Formation of genotoxic nitro-PAH compounds in fish exposed to ambient nitrite and PAH

Toxicological Sciences

Volumn 91, Issue 2, 2006, Pages 440-447

  Shailaja, M S ^a   Rajamanickam, Rani ^a   Wahidulla, Solimabi ^a  

^a NATIONAL INSTITUTE OF OCEANOGRAPHY   (India)

Author keywords

Coastal waters; Fish; Genotoxicity; Nitrite; Nitro PAH

Indexed keywords

DNA FRAGMENT; EPOXIDE; NITRITE; PHENANTHRENE; PHENANTHRENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; BILE; CHEMICAL REACTION; COLLISIONALLY ACTIVATED DISSOCIATION; COMET ASSAY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ELECTROSPRAY MASS SPECTROMETRY; ENVIRONMENTAL EXPOSURE; FISH; GENOTOXICITY; LETHALITY; LIVER CELL; METABOLITE; NITRATION; NONHUMAN; OXIDATION; WATER CONTAMINATION;

ANIMALS; BILE; COMET ASSAY; DNA FRAGMENTATION; DRUG SYNERGISM; LIVER; NITRITES; PHENANTHRENES; SEAWATER; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TILAPIA;

OREOCHROMIS MOSSAMBICUS;

EID: 33744787094     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfj151     Document Type: Article

References (40)

