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Russian Chemical Bulletin

, 59:2219 | Cite as

Synthesis of conjugates of lupane triterpenoids with chromane antioxidants and in vitro study of their influence on the production of nitrogen monoxide and on the arginase activity in activated macrophages

  • A. Yu. Spivak
  • R. R. Khalitova
  • Yu. P. Bel’skii
  • A. N. Ivanova
  • E. R. Shakurova
  • N. V. Bel’skaya
  • V. N. Odinokov
  • M. G. Danilets
  • A. A. Ligacheva
Full Articles

Abstract

Conjugates of lupane triterpenoids (betulin and betulonic and betulinic acids) with synthetic analogs of α-tocopherol were obtained via ester bond formation and tested in vitro. Showing low cytotoxicity, some of them suppress nitrogen monoxide production without affecting the activity of arginase, which suggests their antiinflammatory and immunomodulating properties.

Key words

lupane triterpenoids antioxidants chromanes tocopherols bioconjugates nitrogen monoxide activated macrophages antiinflammatory activity 

References

  1. 1.
    S. V. Vasil’eva, in Khimicheskaya i biologicheskaya kinetika. Novye gorizonty. Biologicheskaya kinetika: Sb. obzornykh statei [Chemical and Biological Kinetics. New Horizons. Biological Kinetics: A Collection of Reviews], Khimiya, Moscow, 2005, 2, p. 579 (in Russian).Google Scholar
  2. 2.
    S. Goerdt, C. E. Orfanos, Immunity, 1999, 10, 137.CrossRefGoogle Scholar
  3. 3.
    S. Ehrt, D. Schnappinger, S. Bekiranov, J. Exp. Med., 2001, 194, 1123.CrossRefGoogle Scholar
  4. 4.
    D. M. Mosser, J. Leukoc. Biol., 2003, 73, 209.CrossRefGoogle Scholar
  5. 5.
    A. Mantovani, Blood, 2006, 108, 408.CrossRefGoogle Scholar
  6. 6.
    M. Munder, K. Eichmann, M. Modolell, J. Immunol., 1998, 160, 5347.Google Scholar
  7. 7.
    T. Kreider, R. M. Anthony, J. F. Urban, Jr., W. C. Gause, Curr. Opin. Immunol., 2007, 19, 448.CrossRefGoogle Scholar
  8. 8.
    H. Maeda, T. Akaike, Biochemistry (Moscow), 1998, 63, 854.Google Scholar
  9. 9.
    T. Akaike, M. Suga, H. Maeda, Pros. Soc. Exp. Biol. Med., 1998, 217, 64.Google Scholar
  10. 10.
    J. Wang, G. Mazza, J. Agric. Food Chem., 2002, 50, 850.CrossRefGoogle Scholar
  11. 11.
    T. Motai, S. Kitanaka, J. Nat. Prod., 2005, 68, 1732.CrossRefGoogle Scholar
  12. 12.
    Li-Yue Nie, J.-J. Qin, Y. Huang, L. Yan, Yu-Bo Liu, Yue-Xing Pan, Hui-Zi Jin, Wei-Dong Zhang, J. Nat. Prod., 2010, 73, 1117.CrossRefGoogle Scholar
  13. 13.
    T. Honda, B.-A. V. Rounds, L. Bore, H. J. Finlay, F. G. Favaloro, N. Suh, Y. Wang, M. B. Sporn, G. W. Gribble, J. Med. Chem., 2000, 43, 4233.CrossRefGoogle Scholar
  14. 14.
    T. Honda, G. W. Gribble, N. Suh, H. J. Finlay, B.-A. V. Rounds, L. Bore, F. G. Favaloro, Jr., Y. Wang, M. B. Sporn, J. Med. Chem., 2000, 43, 1866.CrossRefGoogle Scholar
  15. 15.
    T. Honda, Y. Honda, F. G. Favaloro, G. W. Gribble, N. Suh, A. E. Place, M. H. Rendi, M. B. Sporn, Bioorg. Med. Chem. Lett., 2002, 12, 1027.CrossRefGoogle Scholar
  16. 16.
    T. Honda, K. T. Liby, X. Su, C. Sundararajan, Y. Honda, N. Suh, R. Risingsong, C. R. Williams, D. B. Royce, M. B. Sporn, G. W. Gribble, Bioorg. Med. Chem. Lett., 2006, 15, 6306.CrossRefGoogle Scholar
  17. 17.
    K. Liby, T. Honda, C. R. Williams, R. Risingsong, D. B. Royce, N. Suh, A. T. Dinkova-Kostova, K. K. Stephenson, P. Talalay, C. Sundararajan, G. W. Gribble, M. B. Sporn, Mol. Cancer Ther., 2007, 6, 2123.CrossRefGoogle Scholar
  18. 18.
