Prooxidant activity of aminophenol compounds: copper-dependent generation of reactive oxygen species

Prooxidant properties of aminophenol, the constituent of acetaminophen and mesalamine, were examined. Aminophenol compounds/copper-dependent formation of reactive oxygen species was analyzed by the inactivation of aconitase, the most sensitive enzyme to oxidative stress in permeabilized yeast cells....

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Bibliographic Details
Published in:Biometals 2022-04, Vol.35 (2), p.329-334
Main Authors: Murakami, Keiko, Yoshino, Masataka
Format: Article
Language:English
Subjects:
Acetaminophen
Aconitate Hydratase
Aminophenol
Aminophenols - pharmacology
Analgesics
Biochemistry
Biomedical and Life Sciences
Catalase
Cell Biology
Continuous production
Copper
Copper - pharmacology
Cytotoxicity
Deactivation
Inactivation
Iron constituents
Life Sciences
Medicine/Public Health
Microbiology
Oxidation
Oxidative stress
Oxygen
p-Aminophenol
Pharmacology/Toxicology
Plant Physiology
Radicals
Reactive oxygen species
Reactive Oxygen Species - chemistry
Sodium azide
Sodium azides
Superoxide
Superoxides
Yeasts
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Summary:Prooxidant properties of aminophenol, the constituent of acetaminophen and mesalamine, were examined. Aminophenol compounds/copper-dependent formation of reactive oxygen species was analyzed by the inactivation of aconitase, the most sensitive enzyme to oxidative stress in permeabilized yeast cells. Aminophenol compounds of 2 ( ortho )- and 4 ( para )- substituents, but not 3 ( meta )-isomer produced reactive oxygen species in the presence of copper (cupric) ion or iron. The inactivation required sodium azide the inhibitor of catalase, suggesting that the superoxide radical produced from the 2- and 4-aminophenol in the presence of copper is responsible for the inactivation of aconitase. Aminophenols of 2- and 4-substituents showed a potent reducing activity of copper (cupric) ion, and further potent reactivity with DPPH radical, but 3-aminophenol showed only a little reactivity. Reduced copper ion can generate superoxide radical with the production of oxidized metal. Aminophenols can reduce the copper ion, and further stimulate the continuous production of reactive oxygen species. Cytotoxic effect of acetaminophen, the N -acetylated- p -aminophenol and mesalamine, the 4-aminophenol derivatives may be accounted for by the prooxidant properties of their constituents, aminophenol.
ISSN:0966-0844
1572-8773
DOI:10.1007/s10534-022-00367-8