Chemical analysis of DNA alterations

Rhaese, Hans J.; Freese, Ernst; Melzer, Marvin S.

doi:10.1016/0005-2787(68)90194-9

Cited by 63 publications

(5 citation statements)

References 21 publications

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“…Thus, this reagent is not suitable for a quantitative analysis of the reaction process. In the present study, H202 was used as the reagent, but in this case side reactions, such as alteration of nucleoside other than thiopyrimidines or polynucleotide chain scission, can occur, especially in the presence of metal ions (Phaese et al, 1968), under alkaline conditions or at high temperatures (Priess & Zillig, 1965;Subbaraman et al, 1971), although these reaction rates are much lower than those with thiopyrimidines.…”

Section: Discussionmentioning

confidence: 97%

Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Watanabe¹

1980

Biochemistry

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Section: Discussionmentioning

confidence: 97%

Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Watanabe¹

1980

Biochemistry

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“…The notion that reduced oxygen species are responsible for the B[a]P-dione-induced DNA strand breakage (Table I) is strongly supported by the observed protection of the DNA by superoxide dismutase. It is well known that peroxides, and peroxide and hydroxyl radical generators, cause strand breakage and other inactivating lesions in DNA (Freese et al, 1967;Rhaese et al, 1968;Massie et al, 1972). Metal ion chelation is the most likely process responsible for the complete protection of DNA by EDTA from B[ú]P-dione-induced breakage.…”

Section: Discussionmentioning

confidence: 99%

Benzo[a]pyrenedione/benzo[a]pyrenediol oxidation-reduction couples and the generation of reactive reduced molecular oxygen

Lorentzen¹,

Ts’o²

1977

Biochemistry

154

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The ability of the isomeric quinone metabolites of benzo[a]pyrene, benzo[a]pyrene-6,12-dione, benzo[a]pyrene-1,6-dione, and benzo[a]pyrene-3,6-dione to undergo reversible, univalent oxidation-reduction cycles involving the corresponding benzo[a]pyrenediols and intermediate semiquinone radicals has been characterized. Under anaerobic conditions, all three benzo[a]pyrenediones are easily reduced to benzo[a]pyrenediols, even by mild biological agents such as NAD(P)H, cysteamine, and glutathione. The benzo[a]pyrenediols, in turn, are very rapidly autoxidized to the benzo[a]pyrenediones when exposed to air. Substantial amounts of hydrogen peroxide are produced during these autoxidations, and other reactive reduced oxygen species, such as the superoxide and hydroxyl radicals, are probably formed transiently as well. The benzo[a]pyrenediol-benzo[a]pyrenedione interconversions proceed by one-electron steps; the corresponsing semiquinone radicals can be monitored by electron spin resonance spectroscopy as inter mediates during these reactions carried out at high pH. Benzo[a]pyrenediones induce DNA strand scission when incubated with bacteriophage T7 DNA. This damage is modified by conditions which indicate that reduced oxygen species propagate the free-radical reactions responsible for the strand scission. Benzo[a]pyrenediones are electron-acceptor substrates for NADH dehydrogenase from Clostridium kluyveri. Catalytic amounds of these benzo[a]pyrene metabolites, together with this respiratory enzyme function as cyclic oxidation-reduction couples which link NADH and molecular oxygen in the continuous production of hydrogen peroxide. These data, together with preliminary results with cells in culture, indicate that benzo[a]pyrenediones are potentially harmful metabolites of benzo[a]pyrene, acting by processes which lead to their regeneration rather than depletion; nucleic acid and call damage is probably produced by the reactive reduced oxygen species resulting from such regenerative oxidation-reduction cycles.

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“…These strand breaks are probably caused by hydrogen peroxide, organic peroxides, or other reduced oxygen species generated during autoxidation. Hydrogen peroxide or peroxide and hydroxyl radical generators are known to cause DNA strand breaks, base modifications, cross-linking, and inactivation of transforming principles (Freese et al, 1967;Melzer, 1967;Rhaese and Freese, 1968;Rhaese et al, 1968;Massie et al, 1972). Antioxidants have been used in various studies to reduce chromosomal breaks (Shamberger et al, 1973) and to decrease neoplasia incidences caused by chemical carcinogens (Wattenberg, 1973).…”

Section: Discussionmentioning

confidence: 99%

Autoxidation of 6-hydroxybenzo[a]pyrene and 6-oxobenzo[a]pyrene radical, reactive metabolites of benzo[a]pyrene

Lorentzen¹,

Caspary²,

Lesko³

et al. 1975

Biochemistry

139

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Chemical analysis of DNA alterations

Cited by 63 publications

References 21 publications

Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Reactions of 2-thioribothymidine and 4-thiouridine with hydrogen peroxide in transfer ribonucleic acids from Thermus thermophilus and Escherichia coli as studied by circular dichroism

Benzo[a]pyrenedione/benzo[a]pyrenediol oxidation-reduction couples and the generation of reactive reduced molecular oxygen

Autoxidation of 6-hydroxybenzo[a]pyrene and 6-oxobenzo[a]pyrene radical, reactive metabolites of benzo[a]pyrene

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