    V. N. Odinokov, A. Yu. Spivak, O. V. Knyshenko, Bioorg. Khim., 2007, 33, 387 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2007, 33].Google Scholar
  19. 19.
    A. Detsi, D. Bouloumbasi, K. C. Prousis, M. Koufaki, G. Athanasellis, G. Melagraki, A. Afantitis, O. Igglessi-Markopoulou, Ch. Kontogiorgis, D. J. Hadjipavlou-Litina, J. Med. Chem., 2007, 50, 2450.CrossRefGoogle Scholar
  20. 20.
    A. Di Stefano, P. Sozio, A. Cocco, A. Iannitelli, E. Santussi, M. Costa, L. Pessi, C. Nasuti, F. Cantalamessa, F. Pinnen, J. Med. Chem., 2006, 49, 1486.CrossRefGoogle Scholar
  21. 21.
    M. Nozawa, K. Takhashi, K. Kato, H. Akita, Chem. Pharm. Bull., 2000, 48, 272.Google Scholar
  22. 22.
    S. Genet, A. Strehle, C. Schmidt, G. Boudjelal, A. Lobstein, K. Schoonjans, M. Souchet, J. Auwerx, R. Saladin, A. Wagner, J. Med. Chem., 2010, 53, 178.CrossRefGoogle Scholar
  23. 23.
    A. Yu. Spivak, R. R. Mufazzalova, E. R. Shakurova, V. N. Odinokov, Zh. Org. Khim., 2010, 46, 1355 [Russ. J. Org. Chem. (Engl. Transl.), 2010, 46].Google Scholar
  24. 24.
    G. A. Tolstikov, M. I. Goryaev, Kh. O. Kim, R. A. Khegai, Zh. Prikl. Khim., 1967, 40, 920 [J. Appl. Chem. USSR (Engl. Transl.), 1967, 40].Google Scholar
  25. 25.
    O. B. Flekhter, E. I. Boreko, L. R. Nigmatullina, E. V. Tret’yakova, N. I. Pavlova, L. A. Baltina, S. N. Nikolaeva, O. V. Savinova, V. F. Eremin, F. Z. Galin, G. A. Tolstikov, Bioorg. Khim., 2004, 30, 89 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2004, 30].Google Scholar
  26. 26.
    R. M. Kondratenko, L. A. Baltina, E. V. Vasil’eva, L. A. Baltina, Jr., A. F. Ismagilova, Kh. M. Nasyrov, N. Zh. Baschenko, R. M. Kireeva, S. M. Fridman, G. A. Tolstikov, Bioorg. Khim., 2004, 30, 61 [Russ. J. Bioorg. Chem. (Engl. Transl.), 2004, 30].Google Scholar
  27. 27.
    K. Hiroya, T. Takahashi, N. Miura, A. Naganuma, T. Sakamoto, Bioorg. Med. Chem., 2002, 10, 3229.CrossRefGoogle Scholar
  28. 28.
    S. A. S. Pope, G. E. Burtin, P. T. Clayton, D. J. Madge, D. P. R. Muller, Free Radical Biol. Med., 2002, 33, 807.CrossRefGoogle Scholar
  29. 29.
    H. Lei, J. Atkinson, J. Org. Chem., 2000, 65, 2560.CrossRefGoogle Scholar
  30. 30.
    K. Hiroya, T. Takahashi, N. Miura, A. Naganuma, T. Sakamoto, Bioorg. Med. Chem., 2002, 10, 3229.CrossRefGoogle Scholar
  31. 31.
    K. A. Lawson, K. Anderson, M. Menchaca, J. Atkinson, L. Sun, V. Knight, B. E. Gilbert, C. Conti, B. G. Sanders, K. Kline, Mol. Cancer Therapeutics, 2002, 2, 437.Google Scholar
  32. 32.
    ISO 10993-5. Biological Evaluation of Medical Devices, Pt 5: Tests for Cytotoxicity, in vitro Methods, International Standardization Organisation, Geneva, 1992.Google Scholar
  33. 33.
    M. G. Danilets, Yu. P. Bel’skii, N. V. Bel’skaya, E. S. Trofimova, E. G. Uchasova, V. I. Agafonov, Byull. Eksp. Biol. Med. [Bulletin of Experimental Biological Medicine], 2007, App. 1, 97 (in Russian).Google Scholar

Copyright information

© Springer Science+Business Media, Inc.  2010

Authors and Affiliations

  • A. Yu. Spivak
    • 1
  • R. R. Khalitova
    • 1
  • Yu. P. Bel’skii
    • 2
  • A. N. Ivanova
    • 2
  • E. R. Shakurova
    • 1
  • N. V. Bel’skaya
    • 2
  • V. N. Odinokov
    • 1
  • M. G. Danilets
    • 2
  • A. A. Ligacheva
    • 2
  1. 1.Institute of Petrochemistry and CatalysisRussian Academy of SciencesUfaRussian Federation
  2. 2.Research Institute for PharmacologySiberian Branch of the Russian Academy of Medical SciencesTomskRussian Federation

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