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Biochemistry (Moscow)

, Volume 70, Issue 3, pp 322–329 | Cite as

Inhibition of peroxidase-catalyzed oxidation of 3,3′,5,5′-tetramethylbenzidine by aminophenols

  • I. V. Naumchik
  • E. I. Karasyova
  • D. I. Metelitza
  • I. P. Edimecheva
  • V. L. Sorokin
  • O. I. Shadyro
Article

Abstract

Peroxidase-catalyzed oxidation of 3,3′,5,5′-tetramethylbenzidine (TMB) was inhibited by o-aminophenol (AP), 2-amino-4-tert-butylphenol (ATBP), 2-amino-4,6-di-tert-butylphenol (ADTBP), and 4-tert-butylpyrocatechol (TBP). Inhibitors were characterized by inhibition constant K i and stoichiometric coefficient f, the number of radicals terminated by one inhibitor molecule. The most efficient inhibitor is ADTBP characterized by K i = 36 µM in 0.015 M phosphate citrate buffer, pH 6.0, at 20°C. According to their antiradical efficiency, the studied inhibitors can be arranged as follows: ADTBP > ATBP > AP > TBP. The role of the NH2 group in the inhibitory capacity of aminophenols is discussed. Using gas-liquid chromatography, kinetics of consumption of the initial components and accumulation of the reaction products on peroxidase-catalyzed oxidation of the TMB-TBP pair was studied; the data clarify the stages of a complex process of co-oxidation of amines and phenols.

Key words

horseradish peroxidase tetramethylbenzidine aminophenols inhibition inhibition constants stoichiometric inhibition coefficients 

