The antioxidant action of N-acetylcysteine: Its reaction with hydrogen peroxide, hydroxyl radical, superoxide, and hypochlorous acid

Aruoma, Okezie I.; Halliwell, Barry; Hoey, Brigid M.; Butler, J. A. V.

doi:10.1016/0891-5849(89)90066-x

Cited by 1,631 publications

(942 citation statements)

References 22 publications

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“…Moreover, the increased intracellular peroxides were completely suppressed by preincubation with 10 mM N-acetyl-L-cysteine (Fig. 7C), which is capable of causing an increase in intracellular GSH levels thus resulting in the scavenging of oxidants both directly and indirectly (37)(38)(39). After treatments with aminoguanidine or NAC and 3-DG, similar results were observed in intracellular peroxide production (data not shown).…”

Section: Effects Of Cycloheximide Actinomycin D and Aminoguanidine supporting

confidence: 72%

Selective Induction of Heparin-binding Epidermal Growth Factor-like Growth Factor by Methylglyoxal and 3-Deoxyglucosone in Rat Aortic Smooth Muscle Cells

Che

Asahi

Takahashi

et al. 1997

Journal of Biological Chemistry

103

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Methylglyoxal (MG) and 3-deoxyglucosone (3-DG), reactive dicarbonyl metabolites in the glyoxalase system and glycation reaction, respectively, selectively induced heparin-binding epidermal growth factor (HB-EGF)-like growth factor mRNA in a dose-and time-dependent manner in rat aortic smooth muscle cells (RASMC). A nuclear run-on assay revealed that the dicarbonyl may regulate expression of HB-EGF at the transcription level. The dicarbonyl also increased the secretion of HB-EGF from RASMC. However, platelet-derived growth factor, another known growth factor of smooth muscle cells (SMC), was not induced by both dicarbonyls. The dicarbonyl augmented intracellular peroxides prior to the induction of HB-EGF mRNA as judged by flow cytometric analysis using 2 ,7 -dichlorofluorescin diacetate. N-Acetyl-L-cysteine and aminoguanidine suppressed both dicarbonyl-increased HB-EGF mRNA and intracellular peroxide levels in RASMC. DL-Buthionine-(S,R)-sulfoximine increased the levels of 3-DG-induced HB-EGF mRNA. Furthermore, hydrogen peroxide alone also induced HB-EGF mRNA in RASMC. These results indicate that MG and 3-DG induce HB-EGF by increasing the intracellular peroxide levels. In addition, the pretreatment with 12-O-tetra-decanoylphorbol-13-acetate failed to alter dicarbonyl-induced HB-EGF mRNA expression in RASMC, suggesting that the signal transducing mechanism is not mediated by protein kinase C. Since HB-EGF is known as a potent mitogen for smooth muscle cells and is abundant in atherosclerotic plaques, the induction of HB-EGF by MG and 3-DG, as well as the concomitant increment of intracellular peroxides, may trigger atherogenesis during diabetes.Methylglyoxal (2-oxopropanal; MG), 1 a reactive ␣,␤-dicarbonyl metabolite and physiological substrate for the glyoxalase system (1), is formed by the non-enzymatic and enzymatic elimination of phosphate from dihydroxyacetone phosphate, glyceraldehyde-3-phosphate (2, 3), and by the oxidation of hydroxyacetone and aminoacetone (4 -6). The estimated rate of formation of methylglyoxal in tissues of normal healthy subjects is approximately 125 M/day which can largely be accounted for as a result of fragmentation of triose phosphates (2). The glyoxalase system, using reduced glutathione as a cofactor, catalyzes the conversion of methylglyoxal to D-lactate via the intermediate S-D-lactoylglutathione. The formation of methylglyoxal in cultured human red blood cells is increased under hyperglycemic conditions and by the addition of fructose,

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Section: Effects Of Cycloheximide Actinomycin D and Aminoguanidine supporting

confidence: 72%

Selective Induction of Heparin-binding Epidermal Growth Factor-like Growth Factor by Methylglyoxal and 3-Deoxyglucosone in Rat Aortic Smooth Muscle Cells

