Nowa wersja platformy, zawierająca wyłącznie zasoby pełnotekstowe, jest już dostępna.
Przejdź na https://bibliotekanauki.pl

PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
1999 | 46 | 3 |
Tytuł artykułu

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

Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A series of conjugates containing residues of lipophilic alcohols covalently bound to 5'-end of oligodeoxyribonucleotides targeted against human plasminogen activator inhibitor (PAI-1) mRNA was synthesized via the oxathiaphospholane approach. The highest anti-PAI-1 activity in EA.hy 926 endothelial cell cultures was found for conjugates containing menthyl or heptadecanyl groups linked with an oligonucleotide complementary to a segment of human PAI-1 mRNA. The phosphodiester antisense oligonucleotides, which otherwise exhibit only limited anti-PAI-1 activity, were found to be more active than phosphorothioate oligonucleotides when conjugated to lipophilic alcohol residues. For menthyl conjugates an evidence of antisense mechanism of inhibition was found.
Wydawca
-
Rocznik
Tom
46
Numer
3
Opis fizyczny
p.679-691,fig.
Twórcy
  • Polish Academy of Sciences, H.Sienkiewicza 112, 90-363 Lodz, Poland
autor
autor
autor
autor
autor
autor
Bibliografia
  • 1. Cierniewski, C.S., Babińska, A., Świątkowska, M., Wilczyńska, M., Okruszek, A. & Stec, W.J. (1995) Comparative inhibition of PAI-1 ex­pression in human endothelial cells by modi­fied oligodeoxyribonucleotides. Eur. J. Bio- chem. 227, 494-499.
  • 2. Cierniewski, C.S., Pluskota. E., Krzeslowska, J., Fijałkowska, I., Kobylańska, A., Ko- ziołkiewicz, 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. HaemosL 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 phosphorothio- ate)s. Angew. Chem. Int. Ed EngL 33, 709- 722.
  • 6. Stec, W.J., Ciemiewski, C.S., Okruszek, A., Kobylańska, A., Pawłowska, Z., Koziołkiewicz, M., Pluskota, E., Maciaszek, A., Rębowska, 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. Metłu 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, 3857-3805.
  • 9. Beaucage, S.L. & Iyer, R.P. (1992) Advances in the synthesis of oligonucleotides by phos- phoramidite approach. Tetrahedron 48,2223- 2311.
  • 10. Stec, W.J., Uznański, B., Wilk, A., Hirschbein, B.L., Fearon, K.L. & Bergot, B.J. (1993) Bis- (0,0diisopropoxy phosphinothioyl)disulfide — highly efficient sulfurizing reagent for cost- effective synthesis of oligo(nucleoside phos- phorothioate)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.. Fiirste, J.P., Nordhoff, E., Hil- lenkamp, F., Cech, D. & Erdmann, W A. (1994) Synthesis and properties of oligodeoxy- ribonucleotide-polyethylene glycol conjugates. Nucleic Acids Res. 22, 4810-4817.
  • 13. Jaschke, A., Bald, R., Nordhoff, E., Hillenkamp, F., Cech, D., Erdmann, BA. & Fiirste, 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 oligodeoxyribo- nucleotide 5'-0-conjugates. Nucleosides Nu­cleotides 17, 1977-1982.
  • 15. Błaszczyk, J.f Wieczorek, M.W., Okruszek, A., Sierzchała, A., Kobylańska, A. & Stec, W.J. (1996) The synthesis and X-ray structural studies of 2-cholesteryl-2-thio-l,3,2-oxathia- phospholane and 2-cholesteryl-2-thio-l,3,2-di- thiaphospholane. J. Chem. CrysL 26, 33-42.
  • 16. Stec, W.J., Grajkowski, A., Koziołkiewicz, M. & Uznański, B. (1991) Novel route to oligo- (deoxyribonucleo8ide phosphorothioates). Ste­reocontrolled synthesis of P-chiral oligo (deoxyribonucleoside phosphorothioates). Nu­cleic Acids Res. 19, 5883-5888.
  • 17. Stec, W.J., Grajkowski, A., Kobylańska, A., Koziołkiewicz, M., Misiura, K., Okruszek, A., Wilk, A., Guga, P. & Boczkowska, M. (1995) Diastereomers of nucleoside 3'-<X2-thio- 1,3,2-oxathia (selena)phospholanes): Building blocks for stereocontrolled synthesis of oligo(nucleo8ide 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 sta­bility, and cellular uptake of the oligo- nucleotide-amino-cyclodextrins and adaman- tane 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 waier-soluble meso-tetracarboxypor- phine conjugated to an antisense oligo-deoxy- ribonucleotide. Biochimie 76, 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. Kuyl-Yeheskiely, E., Dreef-Tromp, C.M., Geluk, A., van der Marel, G.A. & van Boom, J.H. (1989) Synthesis of the nucleopeptides H-Phe-TyKpGONHg and H-Phe-SeKpGC> 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. ScL 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 oligodeoxynucleo- tides 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 oiigodeoxynucleotides 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 dimethoxy- trityl residue inhibits HIV-1 replication by spe­cific interaction with the envelope glycopro­tein. Antiviral Res. 31, 137-148.
  • 33. Kobylańska, A., Pluskota, E., Pawłowska. 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. Wolfe, J.L. & Goodchild, J. (1996) Modulation of tetraplex formation by chemical modifica­tion of a G4-containing phosphorothioate uligunucleutide. J. Am. Chem. Soc. 118, G301- 6302.
  • 41. Fang, G. & Cech, T.R. (1993) Characterization of a G-quartet formation reaction promoted by the beta-subunit of the Oxytricha telomere- binding 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. ScL U.S.A. 90. 3157- 3161.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.agro-article-cb4eacd7-c98d-47a8-8ddc-f3d971910203
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.