DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds

Kato, Tetsuta; Kojima, Kazuhiro; Hiramoto, Kazuyuki; Kikugawa, Kiyomi

doi:10.1016/0027-5107(92)90088-j

Cited by 36 publications

(20 citation statements)

References 31 publications

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“…DNA strand breaks induced directly by high PYC concentration may be caused by carbon-centered radicals generated from PYC, such as neocarzinostatin (Saito et al, 1989) and aromatic diazonium salts (Kato et al, 1992). It is also possible that PYC acts as an interceptor of free radical species such as beta-carotene (Ozhogina and Kasaikina, 1995).…”

Section: Protecting Effects Of Pyc Against Dna Damage Caused By Fentomentioning

confidence: 99%

The effects of Pycnogenol on DNA damage in vitro and expression of superoxide dismutase and HP1 in Escherichia coli SOD and catalase deﬁcient mutant cells

Kim¹,

Park²

2004

Phytotherapy Research

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The procyanidin-rich French maritime pine bark extract Pycnogenol (PYC) is believed to be an antioxidant. To access whether PYC protects DNA against Fenton reaction radicals, pUC 19 plasmid DNA was damaged by OH- radicals generated from Fe(II) plus H2O2 in the presence and absence of PYC. DNA damage was quantified by measuring decreases in supercoiled DNA (SC-DNA) using agarose gel electrophoresis. The results showed that PYC (50 microg/mL) did not inhibit DNA damage from Fenton reaction-generated oxyradicals, when the Fenton reaction was allowed to proceed. However, PYC did protect against DNA damage when added prior to the initiation of the Fenton reaction, suggesting that protection resulted from chelation of Fe rather than from the scavenging of radicals. Moreover, we unexpectedly observed PYC-associated DNA breakage, which was dose- and time- dependent. Other antioxidants such as desferrioxamine (DFO) including butylated hydroxyltoluene (BHT), curcumin and alpha-tocopherol exhibited protective effects against DNA damage caused by the Fenton reaction. Subsequently, we assessed the possible pro-oxidant function of PYC on DNA damage in E. coli SOD deficient mutants under oxidative stress, after observing that PYC can induce SOD under oxidative stress. Although, PYC did not enhance DNA damage, it likewise did not protect against oxidative stress-mediated DNA damage. All together, our data indicate that PYC under some circumstances can enhance oxidative stress-mediated DNA damage in vitro and in vivo.

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Section: Protecting Effects Of Pyc Against Dna Damage Caused By Fentomentioning

confidence: 99%

The effects of Pycnogenol on DNA damage in vitro and expression of superoxide dismutase and HP1 in Escherichia coli SOD and catalase deﬁcient mutant cells

Kim¹,

Park²

2004

Phytotherapy Research

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“…Given the large number of reports published in this field in the past 150 years, it is surprising that there is one group of diazonium ions for which radical reactions remained practically unknown. Driven by the interest to find out whether this exclusion is due to the unique reactivity of the hydroxy-substituted aryl radicals 1 [4] and 2, [5,6] or is rather a consequence of special properties of the related arenediazonium ions 3 and 4 (e.g., the possible formation of quinonediazides), we revisited the chemistry of these compounds and their reactive intermediates. Herein, we summarized our first results.…”

mentioning

confidence: 99%

Hydroxy‐ and Aminophenyl Radicals from Arenediazonium Salts

Pratsch

Anger

Ritter

et al. 2011

Chemistry A European J

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A buried polar bilayer interface composed of interdigitated peptide ends and a high density of CF3COO− counterions passifying lysine amines are identified in nanotubes obtained by self‐assembly of short peptides. The structure reveals distinct characteristics that differentiate peptide bilayers and lipid bilayers that can now be exploited for the construction of lipid‐like nanomaterials with protein functionality.

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“…Kikugawa et al have demonstrated that diazoquinone compounds were formed by the reaction between phenols and nitrite, 9) and Kato et al have reported that hydroxyphenyl radicals were generated from diazoquinones. 15) These diazoquinone mutagens acted as mutagens toward S. typhimurium stains TA 98 and TA 100. Schrader et al have revealed that when bisphenol A was treated with nitrite under acidic conditions, electrophiles, which are possible DNA-binding and damaging agents, were formed.…”

Section: Resultsmentioning

confidence: 98%

Changes in the Mutagenic and Estrogenic Activities of 17β-Estradiol after Treatment with Nitrite

Masuda

Terashima

Sano

et al. 2006

Bioscience, Biotechnology, and Biochemistry

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DNA strand breakage by hydroxyphenyl radicals generated from mutagenic diazoquinone compounds

Cited by 36 publications

References 31 publications

The effects of Pycnogenol on DNA damage in vitro and expression of superoxide dismutase and HP1 in Escherichia coli SOD and catalase deﬁcient mutant cells

The effects of Pycnogenol on DNA damage in vitro and expression of superoxide dismutase and HP1 in Escherichia coli SOD and catalase deﬁcient mutant cells

Hydroxy‐ and Aminophenyl Radicals from Arenediazonium Salts

Changes in the Mutagenic and Estrogenic Activities of 17β-Estradiol after Treatment with Nitrite

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