Abstract
Four regioisomeric phenanthrene (PH) quinones (Q) were investigated for their ability to induce chromosomal damage and spindle disturbances. PH 1,4-Q and PH 1,2-Q induced structural as well as numerical chromosomal aberrations, whereas the isomers PH 9,10-Q and PH 3,4-Q were virtually inactive in this respect. However, all four compounds enhanced the frequency of c-mitoses.
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References
Anonymous. Biological Effects of Atmospheric Pollutants. Particulate Polycyclic Organic Matter, National Academy of Sciences, National Research Council, 1972,Washington D.C.
Atsushi H, Hisatoshi M, Yoshie T, Kiyomi Y. Mutagenicity and cytotoxicity of naphthoquinones for Ames Salmonella tester strains. Chem Res Toxicol. 1994;7:559–67.
Beigleiter A. Cytocidal action of the quinone group and its relationship to antitumor activity. Cancer Res. 1983;43: 481–4.
Bücker M, Glatt HR, Platt KL et al. Mutagenicity of phenan-threne and phenanthrene K-region derivatives. Mutat Res. 1979;66:337–48.
Cavalieri E, Rogan E. Role of radical cations in aromatic hydrocarbon carcinogenesis. Environ Health Perspect. 1985;64:69–84.
Chesis PL, Levin DE, Smith MT, Ernster L, Ames BN. Mutagenicity of quinones: pathways of metabolic activation and detoxification. Proc Natl Acad Sci USA. 1984;81:1696–700.
Conney AH. Induction of microsomal enzymes by foreign chemicals and carcinogenesis by polycyclic aromatic hydro-carbons. G.H.A. Clowes Memorial Lecture. Cancer Res. 1982;42:4875–917.
Dipple A. Polynuclear aromatic carcinogens. In: Searle CE, ed. Chemical carcinogens. Washington DC: American Chemi-cal Society; 1976:245–314. (ACS Monograph Series 3).
Ernster L. DT-diaphorase. Methods Enzymol. 1967;10:309–17.
Fieser LF. 1,2-Phenanthrenequinone. J Am Chem Soc. 1929a; 51:1896–906.
Fieser LF. Some derivatives of 3, 4-phenanthrenequinone. J Am Chem Soc. 1929b;51:940–56.
Galloway SM, Ivett JL. Chemically induced aneuploidy in mammalian cells in culture. Mutat Res. 1986;167:80–105.
Glatt HR, Oesch F. Structural and metabolic parameters governing the mutagenicity of polycyclic aromatic hydro-carbons. In: de Serres FJ, ed. Chemical mutagens}, vol.10. New York: Plenum; 1986:73–127.
Glatt HR, Gemperlein G, Turchi G, Heinritz H, Doehmer J, Oesch F. Search for cell culture systems with diverse xenobiotic-metabolizing activities and their use in toxico-logical studies. Mol Toxicol. 1989;1:313–34.
Goeptar AR, Te Koppele JM, Neve EPA, Vermeulen NPE. Reductase and oxidase activity of rat liver cytochrome P450 with 2,3,5,6-tetramethylbenzoquinone as substrate. Chem-Biol Interact. 1992;83:249–69.
Hales BF. Relative mutagenicity and teratogenicity of cyclo-phosphamide and two of its structural analogs. Biochem Pharmacol. 1983;32:3791–5.
Ishii H, Hanaoka T, Harada Y, Ikeda N. Oxidation with Fremy's salt-VIII. Peri-effects of a group located at the C5 position of 1-naphthol and related compounds. Tetra-hedron. 1976;32:2693–8.
Jowa L, Winkle S, Kalf G, Witz G, Snyder R. Deoxyguanosine adducts formed from benzoquinone and hydroquinone. In: Koscsis JJ, Jollow DJ, Witmer CM, Nelson JO, Snyder R, eds. Biological reactive metabolites. vol.3. New York: Ple-num; 1985:825–32.
Kappus H. Oxidative stress in chemical toxicity. Arch Toxicol. 1987;60:144–9.
Lau SS, Hill BA, Highet RJ, Monks TJ. Sequential oxidation and glutathione addition to 1,4-benzoquinone: correlation of toxicity with increased glutathione substitution. Mol Pharmacol. 1988;34:829–36.
Lesko S, Caspary W, Lorentzen R, Ts'o POP. Enzymatic formation of 6-oxobenzo(a)pyrene radical in rat liver homo-genates from carcinogenic benzo(a)pyrene. Biochemistry. 1975;14:3978–84.
Ludewig G, Dogra S, Glatt HR. Genotoxicity of 1,4-benzoqui-none and 1,4-naphthoquinone in relation to effects on glutatione and NAD(P)H levels in V79 cells. Environ Health Perspect. 1989;82:223–8.
