Radiolysis of Glutathione in Oxygen-containing Solutions of pH 7

Quintiliani, M.; Badiello, R.; Tamba, Maurizio; Esfandi, A; Gorin, George

doi:10.1080/09553007714550891

Cited by 97 publications

(43 citation statements)

References 16 publications

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“…GSH + 'OH -> GS°+ H20 [2] NAC + 'OH -> NAC°+ H20 [3] The reported rate constants are k2 = 1.5 x 1010 M-l's-1 (19) and k3 Fig. 1 DMPO-'SG (curve A) and DMPO-NAC-(curve B) adducts observed after the addition of glucose oxidase to generate H202.…”

Section: Resultsmentioning

confidence: 99%

“…Also, the activation of NF-KB is inhibited by the addition of N-acetyl-L-cysteine (NAC), which serves as an oxygen radical scavenger and as a precursor for GSH biosynthesis (4-7). Most of the reaction rates involving GSH in reaction 1 are diffusion controlled (19,20). Therefore, the glutathionyl radical or its cascading radicals, rather than the initial oxygen free radicals, are likely the predominant intracellular radical species.…”

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confidence: 99%

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Endogenous intracellular glutathionyl radicals are generated in neuroblastoma cells under hydrogen peroxide oxidative stress.

Kwak

Yim

Chock

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

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We report the detection of endogenous intracellular glutathionyl (GS') radicals in the intact neuroblastoma cell line (10)(11)(12)(13)(14). As a radical scavenger, glutathione repairs free radical sites, R-, by the following reaction:where GS" is the glutathionyl radical and R* represents *OH, other reactive radicals, or radical sites in proteins and DNA generated by cascading reactions (15,16). When GSH deficiency is produced in newborn rats or guinea pigs, the animals develop multiorgan failure, which is directly related to the loss of essential antioxidant capacity (13,14,17,18). Also, the activation of NF-KB is inhibited by the addition of N-acetyl-L-cysteine (NAC), which serves as an oxygen radical scavenger and as a precursor for GSH biosynthesis (4-7). Most of the reaction rates involving GSH in reaction 1 are diffusion controlled (19,20). Therefore, the glutathionyl radical or its cascading radicals, rather than the initial oxygen free radicals, are likely the predominant intracellular radical species.We attempted to detect and identify free radicals formed under H202 stress in intact cells by using electron paramagnetic resonance (EPR) and spin-trapping methods. Our results show that H202 stress generates endogenous intracellular GS' radicals in intact cells and NAC-originated thiyl radicals (NAC') in NAC-treated cells. In addition, GS' formation exhibited a large increase in its concentration after a lag period, whereas NACG formation did not show this sudden increase. MATERIALS AND METHODSMaterials. The spin trap 5,5-dimethyl-l-pyrroline 1-oxide (DMPO), chromium oxalate, and 2-vinylpyridine were purchased from Aldrich. Horseradish peroxidase (HRP) (type VI), EDTA, GSH, 5,5'-dithiobis(2-nitrobenzoic acid), and cytochrome c (type VI, from horse heart) were obtained from Sigma. Glucose oxidase, glutathione peroxidase (bovine erythrocytes), glutathione reductase (yeast), NADPH, oxidized glutathione, deoxycholate, and NAC were purchased from Calbiochem. Cu/Zn superoxide dismutase (Cu/Zn-SOD), xanthine oxidase, and leupeptin were purchased from Boehringer Mannheim; Chelex 100 resin and SDS were from Bio-

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Endogenous intracellular glutathionyl radicals are generated in neuroblastoma cells under hydrogen peroxide oxidative stress.

Kwak

Yim

Chock

et al. 1995

Proc. Natl. Acad. Sci. U.S.A.

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“…Very similar results were obtained at pH 3 also. The red shift around 250-270 nm in the UV-VIS spectra (Figure 1) is an indication of the formation of disulfide as this has absorbance in the same region [19]. The products from HPLC eluent were also separately collected in the case of CySNO and analyzed by MS which reconfirmed the formation of RSSR.…”

Section: Resultsmentioning

confidence: 99%

Decomposition of S‐Nitrosothiols Induced by UV and Sunlight

Veleeparampil

Aravind

Aravindakumar

2009

Advances in Physical Chemistry

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Photochemical release of nitric oxide (NO) from the S-nitroso derivatives of glutathione, L-cysteine, N-acetyl-L-cysteine, Lcysteinemethylester, D,L-penicillamine, N-acetyl-D,L-penicillamine, and N-acetylcysteamine has been investigated at neutral and acidic pH. The release of NO from RSNO is one of the key reactions that could be utilized in photodynamic therapy. The UV-VIS and HPLC analyses have shown that under argon saturated conditions, disulfide (RSSR) is the major product of UV as well as sunlight induced decomposition. While in aerated conditions, nitirite-the end product of the oxidation of NO-was also observed along with disulfide. The formation of thiyl radical as the intermediate was reconfirmed by laser flash photolysis. The initial rate of formation of NO was on the order of 10 −5 dm 3 mol −1 s −1 . The quantum yields of these reactions were in the range of 0.2-0.8. The high quantum yields observed in the photo induced release of NO from RSNO using both UV and sunlight demonstrate the potential application of these reactions in photodynamic therapy.

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“…4) as well as regenerating the glutathionyl radical (GS') would produce glutathione sulfenyl hydroperoxide (GSOOH). The fate of this species is unknown, but on the basis of extensive work on the radiolysis of thiols in aqueous solution (17,18,22,23) rearrangement to glutathione sulfinic acid (GSO2H) or hydrolysis eventually leading to the generation of GSSG are two possible pathways (Fig. 4).…”

Section: Resultsmentioning

confidence: 99%

Generation of Reactive Species and Fate of Thiols during Peroxidase-Catalyzed Metabolic Activation of Aromatic Amines and Phenols

Ross¹,

Moldéus²

1985

Environmental Health Perspectives

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The horseradish peroxidase (HRP)-catalyzed oxidation of p-phenetidine and acetaminophen was investigated. Studies using the spin probe 2-ethyl-1-hydroxy-2,5,5-trimethyl-3-oxazolidine (OXANOH) suggested these oxidations involve the generation of substrate-derived free radicals. This was confirmed by using glutathione (GSH) in these incubations in the presence of the spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO). DMPO-glutathionyl radical adducts were observed using EPR spectroscopy during HRP-catalyzed oxidation of both p-phenetidine and acetaminophen. Investigations of oxygen uptake and oxidized glutathione (GSSG) formation during HRP-catalyzed oxidations of p-phenetidine and acetaminophen suggested that further reactions of the glutathionyl radical involve glutathione peroxysulfenyl radical and glutathione sulfenyl hydroperoxide production. Quinonoid products of the peroxidatic oxidations of pphenetidine and acetaminophen, and their interaction with GSH via both conjugation and redox mechanisms are described. The relevance of these reactions of GSH with reactive species as detoxification mechanisms is discussed.

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Radiolysis of Glutathione in Oxygen-containing Solutions of pH 7

Cited by 97 publications

References 16 publications

Endogenous intracellular glutathionyl radicals are generated in neuroblastoma cells under hydrogen peroxide oxidative stress.

Endogenous intracellular glutathionyl radicals are generated in neuroblastoma cells under hydrogen peroxide oxidative stress.

Decomposition of S‐Nitrosothiols Induced by UV and Sunlight

Generation of Reactive Species and Fate of Thiols during Peroxidase-Catalyzed Metabolic Activation of Aromatic Amines and Phenols

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