Inhibition of plasminogen activator inhibitor release in endothelial cell cultures by antisense oligodeoxyribonucleotides with a 5′-end lipophilic modification

Acta Biochimica Polonica

Volumn 46, Issue 3, 1999, Pages 679-691

  Kobylańska, Anna ^a   Pluskota, Elzbieta ^b   Świa̧tkowska, Maria ^b   Wójcik, Marzena ^a   Cierniewska Cieślak, Aleksandra ^c   Krakowiak, Agnieszka ^a   Boczkowska, Małgorzata ^a   Pawłowska, Zofia ^b   Okruszek, Andrzej ^a   Koziołkiewicz, Maria ^a   Cierniewski, Czesław S ^a,b   Stec, Wojciech J ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

^b MEDICAL UNIVERSITY OF LODZ   (Poland)

^c POLISH ACADEMY OF SCIENCES   (Poland)

Author keywords

Antisense inhibition; Oligonucleotide conjugates; Plasminogen activator inhibitor

Indexed keywords

ANTISENSE OLIGODEOXYNUCLEOTIDE; MESSENGER RNA; PLASMINOGEN ACTIVATOR INHIBITOR 1; PRIMER DNA;

ARTICLE; CELL LINE; DRUG EFFECT; GENETICS; HUMAN; METABOLISM; NUCLEOTIDE SEQUENCE; SECRETION; SYNTHESIS; VASCULAR ENDOTHELIUM;

BASE SEQUENCE; CELL LINE; DNA PRIMERS; ENDOTHELIUM, VASCULAR; HUMANS; OLIGODEOXYRIBONUCLEOTIDES, ANTISENSE; PLASMINOGEN ACTIVATOR INHIBITOR 1; RNA, MESSENGER;

EID: 0039107898     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.1999_4140     Document Type: Article

References (42)