Matsuoka A, Matsui M, Miyata N, Sofuni T, Ishidate M Jr. Mutagenicity of 3-tert-butyl-4-hydroxyanisole (BHA) and its metabolites in short-term tests in vitro. Mutat Res. 1990;241:125–32.
McKillop A, Young DW. Organic synthesis using supported reagents-Part I. Synthesis. 1979:401–22.
Miller BM, Adler ID. Suspect spindle poisons: analysis of c-mitotic effects in mouse bone marrow cells. Mutagenesis. 1989;4:208–15.
Monks TJ, Lau SS. Toxicology of quinone-thioethers. Crit Rev Toxicol. 1992;22:243–70
O'Brien PJ. Molecular mechanisms of quinone cytotoxicity. Chem-Biol Interact. 1991;80:1–41.
Oesch F, Bücker M, Glatt HR. Activation of phenanthrene to mutagenic metabolites and evidence for at least two differ-ent activation pathways. Mutat Res. 1981;81:1–10.
Pius J, Tao X, Yuehang X, Aniel KJ. NAD(P): quinone oxidoreductase 1 (DT-diaphorase): expression, regulation and role in cancer. Oncol Res. 1994;6:525–32.
Platt KL, Oesch F. Synthesis of non-K-region ortho-quinones of polycyclic aromatic hydrocarbons from cyclic ketones. Tetrahedron Lett. 1982;23:163–6.
Powis G, Svingen AB, Appel P. Quinone stimulated superoxide formation by subcellular fractions, isolated hepatocytes, and other cells. Mol Pharmacol. 1981;20:387–94.
Savage JRK. Annotation: classification and relationship of induced chromosomal structural changes. J Med Genet. 1976;13:103–22.
Sakai M, Yoshida D, Mizusaki S. Mutagenicity of polycyclic aromatic hydrocarbons and quinones on Salmonella typhi-murium TA 97. Mutat Res. 1985;156:61–7.
Sbrana I, Di Sibio A, Lomi A, Scarcelli V. C-Mitosis and numerical chromosome aberration analyses in human lym-phocytes: 10 known or suspect spindle poisons. Mutat Res. 1993;287:57–70.
Sbrana I, Puliti A, Seidel A, Glatt H, Turchi G. Induction of chromosomal aberrations and spindle disturbances in Chi-nese hamster epithelial liver cells in culture by pyrene and benzo(a)pyrene quinones. Mutagenesis. 1995;10:505–12.
Selkirk JK, Croy RG, Gelboin HV. Benzo(a)pyrene metabo-lites: efficient and rapid separation by high-pressure liquid chromatography. Science. 1974;184:169–71.
Smith MT, Evans CG. Inhibitory effect of superoxide-generat-ing quinones on superoxide dismutase. Biochem Pharmacol. 1974;33:3109–10.
Tajima K, Hashizaki M, Yamamoto K, Mizutani T. Metabo-lism of 3-tert-butyl-4-hydroxyanisole by horseradish per-oxidase and hydrogen peroxide. Drug Metab Dispos. 1992;20: 816–20.
Turchi G, Carluccio MA, Oesch F, Gemperlein I, Glatt HR. Characterization of an epithelial, nearly diploid liver cell strain, from Chinese hamster, able to activate promutagens. Mutagenesis. 1987;2:127–35.
Turchi G, Nardone A, Palitti F. Application of an epithelial liver cell line, metabolically competent, for mutation studies of promutagens. Mutat Res. 1992;271:79–88.
Watson WP, Smith RJ, Huckle KR, Right AS. Comparison of hydrocarbon-DNA adducts formed in mouse and human skin following treatment with benzo(a)pyrene. Arch Toxicol Suppl. 1987;11:93–8.
Wislocki PG, Wood AW, Chang RL et al. Mutagenicity and cytotoxicity of benzo(a)pyrene arene oxides, phenols, qui-nones, and dihydrodials in bacterial and mammalian cells. Cancer Res. 1976;36:3350–7.
Wood AW, Chang RL, Levin WL et al. Mutagenicity and tumorigenicity of phenanthrene and chrysene epoxides and diol-epoxides. Cancer Res. 1979;39:4069–77.
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Turchi, G., Glatt, H., Seidel, A. et al. Structure-activity relationship in the induction of chromosomal aberrations and spindle disturbances in Chinese hamster epithelial liver cells by regioisomeric phenanthrene quinones. Cell Biol Toxicol 13, 155–165 (1997). https://doi.org/10.1023/A:1007302111081
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DOI: https://doi.org/10.1023/A:1007302111081