M. (1994) Biologic and therapeutic significance of MYB expression in human melanoma. Proc. Natl. Acad. Sci. U.S.A. 91 (10), 4499-4503.
25. Gewirtz, A. M. (1994) Treatment of chronic myelogenous leukemia (CML) with c-myb antisense oligodeoxynucleotides. Bone Marrow Transplant. 14 (Suppl. 3), S57-S61.
26. Goswami, S. K., and Frey, C. F. (1970) Manganous chloride spray reagent for cholesterol and bile acids on thin-layer chromatograms. J. Chromatogr. 53, 389-390.
27. Graham, M. J., Freier, S. M., Crooke, R. M., Ecker, D. J., Maslova, R. N., and Lesnik, E. A. (1993) Tritium Labeling of Antisense Oligonucleotides by Exchange with Tritiated Water. Nucleic Acids Res. 21 (16), 3737-3743.
28. Redgrave, T. G., Roberts, D. L. K., and West, C. E. (1975) Separation of plasma lipoproteins by density gradient ultracentrifugation. Anal. Biochem. 65, 42-49.
29. McFarlane, A. S. (1958) Efficient trace-labelling of proteins with iodine. Nature 182, 53-54.
30. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
31. Chen, S. H., Yang, C. Y., Chen, P. F., Setzer, D., Tanimura, M., Li, W. H., Gotto, A. M., Jr., and Chan, L. (1986) The complete cDNA and amino acid sequence of human apolipoprotein B-100. J. Biol. Chem. 261 (28), 12918-12921.
32. Manoharan, M. (1993) Designer antisense oligonucleotides: conjugation chemistry and functionality placement. In Antisense Research and Applications (S. T. Crooke, Ed.) pp 303-349, CRC Press, Boca Raton, FL.
33. Goodchild, J. (1990) Conjugates of oligonucleotides and modified oligonucleotides: a review of their synthesis and properties. Bioconjugate Chem. 1, 165-187.
34. Boutorine, A. S., Le Doan, T., Battioni, J. P., Mansuy, D., Dupré, D., and Hélène, C. (1990) Rapid route of synthesis of chemically reactive and highly radioactive labeled α-and β-oligonucleotide derivatives for in vivo studies. Bioconjugate Chem. 1, 350-356.
35. Lukhtanov, E. A., Kutyavin, I. V., Gamper, H. B., and Meyer, R. B. (1995) Oligodeoxyribonucleotides with conjugated dihydropyrroloindole oligopeptides: Preparation and hybridization properties. Bioconjugate Chem. 6 (4), 418-426.
36. Boutorine, A. S., Tokuyama, H., Takasugi, M., Isobe, H., Nakamura, E., and Hélène, C. (1994) Fullerene-oligonuclentide conjugates: photoinduced sequence-specific DNA cleavage Angew. Chem., Int. Ed. Engl. 33, 2462-2465.
37. Oberhauser, B., and Wagner, E. (1992) Effective incorporation of 2′-O-methyl-oligoribonucleotides into liposomes and enhanced cell association through modification with thiocholesterol. Nucleic Acids Res. 20, 533-538.
38. Boutorine, A. S., Brault, D., Takasugi, M., Delgado, O., and Hélène, C. (1996) Chlorin-oligonucleotide conjugates: Synthesis, properties, and red light-induced photochemical sequence-specific DNA cleavage in duplexes and triplexes. J. Am Chem. Soc. 118 (40), 9469-9476.
39. Bannwarth, W., Schmidt, D., Stallard, R. L., Hornung, C., Knorr, R., and Müller, R. (1988) Bathophenanthroline-ruthenium(II) complexes as non-radioactive labels for oligonucleotides which can be measured by time-resolved fluorescence techniques Helv. Chim. Acta 71, 2085-2099.
40. Manoharan, M., Tivel, K. L., and Cook, P. D. (1995) Lipidic nucleic acids. Tetrahedron Lett. 36 (21), 3651-3654.
41. Reed, M. W., Adams, A. D., Nelson, J. S., and Meyer, R. B. (1991) Acridine-and cholesterol-derivatized solid supports for improved synthesis of 3′-modified oligonucleotides. Bioconjugate Chem. 2, 217-225.
42. MacKellar, C., Graham, D., Will, W. W., Burgess, S., and Brown, T. (1992) Synthesis and physical properties of anti-HIV antisense oligonucleotides bearing terminal lipophilic groups. Nucleic Acids Res. 20, 3411-3417.
43. Rensen, P. C. N., Herijgers, N., Netscher, M. H., Meskers, S. C. J., van Eck, M., and van Berkel, Th. J. C. (1997) Particle size determines the specificity of apolipoprotein E-containing triglyceride-rich emulsions for the LDL receptor versus hepatic remnant receptor in vivo. J. Lipid Res. 38, 1070-1084.
44. Rensen, P. C. N., Schiffelers, R. M., Versluis, A. J., Bijsterbosch, M. K., van Kuijk-Meuwissen, M. E. M. J., and van Berkel, Th. J. C. (1997) Human recombinant apolipoprotein E-enriched liposomes can mimic low-density lipoproteins as carriers for the site-specific delivery of anti-tumour agents. Mol. Pharmacol. 52, 445-454.