Advertisement

Russian Chemical Bulletin

, Volume 64, Issue 6, pp 1335–1340 | Cite as

Synthesis and proliferative activity of a new derivative of the lupan pentacyclic triterpenoids, viz., the sulfobetaine based on betulin with a 4-(dimethylammonio)butane-1-sulfonate moiety

  • S. N. Dubovitsky
  • N. G. Komissarova
  • O. V. Shitikova
  • L. V. Spirikhin
  • D. V. Khasanova
  • L. F. Zainullina
  • M. F. Abdullin
  • Y. V. Vakhitova
  • M. S. Yunusov
Full Articles
  • 50 Downloads

Abstract

A new zwitterionic derivative of the lupan pentacyclic triterpenoid series, viz., the sulfobetaine with a 4-(dimethylammonio)butane-1-sulfonate moiety, was synthesized by quaternization of betulin 28-(2-dimethylaminoacetate) with 1,4-butane sultone. The sulfobetaine was found to possess a dose-dependent proliferative effect toward human embrionic kidney cells HEK293 and human T-lymphocytes. Betulin chosen as a comparison compound demonstrated an effect against cells of both the tumor (HepG2, Jurkat) and the normal origin (human HEK293 and T-lymphocytes) which differ from that of the sulfobetaine, inhibiting their proliferation. The new sulfobetaine can prove to be a promising basis for the development of reparative and immunostimulating agents.

Key words

betulin betulin 28-(2-bromoacetate) 1,4-butane sultone sulfobetaine HEK293 Jurkat HepG2 cell lines T-lymphocytes proliferative activity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Russ. J. Bioorg. Chem.Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 32, 37 [Bioorg. Khim., 2006, 32, 42].Google Scholar
  2. 2.
    T. G. Tolstikova, I. V. Sorokina, G. A. Tolstikov, A. G. Tolstikov, O. B. Flekhter, Russ. J. Bioorg. Chem.Russ. J. Bioorg. Chem. (Engl. Transl.), 2006, 32, 261 [Bioorg. Khim., 2006, 32, 291].Google Scholar
  3. 3.
    G. A. Tolstikov, O. B. Flekhter, E. E. Shults, L. A. Baltina, A. G. Tolstikov, Khimiya v interesakh ustoichivogo razvitiya [Chem. Sustain. Dev.], 2005, 13, 1 (in Russian).Google Scholar
  4. 4.
    B. K. Cassels, M. Asencio, Phytochem. Rev., 2011, 10, 545.CrossRefGoogle Scholar
  5. 5.
    H. Kommera, G. N. Kaluderovic, J. Kalbitz, R. Paschke, Arch. Pharm. Chem. Life Sci., 2010, 343, 449.CrossRefGoogle Scholar
  6. 6.
    J. Patocka, J. Appl. Biomed., 2003, 1, 7.Google Scholar
  7. 7.
    US Pat. 20070259839A1, https://www.google.ru/patents/US20070259839.Google Scholar
  8. 8.
    J. Holy, O. Kolomitsyna, D. Krasutsky, P. J. Oliveira, E. Perkins, P. A. Krasutsky, Bioorg. Med. Chem., 2010, 18, 6080.CrossRefGoogle Scholar
  9. 9.
    T. C. Bernardo, T. Cunha-Oliveira, T. L. Serafim, J. Holy, D. Krasutsky, O. Kolomitsyna, P. Krasutsky, A. M. Moreno, P. J. Oliveira, Bioorg. Med. Chem., 2013, 21, 7239.CrossRefGoogle Scholar
  10. 10.
    T. L. Serafim, F. S. Carvalho; T. C. Bernardo, G. C. Pereira, E. Perkins, J. Holy, D. A. Krasutsky, O. N. Kolomitsyna, P. A. Krasutsky, P. J. Oliveira, Bioorg. Med. Chem., 2014, 22, 6270.CrossRefGoogle Scholar
  11. 11.
    WO Pat. 2012160187 A1, https://www.google.ru/patents/WO2012160187A1?cl=en&dq=2012160187+A1&hl=ru&sa=X&ei=vJYBVe3Nom9Pc_AgfAP&ved=0CBwQ6AEwAA.Google Scholar
  12. 12.
    US Pat. 5545667, https://www.google.ru/patents/US5545667.Google Scholar
  13. 13.
    US Pat. 6136857, https://www.google.ru/patents/US6136857.Google Scholar
  14. 14.
    L. Sonnenschein, A. Seubert, Tetrahedron Lett., 2011, 52, 1101.CrossRefGoogle Scholar
  15. 15.
    Th. A. Spencer, Th. J. Onofrey, R. O. Cann, J. S. Russel, L. E. Lee, D. E. Blanchard, A. Castro, P. Gu, G. Jiang, I. Shechter, J. Org. Chem., 1999, 64, 807.CrossRefGoogle Scholar
  16. 16.
    Z. Chu, Y. Feng, Synlett, 2009, 16, 2655.Google Scholar
  17. 17.
    R. S. Ward, J. Davies, G. Hodges, D. W. Roberts, Synthesis, 2002, 16, 2431.CrossRefGoogle Scholar
  18. 18.
    Pat. RF, No. 2270201; Byul. isobret. [Invention Bull.], 2006, 1 (in Russian).Google Scholar
  19. 19.
    D. V. Sergeev, S. N. Proshin, G. I. D´yachuk, Mediko-biolog. sotsial´no-psikholog. problemy bezopasnosti v chrezvych. situatsiyakh [Medicobiol. Social Psychol. Problems of Safety in Emergency Situations], 2011, 3, 76 (in Russian).Google Scholar
  20. 20.
    Pat. RF, No. 2211843; http://www.freepatent.ru/images/patents/107/2357973/patent-2357973.pdf (in Russian).Google Scholar
  21. 21.
    L. Pohjala, S. Alakurtt, T. Ahola, J. Yli-Kauhaluoma, P. Tammela, J. Nat. Prod., 2009, 72, 1917.CrossRefGoogle Scholar
  22. 22.
    A. Boyum, Scand. J. Lab. Clin. Invest., 1968, 21, 77.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • S. N. Dubovitsky
    • 1
  • N. G. Komissarova
    • 1
  • O. V. Shitikova
    • 1
  • L. V. Spirikhin
    • 1
  • D. V. Khasanova
    • 2
  • L. F. Zainullina
    • 2
  • M. F. Abdullin
    • 1
  • Y. V. Vakhitova
    • 2
  • M. S. Yunusov
    • 1
  1. 1.Ufa Institute of ChemistryRussian Academy of SciencesUfaRussian Federation
  2. 2.Institute of Biochemistry and GeneticsUfa Scientific Centre of the Russian Academy of SciencesUfaRussian Federation

Personalised recommendations