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The synthesis of a cobalt(II) tetracarboxyphthalocyanine-deoxyribooligonucleotide conjugate as a reagent for the directed DNA modification

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Abstract

The cobalt(II) tetracarboxyphthalocyanine-deoxyribonucleotide pd(TCTTCCCA) conjugate was synthesized. The phthalocyanineN-succinimide ester prepared from phthalocyanine using DCC was mixed in DMF with an aqueous solution of the oligonucleotide bearing a 1,3-diaminopropane linker at the 5′-phosphate. The resulting conjugate was tested in the intraduplex reaction with target 14-mer and 22-mer oligonucleotides containing conjugate-complementary sequences. In the presence of O2 and a thiol (2-mercaptoethanol or DTT), as a coupled reducer, or H2O2, sequence-specific DNA modification was observed that caused the cleavage of the target upon treatment with piperidine.

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Abbreviations

Ptc:

phthalocyanine residue

DMAP:

4-(dimethylamino)pyridine

References

  1. Belikova, A.M., Zarytova, V.F., and Grineva, N.I.,Tetrahedron Lett., 1967, vol. 37, pp. 3557–3562.

    Article  PubMed  CAS  Google Scholar 

  2. Knorre, D.G., Vlassov, V.V., Zarytova, V.F., Lebedev, A.V., and Fedorova, O.S.,Design and Targeted Reactions of Oligonucleotide Derivatives, Boca Raton, Fl: CRC, 1994.

    Google Scholar 

  3. Topics in Molecular and Structural Biology. V. 12. Oligodeoxynucleotides: Antisense Inhibitors of Gene Expression, Cohen, J.S., Ed., London: Macmillan, 1989.

    Google Scholar 

  4. Uhlman, E. and Peumann, A.,Chem. Rev., 1990, vol. 90, pp. 543–584.

    Article  Google Scholar 

  5. Prospects for Antisense Nucleic Acid Therapy of Cancer and AIDS, Wickstrom, E., Ed., New York: Wiley-Liss, 1991.

    Google Scholar 

  6. Antisense Research and Application, Crooke, S.T. and Lebleu, B., Eds., New York: CRC, 1993.

    Google Scholar 

  7. Kochevar, I. and Dunn, D.A.,Bioorganic Photochemistry, Morrison, H., Ed., New York: Willey, 1990, pp. 273–315.

    Google Scholar 

  8. Fedorova, O.S., Savitskii, A.P., Shoikhet, K.G., and Ponomarev, G.V.,FEBS Lett., 1990, vol. 259, pp. 335–337.

    Article  PubMed  CAS  Google Scholar 

  9. Le Doan, T., Perrouault, L., Héléne, C., Chassignol, M., and Thuong, N.T.,Biochemistry, 1986, vol. 25, pp. 6736–6739.

    Article  PubMed  Google Scholar 

  10. Le Doan, T., Perrouault, L., Chassignol, M., Thuong, N.T., and Héléne, C.,Nucleic Acids Res., 1987, vol. 15, pp. 8643–8659.

    Article  Google Scholar 

  11. Ivanova, E.M., Mamaev, S.V., Fedorova, O.S., and Frolova, E.I.,Bioorg. Khim., 1988, vol. 14, pp. 551–554.

    PubMed  CAS  Google Scholar 

  12. Mastruzzo, L., Woisard, A., Ma, D.D.F., Rizzarelli, E., Favre, A., and Le Doan, T.,Photochem. Photobiol., 1994, vol. 60, pp. 316–322.

    PubMed  CAS  Google Scholar 

  13. Boutorine, A.S., Brault, D., Takasugi, M., Delgado, O., and Héléne, C.,J. Am. Chem. Soc., 1996, vol. 118, pp. 9469–9476.

    Article  CAS  Google Scholar 

  14. Li, H., Fedorova, O.S., Trumble, W.R., Fletcher, T.R., and Czuchajowski, L.,Bioconjugate Chem., 1997, vol. 8, pp. 49–56.

    Article  Google Scholar 

  15. Frolova, E.I., Ivanova, E.M., Zarytova, V.F., Abramova, T.V., and Vlassov, V.V.,FEBS Lett., 1990, vol. 269, pp. 101–104.

    Article  PubMed  CAS  Google Scholar 

  16. Casas, C., Lasey, C.J., and Meunier, B.,Bioconjugate Chem., 1993, vol. 4, pp. 366–371.

    Article  CAS  Google Scholar 

  17. Frolova, E.I., Fedorova, O.S., and Knorre, D.G.,Biochimie, 1993, vol. 75, pp. 5–12.

    Article  PubMed  CAS  Google Scholar 

  18. Mestre, B., Pratviel, G., and Meunier, B.,Bioconjugate Chem., 1995, vol. 6, pp. 466–472.

    Article  CAS  Google Scholar 

  19. Magda, D., Miller, R.A., Sessler, J.L., and Iverson, B.L.,J. Am. Chem. Soc., 1994, vol. 116, pp. 7439–7440.

    Article  CAS  Google Scholar 

  20. Luk’yanets, E.A.,Ross. Khim. Zh., 1998, vol. 42, pp. 9–16.

    CAS  Google Scholar 

  21. Sinha, D.N. and Striepeke, S.,Oligonucleotides and Analogues: A Practical Approach, Eckstein, F., Ed., Oxford: Oxford Univ. Press, 1991, pp. 185–210.

    Google Scholar 

  22. Godovikova, T.S., Zarytova, V.F., and Khalimskaya, L.M.,Bioorg. Khim., 1986, vol. 12, pp. 475–481.

    CAS  Google Scholar 

  23. Borer, P.N.,Handbook of Biochemistry and Molecular Biology: Nucleic Acids, vol. 1, Fasman, G.D., Ed., 3rd ed., Cleveland: CRC, 1975, p. 589.

    Google Scholar 

  24. Knorre, D.G., Vlassov, V.V., Zarytova, V.F., and Karpova, G.G.,Advances in Enzyme Regulation. V. 24, Weber, G., Ed., Oxford: Pergamon, 1985, pp. 277–299.

    Google Scholar 

  25. Maxam, A.M. and Gilbert, M.,Methods Enzymol., 1980, vol. 65, pp. 499–560.

    Article  PubMed  CAS  Google Scholar 

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Correspondence to O. S. Fedorova.

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This article is dedicated to the 25th Anniversary of the journal Bioorganicheskaya Khimiya

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Koval, V.V., Chernonosov, A.A., Abramova, T.V. et al. The synthesis of a cobalt(II) tetracarboxyphthalocyanine-deoxyribooligonucleotide conjugate as a reagent for the directed DNA modification. Russ J Bioorg Chem 26, 104–110 (2000). https://doi.org/10.1007/BF02759155

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  • DOI: https://doi.org/10.1007/BF02759155

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