1. Atkinson, R., and Arey, J. (1994). Atmospheric chemistry of gas-phase polycyclic aromatic hydrocarbons: Formation of atmospheric mutagens. Environ. Health Perspect. 102, 117-126.
2. Budde, C. L., Beyer, A., Munir, I. Z., Dordick, J. S., and Khmelnitsky, Y. L. (2001). Enzymatic nitration of phenols. J. Mol. Catal. B: Enzy. 15, 55-64.
3. Buhler, D. R., and Williams, D. E. (1989). Enzymes involved in metabolism of PAH by fishes and other aquatic animals: Oxidative enzymes (or phase I enzymes). In Metabolism of Polycyclic Aromatic Hydrocarbons in the Aquatic Environment (U. Varanasi, Ed.), pp. 151-184. CRC Press, Boca Raton, FL.
4. Chae, Y. H., Yun, C. H., Guengerich, F. P., Kadlubar, F. F., and El-Bayoumy, K. (1993). Roles of human hepatic and pulmonary cytochrome P450 enzymes in the metabolism of the environmental carcinogen 6-nitrochrysene. Cancer Res. 53, 2028-2034.
5. Chaloupka, K., Harper, N., Krishnan, V., Santostefano, M., Rodriguez, L. V., and Safe, S. (1993). Synergistic activity of polynuclear aromatic hydrocarbon mixtures as aryl hydrocarbon (Ah) receptor agonists. Chem-Biol. Interact. 89, 141-158.
6. Ciccioli, P., Cecinato, A., Brancaleoni, E., Frattoni, M., Zacchei, P., Miguel, A. H., and de Castro Vasconcellos, P. (1996). Formation and transport of 2-nitrofluoranthene and 2-nitropyrene of photochemical origin in the troposphere. J. Geophys. Res. 101, 19567-19582.
7. Collins, A., Dusinska, M., Franklin, M., Somorovska, M., Petrovska, H., Duthie, S., Fillion, L., Panayiotidis, M., Raslova, K., and Vaughan, N. (1997). Comet assay in human biomonitoring studies: Reliability, validation, and applications. Environ. Mol. Mutagen. 30, 139-146.
8. Eddy, F. B., Kunzlik, P. A., and Bath, R. N. (1983). Uptake and loss of nitrite from the blood of rainbow trout, Salmo gairdneri Richardson and Atlantic salmon, Salmo salar L. in fresh water and in dilute seawater. J. Fish Biol. 23, 105-116.
9. Fairbairn, D. W., Olive, P. L., and O'Neill, K. L. (1995). Comet assay: A comprehensive review. Mutat. Res. 339, 37-59.
10. Fent, K. (2001). Fish cell lines as versatile tools in ecotoxicology: Assessment of cytotoxicity, cytochrome P450 1Ainduction potential and estrogenic activity of chemicals and environmental samples. Toxicol. In Vitro 15, 477-488.
11. Fu, P. P., Chou, M. W., Yang, S. K., Beland, F. A., Kadlubar, F. F., Casciano, D. A., Heflich, R. H., and Evans, F. E. (1982). Metabolism of the mutagenic environmental pollutant, 6-nitrobenzo(a)pyrene: Metabolic activation via ring oxidation. Biochem. Biophys. Res. Commun. 105, 1037-1043.
12. Grant, D. M., Josephy, P. D., Lord, H. L., and Morrison, L. D. (1992). Salmonella typhimurium strains expressing human arylamine N-acetyltransferases: Metabolism and mutagenic activation of aromatic amines. Cancer Res. 52, 3961-3964.
13. International Programme on Chemical Safety (IPCS) (1998). Selected non-heterocyclic polycyclic aromatic hydrocarbons. In Environmental Health Criteria, Vol. 202. International Programme on Chemical Safety, WHO Monograph. World Health Organisation, Geneva.
14. Kanoh, T., Fukuda, M., Hayami, E., Kinouchi, T., Nishifuji, K., and Ohnishi, Y. (1990). Nitro reaction in mice injected with pyrene during exposure to nitrogen dioxide. Mutat. Res. 245, 1-4.
15. Kielhorn, J., Wahnschaffe, U., and Mangelsdorf, I. (2003). Selected nitro- and nitroxy-polycyclic aromatic hydrocarbons. In Environmental Health Criteria, Vol. 229, pp. 465. UNEP/ILO/WHO Monograph.World Health Organisation, Geneva.
16. Kitamura, S., and Tatsumi, K. (1996). Metabolism in vivo of 1-nitropyrene, an environmental pollutant in fish. Biol. Pharm. Bull. 19, 1524-1526.
17. Kobayashi, H., Sugiyama, C., Morikawa, Y., Hayashi, M., and Sofuni, T. (1995). A comparison between manual microscopic analysis and computerized image analysis in the single cell gel electrophoresis assay. MMS Commun. 3, 103-115.
18. Lal, H., and Singh, N. P. (1995). Acute low intensity microwave exposure increases DNA single-strand breaks in rat brain cells. Bioelectromagnetics 16, 207-210.
19. Li, E. E., Heflich, R. H., Bucci, T. J., Manjanatha, M. G., Blaydes, B. S., and Delclos, K. B. (1994). Relationships of DNA adduct formation, K-ras activating mutations and tumorigenic activities of 6-nitrochrysene and its metabolites in the lungs of CD-1 mice. Carcinogenesis 15, 1377-1385.
20. Livingstone, D. R. (1998). The fate of organic xenobiotics in aquatic ecosystems: Quantitative and qualitative differences in biotransformation by invertebrates and fish. Comp. Biochem. Physiol. 120, 43-49.
21. McCann, J., Choi, E., Yamasaki, E., and Ames, B. (1975). Detection of carcinogens as mutagens in the salmonells/microsome test: Assay of 300 chemicals. Proc. Natl. Acad. Sci. U.S.A. 72, 5135-5139.
22. Mitchelmore, C. L., and Chipman, J. K. (1998). Detection of DNA strand breaks in brown trout (Salmo trutta) hepatocytes and blood cells using the single cell gel electrophoresis (comet) assay. Aquat. Toxicol. 41, 161-182.
23. 32P-postlabelling. Biomarkers 3, 21-33.
24. Miyanishi, K., Kinouchi, T., Kataoka, K., Kanoh, T., and Ohnishi, Y. (1996). In vivo formation of mutagens by intraperitoneal administration of polycyclic aromatic hydrocarbons in animals during exposure to nitrogen dioxide. Carcinogenesis 17, 1483-1490.
25. Möller, I. (1994). In vivo metabolism and genotoxic effects of nitrated polycyclic aromatic hydrocarbons. Environ. Health Perspect. 102, 139-146.
26. Möller, L., Lax, I., and Eriksson, L. C. (1993). Nitrated polycyclic aromatic hydrocarbons: A risk assessment for the urban citizen. Environ. Health Perspect. 101, 309-315.
27. Möller, L., Rafter, J., and Gustafsson, J.A. (1987). Metabolism of the carcinogenic air pollutant 2-nitrofluorene in the rat. Carcinogenesis 8, 637-645.
28. 2O due to intensifying anoxia on the Indian continental shelf. Nature 408, 346-349.
29. Naqvi, S. W. A., Naik, H., Jayakumar, D. A., Shailaja, M. S., and Narvekar, P. V. (2006). Seasonal oxygen deficiency over the western continental shelf of India. In Past and Present Water Column Anoxia (L. N. Neretin, Ed.), NATO Science Series IV: Earth and Environmental Science, Vol. 64, pp. 195-224. Springer, Dordrecht, The Netherlands.
30. Nixon, S.W. (1995). Coastal marine eutrophication: A definition, social causes, and future concerns. Ophelia 41, 199-219.
31. Ohe, T. (1984). Mutagenicity of photochemical reaction products of polycyclic aromatic hydrocarbons with nitrite. Sci. Total Environ. 39, 161-175.
32. Pangrekar, J., Kandaswami, C., Kole, P., Kumar, S., and Sikka, H. C. (1995). Comparative metabolism of benzo(a)pyrene, chrysene and phenanthrene by brown bullhead liver microsomes. Mar. Environ. Res. 39, 51-55.
33. Pangrekar, J., Kole, P. L., Honey, S. A., Kumar, S., and Sikka, H. C. (2003). Metabolism of phenanthrene by brown bullhead liver microsomes. Aquat. Toxicol. 64, 407-418.
34. Pitts, J. N., Jr., van Cauwenberghe, K. A., Grosjean, D., Schmid, J. P., Fitz, D. R., Belser, W. L., Jr., Knudson, G. B., and Hynds, P.M. (1978). Atmospheric reactions of polycyclic aromatic hydrocarbons: Facile formation of mutagenic nitro derivatives. Science 202, 515-519.
35. Sasaki, J., Arey, J., and Harger, W. (1995). Formation of mutagens from the photooxidations of 2-4-ring PAH. Environ. Sci. Technol. 29, 1324-1335.
36. Shailaja, M. S., Rajamanickam, R., and Wahidulla, S. (2005). Increased formation of carcinogenic PAH metabolites in fish promoted by nitrite. Environ. Pollut. (in press).
37. Shailaja, M. S., and Rodrigues, A. (2003). Nitrite-induced enhancement of toxicity of phenanthrene in fish and its implications for coastal waters. Estuar. Coast. Shelf Sci. 56, 1107-1110.
38. Singh, N. P., McCoy, M. T., Tice, R. R., and Schneider, E. L. (1988). A simple technique for quantitation of low levels of DNA damage in individual cells. Exp. Cell Res. 175, 184-191.
39. Suzuki, J., Hagino, T., and Suzuki, S. (1987). Formation of 1-nitropyrene by photolysis of pyrene in water containing nitrite ion. Chemosphere 16, 859-867.
40. Varanasi, U., Nishimoto, M., Reichart, W. L., and Eberhart, B.-T. L. (1986). Comparative metabolism of benzo(a)pyrene and covalent binding to hepatic DNA in English sole, starry flounder, and rat. Cancer Res. 46, 3817-3824.