1. Cierniewski, C.S., Babińska, A., Świa̧tkowska, M., Wilczyńska, M., Okruszek, A. & Stec, W.J. (1995) Comparative inhibition of PAI-1 expression in human endothelial cells by modified oligodeoxyribonucleotides. Eur. J. Biochem. 227, 494-499.
2. Cierniewski, C.S., Pluskota, E., Krzeslowska, J., Fijalkowska, I., Kobylańska, A., Koziołkiewicz, M., Okruszek, A. & Stec, W.J. (1995) Inhibition by modified oligodeoxyribonucleotides of the expression of the type 1 plasminogen activator inhibitor in human endothelial cells. Thromb. Haemost. 73, 1007.
3. Krishnamurti, C. & Alving, B.M. (1992) Plasminogen activator inhibitor type 1: Biochemistry and evidence for modulation of fibrinolysis in vivo. Semin. Thromb. Haemost. 18, 67-80.
4. Van Meijer, M. & Pannekoek, H. (1995) Structure of plasminogen activator inhibitor 1 (PAI-1) and its function in fibrinolysis: An update. Fibrinolysis 9, 261-276.
5. Stec, W.J. & Wilk, A. (1994) Stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s. Angew. Chem. Int. Ed. Engl. 33, 709-722.
6. Stec, W.J., Cierniewski, C.S., Okruszek, A., Kobylańska, A., Pawłowska, Z., Koziołkiewicz, M., Pluskota, E., Maciaszek, A., Rȩbowska, B. & Stasiak, M. (1997) Stereodependent inhibition of plasminogen activator inhibitor type 1 by phosphorothioate oligonucleotides; Proof of sequence specificity in cell culture and in vivo rats experiments. Antisense Nucleic Acids Drug Dev. 7, 567-573.
7. Wickstrom, E. (1986) Oligodeoxynucleotide stability in subcellular extracts and culture media. Biochem. Biophys. Meth. 13, 97-102.
8. Fisher, T.L., Terhorst, T., Cao, X. & Wagner, R.W. (1993) Intracellular disposition and metabolism of fluorescently-labeled unmodified and modified oligonucleotides microinjected into mammalian cells. Nucleic Acids Res. 21, 3857-3865.
9. Beaucage, S.L. & Iyer, R.P. (1992) Advances in the synthesis of oligonucleotides by phosphoramidite approach. Tetrahedron 48, 2223-2311.
10. Stec, W.J., Uznański, B., Wilk, A., Hirschbein, B.L., Fearon, K.L. & Bergot, B.J. (1993) Bis(O, O-diisopropoxy phosphinothioyl)disulfide - highly efficient sulfurizing reagent for cost-effective synthesis of oligo(nucleoside phosphorothioate)s. Tetrahedron Lett. 34, 5317-5320.
11. Brown, T. & Pritchard, C.E. (1989) A new base-stabile linker for solid-phase oligonucleotide synthesis. J. Chem. Soc., Chem. Commun. 891-893.
12. Jaschke, A., Fürste, J.P., Nordhoff, E., Hillenkamp, F., Cech, D. & Erdmann, V.A. (1994) Synthesis and properties of oligodeoxyribonucleotide-polyethylene glycol conjugates. Nucleic Acids Res. 22, 4810-4817.
13. Jaschke, A., Bald, R., Nordhoff, E., Hillenkamp, F., Cech, D., Erdmann, B.A. & Fürste, J.P. (1996) Synthesis and analytical characterization of RNA-polyethylene glycol conjugates. Nucleosides & Nucleotides 15, 1519-1529.
14. Kobylańska, A., Okruszek, A. & Stec, W.J. (1998) Application of oxathiaphospholane method for the synthesis of oligodeoxyribonucleotide 5′-O-conjugates. Nucleosides Nucleotides 17, 1977-1982.
15. Błaszczyk, J., Wieczorek, M.W., Okruszek, A., Sierzchala, A., Kobylańska, A. & Stec, W.J. (1996) The synthesis and X-ray structural studies of 2-cholesteryl-2-thio-1,3,2-oxathiaphospholane and 2-cholesteryl-2-thio-1,3,2-dithiaphospholane. J. Chem. Cryst. 26, 33-42.
16. Stec, W.J., Grajkowski, A., Koziolkiewicz, M. & Uznański, B. (1991) Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo (deoxyribonucleoside phosphorothioates). Nucleic Acids Res. 19, 5883-5888.
17. Stec, W.J., Grajkowski, A., Kobylańska, A., Koziolkiewicz, M., Misiura, K., Okruszek, A., Wilk, A., Guga, P. & Boczkowska, M. (1995) Diastereomers of nucleoside 3′-O-(2-thio1,3,2-oxathia (selena)phospholanes): Building blocks for stereocontrolled synthesis of oligo(nucleoside phosphorothioate)s. J. Am. Chem. Soc. 117, 12019-12029.
18. Levin, E.G. (1986) Quantitation and properties of the active and latent plasminogen activator inhibitors in cultures of human endothelial cells. Blood 67, 1309-1313.
19. Lewis, M.L., Nachtway, D.S. & Damron, K.L. (1991) A miniaturized fibrinolytic assay for plasminogen activators. Thromb. Res. 64, 223-234.
20. Goodchild, J. (1990) Conjugates of oligonucleotides and modified oligonucleotides: A review of their synthesis and properties. Bioconjug. Chem. 1, 165-187.
