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1998 | 45 | 1 |

Tytuł artykułu

Synthesis, biochemical and biological studies on oligonucleotides bearing a lipophilic dimethoxytrityl group

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Dimethoxytritylphosphono-oligonucleotide conjugates have been prepared. They are totally resistant to nucleases present in human serum and do not affect cleavage of a complementary oligoribonucleotide by RNase H. Conjugates possessing a phosphate backbone gave better antisense inhibition of expression of plasminogen activator inhibitor type-1 within endothelial cells as compared with unconjugated oligonucleotides.

Wydawca

-

Rocznik

Tom

45

Numer

1

Opis fizyczny

p.27-32,fig.

Twórcy

autor
  • Polish Academy of Sciences, H.Sienkiewicza 112, 90-363 Lodz, Poland
autor
autor
autor
autor
autor

Bibliografia

  • 1. Uhlmann, E. & Peyman, A. (1990) Antisense oligonucleotides: A new therapeutic principle. Chem. Rev. 90, 543-584.
  • 2. Wickstrom, E. (1986) Oligonucleotide stability in subcellular extracts and culture media. J. Biochem. Biophys. Meth. 13, 97-101.
  • 3. Stec, W.J. & Zon, G. (1991) Phosphorothioate oligonucleotides; in Oligonucleotides and Ana­logues: A Practical Approach (Eckstein, F., ed.) pp. 87-108, IRL Press, London.
  • 4. Goodchild, J. (1990) Conjugates of oligonu­cleotides and modified oligonucleotides: A re­view of their synthesis and properties. Biocon- jugate Chem. 1, 165-187.
  • 5. Letsinger, R.L., Zhang, G., Sun, D.K., Ikeuchi, T. & Sarin, P.S. (1989) Cholesteryl-conjugated oligonucleotides: Synthesis, properties, and activity as inhibitor of replication of human immunodeficiency virus in cell culture. Proc. Natl Acad. Sci. U.S.A. 86. 6553-6556.
  • 6. Shea, R.G., Morsters, J.C. & Bishofberger, N. (1990) Synthesis, hybridization properties and antiviral activity of lipid-oligonucleotide conjugates. Nucleic Acids Res. 18,3777-3783.
  • 7. McKeUer, 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.
  • 8. Furukawa, H., Mamoto, K., Agatsuma, T., Ya- mamoto, I., Kimara, S. & Shimada. K. (1994) Mechanism of inhibition of HIV-1 infection in vitro by guanine-rich oligonucleotides modi­fied at the 5'-terminal by dimethoxytrityl resi­due. Nucleic Acids Res. 22, 5621-5627.
  • 9. Caruthers, M.H. (1985) Gene synthesis ma­chines: DNA chemistry and its use. Science 230, 281-285.
  • 10. Stec, W.J., Uznahski, B., Wilk, A., Hirschbein, B.L., Fearon, K.L. & Bergot, B.J. (1993) Bis(0,0-diisopropoxy phosphinothioyl)disul- fide — a highly efficient sulfurizing reagent for cost-effective synthesis of oligo(nucleoside phosphorothioate)s. Tetrahedron Lett. 34, 5217-5320.
  • 11. Wilk, A. & Stec, W.J. (1987) Synthesis and separation of diastereoisomers of 5'-CM4,4'- dimethoxytrimethylphenyl)dithymidyl(3' ,5' )- 4,4'-dimethoxy-triphenylmethanephospho- nate. Nucleic Acids Res. Symp. Ser. 18, 289- 292.
  • 12. Nielsen, J., Taagaard, M., Marugg, J.E., van Boom, J.H. & Dahl, O. (1986) Application of 2- cyanoethyl A/,N,./V',W-tetraisopropylphospho- rodiamidite for in situ preparation of deoxyri- bonucleoside phosphoramidites and their use in polymer-supported synthesis of oligode- oxynucleotides. Nucleic Acids Res. 14, 7391- 7403.
  • 13. Atkinson, T. & Smith, M. (1984) Solid phase synthesis of oligodeoxyribonucleotides by the phosphite-triester method; in Oligonucleotide Synthesis (Gait, M.J., ed.) pp. 35-82, IRL Press, Oxford.
  • 14. Koziołkiewicz, M., Wójcik, M., Kobylańska, A., Karwowski, B., Rębowska, B., Guga, P. & Stec, W.J. (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 Acid Drug Dev. 7, 43-48.
  • 15. Cierniewski, C.S., Babińska, A., Świątkowska, M., Wilczyńska, M., Okruszek, A. & Stec, W.J. (1995) Inhibition by modified oligonucleotides of the expression of the type 1 plasminogen ac­tivator inhibitor in human endothelial cells. Eur. J. Biockem. 227, 494-499.
  • 16. Lewis, M.L., Nachtwey, S. & Damron, K.L. (1991) A miniaturized fibrinolytic assay for plasminogen activators. Ihrombosis Res. 64, 223-234.
  • 17. Stec, W.J., Zon, G., Egan, W., Byrd, R.A., Phil- ips, L.R. & Galio, K.A. (1985) Solid-phase syn­thesis, separation, and stereochemical aspects of P-chiral methane- and 4,4'-dimethoxytriph- enylmethanephosphonate analogues of oligo­deoxyribonucleotides. J. Org. Chem. 50, 3908-3913.
  • 18. Walder, R.Y. & Walder, J.A. (1988) Role of RNase-H in hybrid-arrested translation by an­tisense oligonucleotides. Proc. Natl Acad. Sci. U.S.A. 85, 5011-5015.
  • 19. Cierniewski, C.S., Pawłowska, Z., Pluskota, E., Stasiak, M., Kobylańska, A., Misiura, K., Maci­aszek, A., Koziołkiewicz, M. & Stec, W.J. (1996) Antisense oligonucleotides to PAI-1 mRNA as potential agents for therapeutic in­tervention in cardiovascular diseases. Biotech­nologia 4, 141-152.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

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