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Original Article

DNA-breaking versus DNA-protecting activity of four phenolic compounds in vitro

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Pages 551-566 | Received 23 Jul 1998, Published online: 07 Jul 2009

References

  • Thomson R.H. Naturally occurring quinones. Butter Worths Scientific Publications, London 1957, In
  • Ames B.N. Dietary carcinogens and anticarcinogens. Oxygen radicals and degenerative diseases. Science 1983; 221: 1256–1264
  • Yamada K., Shirahata S., Murakami H., Nishiyama K., Shinohara K., Omura H. DNA breakage by phenyl compounds. Agricultural and Biological Chemistry 1985; 49: 1423–1428
  • de Peyster A., Quintanilha A., Packer L., Smith M.T. Oxygen radical formation induced by gossypol in rat liver microsomes and human sperm. Biochemical and Biophysical Research Communications 1984; 118: 573–579
  • Laughton M.J., Halliwell B., Evans P.J., Hoult J.R.S. Antioxidant and pro-oxidant actions of the plant phenolics quercetin, gossypol and myricetin. Effects on lipid peroxidation hydroxyl radical generation and bleomycin-dependent damage to DNA. Biochemical Pharmacology 1989; 38: 2859–2865
  • Srivastava A.K., Padmanaban G. Gossypol mediated DNA degradation. Biochemical and Biophysical Research Communications 1987; 146: 1515–1522
  • Chen Y., Sten M., Nordenskjold M., Lambert B., Matlin S.A., Zhou R.H. The effect of gossypol on the frequency of DNA-strand breaks in human leukocytes in vitro. Mutation Research 1986; 164: 71–78
  • Greenlee W.F., Sun J.D., Bus J.S. A proposed mechanism for benzene toxicity: Formation of reactive intermediates from polyphenol metabolites. Toxicology and Applied Pharmacology 1981; 58: 187–195
  • Kawanishi S., Inoue S., Kawanishi M. Human DNA damage induced by 1,2,4-benzenetriol, a benzene metabolite. Cancer Research 1989; 49: 164–168
  • Zhang L., Smith M.T., Bandy B., Davison A.J. Role of quinones, active oxygen species and metals in the genotoxicity of 1,2,4-benzenetriol, a metabolite of benzene. Free Radicals in the Environment, medicine and Toxicology, H. Nohl, H. Esterbauer, C. Rice-Evans. Richelieu Press, London 1994; 521–561, In
  • Chevion M.A. Site-specific mechanism for free radical induced biological damage: the essential role of redox-active transition metals. Free Radical Biology and Medicine 1988; 5: 27–37
  • Iwahashi H., Morishita H., Ishii T., Sugata R., Kido R. Enhancement by catechols of hydroxyl-radical formation in the presence of ferric ions and hydrogen peroxide. Journal of Biochemistry 1989; 105: 429–434
  • Stich H.F., Rosin M.P., Wu C.H., Powrie W.D. The action of transition metals on the genotoxicity of simple phenols, phenolic acids and cinnamic acids. Cancer Letters 1981; 14: 251–260
  • San R.H.C., Chan R.I.M. Inhibitory effect of phenolic compounds on aflatoxin B1 metabolism and induced mutagenesis. Mutation Research 1987; 177: 229–239
  • Chan R.I.M., San R.H.C., Stich H.F. Mechanism of inhibition of N-methyl-N′-Nitro-N-nitrosoguanidine-induced mutagenesis by phenolic compounds. Cancer Letters 1986; 31: 27–34
  • Wargovich M.J., Eng V.W.S., Newmark H.L. Inhibition by plant phenols of benzo[a]pyrene-induced nuclear aberrations in mammalian intestinal cells: a rapid in vivo assessment method. Food Chemistry and Toxicology 1985; 23: 47–49
  • Raj A.S., Heddle J.A., Newmark H.L., Katz M. Caffeic acid as an inhibitor of DMBA-induced chromosomal breakage in mice assessed by bone-marrow micronucleus test. Mutation Research 1983; 124: 247–253
  • Sasaki Y.F., Imanishi H., Ohta T., Watanabe M., Matsumoto K., Shirasu Y. Suppressing effect of tannic acid on the frequencies of mutagen-induced sister-chromatid exchanges in mammalian cells. Mutation Research 1989; 213: 195–203
  • Iwahashi H., Ishii T., Sugata R., Kido R. The effects of caffeic acid and its related catechols on hydroxyl radical formation by 3-hydroxyanthranilic acid, ferric chloride, and hydrogen peroxide. Archives of Biochemistry and Biophysics 1990; 276: 242–247
  • Duniec Z., Robak J., Gryglewski R. Antioxidant properties of some chemicals vs their influence on cyclooxygenase and lipoxidase activities. Biochemical Pharmacology 1983; 32: 2282–2286
