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Synthesis of steroid analogs of tubuloclustin, their cytotoxicity and effect on microtubules of A549 carcinoma cells

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Abstract

Synthesis of analogs of tubuloclustin (N-(7-adamant-2-yloxy-7-oxoheptanoyl)-N-deacetylcolchicine (1)) with the colchicine fragment replaced with 2-methoxyestradiol scaffold attached via phenolic hydroxy group was described. Esters 3a–c exhibit moderate cytotoxicity (EC50 = 5–6 μmol L–1) and exert a weak effect on the microtubule network in A549 human lung carcinoma cells similar to the clustering effect of tubuloclustin and its derivatives. Conjugates 6a–c and 7a–c with the phenolic ester bond are low stable and compounds 7a–c are inactive to the microtubules of A549 cells, while compounds 6a–c cause an unusual effect of curling of the microtubules.

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References

  1. O. N. Zefirova, H. Lemcke, M. Lantow, E. V. Nurieva, B. Wobith, G. E. Onishchenko, A. Hoenen, G. Griffiths, N. S. Zefirov, S. A. Kuznetsov, ChemBioChem, 2013, 14, 1444.

    Article  CAS  PubMed  Google Scholar 

  2. O. N. Zefirova, E. V. Nurieva, Ya. S. Glazkova, N. A. Zefirov, A. V. Mamaeva, B. Wobith, V. I. Romanenko, N. A. Lesnaya, E. M. Treshchalina, S. A. Kuznetsov, Pharm. Chem. J., 2014, 48,373.

    Article  CAS  Google Scholar 

  3. B. Kumar, R. Kumar, I. Skvortsova, V. Kumar, Curr. Cancer Drug Targets, 2017, 4,357.

    Article  CAS  Google Scholar 

  4. O. N. Zefirova, E. V. Nurieva, B. Wobith, V. V. Gogol, N. A. Zefirov, A. V. Ogonkov, D. V. Shishov, N. S. Zefirov, S. A. Kuznetsov, Mol. Divers., 2017, 21,547.

    Article  CAS  PubMed  Google Scholar 

  5. O. N. Zefirova, Ya. S. Glazkova, E. V. Nurieva, N. A. Zefirov, A. V. Mamaeva, B. Wobith, N. S. Zefirov, S. A. Kuznetsov, Russ. Chem. Bull., 2014, 63, 1126.

    Article  CAS  Google Scholar 

  6. E. V. Nurieva, N. A. Zefirov, N. S. Zefirov, S. A. Kuznetsov, O. N. Zefirova, Russ. Chem. Bull., 2017, 64, 2248.

    Article  CAS  Google Scholar 

  7. B. S. Kumar, D. S. Raghuvanshi, M. Hasanain, S. Alam, J. Sarkar, K. Mitra, F. Khan, A. S. Negi, Steroids, 2016, 110,9.

    Article  CAS  PubMed  Google Scholar 

  8. S. Verenich, P. M. Gerk, Mol. Pharmaceutics, 2010, 7, 2030.

    Article  CAS  Google Scholar 

  9. T. L. Nguyen, C. McGrath, A. R. Hermone, J. C. Burnett, D. W. Zaharevitz, B. W. Day, P. Wirf, E. Hamel, R. Gussio, J. Med. Chem., 2005, 48, 6107.

    Article  CAS  PubMed  Google Scholar 

  10. N. A. Zefirov, O. N. Zefirova, Russ. J. Org. Chem., 2015, 51, 1207.

    Article  CAS  Google Scholar 

  11. M. Rajabi, M. Lanfranchi, F. Campo, L. Panza, Synth. Commun., 2014, 44, 1149.

    Article  CAS  Google Scholar 

  12. J. Klimentova, P. Kosak, K. Vavrova, T. Holas, A. Hrabálek, Bioorg. Med. Chem., 2006, 14, 7681.

    Article  CAS  PubMed  Google Scholar 

  13. L. S. Suwandi, G. E. Agoston, J. H. Shah, A. D. Hanson, X. H. Zhan, T. M. LaVallee, A. M. Treston, Bioorg. Med. Chem. Lett., 2009, 19, 6459.

    Article  CAS  PubMed  Google Scholar 

  14. T. Mosmann, J. Immunol. Methods, 1983, 65,55.

    Article  CAS  PubMed  Google Scholar 

  15. E. V. Nurieva, N. A. Zefirov, A. V. Mamaeva, Y. K. Grishin, S. A. Kuznetsov, O. N. Zefirova, Mendeleev Commun., 2017, 27, 240.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991, Moscow, Russian Federation, Russia

    E. V. Nurieva, N. A. Zefirov, A. V. Mamaeva & O. N. Zefirova

  2. Institute of Physiologically Active Compounds, Russian Academy of Sciences, 1 Severnyi proezd, Chernogolovka, Moscow Region, Russian Federation, 142432, Russia

    N. A. Zefirov & O. N. Zefirova

  3. Institute of Biological Sciences, University of Rostock, 18106, Rostock, Germany

    B. Wobith & S. A. Kuznetsov

Authors
  1. E. V. Nurieva
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  2. N. A. Zefirov
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  3. A. V. Mamaeva
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  4. B. Wobith
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  5. S. A. Kuznetsov
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  6. O. N. Zefirova
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Corresponding author

Correspondence to O. N. Zefirova.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0688–0693, April, 2018.

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Nurieva, E.V., Zefirov, N.A., Mamaeva, A.V. et al. Synthesis of steroid analogs of tubuloclustin, their cytotoxicity and effect on microtubules of A549 carcinoma cells. Russ Chem Bull 67, 688–693 (2018). https://doi.org/10.1007/s11172-018-2123-6

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  • DOI: https://doi.org/10.1007/s11172-018-2123-6

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