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Antioxidant properties of conjugates of polyethylene glycols containing terpenophenolic fragments

Russian Journal of Bioorganic Chemistry volume 40, pages 76–81 (2014)Cite this article

Abstract

A series of water-soluble conjugates has been synthesized from polyethylene glycols of various lengths and 4-bromomethyl-2,6-diisobornylphenol. The membrane protective and antioxidant activities of the synthesized products were evaluated on the model of the H2O2-induced hemolysis of erythrocytes. It was shown that the studied conjugates have a significant antioxidant activity, and a significant membrane protective effect was shown for the conjugates containing 0.2% and 0.8% of the 2,6-diisobornyl-4-methylenephenolic fragments.

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Abbreviations

PEG:

polyethylene glycol

LPO:

lipid peroxidation

TBA-RS:

products reacting with 2-thiobarbituric acid (TBA-reactive substances)

oxyHb:

oxyhemoglobin

metHb:

methemoglobin

ferrylHb:

ferrylhemoglobin

References

  1. Cui, L., Tang, C., and Yin, C., Carbohyd. Polym., 2012, vol. 87, pp. 2505–2511.

    CAS  Article  Google Scholar 

  2. Korshak, V.V. and Shtil’man, M.I., Polimery v protsessakh immobilizatsii i modifikatsii prirodnykh soedinenii (Polymers in Immobilization and Modification of Natural Compounds), Moscow: Nauka, 1984.

    Google Scholar 

  3. Shtilman, M.I., Russ. J. Biopharm., 2009, vol. 1, no. 2, pp. 5–14.

    CAS  Google Scholar 

  4. Abuchowski, A., McCoy, J.R., Palczuk, N.C., van Es, T., and Davis, F.F., J. Biol. Chem., 1977, vol. 252, pp. 3582–3586.

    CAS  PubMed  Google Scholar 

  5. Roberts, M.J., Bentley, M.D., and Harris, J.M., Adv. Drug Deliv. Rev., 2002, vol. 54, pp. 459–476.

    CAS  PubMed  Article  Google Scholar 

  6. Casettari, L., Vllasaliu, D., Castagnino, E., Stolnik, S., Howdle, S., and Illum, L., Prog. Polym. Sci., 2012, vol. 37, pp. 659–685.

    CAS  Article  Google Scholar 

  7. Bildstein, L., Dubernet, C., and Couvreur, P., Adv. Drug Deliv. Rev., 2011, vol. 63, pp. 3–23.

    CAS  PubMed  Article  Google Scholar 

  8. Khandare, J. and Minko, T., Prog. Polym. Sci., 2006, vol. 31, pp. 359–397.

    CAS  Article  Google Scholar 

  9. Anand, P., Thomas, S.G., Kunnumakkara, A.B., Sundaram, C., Harikumar, K.B., Sung, B., Tharakan, S.T., Misra, K., Priyadarsini, I.K., Rajasekharan, K.N., and Aggarwal, B.B., Biochem. Pharmacol., 2008, vol. 76, pp. 1590–1611.

    CAS  PubMed  Article  Google Scholar 

  10. Navath, R.S., Wang, B., Kannan, S., Romero, R., and Kannan, R.M., J. Controlled Release, 2010, vol. 142, pp. 447–456.

    CAS  Article  Google Scholar 

  11. Plotnikov, M.B., Smol’yakova, V.I., Ivanov, I.S., Kuchin, A.V., Chukicheva, I.J., Buravlev, E.V., and Krasnov, E.A., Pharm. Chem. J., 2011, vol. 44, pp. 530–533.

    CAS  Article  Google Scholar 

  12. Plotnikov, M.B., Smolyakova, V.I., Ivanov, I.S., Chernisheva, G.A., Kuchin, A.V., Chukicheva, I.J., and Krasnov, E.A., Bull. Exp. Biol. Med., 2010, vol. 149, pp. 721–723.

