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Polymethylene derivatives of nucleic bases with ω-functional groups: VII. Cytotoxicity in the series of N-(2-oxocyclohexyl)-ω-oxoalkyl-substituted purines and pyrimidines

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Abstract

New polymethylene derivatives of the nucleic bases with β-diketo function in the ω-position have been synthesized by alkylation of uracil, thymine, cytosine, hypoxanthine, adenine, and N 2-isobutyryl guanine with 2-(ω-chloroalkanoyl)cyclohexanones. The physicochemical characteristics of compounds synthesized and their effect on tumor K562 and HCT116 cell lines have been studied.

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Abbreviations

DAPI:

4′,6-diamidimo-2-phenylindole dihydrochloride

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

References

  1. Komissarov, V.V., Panova, N.G., and Kritzyn, A.M., Rus. J. Bioorg. Chem., 2008, vol. 34, pp. 67–73; Bioorg. Khim., 2008, vol.34, pp. 75–82.

    CAS  Google Scholar 

  2. Pragnacharyulu, P.V.P., Varkhedkar, V., Curtis, M.A., Chang, I.F., and Abushanab, E., J. Med. Chem., 2000, vol. 43, pp. 4694–4700.

    Article  PubMed  CAS  Google Scholar 

  3. Boyd, H.F., Fell, S.C.M., Flynn, S.T., Hickey, D.M.B., Ife, R.J., Leach, C.A., Macphee, C.H., Milliner, K.J., Moores, K.E., Pinto, I.L., Porter, R.A., Rawlings, D.A., Smith, S.A., Stansfield, I.G., Tew, D.G., Theobald, C.J., and Whittaker, C.M., Bioorg. Med. Chem. Lett., 2000, vol. 10, pp. 2557–2561.

    Article  PubMed  CAS  Google Scholar 

  4. Wai, J.S., Egbertson, M.S., Payne, L.S., Fisher, T.E., Embrey, M.W., Tran, L.O., Melamed, J.Y., Langford, H.M., Guare, J.P., Zhuang, L., Grey, V.E., Vacca, J.P., Holloway, M.K., Naylor-Olsen, A.M., Hazuda, D.J., Felock, P.J., Wolfe, A.L., Stillmock, K.A., Schleif, W.A., Gabryelski, L.J., and Young, S.D., J. Med. Chem., 2000, vol. 43, pp. 4923–4926.

    Article  PubMed  CAS  Google Scholar 

  5. Grobler, J.A., Stillmock, K., Hu, B., Witmer, M., Felock, P., Espeseth, A.S., Wolfe, A., Egbertson, M., Bourgeois, M., Melamed, J., Wai, J.S., Young, S., Vacca, J., and Hazuda, D.J., Proc. Natl. Acad. Sci. USA, 2002, vol. 99, pp. 6661–6666.

    Article  PubMed  CAS  Google Scholar 

  6. Long, Y.-Q., Jiang, X.-H., Dayam, R., Sanchez, T., Shoemaker, R., Sei, S., and Neamati, N., J. Med. Chem., 2004, vol. 47, pp. 2561–2573.

    Article  PubMed  CAS  Google Scholar 

  7. Summa, V., Petrocchi, A., Matassa, V.G., Taliani, M., Laufer, R., De Francesco, R., Altamura, S., and Pace, P., J. Med. Chem., 2004, vol. 47, pp. 5336–5339.

    Article  PubMed  CAS  Google Scholar 

  8. Biswal, B.K., Cherney, M.M., Wang, M., Chan, L., Yannopoulos, C.G., Bilimoria, D., Nicolas, O., Bedard, J., and James, M.N.G., J. Biol. Chem., 2005, vol. 280, pp. 18 202–18 210.

    CAS  Google Scholar 

  9. Summa, V., Petrocchi, A., Pace, P., Matassa, V.G., De Francesco, R., Altamura, S., Tomei, L., Koch, U., and Neuner, P., J. Med. Chem., 2004, vol. 47, pp. 14–17.

    Article  PubMed  CAS  Google Scholar 

  10. Kopnin, B.P., in Kantserogenez (Cancerogenesis), Zaridze, D.G., Ed., Moscow: Meditsina, 2004, pp. 125–158.

    Google Scholar 

  11. Stavrovskaya, A.A., in Kantserogenez (Cancerogenesis), Zaridze, D.G, Ed., Moscow: Meditsina, 2004, pp. 558–574.

    Google Scholar 

  12. Galmarini, C.M., Mackey, J.R., and Dumontet, C., Lancet Oncol., 2002, vol. 3, pp. 415–424.

    Article  PubMed  CAS  Google Scholar 

  13. Konstantinova, I.D., Leont’eva, N.A., Galegov, G.A., Ryzhova, O.I., Chuvikovsky, D.V., Antonov, K.V., Esipov, R.S., Taran, S.A., Verevkina, K.N., Feofanov, S.A., and Miroshnikov, A.I., Rus. J. Bioorg. Chem., 2004, vol. 30, pp. 553–560; Bioorg. Khim., 2004, vol. 30, pp. 613–620.