Abbreviations

AP

o-aminophenol

ADTBP

2-amino-4,6-di-tert-butylphenol

ATBP

2-amino-4-tert-butylphenol

ANP

2-amino-4-nitrophenol

HP

horseradish peroxidase

TBP

4-tert-butylpyrocatechol

TBBQ

4-tert-butyl-1,2-benzoquinone

TMB

3,3′,5,5′-tetramethylbenzidine

PCB

phosphate citrate buffer

f

stoichiometric inhibition coefficient

Ki

inhibition constant, µM

GLC

gas-liquid chromatography

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REFERENCES

  1. 1.
    Metelitza, D. I., Karasyova, E. I., Grintsevich, E. E., and Thorneley, R. N. F. (2004) J. Inorg. Biochem., 98, 1–9.PubMedGoogle Scholar
  2. 2.
    Metelitza, D. I., Naumchik, I. V., Karasyova, E. I., Polozov, G. I., and Shadyro, O. I. (2003) Prikl. Biokhim. Mikrobiol., 39, 352–362.Google Scholar
  3. 3.
    Metelitza, D. I., Litvinchuk, A. V., and Savenkova, M. I. (1992) Biokhimiya, 57, 103–113.Google Scholar
  4. 4.
    Metelitza, D. I., Eryomin, A. N., Sviridov, D. O., and Kamyshnikov, V. S. (2001) Biochemistry (Moscow), 66, 505–514.Google Scholar
  5. 5.
    Rus’, O. B., and Metelitza, D. I. (2001) Vestsi Akad. Navuk Belarusi. Ser. Khim. Navuk, 4, 75–82.Google Scholar
  6. 6.
    Karasyova, E. I., Nikiforova, T. V., and Metelitza, D. I. (2001) Prikl. Biokhim. Mikrobiol., 37, 472–479.Google Scholar
  7. 7.
    Karasyova, E. I., Losev, Yu. P., and Metelitza, D. I. (1997) Biochemistry (Moscow), 62, 1074–1081.Google Scholar
  8. 8.
    Karasyova, E. I., and Metelitza, D. I. (1999) Biochemistry (Moscow), 64, 54–60.Google Scholar
  9. 9.
    Karasyova, E. I., Nikiforova, T. V., Losev, Yu. P., and Metelitza, D. I. (1999) Bioorg. Khim., 25, 665–672.Google Scholar
  10. 10.
    Karasyova, E. I., Losev, Yu. P., and Metelitza, D. I. (2001) Biochemistry (Moscow), 66, 608–617.Google Scholar
  11. 11.
    Grintsevich, E. E., Senchuk, V. V., Puchkaev, A. V., and Metelitza, D. I. (2000) Biochemistry (Moscow), 65, 924–932.Google Scholar
  12. 12.
    Karasyova, E. I., Losev, Yu. P., and Metelitza, D. I. (2001) Prikl. Biokhim. Mikrobiol., 37, 713–721.Google Scholar
  13. 13.
    Karasyova, E. I., Losev, Yu. P., and Metelitza, D. I. (2002) Bioorg. Khim., 28, 147–155.Google Scholar
  14. 14.
    Naumchik, I. V., Karasyova, E. I., Metelitza, D. I., Polozov, G. I., and Shadyro, O. I. (2004) Bioorg. Khim., 30, 537–546.PubMedGoogle Scholar
  15. 15.
    Metelitza, D. I., Savenkova, M. I., and Kurchenko, V. P. (1987) Prikl. Biokhim. Mikrobiol., 23, 116–124.Google Scholar
  16. 16.
    Nikol’skii, B. P. (ed.) (1967) Chemist’s Handbook [in Russian], Vol. 4, Khimiya, Leningrad, p. 919.Google Scholar
  17. 17.
    Belostotskaya, I. S., and Komissarova, N. L. (1971) Izv. Akad. Nauk SSSR, Ser. Khim., 12, 2816–2817.Google Scholar
  18. 18.
    Magnusson, R. (1960) Acta Chem. Scand., 14, 1643.CrossRefGoogle Scholar
  19. 19.
    Albert, H. E. (1954) J. Am. Chem. Soc., 76, 4985–4988.Google Scholar
  20. 20.
    Vol’eva, B. P., Prokof’eva, T. I., Prokof’ev, A. I., Belostotskaya, I. S., Komissarova, N. L., and Ershov, V. V. (1995) Izv. Akad. Nauk SSSR, Ser. Khim., 9, 1789–1793.Google Scholar
  21. 21.
    Keleti, T. (1990) Basics of Enzyme Kinetics [Russian translation], Mir, Moscow, pp. 183–203.Google Scholar
  22. 22.
    Emanuel, N. M., and Buchachenko, A. L. (1982) Chemical Physics of Aging and Stabilization of Polymers [in Russian], Nauka, Moscow, pp. 239–308.Google Scholar
  23. 23.
    Naumchik, I. V., Karasyova, E. I., Metelitza, D. I., Polozov, G. I., and Shadyro, O. I. (2002) Vestsi Akad. Navuk Belarusi. Ser. Khim. Navuk, 3, 85–91.Google Scholar
  24. 24.
    Ershov, V. V., Nikiforov, G. A., and Volod’kin, A. A. (1972) Sterically-Hindered Phenols [in Russian], Khimiya, Moscow.Google Scholar
  25. 25.
    Valoti, M., Sipe, H. J., Sgragli, G., and Mason, R. P. (1989) Arch. Biochem. Biophys., 269, 423–432.PubMedGoogle Scholar
  26. 26.
    Rodriques-Lopez, J. N., Gilabert, M. A., Tudela, J., Thorneley, R. N. F., and Garcia-Canovas, F. (2000) Biochemistry, 39, 13201–13209.Google Scholar
  27. 27.
    Josephy, P. D., Eling, T., and Mason, R. P. (1982) J. Biol. Chem., 257, 3669–3675.PubMedGoogle Scholar
  28. 28.
    Karpukhina, G. V., Maizus, Z. K., and Emanuel, N. M. (1963) Dokl. Akad. Nauk SSSR, 152, 110–114.Google Scholar
  29. 29.
    Karpukhina, G. V., Maizus, Z. K., and Emanuel, N. M. (1965) Dokl. Akad. Nauk SSSR, 160, 158–162.Google Scholar
  30. 30.
    Kim, B. B. (1992) Advances in Science and Technology. Biotechnology [in Russian], Vol. 36, VINITI, Moscow, pp. 126–146.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • I. V. Naumchik
    • 1
  • E. I. Karasyova
    • 1
  • D. I. Metelitza
    • 1
  • I. P. Edimecheva
    • 2
  • V. L. Sorokin
    • 2
  • O. I. Shadyro
    • 2
  1. 1.Institute of Bioorganic ChemistryNational Academy of Sciences of BelarusMinskBelarus
  2. 2.Faculty of ChemistryBelorussian State UniversityMinskBelarus

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