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Synthesis and properties of 2′,3′-anhydro derivatives of (2′-5′)-oligoadenylates containing modified heterobases

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Chemistry of Natural Compounds Aims and scope

New analogs of natural (2′-5′)-oligoadenylates containing ribavirin or BAP-riboside fragments in addition to adenine 2′,3′-anhydronucleoside units were obtained. The synthesized compounds were highly stable to enzymatic hydrolysis by snake venom phosphodiesterase. It was shown that ribavirin-containing (2′-5′)-oligonucleotides could be used for elimination of pathogenic raspberry ringspot virus in culture in vitro of microrunners of black current and cherry.

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References

  1. M. R. Player and P. F. Torrence, Pharmacol. Ther., 78, No. 2, 55 (1998).

    Article  PubMed  CAS  Google Scholar 

  2. R. H. Silverman, J. Virol., 81, No. 23, 12720 (2007).

    Article  PubMed  CAS  Google Scholar 

  3. J. A. C. Castelli, B. A. Hassel, K. A. Wood, X.-L. Li, K. Amemiya, M. C. Dalakas, P. F. Torrence, and R. J. Youle, J. Exp. Med., 186, No. 6, 967 (1997).

    Article  PubMed  CAS  Google Scholar 

  4. O. N. Kulaeva, A. F. Fedina, E. A. Barkhanova, N. N. Karavaiko, M. Ya. Karpeisky, I. B. Kaplan, M. E. Taliansky, and J. G. Atabekov, Plant Mol. Biol., 20, No. 3, 383 (1992).

    Article  PubMed  CAS  Google Scholar 

  5. Y. Devash, A. Gera, D. H. Willis, M. Reichman, W. Pfleiderer, R. Charubala, I. Sela, and R. J. Suhadolnik, J. Biol. Chem., 259, No. 6, 3482 (1984).

    PubMed  CAS  Google Scholar 

  6. Z. Yu. Tkachuk, V. S. Artemenko, and L. I. Semernikova, Biopolim. Kletka, 11, No. 9, 1227 (1993).

    Google Scholar 

  7. Y. Devash, M. Reichman, I. Sela, N. L. Reichenbach, and R. J. Suhadolnik, Biochemistry, 24, No. 3, 393 (1985).

    Article  Google Scholar 

  8. E. Truve, L. Nigul, T. H. Teeri, and M. Kelve, Nucleosides and Nucleotides, 15, No. 5, 1097 (1996).

    Article  CAS  Google Scholar 

  9. E. I. Kvasyuk, T. I. Kulak, O. V. Tkachenko, S. L. Sentyureva, I. A. Mikhailopulo, R. J. Suhadolnik, E. E. Henderson, S. E. Horvath, M.-X. Guan, and W. Pfleiderer, Helv. Chim. Acta, 80, No. 4, 1053 (1997).

    Article  CAS  Google Scholar 

  10. E. I. Kvasyuk, T. I. Kulak, O. V. Tkachenko, S. L. Sentyureva, I. A. Mikhailopulo, A. I. Zinchenko, and V. N. Barai, Izv. Nat. Akad. Nauk Belarusi, Ser. Khim. Nauk, 3, 73 (1996).

    Google Scholar 

  11. E. I. Kvasyuk, T. I. Kulak, A. I. Zinchenko, V. N. Barai, and I. A. Mikhailopulo, Bioorg. Khim., 22, No. 3, 208 (1996).

    CAS  Google Scholar 

  12. R. Charubala, W. Pfleiderer, R. J. Suhadolnik, K. T. Iacono, N. F. Muto, J. W. Homan, C. Martinand-Mari, S. E. Horvath, E. E. Henderson, A. Steele, and T. J. Rogers, Helv. Chim. Acta, 85, No. 8, 2284 (2002).

    Article  CAS  Google Scholar 

  13. I. A. Mikhailopulo, Z. Yu. Tkachuk, E. A. Baran, L. V. Tkachuk, A. V. Kozlov, I. I. Slukvin, T. I. Kulak, E. I. Kvasyuk, and G. K. Matsuka, Nucleosides and Nucleotides, 14, No. 3–5, 1105 (1995).

    CAS  Google Scholar 

  14. G. S. Ti, B. L. Gaffney, and R. A. Jones, J. Am. Chem. Soc., 104, No. 5, 1316 (1982).

    Article  CAS  Google Scholar 

  15. G. G. Sivets, E. N. Kalinichenko, and I. A. Mikhailopulo, Lett. Org. Chem., 3, No. 5, 402 (2006).

    Article  CAS  Google Scholar 

  16. M. J. Robins, Y. Fouron, and R. Mengel, J. Org. Chem., 39, No. 11, 1564 (1974).

    Article  PubMed  CAS  Google Scholar 

  17. H. Sawai, K. Kuroda, J. Seki, and H. Ozaki, Biopolymers, 39, No. 2, 173 (1996).

    Article  PubMed  CAS  Google Scholar 

  18. A. V. Itkes, M. Ya. Karpeisky, O. N. Kartasheva, S. N. Mikhailov, G. P. Moiseyev, W. Pfleiderer, R. Charubala, and G. I. Yakovlev, FEBS Lett., 236, No. 2, 325 (1988).

    Article  PubMed  CAS  Google Scholar 

  19. K. Kubota, K. Nakahara, T. Ohtsuka, S. Yoshida, J. Kawaguchi, Y. Fujita, Y. Ozeki, A. Hara, C. Yoshimura, H. Furukawa, H. Haruyama, K. Ichikawa, M. Yamashita, T. Matsuoka, and Y. Iijima, J. Biol. Chem., 279, No. 36, 37832 (2004).

    Article  PubMed  CAS  Google Scholar 

  20. J. B. Poulsen, K. R. Andersen, K. H. Kjaer, F. Durand, P. Faou, A. L. Vestergard, G. H. Talbo, N. Hoogenraad, D. E. Brodersen, J. Justesen, and P. M. Martensen, Nucleic Acid Res., 39, No. 9, 3754 (2011).

    Article  PubMed  CAS  Google Scholar 

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Correspondence to T. I. Kulak.

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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2013, pp. 613–618.

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Kulak, T.I., Tsibul′skaya, I.A., Tkachenko, O.V. et al. Synthesis and properties of 2′,3′-anhydro derivatives of (2′-5′)-oligoadenylates containing modified heterobases. Chem Nat Compd 49, 716–722 (2013). https://doi.org/10.1007/s10600-013-0715-9

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  • DOI: https://doi.org/10.1007/s10600-013-0715-9

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