  • Zhou Y.C., Zheng R.L. Phenolic compounds and an analog as superoxide anion scavengers and antioxidants. Biochemical Pharmacology 1991; 42: 1177–1179
  • Hamasaki Y., Tai H.H. Gossypol, a potent inhibitor of arachidonate 5- and 12-lipoxygenases. Biochimica Biophysica Acta 1985; 834: 37–41
  • Skutches C.L., Smith F.H. Effect of phenobarbital on the level of gossypol in the liver and the effect of gossypol and phenobarbital on the liver microsomal O-demethylation and lipid peroxidation activities in the rat. Journal of Nutrition 1974; 104: 1567–1575
  • Pellack-Walker P., Walker J.K., Evans H.H., Blumey J.L. Relationship between the oxidation potential of benzene metabolites and their inhibitory effect on DNA synthesis in L5178YS cells. Molecular Pharmacology 1985; 28: 560–566
  • Lee E.W., Johnson J.T., Garner C.D. Inhibitory effect of benzene metabolites on nuclear DNA synthesis in bone marrow cells. Journal of Toxicology and Environmental Health 1989; 26: 277–291
  • Lewis J.G., Stewart W., Adams D.O. Role of oxygen radicals in induction of DNA damage by metabolites of benzene. Cancer Research 1988; 48: 4762–4765
  • Maniatis T., Fitsch E.F., Sambrook J. Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratories, Cold Spring Harbor, NY 1989; 1: 2.73–2.73, In
  • Espejo R.T., Canelo E.S. Properties of bacteriophage PM2, a lipid-containing bacterial virus. Virology 1968; 34: 738–747
  • Espejo R.T., Canelo E.S., Sinsheimer R.L. DNA of bacteriophage PM2: A closed circular double-stranded molecule. Proceedings of the National Academy of Sciences of the USA 1969; 63: 1164–1168
  • Tsang S.S. A DNA binding activity from HeLa cells which binds preferentially to DNA damage with ultraviolet light and N-acetoxy-N-acetyl-2-aminofluorene. University of British Columbia, VancouverCanada 1980, Thesis
  • Kuhnlein U., Penhoet E.E., Linn S. An altered apurinic DNA endonuclease activity in group A and group D xeroderma pigmentosum fibroblasts. Proceedings of the National Academy of Sciences of the USA 1976; 73: 1169–1173
  • Smith R.M., Martell A.E. Critical Stability Constants. Amines, Plenum, New York 1975; 2
  • Martell A.E., Smith R.M. Critical Stability Constants. Other Organic Ligands, Plenum, New York 1977; 3
  • 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. Journal of Biological Chemisty 1991; 25: 1509–1515
  • Ehrenfeld G.M., Shipley J.B., Heimbrook D.C., Sugiyama H., Long E.C., vanBoom J.H., van der Marel G.A., Oppenheimer N.J., Hecht S.M. Copper-dependent cleavage of DNA by bleomycin. Biochemistry 1987; 26: 931–942
  • Eliot H., Gianni L., Myers C. Oxidative destruction of DNA by adriamycin-iron complex. Biochemistry 1984; 23: 928–936
  • Haidle C.W., McKinney S.H. Agarose gel electrophoretic analysis of damage to supercoiled DNA by adriamycin in the presence of beta-NADH dehydrogenase. Cancer Biochemistry and Biophysics 1985; 8: 47–59
  • Gutteridge J.M.C., Halliwell B. The role of superoxide and hydroxyl radicals in the degradation of DNA and deoxyribose induced by a copper-phenanthroline complexes. Biochemical Pharmacology 1982; 31: 2801–2805
  • Rahman A., Shahabuddin H.S.M., Parish J.H., Ainley K. Strand scission in DNA induced by quercetin and Cu(II): role of Cu(I) and oxygen free radicals. Carcinogenesis 1989; 10: 1833–1839
  • Schneider J.E., Browning M.M., Floyd R.A. Ascorbate/iron mediation of hydroxyl free radical damage to pBR322 plasmid DNA. Free Radical Biology and Medicine 1988; 5: 287–295
  • Bandy B., Moon J., Davison A.J. Multiple actions of superoxide dismutase: Why can it both inhibit and stimulate reduction of oxygen by hydroquinones?. Free Radical Biology and Medicine 1990; 9: 143–148
  • Zhang L., Bandy B., Davison A.J. Effects of metals, ligands and antioxidants on the reaction of oxygen with 1,2,4-benzenetriol. Free Radiological Biology and Medicine 1996; 20: 495–505
  • Tachon P. Ferric and cupric ions requirement for DNA single-strand breakage by H2O2. Free Radical Research Communications 1989; 7: 1–10
  • Aruoma O.I., Halliwell B., Gajewski E., Dizdaroglu M. Copper-ion-dependent damage to the bases in DNA in the presence of hydrogen peroxide. Biochemical Journal 1991; 273: 601–604

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