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

Free Radical Research

Volumn 40, Issue 1, 2006, Pages 31-39

  Oikawa, Shinji ^a   Ito, Takahiro ^a   Iwayama, Michiko ^a   Kawanishi, Shosuke ^a  

^a MIE UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

4 hydrazinobenzoic acid; 8 dihydro 2 deoxyguanosine; 8 oxo 7; Adduct formation; Copper; DNA damage; Reactive oxygen species

Indexed keywords

4 HYDRAZINOBENZOIC ACID; 8 HYDROXYDEOXYGUANOSINE; ADENINE; ADENOSINE; BENZOIC ACID DERIVATIVE; CARCINOGEN; CATALASE; COPPER; CYTOSINE; DNA FRAGMENT; FREE RADICAL; GUANINE; GUANOSINE; HYDRAZINE DERIVATIVE; HYDROGEN PEROXIDE; PHOSPHORUS 32; PIPERIDINE; PROTEIN P16; PROTEIN P53; REACTIVE OXYGEN METABOLITE; THYMINE; UNCLASSIFIED DRUG;

AGARICUS BISPORUS; ANTIOXIDANT ACTIVITY; ARTICLE; AUTOOXIDATION; CARCINOGENESIS; CARCINOGENICITY; CONTROLLED STUDY; DNA ADDUCT; DNA DAMAGE; ELECTRON SPIN RESONANCE; HUMAN; ISOTOPE LABELING; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; OXIDATIVE STRESS; SPIN TRAPPING;

ADENOSINE; AGARICUS; ANIMALS; BENZOIC ACIDS; CARCINOGENS; CATALASE; CATTLE; COPPER; DEOXYGUANOSINE; DNA; DNA ADDUCTS; DNA DAMAGE; ELECTRON SPIN RESONANCE SPECTROSCOPY; GENES, TUMOR SUPPRESSOR; GUANOSINE; HUMANS; REACTIVE OXYGEN SPECIES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; SUBSTRATE SPECIFICITY;

AGARICUS BISPORUS; BASIDIOMYCOTA; RODENTIA;

EID: 29744431567     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760500329994     Document Type: Article

References (42)