21. Manoharan, M. (1993) Designer antisense oligonucleotides: Conjugation chemistry and functionality placement; in Antisense Research and Applications (Crooke, S.T. & Lebleu, B., eds.) pp. 303-349, CRC Press, Boca Raton, FL.
22. Ramirez, F., Mandal, S.B. & Marecek, J.F. (1982) Nucleotidophospholipids: Oligonucleotide derivatives with membrane-recognition groups. J. Am. Chem. Soc. 104, 5483-5486.
23. Habus, I., Zhao, Q. & Agrawal, S. (1995) Synthesis, hybridization properties, nuclease sta3 bility, and cellular uptake of the oligonucleotide-amino-cyclodextrins and adamantane conjugates. Bioconjug. Chem. 6, 327-331.
24. MacKellar, C., Graham, D., Will, D.W., Burgess, S. & Brown, T. (1992) Synthesis and physical properties of anti-HIV antisense oligonucleotides bearing terminal lipophilic groups. Nucleic Acids Res, 20, 3411-3417.
25. Ortigao, J.F., Ruck, A., Gupta, K.C., Rosch, R., Steiner, R. & Seliger, H. (1993) Solid-phase introduction and intracellular photoinduced reaction of water-soluble meso-tetracarboxyporphine conjugated to an antisense oligo-deoxyribonucleotide. Biochimie 75, 29-34.
26. Boiziau, C. & Toulme, J.-J. (1991) Modified oligonucleotides in rabbit reticulocytes: Uptake, stability and antisense properties. Biochimie 73, 1403-1408.
27. Leonetti, J.P., Raynier, B., Lemaitre, M., Gagnor, C., Milhaud, P.G., Imbach, J.-L. & Lebleu, B. (1988) Antiviral activity of conjugates between poly(L-lysine) and synthetic oligodeoxyribo-nucleotides. Gene 72, 323-332.
28. 2 and H-Phe-Ser(pGC)-Ala-OH via a phosphotriester approach. Nucleic Acids Res. 17, 2897-2905.
29. Letsinger, R.L., Zhang, G.R, Sun, D.K., Ikeuchi, T. & Sarin, P.S. (1989) Cholesteryl-conjugated oligonucleotides: Synthesis, properties, and activity as inhibitors of replication of human immunodeficiency virus in cell culture. Proc. Natl. Acad. Sci. U.S.A. 86, 6553-8556.
30. Krieg, A.M., Tonkinson, J., Matson, S., Zhao, Q., Saxon, M., Zhang, L.M., Bhanja, U., Yakubov, L. & 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.
31. Stein, C.A., Pal, R., Devico, A.L., Hoke, G., Mumbauer, S., Kinstler, O., Sarngadharan, M.G. & Letsinger, R.L. (1991) Mode of action of 5′-linked cholesteryl phosphorothioate oligodeoxynucleotides in inhibiting syncytia formation and infection by HIV-1 and HIV-2 in vitro. Biochemistry 30, 2439-2444.
32. Agatsuma, T., Yamamoto, I., Furukawa, H. & Nishigaki, T. (1996) Guanine-rich oligonucleotide modified at the 5′ terminal by dimethoxytrityl residue inhibits HIV-1 replication by specific interaction with the envelope glycoprotein. Antiviral Res. 31, 137-148.
33. Kobylańska, A., Pluskota, E., Pawlowska, Z., Okruszek, A., Cierniewski, C.S. & Stec, W.J. (1999) The cytotoxicity of anti-PAI-1 oligonucleotides and their conjugates. Nucleosides Nucleotides 18, 1709-1710.
34. Eder, P.S., Devine, R.J., Dagile, J.M. & Walder, J.A. (1991) Substrate specificity and kinetics of degradation of antisense oligonucleotides by a 3′-exonuclease in plasma. Antisense Res. Dev. 1, 141-151.
35. Hardin, C.C., Corregan, M.J., Lieberman, D.V. & Brown II, B.A. (1997) Allosteric interactions between DNA strands and monovalent cations in DNA quadruplex assembly: Thermodynamic evidence for three linked association pathways. Biochemistry 36, 15428-15450.
36. Stein, C.A. & Cheng, Y.-C. (1993) Antisense oligonucleotides as therapeutic agents - is the bullet really magical? Science 261, 1004-1012.
37. Gao, W., Han, F., Storm, C., Egan, W. & Cheng, Y. (1991) Phosphorothioate oligonucleotides are inhibitors of human DNA polymerases and RNase H: Implications for anti-sense technology. Mol. Pharmacol. 41, 223-229.
38. Stein, C.A. (1995) Does antisense exist? Nature Med. 1, 1119-1121.
39. Sen, D. & Gilbert, W. (1992) Guanine quartet structures. Methods Enzymol. 211, 191-199.
40. 4-containing phosphorothioate oligonucleotide. J. Am. Chem. Soc. 118, 6301-6302.
41. Fang, G. & Cech, T.R. (1993) Characterization of a G-quartet formation reaction promoted by the beta-subunit of the Oxytricha telomerebinding protein. Biochemistry 32, 11646-11657.
42. Liu, Z., Frantz, J.D., Gilbert, W. & Tye, B.K. (1993) Identification and characterization of a nuclease activity specific for G4 tetrastranded DNA. Proc. Natl. Acad. Sci. U.S.A. 90, 3157-3161.