Mechanism of oxidative DNA damage induced by quercetin in the presence of Cu(II)

Yamashita, Naruto; Takahashi, Hiroshi; Kawanishi, Shosuke

doi:10.1016/s0027-5107(99)00029-9

Cited by 151 publications

(97 citation statements)

References 33 publications

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“…20 To minimize artificial formation of 8-oxodG, several complicated manipulations involving oxygen removal, a lower workup temperature and the elimination of transition metals by nitroxides or deferoxamine mesylate (DFO) have been applied. 21,22 Recently, enzyme-immobilized bioreactors have been used in many applications including the chemical analysis of proteins, kinetic studies and biocatalysis. 28−32,38−44 Online analysis platform included trypsin-immobilized reactor coupled to LC-MS/MS or capillary electrophoresis (CE), which could digest proteins and identify peptides automatically, demonstrating an increasing stability and improved enzymatic activity of trypsin.…”

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confidence: 99%

Three-Enzyme Cascade Bioreactor for Rapid Digestion of Genomic DNA into Single Nucleosides

Yin

Zhang

et al. 2016

Anal. Chem.

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Structure-based DNA modification analysis provides accurate and important information on genomic DNA changes from epigenetic modifications to various DNA lesions. However, genomic DNA strands are often required to be efficiently digested into single nucleosides. It is an arduous task because of the involvement of multiple enzymes with different catalytic acitivities. Here we constructed a three-enzyme cascade capillary monolithic bioreactor that consists of immobilized deoxyribonuclease I (DNase I), snake venom phosphodiesterase (SVP), and alkaline phosphatase (ALPase). By the use of this cascade capillary bioreactor, genomic DNA can be efficiently digested into single nucleosides with an increasing rate of ∼20 folds. The improvement is mainly attributed to dramatically increase enzymatic capacity and activity. With a designed macro-porous structure, genomic DNA of 5−30 Kb (∼1.6−10 million Daltons) can be directly passed through the bioreactor simply by hand pushing or a low-pressure microinjection pump. By coupling with liquid chromatography-tandem mass spectrometry (LC-MS/MS), we further developed a sensitive assay for detection of an oxidative stress biomarker 8-oxo-7,8-dihydro-2′-deoxyguanosine (8-oxodG) in DNA. The proposed three-enzyme cascade bioreactor is also potentially applicable for fast identification and quantitative detection of other lesions and modifications in genomic DNA.E xposure to chemical carcinogens may result in DNA damages, a key step toward the onset of cancer. 1−4 DNA damages can occur via structural modification of the nucleosides and phosphate moieties in DNA chains. 5 It is difficult to directly search for various modifications in genomic DNA since DNA strands are long biopolymers consisting of a large number of normal nucleosides (deoxyadenosine, dA; deoxygunosine, dG; deoxycytidine, dC; and thymidine monophosphates, dT) interspersing with a small quantity of modified nucleosides (e.g., 5-methylcytosine, 5mC) or trace modifications (e.g., 5-hydroxymethylcytosine, 5-formalcytosine, and 5-carboxylcytosine). To determine these DNA modifications, genomic DNA samples were often required to be efficiently digested into mononucleotides or single nucleosides. 6−10 Liquid chromatography-mass spectrometry (LC-MS) can explore whether nucleotide is modified, and is sensitive enough to quantify these modifications on DNA chains. 9,11−15 For example, during LC-MS/MS analysis of global DNA methylation and hydroxylmethylation, genomic DNA was digested into the mixture of classical DNA nucleosides (dA, dT, dG, dC) and modified nucleosides. 16−18 Recently, we discovered a new DNA modification in drosophila, N6-methyladenine. 19 To accurately identify its structure and validate its identity, the Drosophila genomic DNA was also required to be digested into single nucleosides for high sensitivity analysis. Another example, identification and analysis of oxidative damaged DNA (e.g., 8-oxo-7,8-dihydro-2′-deoxyguanosine, 8-oxodG) completely digestion of genomic DNA to maximal release 8-oxodG w...

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confidence: 99%

Three-Enzyme Cascade Bioreactor for Rapid Digestion of Genomic DNA into Single Nucleosides

Yin

Zhang

et al. 2016

Anal. Chem.

