Copper-catalyzed dna damage by ascorbate and hydrogen peroxide: Kinetics and yield

Stoewe, Reinhard; Prütz, Walter A.

doi:10.1016/s0891-5849(87)80003-5

Cited by 113 publications

(59 citation statements)

References 43 publications

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“…Since Thus neither the lack of protection by "OH scavengers (nor the inability to show 'OH formation) exclude "OH as a mediator ofoxidant-induced injury. It has been speculated that small amounts of transition metal are bound to DNA (68,69). Although this has not been proven, it would explain the formation of DNA strand breaks and the inability of-OH scavengers to prevent these DNA strand breaks.…”

Section: Methodsmentioning

confidence: 99%

Oxidant-induced DNA damage of target cells.

Schraufstätter¹,

Hyslop²,

Jackson³

et al. 1988

J. Clin. Invest.

348

133

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In this study we examined the leukocytic oxidant species that induce oxidant damage of DNA in whole cells. H202 added extracellularly in micromolar concentrations (10-100 MM) induced DNA strand breaks in various target cells. The sensitivity of a specific target cell was inversely correlated to its catalase content and the rate of removal of H202 by the target cell. Oxidant species produced by xanthine oxidase/purine or phorbol myristate acetate-stimulated monocytes induced DNA breakage of target cells in proportion to the amount of H202 generated. These DNA strand breaks were prevented by extracellular catalase, but not by superoxide dismutase.Cytotoxic doses of HOCI, added to target cells, did not induce DNA strand breakage, and myeloperoxidase added extracellularly in the presence of an H202-generating system, prevented the formation of DNA strand breaks in proportion to its H202 degrading capacity.The studies also indicated that H202 formed hydroxyl radical (OH) intracellularly, which appeared to be the most likely free radical responsible for DNA damage: OH was detected in cells exposed to H202; the DNA base, deoxyguanosine, was hydroxylated in cells exposed to H202; and intracellular iron was essential for induction of DNA strand breaks.

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Section: Methodsmentioning

confidence: 99%

Oxidant-induced DNA damage of target cells.

Schraufstätter¹,

Hyslop²,

Jackson³

et al. 1988

J. Clin. Invest.

348

133

View full text Add to dashboard Cite

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“…[4,5] Moreover, copper is an important structural metal ion in chromatin, [6][7][8] which contains about one copper ion per kilobase. [6] For these reasons, there is an increased interest in the ability of copper ion to participate in DNA-damaging reactions in vivo.…”

Section: Introductionmentioning

confidence: 99%

“…[6] For these reasons, there is an increased interest in the ability of copper ion to participate in DNA-damaging reactions in vivo. [8,9] Kinetic, [9][10][11] inhibitor, [4,5,9] and sequence-context [12][13][14][15] studies have all suggested that DNA damage induced by copper ion in the presence of H 2 O 2 occurs site-specifically at the sites of DNA-associated copper. However, the nature of the last DNA-oxidizing species produced by the interaction of the DNA-Cu I complex with H 2 O 2 remains uncertain.…”

Section: Introductionmentioning

confidence: 99%

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

et al. 2007

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The reaction of 2,4,6‐tri(pyridyl)‐1,3,5‐triazine (ptz) and copper(II) salts in dmf/water (1:1) results in the hydrolysis of ptz and formation of the anions bis(2‐pyridylcarbonyl)amide (ptO2–) and bis(2‐pyridylamine)amide (ptN2–), which are found in the complexes [Cu(ptN2)(OAc)]·3H2O (1), [Cu(ptO2)(OAc)(H2O)]·H2O (2), [Cu(ptN2)(for)]·3H2O (3) (for = formate), [Cu(ptO2)(for)(H2O)] (4), [Cu(ptO2)(benz)]·H2O (5) (benz = benzoate), and [Cu(ptO2)F(H2O)]2·3H2O (6). This report includes the chemical and spectroscopic characterization of all these complexes along with the crystal structures of 4–6. The coordination spheres of CuII in 4 and 5 are best described as distorted tetragonal square pyramidal for the former and distorted square planar for the latter. The crystal structure of 6 shows the presence of two discrete monomeric [Cu(ptO2)F(H2O)] entities in the crystallographic asymmetric unit in which both copper(II) ions have a distorted square‐pyramidal coordination geometry. The binding of the complexes to DNA has been investigated with the aid of viscosity and thermal denaturation studies, both of which indicate that the interaction is probably due to the outer‐sphere mechanism. The ability of the compounds to cleave DNA has also been tested. Efficient oxidative cleavage was observed in the presence of a mild reducing agent (ascorbate) and dioxygen. Mechanistic studies with reactive oxygen species (ROS) scavengers confirm that hydrogen peroxide, the hydroxyl radical, singlet oxygen‐like species, and the superoxide anion are necessary diffusible intermediates in the scission process. A mechanism involving either the Fenton or theHaber–Weiss reaction plus the formation of copper oxene species is proposed for the DNA cleavage mediated by these compounds.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…The ethidium bromide (EB) binding assay, based on the formation of a fluorescent complex between double-stranded DNA and EB, was used to measure DNA damage (Stoewe and Prutz, 1987). Damaged DNA thus inhibits the binding of EB to DNA and results in a decrease in intensity of fluorescence.…”

Section: Introductionmentioning

confidence: 99%

Protective effect of water yam (Dioscorea alata L.) extract on the copper‐driven fenton reaction and X‐ray induced DNA damage in vitro

Wang

Liang

Lii

et al. 2004

Phytotherapy Research

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The rhizome extract of Dioscorea has been shown to possess radical scavenging activity. In this study, the protective effect of water yam (Dioscorea alata L.) rhizome extract on calf thymus DNA and plasmid DNA strand breakage by the copper-driven Fenton reaction and X-irradiation was examined. The protective activity in vitro of four lyophilized extracts obtained from yam rhizomes: (1) aqueous extract (YAE); (2) 30% ethanolic extract (YEE); (3) aqueous extract boiled for 30 min (BYAE); and (4) 30% ethanolic extract boiled for 30 min (BYEE) were evaluated by ethidium bromide binding assay and DNA nicking assay. The YAE, YEE, and BYEE effectively inhibited the copper-driven Fenton reaction-induced damage of calf thymus DNA, while inhibition was less pronounced in the case of X-ray induced strand breakage of plasmid DNA. While BYAE potently inhibited X-ray induced strand breaks in plasmid pGL3 DNA, it failed to inhibit, and even greatly enhanced copper-H(2)O(2) induced damage of calf thymus DNA. The present results demonstrate strong copper chelating and weak hydroxyl radical scavenging activities in yam rhizome extracts, and these activities may vary depending on the procedures used in preparing the extract.

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Copper-catalyzed dna damage by ascorbate and hydrogen peroxide: Kinetics and yield

Cited by 113 publications

References 43 publications

Oxidant-induced DNA damage of target cells.

Oxidant-induced DNA damage of target cells.

Efficient DNA Cleavage Induced by Copper(II) Complexes of Hydrolysis Derivatives of 2,4,6‐Tri(2‐pyridyl)‐1,3,5‐triazine in the Presence of Reducing Agents

Protective effect of water yam (Dioscorea alata L.) extract on the copper‐driven fenton reaction and X‐ray induced DNA damage in vitro

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