Che

Asahi

Takahashi

et al. 1997

Journal of Biological Chemistry

103

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“…The released Å OH radicals attack DNA molecules before it is scavenged by NAC. Furthermore, the deleterious biological effects of thiyl and other sulfur-containing radicals produced by hydrogen atom abstraction from NAC may also contribute to the observed effects on DNA damage [13].…”

Section: The Effect Of N-acetyl-l L-cysteine On Dna Damagementioning

confidence: 99%

“…It has been proposed that the beneficial effect of NAC mainly comes from its capability of directly scavenging Å OH radicals as well as its function as a glutathione precursor [12][13][14][15][16][17]. However, there are still considerable controversies regarding the antioxidant efficacy of NAC.…”

Section: Introductionmentioning

confidence: 99%

Quantitative measurement of hydroxyl radical induced DNA double‐strand breaks and the effect of N‐acetyl‐l‐cysteine

Yang

2006

FEBS Letters

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Reactive oxygen species, such as hydroxyl or superoxide radicals, can be generated by exogenous agents as well as from normal cellular metabolism. Those radicals are known to induce various lesions in DNA, including strand breaks and base modifications. These lesions have been implicated in a variety of diseases such as cancer, arteriosclerosis, arthritis, neurodegenerative disorders and others. To assess these oxidative DNA damages and to evaluate the effects of the antioxidant N-acetyl-L L-cysteine (NAC), atomic force microscopy (AFM) was used to image DNA molecules exposed to hydroxyl radicals generated via Fenton chemistry. AFM images showed that the circular DNA molecules became linear after incubation with hydroxyl radicals, indicating the development of double-strand breaks. The occurrence of the double-strand breaks was found to depend on the concentration of the hydroxyl radicals and the duration of the reaction. Under the conditions of the experiments, NAC was found to exacerbate the free radical-induced DNA damage.

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“…Superoxide anion radicals were produced by using the hypoxanthine-xanthine oxidase system (27,30,31). The composition of the reaction mixture (1.0 ml) was as follows: 50 mM KH 2 PO 4 -KOH, pH 7.4, 1 mM EDTA, 100 µM hypoxanthine, and 100 µM NBT.…”

Section: Superoxide Anion Profilementioning

confidence: 99%

The antioxidant action of Polypodium leucotomos extract and kojic acid: reactions with reactive oxygen species

Gomes

Lunardi

González

et al. 2001

Braz J Med Biol Res

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Two natural products Polypodium leucotomos extract (PL) and kojic acid (KA) were tested for their ability to scavenge reactive oxygen species (in phosphate buffer. Hydroxyl radicals were generated by the Fenton reaction, and the rate constants of scavenging were 1.6 x 10 9 M -1 s -1 for KA and 1.0 x 10 9 M -1 s -1 for PL, similar to that of ethanol (1.4 x 10 9 M -1 s -1 ). With superoxide anions generated by the xanthine/hypoxanthine system, KA and PL (0.2-1.0 mg/ml) inhibited · O 2 -dependent reduction of nitroblue tetrazolium by up to 30 and 31%, respectively. In the detection of 1 O 2 by rose bengal irradiation, PL at 1.0 mg/ml quenched singlet oxygen by 43% relative to azide and KA by 36%. The present study demonstrates that PL showed an antioxidant effect, scavenging three of four reactive oxygen species tested here. Unlike KA, PL did not significantly scavenge hydrogen peroxide. Correspondence

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The antioxidant action of N-acetylcysteine: Its reaction with hydrogen peroxide, hydroxyl radical, superoxide, and hypochlorous acid

Cited by 1,631 publications

References 22 publications

Selective Induction of Heparin-binding Epidermal Growth Factor-like Growth Factor by Methylglyoxal and 3-Deoxyglucosone in Rat Aortic Smooth Muscle Cells

Selective Induction of Heparin-binding Epidermal Growth Factor-like Growth Factor by Methylglyoxal and 3-Deoxyglucosone in Rat Aortic Smooth Muscle Cells

Quantitative measurement of hydroxyl radical induced DNA double‐strand breaks and the effect of N‐acetyl‐l‐cysteine

The antioxidant action of Polypodium leucotomos extract and kojic acid: reactions with reactive oxygen species

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