    CAS  PubMed  Article  Google Scholar 

  13. Logvinov, S.V., Plotnikov, M.B., Zhdankina, A.A., Smolyakova, V.I., Ivanov, I.S., Kuchin, A.V., Chukicheva, I.Yu., and Varakuta, E.Yu., Neurosci. Behav. Physiol., 2010, vol. 40, pp. 779–782.

    CAS  PubMed  Article  Google Scholar 

  14. Yan, Y., Yu, C., Chen, J., Li, X., Wang, W., and Li, S., Carbohyd. Polym., 2011, vol. 83, pp. 217–224.

    CAS  Article  Google Scholar 

  15. Ke, M., Zhang, X.-J., Han, Z.-H., Yu, H.-Y., Lin, Y., Zhang, W.-G., Sun, F.-H., and Wang, T.-J., Carbohyd. Polym., 2011, vol. 86, pp. 136–141.

    CAS  Article  Google Scholar 

  16. Li, X.M., Li, X.L., and Zhou, A.G., Eur. Polym. J., 2007, vol. 43, pp. 488–497.

    CAS  Article  Google Scholar 

  17. Epstein, W.W. and Sweat, F.W., Chem. Rev., 1967, vol. 67, pp. 247–260.

    CAS  Article  Google Scholar 

  18. Shevchenko, O.G., Plyusnina, S.N., Shishkina, L.N., Chukicheva, I.Yu., Fedorova, I.V., and Kuchin, A.V., Biol. Membr., 2013, vol. 30, pp. 40–51.

    CAS  Google Scholar 

  19. Fernandes, J.C., Eaton, P., Nascimento, H., Giao, M.S., Ramos, O.S., Belo, L., Santos-Silva, A., Pintado, M.E., and Malcata, F.X., Carbohyd. Polym., 2010, vol. 79, pp. 1101–1106.

    CAS  Article  Google Scholar 

  20. Coppinger, G.M. and Campbell, T.W., J. Am. Chem. Soc., 1953, vol. 75, pp. 734–736.

    CAS  Article  Google Scholar 

  21. Takebayashi, J., Chen, J., and Tai, A., Advanced Protocols in Oxidative Stress. II. Methods in Molecular Biology, Armstrong, D., Ed., New York: Humana Press, 2010, vol. 594, pp. 287–296.

    Google Scholar 

  22. Asakawa, T. and Matsushita, S., Lipids, 1980, vol. 15, pp. 137–140.

    CAS  Article  Google Scholar 

  23. Berg, J.J.M., Op den Kamp, J.A.F., Lubin, B.H., Roelofsen, B., and Kuypers, F.A, Free Radical Biol. Med., 1992, vol. 12, pp. 487–498.

    Article  Google Scholar 

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, ul. Pervomayskaya 48, Syktyvkar, 167982, Russia

    I. Yu. Chukicheva, M. A. Torlopov, E. V. Buravlev & A. V. Kuchin

  2. Institute of Biology, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, Syktyvkar, 167982, Russia

    O. G. Shevchenko

Authors
  1. I. Yu. Chukicheva
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  2. M. A. Torlopov
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  3. E. V. Buravlev
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  4. O. G. Shevchenko
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  5. A. V. Kuchin
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Corresponding author

Correspondence to E. V. Buravlev.

Additional information

Original Russian Text © I.Yu. Chukicheva, M.A. Torlopov, E.V. Buravlev, O.G. Shevchenko, A.V. Kuchin, 2014, published in Bioorganicheskaya Khimiya, 2014, Vol. 40, No. 1, pp. 85–91.

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Chukicheva, I.Y., Torlopov, M.A., Buravlev, E.V. et al. Antioxidant properties of conjugates of polyethylene glycols containing terpenophenolic fragments. Russ J Bioorg Chem 40, 76–81 (2014). https://doi.org/10.1134/S1068162014010026

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  • DOI: https://doi.org/10.1134/S1068162014010026

Keywords

  • polyethylene glycols
  • terpenophenols
  • antioxidants
  • membrane protective properties
  • red blood cells
  • oxidative hemolysis