Biochemistry (Moscow)

, Volume 74, Issue 9, pp 1021–1026 | Cite as

Interaction of tetrasubstituted cationic aluminum phthalocyanine with artificial and natural membranes

  • A. A. Pashkovskaya
  • I. V. Perevoshchikova
  • V. E. Maizlish
  • G. P. Shaposhnikov
  • E. A. Kotova
  • Yu. N. AntonenkoEmail author


A study of the properties of water-soluble tetrasubstituted cationic aluminum phthalocyanine (AlPcN4) revealed efficient binding of this photosensitizer to phospholipid membranes as compared with tetrasulfonated aluminum and zinc phthalocyanine complexes. This also manifested itself in enhanced photodynamic activity of AlPcN4 as measured by the photosensitized damage of gramicidin channels in a planar bilayer lipid membrane. The largest difference in the photodynamic activity of cationic and anionic phthalocyanines was observed in a membrane containing negatively charged lipids, thereby pointing to significant contribution of electrostatic interactions to the binding of photosensitizers to a membrane. Fluoride anions suppressed the photodynamic activity and binding to membrane of both tetraanionic and tetracationic aluminum phthalocyanines, which supports our hypothesis that interaction of charged metallophthalocyanines with phospholipid membranes is mostly determined by coordination of the central metal atom with the phosphate group of lipid.

Key words

planar bilayer lipid membrane photosensitizer phthalocyanine singlet oxygen ion channels gramicidin A liposomes mitochondria 



tetra-tributylammonium salt of hydroxyaluminum tetra-4-chloromethylphthalocyanine


