Fungal metabolism of nitrofluoranthenes

Journal of Toxicology and Environmental Health - Part A

Volumn 53, Issue 2, 1998, Pages 153-174

  Pothuluri, Jairaj V ^a   Doerge, Daniel R ^a   Churchwell, Mona I ^a   Fu, Peter P ^a   Cerniglia, Carl E ^a  

^a NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 NITROFLUORANTHENE; 3 NITROFLUORANTHENE; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

AIR POLLUTANT; ARTICLE; BIOTRANSFORMATION; CUNNINGHAMELLA; DETOXIFICATION; GENOTOXICITY; LIVER METABOLISM; LIVER MICROSOME; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; XENOBIOTIC METABOLISM;

AIR POLLUTANTS; ANIMALS; BIOTRANSFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORENES; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES, LIVER; MUCORALES; RATS; RATS, SPRAGUE-DAWLEY;

CUNNINGHAMELLA ELEGANS; FUNGI; MAMMALIA;

EID: 0032559353     PISSN: 15287394     EISSN: 10872620     Source Type: Journal    
DOI: 10.1080/009841098159420     Document Type: Article

References (34)

1. X. Atmos. Environ. 20:2339-2345.
2. Atlas, R. M., and Cerniglia, C. E. 1995. Bioremediation of petroleum pollutants. BioScience 45:332-338.
3. Belisario, M. A., Pecce, R., Della Morte, R., Arena, A. R., Cecinato, A., Ciccioli, P., and Staiano, N. 1990. Characterization of oxidative and reductive metabolism in vitro of nitrofluo-ranthenes by rat liver enzymes. Carcinogenesis 7:1135-1141.
4. Ball, L. M., Nishioka, M. G., and Lewtas, J. 1991. Hepatic metabolism of the environmental mutagen 2-nitrofluoranthene. In Polynuclear aromatic hydrocarbons: Measurements, means, and metabolism, eds. M. Cooke, L. Loening, and J. Merritt, pp. 109-119. Columbus, OH: Battelle Press.
5. Boyd, D. R., Greene, R. M. E., Neill, J. D., and Stubbs, M. E. 1981. Racemization of phenanthrene 3,4-oxide. Absolute stereochemistry of cis- and trans-phenanthrene 3,4, dihydrodiols. J. Chem. Soc. Perkin Trans. I:1477-1482.
6. Cerniglia, C. E., and Gibson, D. T. 1978. Metabolism of naphthalene by cell extracts of Cunning-hamella elegans. Arch. Biochem. Biophys. 186:121-127.
7. Cerniglia, C. E., and Somerville, C. C. 1995. Reductive metabolism of nitroaromatic and nitropoly-cyclic aromatic hydrocarbons. In Biodegradation of nitroaromatic compounds, ed. J. Spain, pp. 99-115. New York: Plenum Press.
8. Cerniglia, C. E., Fu, P. P., and Yang, S. K. 1983. Regio- and stereoselective metabolism of 4-methylbenz[a]anthracene by the fungus Cunninghamella elegans. Biochem. J. 216:377-384.
9. Cerniglia, C. E., Freeman, J. P., White, G. L., Heflich, R. F., and Miller, D. W. 1985. Fungal metabolism and detoxification of the nitropolycyclic aromatic hydrocarbon 1-nitropyrene. Appl. Environ. Microbiol. 50:649-655.
10. Cerniglia, C. E., Campbell, W. L., Fu, P. P., Freeman, J. P., and Evans, F. E. 1990. Stereoselective fungal metabolism of methylated anthracenes. Appl. Environ. Microbiol. 56:661-668.
11. Cerniglia, C. E., Sutherland, J. B., and Crow, S. A. 1992. Fungal metabolism of aromatic hydrocarbons. In Microbial degradation of natural products, ed. G. Winkelmann, pp. 193-217. Weinheim, Germany: VCH.
12. Chou, M. W., and Yang, S. K. 1979. Combined reversed-phase and normal-phase high-performance liquid chromatography in the purification and identification of 7,12-dimethylbenz[a]anthra-cene metabolites. J. Chromatog. 185:635-654.
13. Consolo, M. C., Anders, M., and Howard, P. C. 1989. Mutagenicity of the phenolic microsomal metabolites of 3-nitrofluoranthene and 1-nitropyrene in strains of Salmonella typhimurium. Mutat. Res. 210:263-269.
14. Evans, F. E., Deck, J., and Howard, P. C. 1994. Structure of phenolic isomers of 2- and 3-nitrofluo-ranthene studied by one- and two-dimensional ^ NMR spectroscopy. Comparative analysis of mutagenicity. Chem. Res. Toxicol. 7:352-357.
