Additions and Corrections: Deuterium-isotope Effects in the Autoxidation of Aralkyl Hydrocarbons. Mechanism of the Interaction of Peroxy Radicals.

Russell, Glen A.

doi:10.1021/ja01557a616

Cited by 156 publications

(249 citation statements)

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“…A previous investigation [31] reports high k 6 values even at 30°C for different substrates in which termination is due to secondary peroxyl radicals. According to Howard and Ingold [31], those substrate would terminate by disproproportionation [32] and the ease with which H is transferred plays a very important role in determining the rate constant for termination. Polyamide termination would thus display an interesting similarity with those reactions.…”

Section: Assessment Of Kinetic Parametersmentioning

confidence: 99%

Molecular and macromolecular structure changes in polyamide 11 during thermal oxidation

Okamba-Diogo

Richaud

Verdú

et al. 2014

Polymer Degradation and Stability

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Section: Assessment Of Kinetic Parametersmentioning

confidence: 99%

Molecular and macromolecular structure changes in polyamide 11 during thermal oxidation

Okamba-Diogo

Richaud

Verdú

et al. 2014

Polymer Degradation and Stability

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“…After purification of the BOOH, we found that the extent of damage to both pBR 322 and pUC 19 DNA induced by HRP (1.8 and 9.0 µM) was identical (within our experimental accuracy) to that induced by the same concentration of HRP + 60 mM pure BOOH (compare lanes 2 and 3 with lanes 7 and 8 in Figures 4 and 5) (for duplicate experiments, see Figures S7-S9 in the Supporting Information). Furthermore, even in such 'clean' systems 10 mM Trolox exerted little or no protective effect on the SC DNA (see Figures 4,5, and S7-S9). Damage to pUC 19 by 9 µM HRP and 60 mM pure BOOH was essentially the same for BOOH purified by azeotropic distillation and for that further purified by recrystallization from hexane (see Figure S12).…”

Section: Resultsmentioning

confidence: 99%

Cleavage of Supercoiled DNA by Horseradish Peroxidase plus tert-Butyl Hydroperoxide Is Not Due to tert-Butylperoxyl Radicals

2002

Chem. Res. Toxicol.

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Two supercoiled (SC), double-stranded DNAs, pBR 322 and pUC 19, have been subjected to oxidative stress using horseradish peroxidase (HRP) and HRP + tert-butyl hydroperoxide (BOOH). HRP alone causes single-strand cleavage of these SC DNAs. Strand cleavage is enhanced substantially in the presence of commercial BOOH (which contains H 2 O 2 ) but is, at best, only very slightly enhanced in the presence of pure BOOH. In the HRP/pure BOOH system, the DNA single-strand-scission which does occur appears to be due to a direct action of oxidized HRP. It is not due to tert-butylperoxyl radicals because strand-scision is not even retarded by 10 mM Trolox, an outstanding water-soluble trap for peroxyl radicals. The present results are congruent with our earlier conclusion [Paul, T., et al. (2000) Biochemistry 39, 4129] that neutral alkylperoxyl radicals produce little or no direct single-strand-scission in SC DNAs.It was recently demonstrated in this laboratory that direct single-strand cleavage of (double-strand) supercoiled DNA by water-soluble alkylperoxyl radicals (1) 1 at 37°C was relatively facile when the peroxyl carried a positive charge but was generally below the level of detection when the peroxyl was uncharged or carried a negative charge (2). For example, with the positively charged peroxyl radical, (H 2 N) 2 + CC(CH 3 ) 2 OO • ( + ROO • ), 2 and the supercoiled (SC) plasmid DNA, pBR 322, it was found that ca. 50% of the SC DNA suffered a singlestrand break to afford relaxed (R) DNA at a + ROO • /bp ratio of 0.2 (2). Strand cleavage by a different positively changed peroxyl occurred with a similar efficiency (2). In contrast, the neutral, water-soluble peroxyl radical, HOCH 2 CH 2 NHC(O)C(CH 3 ) 2 OO • , generally produced no detectable strand-scission (i.e., no detectable R DNA) at a ROO • /bp ratio as high as 5:1 (2, 3), 3 and the negatively charged peroxyl radical, -O 3 SCH 2 CH 2 C(CH 3 )(CN)OO • , generally produced no strand-scission even at a ROO • / bp ratio of 24:1 (2). Essentially identical results were obtained with another SC DNA, pUC 19 (2). The uniquely strong DNA strand cleaving abilities of the positively charged peroxyl radicals was attributed to their Coulombic attraction to the negatively charged SC DNA polyanion (2).After these null-results on the neutral ROO • /DNA reaction were published (2), a paper appeared which caused us surprise and concern because it claimed that neutral alkylperoxyl radicals "generated in situ" from five different alkyl hydroperoxides and three different peroxidases generally produced single-strand breaks in pBR 322 (4). This strand-scission was not a consequence of the DNA having been subjected to very much higher ROO • /bp ratios than we had employed. 4 We were therefore prompted to investigate one of the peroxidase/alkyl hydroperoxide systems. We chose horseradish peroxidase (HRP) and tert-butyl hydroperoxide (BOOH) because both are readily available commercially and because the HRP/ BOOH pair had been reported to have "a substantial DNA-cleaving activity"(4). 5...

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“…Parts of the observed DMPO-OH and DEPMPO-OH might be produced via other pathways. Koga et al reported (26) that 1 O 2 is formed during the Fe 3+ -catalyzed decomposition of LOOH, probably via the Russell mechanism (27). The formation of DMPO-OH during the reaction between DMPO and 1 O 2 has also been reported (10,11).…”

Section: Discussionmentioning

confidence: 96%

Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions

Kambayashi

Tero‐Kubota

Yamamoto

et al. 2003

Journal of Biochemistry

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Additions and Corrections: Deuterium-isotope Effects in the Autoxidation of Aralkyl Hydrocarbons. Mechanism of the Interaction of Peroxy Radicals.

Cited by 156 publications

References 0 publications

Molecular and macromolecular structure changes in polyamide 11 during thermal oxidation

Molecular and macromolecular structure changes in polyamide 11 during thermal oxidation

Cleavage of Supercoiled DNA by Horseradish Peroxidase plus tert-Butyl Hydroperoxide Is Not Due to tert-Butylperoxyl Radicals

Formation of Superoxide Anion during Ferrous Ion-Induced Decomposition of Linoleic Acid Hydroperoxide under Aerobic Conditions

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