Radical production from free and peptide‐bound methionine sulfoxide oxidation by peroxynitrite and hydrogen peroxide/iron(II)

Nakao, Lia S.; Iwai, Leo Kei; Kalil, Jorge; Augusto, Ohára

doi:10.1016/s0014-5793(03)00674-4

Cited by 48 publications

(33 citation statements)

References 32 publications

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“…Endogenous MetO formation in proteins is a potential pathological biomarker related to in‰ammation (17), aging (18) and smoking (19). Methyl radicals are generated from free and peptide-bound MetO oxidation by peroxynitrite and hydrogen peroxide/iron(II) in vitro (20). Therefore, MetO may be involved in cytosine methylation and the following epigenetic changes.…”

Section: Discussionmentioning

confidence: 99%

Analyses of 8-Methyldeoxyadenosine and 8-Methyldeoxyguanosine as Markers of Free Radical-mediated DNA Methylation in Mouse

Kasai¹,

Kawai²,

Song³

et al. 2013

Genes and Environment

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To examine whether methyl radical-induced DNA damage occurs in vivo, cumene hydroperoxide (CuOOH) and methionine sulfoxide (MetO) were administered to mice as methyl radical generators, and 8-methyldeoxyadenosine (m 8 dA) and 8-methyldeoxyguanosine (m 8 dG) in the tissue DNA were analyzed by the LC/MS/MS method. After mouse skin was treated with CuOOH and Fe 2＋ , both m 8 dA and m 8 dG were detected in the epidermal DNA. m 8 dA formation was also detected in the liver DNA from MetO-treated, non-alcoholic steatohepatitis (NASH) mice. Since 5-methyldeoxycytidine, m 8 dA, and m 8 dG are formed in DNA by methyl radicals, these results support our hypothesis that de novo DNA methylation at the cytosine C-5 position is triggered by a free radical mechanism and may initiate epigenetic changes.

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Section: Discussionmentioning

confidence: 99%

Analyses of 8-Methyldeoxyadenosine and 8-Methyldeoxyguanosine as Markers of Free Radical-mediated DNA Methylation in Mouse

Kasai¹,

Kawai²,

Song³

et al. 2013

Genes and Environment

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“…Methyl radicals are generated from free and peptide- U: U band was predominant, U＋M: both U band and M band were detected, M: M band was predominant. bound methionine sulfoxide (MetO) oxidation by peroxynitrite and hydrogen peroxide/iron(II) in vitro (25). Furthermore, we have reported the formation of 5-methylcytosine in DNA by free radical mechanisms in vitro, using methyl radical generating systems such as methionine sulfoxide (MetO)/Fenton reagent (12).…”

Section: Discussionmentioning

confidence: 99%

Methionine Sulfoxide Stimulates Hepatocarcinogenesis in Non-alcoholic Steatohepatitis (NASH) Mouse: Possible Role of Free Radical-mediated DNA Methylation

Kawai¹,

Li²,

Song³

et al. 2012

Genes and Environment

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We have reported the formation of 5-methylcytosine from cytosine in vitro, with methyl radicals generated from methionine sulfoxide (MetO). To conˆrm this reaction in vivo, MetO was added to the drinking water and administered to non-alcoholic steatohepatitis (NASH) mice, which develop hepatitis caused by endogenous oxidative stress. Histopathological examinations revealed incidences of hepatocellular carcinoma of 16.7% and 90% in the 0% and 3% MetO groups, respectively. Higher DNA methylation was detected in the promoter region of the p16 gene isolated from the livers of MetO-treated mice. The higher incidence of liver tumors may be due to the methyl radical-mediated formation of 5-methylcytosine in DNA, which triggers epigenetic changes.

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“…It is known that many reactions take place in organisms that may form peroxide which is an oxidant and can oxidize some amino acids such as cysteine, tyrosine, tryptophan and methionine in proteins [11,20]. When these amino acid residues are oxidized, the protein conformation and its function will change.…”

Section: Discussionmentioning

confidence: 99%

“…Specific protein activities have been shown to be both up-and down-regulated following methionine oxidation. Also, in specially designed model peptides, methionine oxidation has been shown to serve as a conformational switch between a-helical and b-sheet structures [11]. At present, the effect of H 2 O 2 on prawn NAGase has been little reported.…”

Section: Inhibition Kinetics Of Hydrogen Peroxide On B-n-acetyl-dglucmentioning

confidence: 99%

Inhibition kinetics of hydrogen peroxide on β-N-acetyl-d-glucosaminidase from prawn (Penaeus vannamei)

Xie

Ming

Chen

2006

Journal of Enzyme Inhibition and Medicinal Chemistry

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The effects of hydrogen peroxide (H 2 O 2 ) on prawn NAGase activity for the hydrolysis of pNP-b-D-GlcNAc have been studied. The results show that H 2 O 2 can reversible inhibit the enzyme (IC 50°0 .85 M) and the inhibition is of a mixed type. The kinetics show that k þ0 is much larger than k 0 þ0 ; indicating the free enzyme is more susceptible than the enzyme-substrate complex in the H 2 O 2 solution. It is suggested that the presence of the substrate offers marked protection against inhibition by H 2 O 2 . Changes of activity and conformation of the enzyme in different concentrations of H 2 O 2 have been compared by measuring the fluorescence spectra and residual activity and show that the change of conformation is more rapidly than that of the residual activity, which implies that the whole conformation of the enzyme changes more rapidly than the conformation of the active centre of the enzyme in the H 2 O 2 solution.

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Radical production from free and peptide‐bound methionine sulfoxide oxidation by peroxynitrite and hydrogen peroxide/iron(II)

Cited by 48 publications

References 32 publications

Analyses of 8-Methyldeoxyadenosine and 8-Methyldeoxyguanosine as Markers of Free Radical-mediated DNA Methylation in Mouse

Analyses of 8-Methyldeoxyadenosine and 8-Methyldeoxyguanosine as Markers of Free Radical-mediated DNA Methylation in Mouse

Methionine Sulfoxide Stimulates Hepatocarcinogenesis in Non-alcoholic Steatohepatitis (NASH) Mouse: Possible Role of Free Radical-mediated DNA Methylation

Inhibition kinetics of hydrogen peroxide on β-N-acetyl-d-glucosaminidase from prawn (Penaeus vannamei)

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