15. Fu, P. P. 1990. Metabolism of nitro-polycyclic aromatic hydrocarbons. Drug Metab. Rev. 22:209-268.
16. Herreno-Saenz, D., Evans, F. E., Heinze, T., Lewtas, J., and Fu, P. P. 1992. In vitro metabolism and DNA adduct formation from the mutagenic environmental contaminant 2-nitrofluoranthene. Toxicology 6:863-869.
17. 1mice. Polycyclic Aromatic Compounds 6:79-85.
18. Howard, P. C., Mateescu, G. D., and Consolo, M. C. 1988. Liver microsomal metabolism of the environmental carcinogen 3-nitrofluoranthene, I. Phenolic metabolites. Carcinogenesis 9:911-917.
19. International Agency for Research on Cancer. 1989. Diesel and gasoline exhausts and some nitroarenes. IARC Monogr. Eval. Carcinog. Chem. Hum. 46, Lyon: IARC.
20. Lewtas, J. 1988. Genotoxicity of complex mixtures: Strategies for the identification and comparative assessment of airborne mutagens and carcinogens from combustion sources. Fundam. Appl. Toxicol. 10:571-589.
21. Lowry, O. H., Rosenbrough, N. J., Farr, A. L., and Randall, R. J. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:265-275.
22. Millner, G. C., Fu, P. P., and Cerniglia, C. E. 1986. Microbial transformation of 6-nitrobenzo[a]-pyrene. J. Toxicol. Environ. Health 19:519-530.
23. Pitts, J. N., Jr., Sweetman, J. A., Zielinska, B., Winer, A. M., and Atkinson, R. 1985. Determination of 2-nitrofluoranthene and 2-nitropyrene in ambient particulate organic matter: Evidence for atmospheric reactions. Atmos. Environ. 19:1601-1608.
24. Pothuluri, J. V., and Cerniglia, C. E. 1998. Current aspects on polycyclic aromatic hydrocarbons biodegradation processes. In Bioremediation: Principles and practices, biodegradation technology development, eds. R. L. Irving and S. K. Sikdar, Vol. 2, pp. 461-520. Lancaster, PA: Technomic.
25. Pothu luri, J. V., Freeman, J. P., Evans, F. E., and Cerniglia, C. E. 1990. Fungal transformation of flu-oranthene. Appl. Environ. Microbiol. 56:2974-2983.
26. Pothu luri, J. V., Freeman, J. P., Evans, F. E., and Cerniglia, C. E. 1992a. Fungal metabolism of ace-naphthene by Cunninghamella elegans. Appl. Environ. Microbiol. 58:3654-3659.
27. Pothu luri, J. V., Heflich, R. H., Fu, P. P., and Cerniglia, C. E. 1992b. Fungal metabolism and detoxification of fluoranthene. Appl. Environ. Microbiol. 58:937-941.
28. Pothuluri, J. V., Evans, F. E., Freeman, J. P., and Cerniglia, C. E. 1994. Fungal metabolism of 3-nitrofluoranthene. J. Toxicol. Environ. Health 42:209-218.
29. Ramdahl, T., Zielinska, B., Arey, J., Atkinson, R., Winer, A. M., and Pitts, J. N., Jr. 1986. A possible formation pathway for the nitrofluoranthenes and nitropyrenes in ambient air and their contribution to direct mutagenicity. 10th Int. Symp. PAH, Battelle, Columbus, OH, 21-23 October 1985.
30. Sutherland, J. B. 1992. Detoxification of polycyclic aromatic hydrocarbons by fungi. J. Ind. Microbiol. 9:53-62.
31. Tokiwa, H., and Ohnishi, Y. 1986. Mutagenicity and carcinogenicity of nitroarenes and their sources in the environment. CRC Crit. Rev. Toxicol. 17:23-60.
32. Zhang, D., Yang, Y., Leakey, J. E. A., and Cerniglia, C. E. 1996. Phase I and phase II enzymes produced by Cunninghamella elegans for the metabolism of xenobiotics. FEMS Microbiol. Lett. 138:221-226.
33. Zielinska, B., Arey, J., Atkinson, R., Ramdahl, T., Winer, A. M., and Pitts, J. N., Jr. 1986. Reactions of dinitrogen pentoxide with fluoranthene. J. Am. Chem. Soc. 108:4126-4132.
34. Zielinska, B., Harger, W. P., Arey, J., Winer, A. M., Haas, R. A., and Hanson, C. V. 1987. The mutagenicity of 2-nitrofluoranthene and its in vitro hepatic metabolites. Mutat. Res. 190:259-266.