1. Toth, B Erickson, J and Gannett, P. (1997) Lack of carcinogenesis superfluous by the baked mushroom Agaricus bisporus in mice: Different feeding regimen In vivo, 11, pp. 227 - 232.
2. Toth, B Gannett, PM Visek, WJ and Patil, K. (1998) Carcinogenesis studies with the lyophilized mushroom Agaricus bisporus in mice In vivo,, 12, pp. 239 - 244.
3. Toth, B and Erickson, J. (1986) Cancer induction in mice by feeding of the fresh uncooked cultivated mushroom of commerce Agaricus bisporus mushroom Cancer Res, 46, pp. 4007 - 4011.
4. Toth, B. (1995) Mushroom toxins and cancer Int J Oncol, 6, pp. 137 - 145.
5. Toth, B. (1987) Cancer induction by the sulfate form of 4-(hydroxymethyl) benzenediazonium ion of Agaricus bisporus In vivo, 1, pp. 39 - 42.
6. Ross, AE Nagel, D and Toth, B. (1982) Evidence for the occurrence and formation of diazonium ions in the Agaricus bisporus mushroom and its extracts J Agric Food Chem, 30, pp. 521 - 525.
7. Toth, B and Gannett, P. (1993) An assessment of its carcinogenic potency Mycopathologia, 124, pp. 73 - 77.
8. Toth, B and Sornson, H. (1984) Lack of carcinogenicity of agaritine by subcutaneous administration in mice Mycopathologia, 85, pp. 75 - 79.
9. Friederich, U Fischer, B Luthy, J Hann, D Schlatter, C and Wurgler, FE. (1986) 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, 183, pp. 85 - 89.
10. Hiramoto, K Kaku, M Sueyoshi, A Fujise, M and Kikugawa, K. (1995) DNA base and deoxyribose modification by the carbon-centered radical generated from 4-(hydroxymethyl)benzenediazonium salt, a carcinogen in mushroom Chem Res Toxicol, 8, pp. 356 - 362.
11. Hiramoto, K Kaku, M Kato, T and Kikugawa, K. (1995) DNA strand breaking by the carbon-centered radical generated from 4-(hydroxymethyl) benzenediazonium salt, a carcinogen in mushroom Agaricus bisporus Chem Biol Interact, 94, pp. 21 - 36.
12. Chauhan, Y Nagel, D and Toth, B. (1984) Identification of p-hydrazinobenzoic acid in the commercial mushroom Agaricus bisporus J Agric Food Chem, 32, pp. 1067 - 1069.
13. McManus, B Toth, B and Patil, K. (1987) Aortic rupture and aortic smooth muscle tumors in mice. Induction by p-hydrazinobenzoic acid hydrochloride of the cultivated mushroom Agaricus bisporus Lab Invest, 57, pp. 78 - 85.
14. Walton, K Coombs, MM Walker, R and Ioannides, C. (1997) Bioactivation of mushroom hydrazines to mutagenic products by mammalian and fungal enzymes Mutat Res, 381, pp. 131 - 139.
15. Shibutani, S Takeshita, M and Grollman, AP. (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG Nature, 349, pp. 431 - 434.
16. Cheng, KC Cahill, DS Kasai, H Nishimura, S and Loeb, LA. (1992) 8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G-T and A-C substitutions J Biol Chem, 267, pp. 166 - 172.
17. Serrano, M Hannon, GJ and Beach, D. (1993) A new regulatory motif in cell-cycle control causing specific inhibition of cyclin D/CDK4 Nature 366, pp. 704 - 707.
18. Oikawa, S Murakami, K and Kawanishi, S. (2003) Oxidative damage to cellular and isolated DNA by homocysteine: Implications for carcinogenesis Oncogene, 22, pp. 3530 - 3538.
19. Chumakov P. 1990., EMBL Data Library accession number X54156
20. Yamashita, N Murata, M Inoue, S Hiraku, Y Yoshinaga, T and Kawanishi, S. (1998) Superoxide formation and DNA damage induced by a fragrant furanone in the presence of copper(II) Mutat Res, 397, pp. 191 - 201.
21. Yamamoto, K and Kawanishi, S. (1991) 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, 266, pp. 1509 - 1515.
22. Kawanishi, S and Yamamoto, K. (1991) Mechanism of site-specific DNA damage induced by methylhydrazines in the presence of copper(II) or manganese(III) Biochemistry, 30, pp. 3069 - 3075.
23. Maxam, AM and Gilbert, W. (1980) Sequencing end-labeled DNA with basespecific chemical cleavages Methods Enzymol, 65, pp. 499 - 560.
24. Kasai, H Crain, PF Kuchino Y Nishimura, S Ootsuyama, A and Tanooka, H. (1986) Formation of 8-hydroxyguanine moiety in cellular DNA by agents producing oxygen radicals and evidence for its repair Carcinogenesis, 7, pp. 1849 - 1851.
25. Ito, K Inoue, S Yamamoto, K and Kawanishi, S. (1993) 8-Hydroxydeoxyguanosine formation at the 5′ site of 5′-GG-3′ sequences in doublestranded DNA by UV radiation with riboflavin J Biol Chem, 268, pp. 13221 - 13227.
26. Yamamoto, K and Kawanishi, S. (1991) Free radical production and site-specific DNA damage induced by hydralazine in the presence of metal ions or peroxidase/hydrogen peroxide Biochem Pharmacol, 41, pp. 905 - 914.
27. Pryor, WA and Tang, RH. (1978) Ethylene formation from methional Biochem Biophys Res Comm, 81, pp. 498 - 503.
28. Buettner, GR. (1987) Spin trapping: ESR parameters of spin adducts Free Radic Biol Med, 3, pp. 259 - 303.
29. Burkitt, MJ. (1994) Copper-DNA adducts Methods Enzymol, 234, pp. 66 - 79.
30. 2-induced DNA damage is enhanced by packaging of DNA as a nucleosome Chem Res Toxicol, 14, pp. 416 - 422.
31. Nunez, ME Noyes, KT and Barton, JK. (2002) Oxidative charge transport through DNA in nucleosome core particles Chem Biol, 9, pp. 403 - 415.
32. Cullis, PM Jones, GD Symons MC and Lea, JS. (1987) Electron transfer from protein to DNA in irradiated chromatin Nature 330, pp. 773 - 774.
33. 2-induced DNA damage and alters its site specificity Biochem Biophys Res Comm, 333, pp. 1073 - 1077.
34. Kawanishi, S Hiraku, Y Murata, M and Oikawa, S. (2002) The role of metals in site-specific DNA damage with reference to carcinogenesis Free Radic Biol Med, 32, pp. 822 - 832.
35. Ito, K Yamamoto, K and Kawanishi, S. (1992) Manganese-mediated oxidative damage of cellular and isolated DNA by isoniazid and related hydrazines: Non-Fenton-type hydroxyl radical formation Biochemistry, 31, pp. 11606 - 11613.
36. Toth, B. (1975) Synthetic and naturally occurring hydrazines as possible cancer causative agents Cancer Res, 35, pp. 3693 - 3697.
37. Parodi, S De Flora, S Cavanna, M Pino, A Robbiano, L Bennicelli, C and Brambilla, G. (1981) DNA-damaging activity in vivo and bacterial mutagenicity of sixteen hydrazine derivatives as related quantitatively to their carcinogenicity Cancer Res, 41, pp. 1469 - 1482.
38. Ferrali, M Signorini, C Sugherini, L Pompella, A Lodovici, M Caciotti, B Ciccoli, L and Comporti, M. (1997) Release of free, redox-active iron in the liver and DNA oxidative damage following phenylhydrazine intoxication Biochem Pharmacol, 53, pp. 1743 - 1751.
39. Sun, Y Li, Y and Oberley, LW. (1988) Superoxide dismutase activity during dimethylhydrazine colon carcinogenesis and the effects of cholic acid and indole Free Radic Res Commun, 4, pp. 299 - 309.
40. Lodovici, M Casalini, C De Filippo, C Copeland, E Xu, X Clifford, M and Dolara, P. (2000) Inhibition of 1,2-dimethylhydrazine-induced oxidative DNA damage in rat colon mucosa by black tea complex polyphenols Food Chem Toxicol, 38, pp. 1085 - 1088.
41. Ogawa, K Hiraku, Y Oikawa, S Murata, M Sugimura, Y Kawamura, J and Kawanishi, S. (2003) Molecular mechanisms of DNA damage induced by procarbazine in the presence of Cu(II) Mutat Res, 539, pp. 145 - 155.
42. Hirakawa, K Midorikawa, K Oikawa, S and Kawanishi, S. (2003) Carcinogenic semicarbazide induces sequence-specific DNA damage through the generation of reactive oxygen species and the derived organic radicals Mutat Res, 536, pp. 91 - 101.