tetrasulfonated aluminum phthalocyanine


bilayer lipid membrane




diphytanoyl phosphatidylcholine


diphytanoyl phosphatidylglycerol


tetrasulfonated zinc phthalocyanine


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  1. 1.
    Kaliya, O. L., Lukyanets, E. A., and Vorozhtsov, G. N. (1999) J. Porphyrins Phthalocyanines, 3, 592–610.CrossRefGoogle Scholar
  2. 2.
    Valli, L. (2005) Adv. Colloid Interface Sci., 116, 13–44.PubMedCrossRefGoogle Scholar
  3. 3.
    Ou, Z., Shen, J., and Kadish, K. M. (2006) Inorg. Chem., 45, 9569–9579.PubMedCrossRefGoogle Scholar
  4. 4.
    Tolbin, A. Yu., Tomilova, L. G., and Zefirov, N. S. (2007) Uspekhi Khim., 76, 732–744.Google Scholar
  5. 5.
    Claessens, C. G., Hahn, U., and Torres, T. (2008) Chem. Rec., 8, 75–97.PubMedCrossRefGoogle Scholar
  6. 6.
    Spikes, J. D. (1986) Photochem. Photobiol., 43, 691–699.PubMedCrossRefGoogle Scholar
  7. 7.
    Nyokong, T. (2007) Coord. Chem. Rev., 251, 1707–1722.CrossRefGoogle Scholar
  8. 8.
    Fernandez, D. A., Awruch, J., and Dicelio, L. E. (1997) J. Photochem. Photobiol. B, 41, 227–232.PubMedCrossRefGoogle Scholar
  9. 9.
    Minnock, A., Vernon, D. I., Schofield, J., Griffiths, J., Parish, J. H., and Brown, S. T. (1996) J. Photochem. Photobiol. B, 32, 159–164.PubMedCrossRefGoogle Scholar
  10. 10.
    Segalla, A., Borsarelli, C. D., Braslavsky, S. E., Spikes, J. D., Roncucci, G., Dei, D., Chiti, G., Jori, G., and Reddi, E. (2002) Photochem. Photobiol. Sci., 1, 641–648.PubMedCrossRefGoogle Scholar
  11. 11.
    Jori, G., and Brown, S. B. (2004) Photochem. Photobiol. Sci., 3, 403–405.PubMedCrossRefGoogle Scholar
  12. 12.
    Scalise, I., and Durantini, E. N. (2005) Bioorg. Med. Chem., 13, 3037–3045.PubMedCrossRefGoogle Scholar
  13. 13.
    Kuznetsova, N. A., Makarov, D. A., Kaliya, O. L., and Vorozhtsov, G. N. (2007) J. Hazard. Mater., 146, 487–491.PubMedCrossRefGoogle Scholar
  14. 14.
    Makarov, D. A., Yuzhakova, O. A., Slivka, L. K., Kuznetsova, N. A., Negrimovsky, V. M., Kaliya, O. L., and Lukyanets, E. A. (2007) J. Porphyrins Phthalocyanines, 11, 586–595.CrossRefGoogle Scholar
  15. 15.
    Valenzeno, D. P., and Tarr, M. (1991) Photochemistry and Photophysics (Rabek, J. F., ed.) CRC Press, Boca Raton-Ann Arbor-Boston.Google Scholar
  16. 16.
    Dougherty, T. J., Gomer, C. J., Henderson, B. W., Jori, G., Kessel, D., Korbelik, M., Moan, J., and Peng, Q. (1998) J. Natl. Cancer Inst., 90, 889–905.PubMedCrossRefGoogle Scholar
  17. 17.
    Kepczynski, M., Pandian, R. P., Smith, K. M., and Ehrenberg, B. (2002) Photochem. Photobiol., 76, 127–134.PubMedCrossRefGoogle Scholar
  18. 18.
    Engelmann, F. M., Mayer, I., Gabrielli, D. S., Toma, H. E., Kowaltowski, A. J., Araki, K., and Baptista, M. S. (2007) J. Bioenerg. Biomembr., 39, 175–185.PubMedCrossRefGoogle Scholar
  19. 19.
    Ben-Hur, E., Dubbelman, T. M., and van Lier, J. E. (1991) Photochem. Photobiol., 54, 703–707.PubMedCrossRefGoogle Scholar
  20. 20.
    Ben-Hur, E., Malik, Z., Dubbelman, T. M., Margaron, P., Ali, H., and van Lier, J. E. (1993) Photochem. Photobiol., 58, 351–355.PubMedCrossRefGoogle Scholar
  21. 21.
    Rosenthal, I., Shafirovich, V. Y., Geacintov, N. E., Ben-Hur, E., and Horowitz, B. (1994) Photochem. Photobiol., 60, 215–220.PubMedCrossRefGoogle Scholar
  22. 22.
    Rokitskaya, T. I., Block, M., Antonenko, Y. N., Kotova, E. A., and Pohl, P. (2000) Biophys. J., 78, 2572–2580.PubMedCrossRefGoogle Scholar
  23. 23.
    Shapovalov, V. L., Rokitskaya, T. I., Kotova, E. A., Krokhin, O. V., and Antonenko, Y. N. (2001) Photochem. Photobiol., 74, 1–7.PubMedCrossRefGoogle Scholar
  24. 24.
    Pashkovskaya, A. A., Sokolenko, E. A., Sokolov, V. S., Kotova, E. A., and Antonenko, Y. N. (2007) Biochim. Biophys. Acta, 1768, 2459–2465.PubMedCrossRefGoogle Scholar
  25. 25.
    Mueller, P., Rudin, D. O., Tien, H. T., and Wescott, W. C. (1963) J. Phys. Chem., 67, 534–535.Google Scholar
  26. 26.
    Bronshtein, I., Afri, M., Weitman, H., Frimer, A. A., Smith, K. M., and Ehrenberg, B. (2004) Biophys. J., 87, 1155–1164.PubMedCrossRefGoogle Scholar
  27. 27.
    Gomes, A., Fernandes, E., and Lima, J. L. (2005) J. Biochem. Biophys. Meth., 65, 45–80.PubMedCrossRefGoogle Scholar
  28. 28.
    Sholto, A., and Ehrenberg, B. (2008) Photochem. Photobiol. Sci., 7, 344–351.PubMedCrossRefGoogle Scholar
  29. 29.
    Kuznetsova, N. A., Gretsova, N. S., Derkacheva, V. M., Kaliya, O. L., and Lukyanets, E. A. (2003) J. Porphyrins Phthalocyanines, 7, 147–154.CrossRefGoogle Scholar
  30. 30.
    Rokitskaya, T. I., Antonenko, Y. N., and Kotova, E. A. (1996) Biochim. Biophys. Acta, 1275, 221–226.PubMedCrossRefGoogle Scholar
  31. 31.
    Antonenko, Yu. N., Kotova, E. A., and Rokitskaya, T. I. (2005) Biol. Membr. (Moscow), 22, 275–289.Google Scholar
  32. 32.
    Perevoshchikova, I. V., Zorov, D. B., and Antonenko, Y. N. (2008) Biochim. Biophys. Acta, 1778, 2182–2190.PubMedCrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2009

Authors and Affiliations

  • A. A. Pashkovskaya
    • 1
  • I. V. Perevoshchikova
    • 1
  • V. E. Maizlish
    • 2
  • G. P. Shaposhnikov
    • 2
  • E. A. Kotova
    • 1
  • Yu. N. Antonenko
    • 1
    Email author
  1. 1.Belozersky Institute of Physico-Chemical BiologyLomonosov Moscow State UniversityMoscowRussia
  2. 2.Ivanovo State University of Chemistry and TechnologyIvanovoRussia

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