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

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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.

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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

K i :

inhibition constant, µM

GLC:

gas-liquid chromatography

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Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, ul. Akademika Kuprevicha 5/2, 220141, Minsk, Belarus

    I. V. Naumchik, E. I. Karasyova & D. I. Metelitza

  2. Faculty of Chemistry, Belorussian State University, ul. Leningradskaya 14, 220050, Minsk, Belarus

    I. P. Edimecheva, V. L. Sorokin & O. I. Shadyro

Authors
  1. I. V. Naumchik
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  2. E. I. Karasyova
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  3. D. I. Metelitza
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  4. I. P. Edimecheva
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  5. V. L. Sorokin
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  6. O. I. Shadyro
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Correspondence to D. I. Metelitza.

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Translated from Biokhimiya, Vol. 70, No. 3, 2005, pp. 397–405.

Original Russian Text Copyright © 2005 by Naumchik, Karasyova, Metelitza, Edimecheva, Sorokin, Shadyro.

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Naumchik, I.V., Karasyova, E.I., Metelitza, D.I. et al. Inhibition of peroxidase-catalyzed oxidation of 3,3′,5,5′-tetramethylbenzidine by aminophenols. Biochemistry (Moscow) 70, 322–329 (2005). https://doi.org/10.1007/s10541-005-0118-z

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  • DOI: https://doi.org/10.1007/s10541-005-0118-z

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