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Evaluation of cytotoxicity and efficiency of antioxidant protection of hydrophilic derivatives of 2,4,6-trialkylphenols in Escherichia coli cells

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Abstract

The effects of five new derivatives of 2,6-dialkyl-4-propylphenol containing different ionogenic groups (-SO3Na, -S-SO3Na, -S-(NH2)2Cl) in the para position on survival of the E. coli AB1157 strain and its isogenic strain deficient in repair enzyme genes have been investigated in the presence and in the absence of hydrogen peroxide. Survival of cells treated with hydrogen peroxide was markedly increased in the presence of sodium (3-(3,5-dimethyl-4-hydroxyphenyl)propyl)-1-sulphonate (C1). Replacement of methyl substituents at ortho-position of C1 for tert-butyl or cyclohexyl groups decreased cell protection against exogenous hydrogen peroxide. Among 2,6-di-tert-buthylphenol the compound with the thiosulphonate group demonstrated properties similar to its sulphonate analog, whereas 3 mM isothiuronium chloride completely suppressed cell growth both in the absence and in the presence of hydrogen peroxide. Thus, among the tested compounds C1 may be considered as the most promising antioxidant.

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Abbreviations

AO:

antioxidant

CFU:

colony forming unit

ROS:

reactive oxygen species

References

  1. Sies, H., Oxidative Stress, London: Academic Press, 1985, pp. 1–8.

    Google Scholar 

  2. Sies, H., Amer. J. Med., 1991, vol. 91, pp. 313–323.

    Article  Google Scholar 

  3. Seyfulla, R.D. and Borisova, I.G., Farmakol. Toksikol., 1990, no. 6, pp. 3–10.

  4. Men’schikova, E.B., Lankin, V.Z. Zenkov, N.K., Bondar’, I.A., Krugovykh, I.F., and Trufakin, V.A., Okislitel’nyi stress. Prooksidanty i antioksidanty (Oxidative Stress. Prooxidants and Antioxidants), Moscow: Slovo, 2006.

    Google Scholar 

  5. Vol’skii, N.N., Kashlakova, N.V., and Kozlov, V.A., Tsitologiya, 1988, vol. 30, pp. 895–902.

    Google Scholar 

  6. Richards, D.M.S., Dean, R.T., and Jessup, W., Biochim. Biophys. Acta, 1988, vol. 946, pp. 281–288.

    Article  CAS  Google Scholar 

  7. Drapier, J.-C. and Hibbs, J.B., J. Immunol., 1988, vol. 140, pp. 2829–2838.

    CAS  Google Scholar 

  8. Hoffman, M.E., Mello-Filho, A.C., and Meneghini, R., Biochim. Biophys. Acta, 1984, vol. 781, pp. 234–238.

    Google Scholar 

  9. Harman, D., Mutat. Res., 1992, vol. 275, pp. 257–266.

    CAS  Google Scholar 

  10. Beckman, K.B. and Ames, B.N., Physiol. Rev., 1998, vol. 78, pp. 547–581.

    CAS  Google Scholar 

  11. Grollman, A.P. and Moriya, M., Trends Genet., 1993, vol. 9, pp. 246–249.

    Article  CAS  Google Scholar 

  12. Halliwell, B., Lancet, 1994, vol. 344, pp. 721–724.

    Article  CAS  Google Scholar 

  13. Zhuravlev, A.I., Bioantiokisliteli v regulyatsii metabolisma v norme i patologii, (Bioantioxidants in the regulation of metabolism in norm and pathology), Moscow: Nauka, 1982, pp. 3–37.

    Google Scholar 

  14. Bast, A. and Haenen, G.R., Antioxidants in Therapy and Preventive Medicine, N.-Y.: Plenum Press, 1990, pp. 111–116.

    Google Scholar 

  15. Munday, R. and Winterboume, C.C., Biochem. Pharmacol., 1989, vol. 38, pp. 4349–4352.

    Article  CAS  Google Scholar 

  16. Wengel, A., Enzymes — Tools and Targets, Basel: Karget, 1988, pp. 161–167.

    Google Scholar 

  17. Kenya, M.V., Lukash, A.I., Gus’kov, E.P., Usp. Sovr. Biol., 1993, vol. 113, pp. 456–470.

    Google Scholar 

  18. Abramova, Zh.I. and Oksengendler, G.I., Chelovek i protivookislitel’nye veshchestva, (Man and Antioxidant Substances), Leningrad; Nauka, 1985.

    Google Scholar 

  19. Beyer, R.E., Free Radical Biol. Med., 1990, vol. 8, pp. 545–565.

    Article  CAS  Google Scholar 

  20. Roginskii, V.A., Fenol’nyie antioksidanty: reaktsionnaya sposobnost’ i effektivnost’ (Phenolic Antioxidants: Reactivity and Effectiveness), Moscow: Nauka, 1988.

    Google Scholar 

  21. Mickle, D.A.G., Li, R.K., Weisel, R.D., Tumiati, L.C., and Wu, T.W., J. Mol. Cell. Cardiol., 1990, vol. 22, pp. 1297–1304.