    Article  CAS  Google Scholar 

  14. Manikowski, A., Verri, A., Lossani, A., Gebhardt, B.M., Gambino, J., Focher, F., Spadari, S., and Wright, G.E., J. Med. Chem., 2005, vol. 48, pp. 3919–3929.

    Article  PubMed  CAS  Google Scholar 

  15. Esteban-Gamboa, A., Balzarini, J., Esnouf, R., and De Clercq, E., Camarasa M.-J., and Perez-Perez M.-J, J. Med. Chem., 2000, vol. 43, pp. 971–983.

    Article  PubMed  CAS  Google Scholar 

  16. Halazy, S., Ehrhard, A., and Danzin, C., J. Am. Chem. Soc., 1991, vol. 113, pp. 315–317.

    Article  CAS  Google Scholar 

  17. Beauchamp, L.M., Tuttle, J.V., Rodriguez, M.E., and Sznaidman, M.L., J. Med. Chem., 1996, vol. 39, pp. 949–956.

    Article  PubMed  CAS  Google Scholar 

  18. Kelley, J.L., Bullock, R.M., Krochmal, M.P., McLean, E.W., Linn, J.A., Durcan, M.J., and Cooper, B.R., J. Med. Chem., 1997, vol. 40, pp. 3207–3216.

    Article  PubMed  CAS  Google Scholar 

  19. Zacharie, B., Gagnon, L., Attrado, G., Connolly, T.P., St-Dennis, Y., and Penney, C.L., J. Med. Chem., 1997, vol. 40, pp. 2883–2894.

    Article  PubMed  CAS  Google Scholar 

  20. Kritzyn, A.M. and Komissarov, V.V., Rus. J. Bioorg. Chem., 2004, vol. 30, pp. 436–440; Bioorg. Khim., 2004, vol. 30, pp. 487–492.

    Article  CAS  Google Scholar 

  21. Kritzyn, A.M., Vepsalainen, J., and Komissarov, V.V., Rus. J. Bioorg. Chem., 2005, vol. 31, pp. 256–262; Bioorg. Khim., 2005, vol. 31, pp. 288–294.

    Article  CAS  Google Scholar 

  22. Nesmeyanov, A.N. and Zakharkin, L.I., in: A.N. Nesmeyanov, Izbrannye trudy (Selected Works), Moscow, 1959, vol. 3, pp. 276–286.

  23. Meszarosova, K., Holy, A., and Masojidkova, M., Coll. Czech. Chem. Communs., 2000, vol. 65, pp. 1109–1125.

    Article  CAS  Google Scholar 

  24. Tietze, L. and Eicher, T., Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, New York: Georg Thieme Verlag Stuttgart, 1991. Preparativnaya organicheskaya khimiya: Per. s nem (Preparative Organic Chemistry), Moscow: Mir, 1999.

    Google Scholar 

  25. Sidorova, T.A., Nigmatov, A., Kakpakova, E.S., Stavrovskaya, A.A., Gerassimova, G.K., Shtil, A.A., and Serebryakov, E.P., J. Med. Chem., 2002, vol. 45, pp. 5330–5339.

    Article  PubMed  CAS  Google Scholar 

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Authors and Affiliations

  1. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 119991, Russia

    V. V. Komissarov & A. M. Kritzyn

  2. Blokhin Russian Cancer Research Center of Oncology, Russian Academy of Medical Sciences, Kashirskoe sh. 24, Moscow, 115478, Russia

    G. M. Volgareva, Ya. S. Ol’shanskaya, M. E. Chernyshova & A. A. Shtil’

  3. Moscow Hertzen Institute of Oncology, Russian Academy of Medical Sciences, Moscow, Russia

    L. E. Zavalishina & G. A. Frank

Authors
  1. V. V. Komissarov
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  2. G. M. Volgareva
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  3. Ya. S. Ol’shanskaya
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  4. M. E. Chernyshova
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  5. L. E. Zavalishina
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  6. G. A. Frank
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  7. A. A. Shtil’
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  8. A. M. Kritzyn
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Corresponding author

Correspondence to A. M. Kritzyn.

Additional information

Original Russian Text © V.V. Komissarov, G.M. Volgareva, Ya.S. Ol’shanskaya, M.E. Chernyshova, L.E. Zavalishina, G.A. Frank, A.A. Shtil’, A.M. Kritzyn, 2009, published in Bioorganicheskaya Khimiya, 2009, Vol. 35, No. 1, pp. 84–94.

For communication VI see [1].

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Komissarov, V.V., Volgareva, G.M., Ol’shanskaya, Y.S. et al. Polymethylene derivatives of nucleic bases with ω-functional groups: VII. Cytotoxicity in the series of N-(2-oxocyclohexyl)-ω-oxoalkyl-substituted purines and pyrimidines. Russ J Bioorg Chem 35, 75–85 (2009). https://doi.org/10.1134/S1068162009010105

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  • DOI: https://doi.org/10.1134/S1068162009010105

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