Radical production and DNA damage induced by carcinogenic 4-hydrazinobenzoic acid, an ingredient of mushroom Agaricus bisporus

References

• Toth B, Erickson J, Gannett P. Lack of carcinogenesis superfluous by the baked mushroom Agaricus bisporus in mice: Different feeding regimen. In vivo 1997; 11: 227–232
   PubMed Web of Science ®Google Scholar
• Toth B, Gannett PM, Visek WJ, Patil K. Carcinogenesis studies with the lyophilized mushroom Agaricus bisporus in mice. In vivo 1998; 12: 239–244
   PubMed Web of Science ®Google Scholar
• Toth B, Erickson J. Cancer induction in mice by feeding of the fresh uncooked cultivated mushroom of commerce Agaricus bisporus mushroom. Cancer Res 1986; 46: 4007–4011
   PubMed Web of Science ®Google Scholar
• Toth B. Mushroom toxins and cancer. Int J Oncol 1995; 6: 137–145
   PubMed Web of Science ®Google Scholar
• Toth B. Cancer induction by the sulfate form of 4-(hydroxymethyl) benzenediazonium ion of Agaricus bisporus. In vivo 1987; 1: 39–42
   PubMedGoogle Scholar
• Ross AE, Nagel D, Toth B. Evidence for the occurrence and formation of diazonium ions in the Agaricus bisporus mushroom and its extracts. J Agric Food Chem 1982; 30: 521–525
   PubMed Web of Science ®Google Scholar
• Toth B, Gannett P. An assessment of its carcinogenic potency. Mycopathologia 1993; 124: 73–77
   PubMed Web of Science ®Google Scholar
• Toth B, Sornson H. Lack of carcinogenicity of agaritine by subcutaneous administration in mice. Mycopathologia 1984; 85: 75–79
   PubMed Web of Science ®Google Scholar
• Friederich U, Fischer B, Luthy J, Hann D, Schlatter C, Wurgler FE. The mutagenic activity of agaritine-a constituent of the cultivated mushroom Agaricus bisporus- and its derivatives detected with the Salmonella/mammalian microsome assay (Ames Test). Z Lebensm Unters Forsch 1986; 183: 85–89
   PubMedGoogle Scholar
• Hiramoto K, Kaku M, Sueyoshi A, Fujise M, Kikugawa K. DNA base and deoxyribose modification by the carbon-centered radical generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom. Chem Res Toxicol 1995; 8: 356–362
   PubMed Web of Science ®Google Scholar
• Hiramoto K, Kaku M, Kato T, Kikugawa K. DNA strand breaking by the carbon-centered radical generated from 4-(hydroxymethyl) benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus. Chem Biol Interact 1995; 94: 21–36
   PubMed Web of Science ®Google Scholar
• Chauhan Y, Nagel D, Toth B. Identification of p-hydrazinobenzoic acid in the commercial mushroom Agaricus bisporus. J Agric Food Chem 1984; 32: 1067–1069
   Web of Science ®Google Scholar
• McManus B, Toth B, Patil K. Aortic rupture and aortic smooth muscle tumors in mice. Induction by p-hydrazinobenzoic acid hydrochloride of the cultivated mushroom Agaricus bisporus. Lab Invest 1987; 57: 78–85
   PubMed Web of Science ®Google Scholar
• Walton K, Coombs MM, Walker R, Ioannides C. Bioactivation of mushroom hydrazines to mutagenic products by mammalian and fungal enzymes. Mutat Res 1997; 381: 131–139
   PubMed Web of Science ®Google Scholar
• Shibutani S, Takeshita M, Grollman AP. Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 1991; 349: 431–434
   PubMed Web of Science ®Google Scholar
• Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA. 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G-T and A-C substitutions. J Biol Chem 1992; 267: 166–172
   PubMed Web of Science ®Google Scholar
• Serrano M, Hannon GJ, Beach D. A new regulatory motif in cell-cycle control causing specific inhibition of cyclin D/CDK4. Nature 1993; 366: 704–707
   PubMed Web of Science ®Google Scholar
• Oikawa S, Murakami K, Kawanishi S. Oxidative damage to cellular and isolated DNA by homocysteine: Implications for carcinogenesis. Oncogene 2003; 22: 3530–3538
   PubMed Web of Science ®Google Scholar
• Chumakov P. 1990., EMBL Data Library accession number X54156
   Google Scholar
• Yamashita N, Murata M, Inoue S, Hiraku Y, Yoshinaga T, Kawanishi S. Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II). Mutat Res 1998; 397: 191–201
   PubMed Web of Science ®Google Scholar
• Yamamoto K, Kawanishi S. Site-specific DNA damage induced by hydrazine in the presence of manganese and copper ions. The role of hydroxyl radical and hydrogen atom. J Biol Chem 1991; 266: 1509–1515