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“…Several studies have revealed prooxidant effects of vitamin E (13,14) and vitamin C (15)(16)(17) under certain circumstances. Other antioxidants such as N-acetylcysteine (18) and quercetin (19,20) can cause oxidative damage to cellular and isolated DNA. ␤-Carotene may also act as both an antioxidant and a prooxidant under various oxygen partial pressures (21)(22)(23).…”

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confidence: 99%

Oxidative DNA Damage by Vitamin A and Its Derivative via Superoxide Generation

Murata

Kawanishi²

2000

Journal of Biological Chemistry

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174

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Recent intervention studies revealed that ␤-carotene supplement to smokers resulted in a higher incidence of lung cancer. However, the causal mechanisms remain to be clarified. We reported here that vitamin A (retinol) and its derivative (retinal) caused cellular DNA cleavage detected by pulsed field gel electrophoresis. Retinol and retinal significantly induced 8-oxo-7,8-dihydro-2-deoxyguanosine formation in HL-60 cells but not in H 2 O 2 -resistant HP100 cells, suggesting the involvement of H 2 O 2 in cellular DNA damage. Experiments using 32 P-labeled isolated DNA demonstrated that retinol and retinal caused Cu(II)-mediated DNA damage, which was inhibited by catalase. UV-visible spectroscopic and electron spin resonance-trapping studies revealed the generation of superoxide and carbon-centered radicals, respectively. The superoxide generation during autoxidation of retinoids was significantly correlated with the formation of 8-oxo-7,8-dihydro-2-deoxyguanosine, although the yield of carbon-centered radicals was not necessarily related to the intensity of DNA damage. These findings suggest that superoxide generated by autoxidation of retinoids was dismutated to H 2 O 2 , which was responsible for DNA damage in the presence of endogenous metals. Retinol and retinal have prooxidant abilities, which might lead to carcinogenesis of the supplements of ␤-carotene.

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“…The obtained results indicate that phenolic compounds can switch from antioxidants to pro-oxidants in the presence of Cu(II) ions to induce ROS production and subsequently DNA damage. Phenolic antioxidants, including quercetin (Yamashita et al, 1999), curcumin (Ahsan and Hadi, 1998), and salsolinol (Jung and Surh, 2001) were reported to act as pro-oxidants in the presence of cupric ions. If phenolic compounds such as PA and copper were absorbed by the body, they would interact with each other to generate ROS.…”

Section: Resultsmentioning

confidence: 99%

“…Phenolic anti-oxidants, including quercetin (Yamashita et al, 1999), salsolinol (Jung and Surh, 2001), and resveratrol (Ahmad et al, 2005), were reported to induce lipid peroxidation and/or DNA damage in the presence of cupric ions. In this reaction, Cu(II) ions is reduced to Cu(I) ions by phenolic compounds and the re-oxidation of Cu(I) ions to Cu(II) ions is accompanied by the formation of ROS.…”

mentioning

confidence: 99%

Effect of Interaction between Protocatechualdehyde Produced from Streptomyces lincolnensis M-20 and Copper Ions on Antioxidant and Pro-oxidant Activities

Kim¹,

Lee²,

Yang³

2014

The Korean Journal of Microbiology

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Protocatechualdehyde (PA) is phenolic compound having antioxidative and antitumor activities. PA was purified from supernatant of Streptomyces lincolnensis M-20. In the presence of copper ion, PA acted as pro-oxidant. The antioxidant activity was assessed with the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, and the pro-oxidant effect of PA on DNA damage as pBR322 plasmid DNA-cleaving agents in the presence of Cu(II) ions was investigated. The involvement of reactive oxygen species (ROS) in the DNA damage was confirmed by the inhibition of the DNA breakage by using glutathione (GSH), specific scavenger of ROS. When the increase in ROS reaches a certain level (the toxic threshold), it may trigger cell death. The formation of the PA/Cu(II) chelate complex was confirmed by reaction with ethylenediamine-tetraacetic acid (EDTA), a well-known chelating agent for metal ions, by using UV/Vis spectroscopic analysis.

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Mechanism of oxidative DNA damage induced by quercetin in the presence of Cu(II)

Cited by 151 publications

References 33 publications

Three-Enzyme Cascade Bioreactor for Rapid Digestion of Genomic DNA into Single Nucleosides

Three-Enzyme Cascade Bioreactor for Rapid Digestion of Genomic DNA into Single Nucleosides

Oxidative DNA Damage by Vitamin A and Its Derivative via Superoxide Generation

Effect of Interaction between Protocatechualdehyde Produced from Streptomyces lincolnensis M-20 and Copper Ions on Antioxidant and Pro-oxidant Activities

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