    Article  CAS  Google Scholar 

  22. Voskresenskii, O.N., Zhutaev, I.A., Bobyrev, V.N., and Bezuglyi, Yu.V., Vopr. Med. Khim., 1982, no. 1, pp. 14–27.

  23. Sokolovskii, V.V., Vopr. Med. Khim., 1988, no. 6, pp. 3–10.

  24. Maron, D.M. and Ames, B.N., Mutat. Res., 1983, vol. 113, pp. 173–215.

    CAS  Google Scholar 

  25. Quillardet, P. and Hofnung, M., Mutat. Res., 1985, vol. 147, pp. 65–78.

    CAS  Google Scholar 

  26. Asad, N.R., CEB de Almedia, LMBO Asad, Felzeswalb, I., and Leitao, A.C., Biochimie, 1995, vol. 77, pp. 262–264.

    Article  CAS  Google Scholar 

  27. Gomes, E.M., Souto, P.R., and Felzeswalb, I., Mutat. Res., 1996, vol. 367, pp. 203–208.

    Article  CAS  Google Scholar 

  28. Imlay, J., and Linn, S., Science, 1988, vol. 240, pp. 640–642, 1302–1309.

    Article  CAS  Google Scholar 

  29. Asad, N.R. and Leitao, A.C., J. Bacteriol., 1991, vol. 173, pp. 2562–2568.

    CAS  Google Scholar 

  30. Kemeleva, E.A., Vasyunina, E.A., Sinitsyna, O.I., Khomchenko, A.S., Gross, M.A., Kandalintseva, N.V., Prosenko, A.E., and Nevinsky, G.A., Bioorgan. Khim., 2008, vol. 34, pp. 499–509.

    Article  CAS  Google Scholar 

  31. DeWitt, S.K. and Adelbeg, E.A., Genetics, 1962, vol. 47, pp. 577–585.

    CAS  Google Scholar 

  32. Oleinick, A.S., Kuprina, T.S., Pevneva, N.Yu., Markov, A.F., Kandalintseva, N.V., Prosenko, A.E., and Grigor’ev, I.A., Izv. Akad. Nauk, Ser. Khim., 2007, vol. 6, pp. 1094–1101.

    Google Scholar 

  33. Kandalintseva, N.V., Prosenko, A.E., Dyubchenko, O.I., and Stoyanov, E.S., Zh. Org. Khim., 2001, vol. 9, pp. 1317–1320.

    Google Scholar 

  34. Miller, J., Eksperimenty v molekulyarnoi genetike, (Experiments in Molecular Genetics), Mir: Moscow, 1976.

    Google Scholar 

  35. Bhatnagar, S.K. and Bessman, M.J., J. Biol. Chem., 1988, vol. 263, pp. 8953–8957.

    CAS  Google Scholar 

  36. Miller, J.H. and Michael, M., Gene, 1996, vol. 179, pp. 129–132.

    Article  CAS  Google Scholar 

  37. Lin, J.J. and Sancar, A., Bochemistry, 1989, vol. 28, pp. 7979–7984.

    Article  CAS  Google Scholar 

  38. Oleinik, A.S., Pevneva, N.Yu., Kandalintseva, N.V., Prosenko, A.E., Khoschenko, O.M., and Dushkin, M.I., Khimiya v Interesakh Ustoichivogo Razvitiya, 2008, vol. 5, pp. 559–564.

    Google Scholar 

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Authors and Affiliations

  1. Institute of Cytology and Genetics, Siberian Branch of Russian Academy of Sciences, Novosibirsk, 630090, Russia

    U. N. Rotskaya, L. P. Ovchinnikova, E. A. Vasunina, O. I. Sinitsina & G. A. Nevinsky

  2. Novosibirsk State Pedagogic University, Novosibirsk, 630090, Russia

    N. V. Kandalintseva & E. A. Prosenko

  3. Institute of Chemical Biology and Fundamental Medicine, Siberian Branch of Russian Academy of Sciences, ul. Lavrentyeva 8, Novosibirsk, 630090, Russia

    G. A. Nevinsky

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  1. U. N. Rotskaya
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  2. L. P. Ovchinnikova
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  3. E. A. Vasunina
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  4. O. I. Sinitsina
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  5. N. V. Kandalintseva
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  7. G. A. Nevinsky
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Correspondence to G. A. Nevinsky.

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Original Russian Text © U.N. Rotskaya, L.P. Ovchinnikova, E.A. Vasunina, O.I. Sinitsina, N.V. Kandalintseva, E.A. Prosenko, G.A. Nevinsky, 2010, published in Biomeditsinskaya Khimiya.

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Rotskaya, U.N., Ovchinnikova, L.P., Vasunina, E.A. et al. Evaluation of cytotoxicity and efficiency of antioxidant protection of hydrophilic derivatives of 2,4,6-trialkylphenols in Escherichia coli cells. Biochem. Moscow Suppl. Ser. B 4, 377–382 (2010). https://doi.org/10.1134/S1990750810040098

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  • DOI: https://doi.org/10.1134/S1990750810040098

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