Enhancement of the peroxidase-mediated oxidation of butylated hydroxytoluene to a quinone methide by phenolic and amine compounds

Chemico-biological Interactions
D C Thompson, M A Trush

Abstract

We have recently demonstrated that butylated hydroxyanisole (BHA) markedly stimulates the peroxidase-dependent oxidation of butylated hydroxytoluene (BHT) to the potentially toxic BHT-quinone methide. Using both horseradish peroxidase and prostaglandin H synthase we now report the ability of a wide variety of compounds to stimulate peroxidase-dependent activation of BHT. These compounds include several phenolic compounds commonly present in pharmacologic preparations or occurring naturally in foods. The ability of a given compound to stimulate BHT oxidation was found to depend on the type of radical it forms upon peroxidase oxidation. Compounds which have been shown to form phenoxy radicals or nitrogen-centered cation radicals were observed to enhance BHT oxidation. Conversely, compounds which are known to form peroxy radicals or semiquinone radicals either inhibited or had no effect on BHT oxidation. Compounds which enhanced BHT oxidation (monitored by covalent binding of [14C]BHT to protein) were also observed to stimulate the formation of BHT-quinone methide and stilbenequinone. This suggested a common mechanism of interaction of these compounds with BHT. The stimulation of BHT covalent binding by BHA was also seen in variou...Continue Reading

References

Feb 1, 1978·Toxicology and Applied Pharmacology·O Takahashi, K Hiraga
Oct 1, 1987·Toxicology and Applied Pharmacology·D A EastmondR D Irons
Jun 1, 1988·Archives of Biochemistry and Biophysics·S Liochev, I Fridovich
Dec 1, 1985·Environmental Health Perspectives·B KalyanaramanR C Sealy
Oct 1, 1988·Toxicology and Applied Pharmacology·D C Thompson, M A Trush
Oct 1, 1986·Proceedings of the National Academy of Sciences of the United States of America·G A ReedR P Mason
Jan 1, 1987·Toxicology and Applied Pharmacology·T MizutaniS Fujita
Oct 1, 1986·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·D C Thompson, M A Trush
Oct 1, 1985·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·V V Subrahmanyam, P J O'Brien
Feb 1, 1973·Archives of Biochemistry and Biophysics·T Shiga, K Imaizumi
Jul 20, 1971·Biochimica Et Biophysica Acta·G S Bayse, M Morrison
Sep 15, 1984·Biochemical Pharmacology·P R WestR P Mason
Aug 15, 1984·Biochemical Pharmacology·Y NakagawaK Hiraga
Oct 1, 1982·Environmental Research·H Babich
Oct 1, 1980·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·M E McManus, D S Davies
Aug 1, 1982·The Biochemical Journal·S Kimura, P H Jellinck

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Citations

Jan 1, 1991·Chemico-biological Interactions·B J SmithT E Eling
Feb 1, 1993·Chemico-biological Interactions·D C ThompsonP Moldéus
Aug 1, 1992·Proceedings of the National Academy of Sciences of the United States of America·G Lévay, W J Bodell
Feb 1, 1992·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·O I AruomaJ Löligers
Oct 25, 2002·International Journal of Toxicology·Rebecca S Lanigan, Torill A Yamarik
Nov 7, 2020·International Journal of Biological Macromolecules·Fengmao LiYunming Tang

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