   PubMed Web of Science ®Google Scholar
• Kawanishi S, Yamamoto K. Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper(II) or manganese(III). Biochemistry 1991; 30: 3069–3075
   PubMed Web of Science ®Google Scholar
• Maxam AM, Gilbert W. Sequencing end-labeled DNA with basespecific chemical cleavages. Methods Enzymol 1980; 65: 499–560
   PubMedGoogle Scholar
• Kasai H, Crain PF, Kuchino Y, Nishimura S, Ootsuyama A, Tanooka H. Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair. Carcinogenesis 1986; 7: 1849–1851
   PubMed Web of Science ®Google Scholar
• Ito K, Inoue S, Yamamoto K, Kawanishi S. 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in doublestranded DNA by UV radiation with riboflavin. J Biol Chem 1993; 268: 13221–13227
   PubMed Web of Science ®Google Scholar
• Yamamoto K, Kawanishi S. Free radical production and site-specific DNA damage induced by hydralazine in the presence of metal ions or peroxidase/hydrogen peroxide. Biochem Pharmacol 1991; 41: 905–914
   PubMed Web of Science ®Google Scholar
• Pryor WA, Tang RH. Ethylene formation from methional. Biochem Biophys Res Comm 1978; 81: 498–503
   PubMed Web of Science ®Google Scholar
• Buettner GR. Spin trapping: ESR parameters of spin adducts. Free Radic Biol Med 1987; 3: 259–303
   PubMed Web of Science ®Google Scholar
• Burkitt MJ. Copper-DNA adducts. Methods Enzymol 1994; 234: 66–79
   PubMed Web of Science ®Google Scholar
• Liang Q, Dedon PC. Cu(II)/H2O2-induced DNA damage is enhanced by packaging of DNA as a nucleosome. Chem Res Toxicol 2001; 14: 416–422
   PubMed Web of Science ®Google Scholar
• Nunez ME, Noyes KT, Barton JK. Oxidative charge transport through DNA in nucleosome core particles. Chem Biol 2002; 9: 403–415
   PubMedGoogle Scholar
• Cullis PM, Jones GD, Symons MC, Lea JS. Electron transfer from protein to DNA in irradiated chromatin. Nature 1987; 330: 773–774
   PubMed Web of Science ®Google Scholar
• Midorikawa K, Murata M, Kawanishi S. Histone peptide AKRHRK enhances H2O2-induced DNA damage and alters its site specificity. Biochem Biophys Res Comm 2005; 333: 1073–1077
   PubMed Web of Science ®Google Scholar
• Kawanishi S, Hiraku Y, Murata M, Oikawa S. The role of metals in site-specific DNA damage with reference to carcinogenesis. Free Radic Biol Med 2002; 32: 822–832
   PubMed Web of Science ®Google Scholar
• Ito K, Yamamoto K, Kawanishi S. Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: Non-Fenton-type hydroxyl radical formation. Biochemistry 1992; 31: 11606–11613
   PubMed Web of Science ®Google Scholar
• Toth B. Synthetic and naturally occurring hydrazines as possible cancer causative agents. Cancer Res 1975; 35: 3693–3697
   PubMed Web of Science ®Google Scholar
• Parodi S, De Flora S, Cavanna M, Pino A, Robbiano L, Bennicelli C, Brambilla G. DNA-damaging activity in vivo and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity. Cancer Res 1981; 41: 1469–1482
   PubMed Web of Science ®Google Scholar
• Ferrali M, Signorini C, Sugherini L, Pompella A, Lodovici M, Caciotti B, Ciccoli L, Comporti M. Release of free, redox-active iron in the liver and DNA oxidative damage following phenylhydrazine intoxication. Biochem Pharmacol 1997; 53: 1743–1751
   PubMed Web of Science ®Google Scholar
• Sun Y, Li Y, Oberley LW. Superoxide dismutase activity during dimethylhydrazine colon carcinogenesis and the effects of cholic acid and indole. Free Radic Res Commun 1988; 4: 299–309
   PubMed Web of Science ®Google Scholar
• Lodovici M, Casalini C, De Filippo C, Copeland E, Xu X, Clifford M, Dolara P. Inhibition of 1,2-dimethylhydrazine-induced oxidative DNA damage in rat colon mucosa by black tea complex polyphenols. Food Chem Toxicol 2000; 38: 1085–1088
   PubMed Web of Science ®Google Scholar
• Ogawa K, Hiraku Y, Oikawa S, Murata M, Sugimura Y, Kawamura J, Kawanishi S. Molecular mechanisms of DNA damage induced by procarbazine in the presence of Cu(II). Mutat Res 2003; 539: 145–155
   PubMed Web of Science ®Google Scholar
• Hirakawa K, Midorikawa K, Oikawa S, Kawanishi S. Carcinogenic semicarbazide induces sequence-specific DNA damage through the generation of reactive oxygen species and the derived organic radicals. Mutat Res 2003; 536: 91–101
   PubMed Web of Science ®Google Scholar