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Synthesis and Inhibitory Properties of Imines Containing Monoterpenoid and Adamantane Fragments Against DNA Repair Enzyme Tyrosyl-DNA Phosphodiesterase 1 (Tdp1)

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Chemistry of Natural Compounds Aims and scope

Six imines including four new ones were synthesized via the reaction of monoterpenoid aldehydes with aminoadamantanes. The inhibitory activities of the synthesized compounds against purified human recombinant DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 (Tdp1) fell in the range IC50 = 5.5–7.1 μM.

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References

  1. E. Q. Comeaux and R. C. Van Waardenburg, Drug Metab. Rev., 46, 494 (2014).

    Article  PubMed  CAS  Google Scholar 

  2. F. Cortes Ledesma, S. F. El Khamisy, M. C. Zuma, K. Osborn, and K. W. Caldecott, Nature, 461, 674 (2009).

    Article  PubMed  CAS  Google Scholar 

  3. L. F. Povirk, ISRN Mol. Biol., 1 (2012).

  4. T. S. Dexheimer, S. Antony, C. Marchand, and Y. Pommier, Anti-Cancer Agents Med. Chem., 8, 381 (2008).

    Article  CAS  Google Scholar 

  5. G. L. Beretta, G. Cossa, L. Gatti, F. Zunino, and P. Perego, Curr. Med. Chem., 17, 1500 (2010).

    Article  PubMed  CAS  Google Scholar 

  6. D. R. Davies, H. Interthal, J. J. Champoux, and W. G. J. Hol, J. Mol. Biol., 324, 917 (2003).

    Article  Google Scholar 

  7. C. Meisenberg, D. C. Gilbert, A. Chalmers, V. Haley, S. Gollins, S. E. Ward, and S. F. El-Khamisy, Mol. Cancer Ther., 14, 575 (2015).

    Article  PubMed  CAS  Google Scholar 

  8. J. H. Jun, V. Kumar, T. S. Dexheimer, I. Wedlich, M. C. Nicklaus, Y. Pommier, and S. V. Malhotra, Eur. J. Pharm. Sci., 111, 337 (2018).

    Article  PubMed  CAS  Google Scholar 

  9. T. X. Nguyen, A. Morrell, M. Conda-Sheridan, C. Marchand, K. Agama, A. Bermingam, A. G. Stephen, A. Chergui, A. Naumova, R. Fisher, B. R. O′Keefe, Y. Pommier, and M. Cushman, J. Med. Chem., 55, 4457 (2012).

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  10. S. Antony, C. Marchand, A. G. Stephen, L. Thibaut, K. K. Agama, R. J. Fisher, and Y. Pommier, Nucleic Acids Res., 35, 4474 (2007).

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  11. A. Bermingham, E. Price, C. Marchand, A. Chergui, A. Naumova, E. L. Whitson, L. R. H. Krumpe, E. I. Goncharova, J. R. Evans, T. C. McKee, C. J. Henrich, Y. Pommier, and B. R. O′Keefe, SLAS Discovery, 22, 1093 (2017).

    CAS  Google Scholar 

  12. A. L. Zakharenko, T. M. Khomenko, S. V. Zhukova, O. A. Koval, O. D. Zakharova, R. O. Anarbaev, N. A. Lebedeva, D. V. Korchagina, N. I. Komarova, V. G. Vasiliev, J. Reynisson, K. P. Volcho, N. F. Salakhutdinov, and O. I. Lavrik, Bioorg. Med. Chem., 23, 2044 (2015).

    Article  PubMed  CAS  Google Scholar 

  13. A. Zakharenko, O. Luzina, O. Koval, D. Nilov, I. Gushchina, N. Dyrkheeva, V. Svedas, N. Salakhutdinov, and O. Lavrik, J. Nat. Prod., 79, 2961 (2016).

    Article  PubMed  CAS  Google Scholar 

  14. T. Khomenko, A. Zakharenko, T. Odarchenko, H. J. Arabshahi, V. Sannikova, O. Zakharova, D. Korchagina, J. Reynisson, K. Volcho, N. Salakhutdinov, and O. Lavrik, Bioorg. Med. Chem., 24, 5573 (2016).

    Article  PubMed  CAS  Google Scholar 

  15. A. L. Zakharenko, K. Yu. Ponomarev, E. V. Suslov, D. V. Korchagina, K. P. Volcho, I. A. Vasil′eva, N. F. Salakhutdinov, and O. I. Lavrik, Russ. J. Bioorg. Chem., 41, 657 (2015).

    Article  CAS  Google Scholar 

  16. K. Y. Ponomarev, E. V. Suslov, A. L. Zakharenko, O. D. Zakharova, A. D. Rogachev, D. V. Korchagina, A. Zafar, J. Reynisson, A. A. Nefedov, K. P. Volcho, N. F. Salakhutdinov, and O. I. Lavrik, Bioorg. Chem., 76, 392 (2018).

    Article  PubMed  CAS  Google Scholar 

  17. A. S. Sokolova, O. I. Yarovaya, D. S. Baev, A. V. Shernyukov, A. A. Shtro, V. V. Zarubaev, and N. F. Salakhutdinov, Eur. J. Med. Chem., 127, 661 (2017).

    Article  PubMed  CAS  Google Scholar 

  18. V. V. Zarubaev, A. V. Garshinina, T. S. Tretiak, V. A. Fedorova, A. A. Shtro, A. S. Sokolova, O. I. Yarovaya, and N. F. Salakhutdinov, Antiviral Res., 120, 126 (2015).

    Article  PubMed  CAS  Google Scholar 

  19. D. H. R. Barton and G. Fontana, Synth. Commun., 26, 1953 (1996).

    Article  CAS  Google Scholar 

  20. P. W. Jensen, M. Falconi, E. L. Kristoffersen, A. T. Simonsen, J. B. Cifuentes, L. B. Marcussen, R. Frohlich, J. Vagner, C. Harmsen, S. Juul, Y. P. Ho, M. A. Withers, J. R. Lupski, J. Koch, A. Desideri, B. R. Knudsen, and M. Stougaard, Biosens. Bioelectron., 15, 230 (2013).

    Article  CAS  Google Scholar 

  21. E. Suslov, K. Ponomarev, A. Rogachev, M. Pokrovsky, A. Pokrovsky, M. Pykhtina, A. Beklemishev, D. Korchagina, K. Volcho, and N. Salakhutdinov, Med. Chem., 11, 629 (2015).

    Article  PubMed  CAS  Google Scholar 

  22. N. A. Lebedeva, N. I. Rechkunova, and O. I. Lavrik, FEBS Lett., 585, 683 (2011).

    Article  PubMed  CAS  Google Scholar 

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Acknowledgment

The research was sponsored by a Grant of the Russian Science Foundation (Project No. 16-13-10074). We thank the Khimiya Common Use Center of NIOCh SB RAS for taking the spectral and analytical measurements.

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Correspondence to E. V. Suslov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2018, pp. 569–572.

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Zakharenko, A.L., Mozhaitsev, E.S., Suslov, E.V. et al. Synthesis and Inhibitory Properties of Imines Containing Monoterpenoid and Adamantane Fragments Against DNA Repair Enzyme Tyrosyl-DNA Phosphodiesterase 1 (Tdp1). Chem Nat Compd 54, 672–676 (2018). https://doi.org/10.1007/s10600-018-2443-7

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  • DOI: https://doi.org/10.1007/s10600-018-2443-7

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