Abstract
4-Mercaptoimidazoles derived from the naturally occurring antioxidants, ovothiols, were tested for their glutathione peroxidase-like (GSH Px-like) activity and protection against peroxynitrite-induced damage. All the thiol compounds displayed similar significant GSH Px-like activities, which are however weaker than that of the reference compound, ebselen. The inhibitions of the peroxynitrite-dependent oxidation of Evans blue dye and dihydrorhodamine 123 showed that the thiol compounds substituted on position 5 of the imidazole ring were nearly as effective as ebselen while the C-2 substituted ones were less effective. Both assays corroborate the large superiority of mercaptoimidazoles over glutathione as inhibitors of peroxynitrite-dependent oxidation.
MeSH terms
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Antioxidants / chemistry
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Antioxidants / metabolism*
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Antioxidants / pharmacology
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Azoles / metabolism
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Azoles / pharmacology
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Catalysis / drug effects
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Chromans / metabolism
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Chromans / pharmacology
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Evans Blue / metabolism
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Free Radical Scavengers / metabolism
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Free Radical Scavengers / pharmacology
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Glutathione / metabolism
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Glutathione / pharmacology
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Glutathione Peroxidase / metabolism*
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Hydrogen Peroxide / metabolism
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Imidazoles / chemistry
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Imidazoles / metabolism*
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Imidazoles / pharmacology
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Inhibitory Concentration 50
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Isoindoles
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Kinetics
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Methylhistidines / metabolism*
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NADP / metabolism
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Nitrates / antagonists & inhibitors*
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Nitrates / metabolism
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Nitrates / pharmacology
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Organoselenium Compounds / metabolism
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Organoselenium Compounds / pharmacology
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Oxidants / antagonists & inhibitors
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Oxidants / metabolism
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Oxidants / pharmacology
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Oxidation-Reduction / drug effects
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Rhodamines / metabolism
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Sulfhydryl Compounds / chemistry
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Sulfhydryl Compounds / metabolism*
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Sulfhydryl Compounds / pharmacology
Substances
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Antioxidants
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Azoles
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Chromans
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Free Radical Scavengers
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Imidazoles
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Isoindoles
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Methylhistidines
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Nitrates
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Organoselenium Compounds
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Oxidants
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Rhodamines
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Sulfhydryl Compounds
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ovothiol C
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dihydrorhodamine 123
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peroxynitric acid
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ebselen
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Evans Blue
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NADP
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Hydrogen Peroxide
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Glutathione Peroxidase
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Glutathione
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6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid