Lipid hydroperoxides initiate the autoxidation of sulfite with concomitant production of superoxide

Brestel, Eric P.; Petrone, William F.; Cohen, Reuben A.

doi:10.1016/s0748-5514(86)80073-3

Cited by 8 publications

(4 citation statements)

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“…This result has at least two significant implications: (i) it suggests a new property for xanthine oxidase; and (ii) it provides a possible new metabolic pathway for SO;-generation in cellular systems, where both H,O, and xanthine oxidase are present. As mentioned in the Introduction, it is generally believed that SO;-radicals play an important role in the biochemical mechanism of SO~-toxicity [2][3][4][5][6][7][8][9]. For example, SO;" radicals are known to cause many adverse reactions with biological molecules, including methionine and diphosphopyridine nucleotide oxidation [8,31], fl-carotene and tryptophan destruction [7,8], double bond addition in alkenes [32], fatty acid peroxidation [33], nucleic acid modification [3], and DNA cleavage [34].…”

Section: Discussionmentioning

confidence: 99%

“…Our current finding that the xanthine oxidase/H.,O, system can generate SO~-radical from SOl-suggests a new property of this enzyme. Second, this result points to a new enzymatic pathway for salfite metabolism and toxicity, since the SO;-radical has been implicated in the mechanism of toxic reactions resulting from sulfite exposure [2][3][4][5][6][7][8][9]. Third, we noted that while the mechanism of SO;-generation from SOl-via autoxidation and trace-metal catalyzed oxidation has been studied in detail [10][11][12][13][14], relatively little is known about the mechanism of SO;-generation through enzymatic pathway, with the exception of some recent studies [15][16][17][18][19].…”

Section: Introductionmentioning

confidence: 94%

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Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO^.−₃) from sulfite (SO²⁻₃)

1992

FEBS Letters

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In the presence of hydrogen peroxide (H20:), xanthine oxidase has been found to catalyze sulfur trioxide anion radical (SO;-) formation from sullite anion (SO]-), The SO]" radical was identified by ESR (electron spin resonance) spin trapping, utilizing 5,5-dimethyl-l-pyrroline-l-oxide (DMPO) as the spin trap, Inactivated xanthin~ oxidase does not catalyze SO;-radical formation, implying a specific role for this enzyme. The initial rate ofSO]-radical formation increases linearly with xanth ine oxidasc concentration, To~ethcr, thes¢ observations indicate that the $07 generation occurs enzymatic.ally. These results suggest a new property of xanthine oxidase and perhaps also a significant step in the m~hanism of sulfitc toxicity in cellular systems.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO^.−₃) from sulfite (SO²⁻₃)

1992

FEBS Letters

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“…It can act as a mutagen or co-mutagen (4) and a co-carcinogen (5). The mechanism of sulfite toxicity is believed to be related to sulfite oxidation processes involving sulfur trioxide radical ion (-SO;) formation (1,(6)(7)(8) (-OH) radical is also generated in the sulfite oxidation pathway (9). This radical may play an important role in sulfiteinduced genetic damage.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Generation of Hydroxyl Radical and Sulfur Trioxide Anion Radical from Oxidation of Sodium Sulfite, Nickel(II) Sulfite, and Nickel Subsulfide in the Presence of Nickel(II) Complexes

Shi¹,

Dalal²,

Kasprzak³

1994

Environmental Health Perspectives

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Electron spin resonance (ESR) spin trapping was utilized to investigate the generation of free radicals from oxidation of sodium sulfite, nickel(ll) sulfite, and nickel subsulfide (Ni3S2) by ambient oxygen or H202 at pH 7.4. The spin trap used was 5,5-dimethyl-1-pyrroline-N-oxide (DMPO). Under ambient oxygen, a solution of sodium sulfite alone generated predominantly sulfur trioxide anion radical (-SO0) due to the autoxidation of sulfite.Addition of nickel(ll) chloride [NiOllW] enhanced the -SO; yield about 4-fold. Incubation of sulfite with Ni(ll) in the presence of chelators such asand penicillamine did not have any significant effect on that enhancement. In contrast, albumin, and especially glycylglycylhistidine (GlyGlyHis), augmented the enhancing effect of Ni(ll) by factors of 1.4 and 4, respectively. Computer simulation analysis of the spin-adduct spectrum and formate scavenging experiment showed that the mixture of sodium sulfite, Ni(ll), and GlyGlyHis generated both hydroxyl (-OH) radical and -SO; radical, in the ratio of approximately 1:2. The free-radical spin adduct intensity reached its saturation level in about 5 min. The yield of the radical adducts could be slightly reduced by deferoxamine and very strongly reduced by diethylenetriaminepentaacetic acid (DTPA). Aqueous suspensions of sparingly soluble nickel(ll) sulfite in the presence of air and GlyGlyHis generated surface-located *SO-and 'OH radicals. The same radicals were generated in Ni3S2 suspension in the presence of GlyGlyHis and H202, indicating sulfite production by oxidation of the sulfide moiety of this compound. In view of the present results, the exceptionally high carcinogenic potential of Ni3S2 appears to be due to the ability of both the nickel and sulfide constituents of the molecule to facilitate the generation of genotoxic radicals. -Environ Health Perspect 102 (Suppl 31:91-96 (1994)

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Section: Introductionmentioning

confidence: 99%

Enhanced generation of hydroxyl radical and sulfur trioxide anion radical from oxidation of sodium sulfite, nickel(II) sulfite, and nickel subsulfide in the presence of nickel(II) complexes.

Shi

Dalal

Kasprzak

1994

Environ Health Perspect

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Electron spin resonance (ESR) spin trapping was utilized to investigate the generation of free radicals from oxidation of sodium sulfite, nickel(II) sulfite, and nickel subsulfide (Ni3S2) by ambient oxygen or H2O2 at pH 7.4. The spin trap used was 5,5-dimethyl-1-pyrroline-N-oxide (DMPO). Under ambient oxygen, a solution of sodium sulfite alone generated predominantly sulfur trioxide anion radical (.SO3-) due to the autoxidation of sulfite. Addition of nickel(II) chloride [Ni(II)] enhanced the .SO3- yield about 4-fold. Incubation of sulfite with Ni(II) in the presence of chelators such as tetraglycine, histidine, beta-alanyl-3-methyl-L-histidine (anserine), beta--L-histidine (carnosine), gamma-aminobutyryl-L-histidine (homocarnosine), glutathione, and penicillamine did not have any significant effect on that enhancement. In contrast, albumin, and especially glycylglycylhistidine (GlyGlyHis), augmented the enhancing effect of Ni(II) by factors of 1.4 and 4, respectively. Computer simulation analysis of the spin-adduct spectrum and formate scavenging experiment showed that the mixture of sodium sulfite, Ni(II), and GlyGlyHis generated both hydroxyl (.OH) radical and .SO3- radical, in the ratio of approximately 1:2. The free-radical spin adduct intensity reached its saturation level in about 5 min. The yield of the radical adducts could be slightly reduced by deferoxamine and very strongly reduced by diethylenetriaminepentaacetic acid (DTPA). Aqueous suspensions of sparingly soluble nickel(II) sulfite in the presence of air and GlyGlyHis generated surface-located .SO3- and .OH radicals. The same radicals were generated in Ni3S2 suspension in the presence of GlyGlyHis and H2O2, indicating sulfite production by oxidation of the sulfide moiety of this compound.(ABSTRACT TRUNCATED AT 250 WORDS)

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Lipid hydroperoxides initiate the autoxidation of sulfite with concomitant production of superoxide

Cited by 8 publications

References 0 publications

Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO^.−₃) from sulfite (SO²⁻₃)

Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO^.−₃) from sulfite (SO²⁻₃)

Enhanced Generation of Hydroxyl Radical and Sulfur Trioxide Anion Radical from Oxidation of Sodium Sulfite, Nickel(II) Sulfite, and Nickel Subsulfide in the Presence of Nickel(II) Complexes

Enhanced generation of hydroxyl radical and sulfur trioxide anion radical from oxidation of sodium sulfite, nickel(II) sulfite, and nickel subsulfide in the presence of nickel(II) complexes.

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Lipid hydroperoxides initiate the autoxidation of sulfite with concomitant production of superoxide

Cited by 8 publications

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Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO.−3) from sulfite (SO2−3)

Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO.−3) from sulfite (SO2−3)

Enhanced Generation of Hydroxyl Radical and Sulfur Trioxide Anion Radical from Oxidation of Sodium Sulfite, Nickel(II) Sulfite, and Nickel Subsulfide in the Presence of Nickel(II) Complexes

Enhanced generation of hydroxyl radical and sulfur trioxide anion radical from oxidation of sodium sulfite, nickel(II) sulfite, and nickel subsulfide in the presence of nickel(II) complexes.

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Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO^.−₃) from sulfite (SO²⁻₃)

Xanthine oxidase/hydrogen peroxide generates sulfur trioxide anion radical (SO^.−₃) from sulfite (SO²⁻₃)