Detection and mechanistic investigation of halogenated benzoquinone induced DNA damage by photoelectrochemical DNA sensor

Jia, Suping; Zhu, Ben-Zhan; Guo, Liang

doi:10.1007/s00216-010-3796-3

Cited by 38 publications

(23 citation statements)

References 26 publications

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“…Thus, the oxidative DNA damage contributes to carcinogenesis 24, 25. The DNA biosensors can be used for the detection of reactive oxygen species 25, UV exposure 26, and mutagens 27–29.…”

Section: Introductionmentioning

confidence: 99%

Organic Acid and DNA Sensing with Electrochemical Sensor Based on Carbon Black and Pillar[5]arene

et al. 2016

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Electrochemical sensor has been proposed on the base of glassy carbon electrode (GCE) modified with carbon black (CB) and pillar[5]arene (P[5]A). The characteristics of the peak currents were found to be sensitive to the incubation of the sensor in organic acid and DNA solution. The detection of n×(10−8–10−5) M of organic acid and down to (1–5)×10−18 g of DNA was attributed to the effect of the analytes on the aggregation and relative stability of oxidized and reduced forms of P[5]A. No signal interference with the alkali and alkali‐earth metal ions was found. The electrochemical sensor was tested in the detection of specific DNA interactions, i.e. reactive oxygen species damage and intercalating pharmaceuticals detection.

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“…Thus, the oxidative DNA damage contributes to carcinogenesis 24, 25. The DNA biosensors can be used for the detection of reactive oxygen species 25, UV exposure 26, and mutagens 27–29.…”

Section: Introductionmentioning

confidence: 99%

Organic Acid and DNA Sensing with Electrochemical Sensor Based on Carbon Black and Pillar[5]arene

et al. 2016

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“…In our previous studies, we found that TCBQ and H 2 O 2 can produce highly reactive hydroxyl radicals via a metal-independent mechanism5640414243, which can cause oxidative damage to DNA and other macromolecules44454647. Based on our finding that NHPI can effectively detoxify TCBQ, we expect that NHPI should also effectively protect plasmid pBR322 DNA from single-strand and double-strand breakage induced by TCBQ/H 2 O 2 .…”

Section: Resultsmentioning

confidence: 87%

An Exceptionally Facile Two-Step Structural Isomerization and Detoxication via a Water-Assisted Double Lossen Rearrangement

Huang

Xie

et al. 2016

Sci Rep

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N-hydroxyphthalimide (NHPI), which is best known as an organocatalyst for efficient C-H activation, has been found to be oxidized by quinoid compounds to its corresponding catalytically active nitroxide-radical. Here, we found that NHPI can be isomerized into isatoic anhydride by an unusually facile two-step method using tetrachloro-1,4-benzoquinone (TCBQ, p-chloranil), accompanied by a two-step hydrolytic dechlorination of highly toxic TCBQ into the much less toxic dihydroxylation product, 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone (chloranilic acid). Interestingly, through the complementary application of oxygen-18 isotope-labeling, HPLC combined with electrospray ionization quadrupole time-of-flight and high resolution Fourier transform ion cyclotron resonance mass spectrometric studies, we determined that water was the source and origin of oxygen for isatoic anhydride. Based on these data, we proposed that nucleophilic attack with a subsequent water-assisted Lossen rearrangement coupled with rapid intramolecular addition and cyclization in two consecutive steps was responsible for this unusual structural isomerization of NHPI and concurrent hydroxylation/detoxication of TCBQ. This is the first report of an exceptionally facile double-isomerization of NHPI via an unprecedented water-assisted double-Lossen rearrangement under normal physiological conditions. Our findings may have broad implications for future research on hydroxamic acids and polyhalogenated quinoid carcinogens, two important classes of compounds of major chemical and biological interest.

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“…Ru(bpy) 2 dppz 2+ is a DNA intercalator and binds selectively to the stacked base pairs in double-stranded DNA. Our previous study has shown that DNA damage including DNA adducts and base oxidation results in DNA structural changes and reduces its binding sites for Ru(bpy) 2 dppz 2+ [29]. Similarly, PSNS might also cause DNA damage and lead to lower photocurrent.…”

Section: Resultsmentioning

confidence: 98%

Rapid assessment of DNA damage induced by polystyrene nanosphere suspension using a photoelectrochemical DNA sensor

Zhang

Jia

et al. 2011

Sci. China Chem.

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Nanomaterials have been used increasingly in a wide variety of applications, and some of them have shown toxic effects on experimental animals and cells. In this study, a previously established photoelectrochemical DNA sensor was employed to rapidly detect DNA damage induced by polystyrene nanosphere (PSNS) suspensions. In the sensor, a double-stranded DNA film was assembled on a semiconductor electrode, and a DNA intercalator, Ru(bpy) 2 (dppz) 2+ (bpy = 2,2'-bipyridine, dppz = dipyrido[3,2-a:2',3'-c]phenazine) was used as the photoelectrochemical signal indicator. After the DNA-modified electrode was exposed to 2.0 mg/mL PSNS suspension, photocurrent of DNA-bound Ru(bpy) 2 (dppz) 2+ decreased by about 20%. The decrease is attributed to the chemical damage of DNA and consequently less binding of Ru(bpy) 2 (dppz) 2+ molecules to the electrode. Gel electrophoresis of DNA samples incubated with PSNS suspension confirmed DNA damage after the chemical exposure. However, in both photoelectrochemical and gel electrophoresis experiments, extensively washed PSNS did not induce any DNA damage, and the supernatant of PSNS suspension exhibited comparable DNA damage as the unwashed PSNS suspension. Furthermore, UV-visible absorption spectrum of the supernatant displayed a pattern very similar to that of styrene oxide (SO), a compound which has been shown to induce DNA damage by forming covalent DNA adducts. It is therefore suggested that styrene oxide and other residual chemicals in the PSNS may be responsible for the observed DNA damage. The results highlight the importance of full characterization of nanomaterials before their toxicity study, and demonstrate the utility of photoelectrochemical DNA sensors in the rapid assessment of DNA damage induced by chemicals and nanomaterials. nanomaterial, toxicity, DNA damage, sensor

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Detection and mechanistic investigation of halogenated benzoquinone induced DNA damage by photoelectrochemical DNA sensor

Cited by 38 publications

References 26 publications

Organic Acid and DNA Sensing with Electrochemical Sensor Based on Carbon Black and Pillar[5]arene

Organic Acid and DNA Sensing with Electrochemical Sensor Based on Carbon Black and Pillar[5]arene

An Exceptionally Facile Two-Step Structural Isomerization and Detoxication via a Water-Assisted Double Lossen Rearrangement

Rapid assessment of DNA damage induced by polystyrene nanosphere suspension using a photoelectrochemical DNA sensor

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