Pharmaceutical Chemistry Journal

, Volume 46, Issue 2, pp 82–85 | Cite as

Influence of hydrophobic properties of IKhFAN antioxidants on their membranotropic activity

  • E. Yu. Parshina
  • L. Ya. Gendel’
  • A. B. Rubin

The echinocytogenic and stomatocytogenic action on erythrocytes, the structure-modifying effect on erythrocyte membranes, and the hemolytic activity of IKhFAN antioxidants were established as functions of their hydrophobicity. The functions are nonlinear. The echinocytogenic, stomatocytogenic, and hemolytic activities first increase, pass through a maximum, and then decrease as the hydrophobicity parameter increases whereas the microviscosity of erythrocyte membranes varies in the opposite manner. These results may be useful in developing approaches to the synthesis of hybrid biologically active compounds including drugs with controlled and targeted delivery to the corresponding cell membrane structures.

Key words

IKhFAN antioxidants echinocytogenic stomatocytogenic and hemolytic activity hydrophobicity 


  1. 1.
    E. M. Molotchkina, I. B. Ozerova, and E. B. Burlakova, Free Radical Biol. Med., 33, Issue 2S1, No. 610, S229–S230 (2002).Google Scholar
  2. 2.
    N. M. Storozhok, M. G. Perevozkina, G. A. Nikiforov, et al., Kinet. Katal., 45(6), 863–871 (2004).CrossRefGoogle Scholar
  3. 3.
    E. Burlakova, E. Molochkina, and G. Nikiforov, Chem. Chem. Technol., 2(3), 163–173 (2008).Google Scholar
  4. 4.
    E. B. Burlakova, E. M. Molochkina, A. N. Goloshchapov, et al., in: Abstracts of Papers of the Conference “Basic Sciences – Medicine” [in Russian], Moscow (2003), pp. 15–17.Google Scholar
  5. 5.
    E. Yu. Parshina, L. Ya. Gendel’, and A. B. Rubin, Biofizika, 49(6), 1094–1098 (2004).PubMedGoogle Scholar
  6. 6.
    E. Yu. Parshina, L. Ya. Gendel’, and A. B. Rubin, Izv. Ross. Akad. Nauk, Ser. Biol., No. 6, 645–649 (2007).Google Scholar
  7. 7.
    E. Yu. Parshina, L. Ya. Gendel’, and A. B. Rubin, Biofizika, 54(6), 1051–1054 (2009).PubMedGoogle Scholar
  8. 8.
    G. A. Nikiforov, I. S. Belostotskaya, V. B. Vol’eva, et al., Nauchn. Vestn. Tyumenskoi Med. Akad., Spets. Vypusk “Bioantioksidanty”, 50–51 (2003).Google Scholar
  9. 9.
    O. G. Luneva, L. Ya. Gendel’, and K. E. Kruglyakova, Biofizika, 47(1), 38–44 (2002).PubMedGoogle Scholar
  10. 10.
    L. I. Antsiferova, A. M. Vasserman, A. N. Ivanova, et al., Atlas of Electron Paramagnetic Resonance Spectra of Spin Labels and Probes [in Russian], Nauka, Moscow (1977).Google Scholar
  11. 11.
    C. Hansch and T. Fujita, J. Am. Chem. Soc., 86, 1616–1626 (1964).CrossRefGoogle Scholar
  12. 12.
    C. Hansch and A. Leo, Exploring QSAR, Vol. 2, Hydrophobic, Electronic and Steric Constants, Wiley, New York (1995).Google Scholar
  13. 13.
    A. A. Klesov and I. V. Berezin, Enzymatic Catalysis [in Russian], Izd. Mosk. Univ., Moscow (1980).Google Scholar
  14. 14.
    M. A. Landau, Molecular Mechanisms of Activity of Physiologically Active Substances [in Russian], Nauka, Moscow (1981).Google Scholar
  15. 15.
    O. M. Panasenko, L. Ya. Gendel’, K. E. Kruglyakova, et al., Izv. Akad. Nauk SSSR, Ser. Biol., No. 4, 607–611 (1981).Google Scholar
  16. 16.
    K. E. Kilivnik, O. S. Khmarskaya, and O. S. Ksenzhek, Biofizika, 54(2), 242–248 (2009).PubMedGoogle Scholar
  17. 17.
    W. M. Meylan and P. H. Howard, Perspect. Drug Discovery Des., 19, 67–84 (2000).CrossRefGoogle Scholar
  18. 18.
    M. P. Sheetz and S. J. Singer, Proc. Natl. Acad. Sci. USA, 71, 4457–4461 (1974).PubMedCrossRefGoogle Scholar
  19. 19.
    M. P. Sheetz and S. J. Singer, J. Cell Biol., 70, 247–251 (1976).PubMedCrossRefGoogle Scholar
  20. 20.
    B. Isomaa, H. Hagerstrand, G. Paatero, and A. C. Engblom, Biochim. Biophys. Acta, 860(3), 510–524 (1986).PubMedCrossRefGoogle Scholar
  21. 21.
    P. G. Kury and H. M. McConnell, Biochemistry, 14(13), 2798–2803 (1975).PubMedCrossRefGoogle Scholar
  22. 22.
    A. Kotyk and K. Janacek, Cell Membrane Transport: Principles and Techniques, Plenum Press, New York (1970).Google Scholar
  23. 23.
    L. Ya. Gendel’ and K. E. Kruglyakova, Spin Label and Probe Method [in Russian], Nauka, Moscow (1986), pp. 163–194.Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • E. Yu. Parshina
    • 1
  • L. Ya. Gendel’
    • 2
  • A. B. Rubin
    • 1
  1. 1.Department of BiologyMoscow State UniversityMoscowRussia
  2. 2.Emanuel Institute of Biochemical PhysicsRussian Academy of SciencesMoscowRussia

Personalised recommendations