Atmospheric chemistry of polycyclic aromatic hydrocarbons and related compounds

Journal of Health Science

Volumn 57, Issue 6, 2011, Pages 504-511

  Kameda, Takayuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Atmospheric reaction; Photolysis; Polycyclic aromatic compound; Secondary formation

Indexed keywords

1 NITROPYRENE; 1 NITROTRIPHENYLENE; 2 NITROTRIPHENYLENE; ENVIRONMENTAL CHEMICAL; HYDROXYNITROPYRENE DERIVATIVE; NITRATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRENE DERIVATIVE; RADICAL; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERE; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DECOMPOSITION; GAS; HUMAN; NITRATION; NONHUMAN; OXYGENATION; PHOTOCHEMISTRY; PHOTOREACTIVITY; PHYSICAL CHEMISTRY; POLLUTANT; RADIATION EXPOSURE; REPRODUCTIVE TOXICITY; SIMULATION; SUSPENDED PARTICULATE MATTER; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 82855175356     PISSN: 13449702     EISSN: 13475207     Source Type: Journal    
DOI: 10.1248/jhs.57.504     Document Type: Article

References (39)

1. Schuetzle, D. (1983) Sampling of vehicle emissions for chemical analysis and biological testing. Environ. Health Perspect., 47, 65-80.
2. Salmeen, I. T., Pero, A. M., Zator, R., Schuetzle D. and Riley, T. L. (1984) Ames assay chromatograms and the identification of mutagens in diesel particle extracts. Environ. Sci. Technol., 18, 375-382.
3. Schuetzle, D., Riley, T. L., Prater, T. J., Harvey, T. M. and Hunt, D. F. (1982) Analysis of nitrated polycyclic aromatic-hydrocarbons in diesel particulates. Anal. Chem., 54, 265-271.
4. Bamford, H. A., Bezabeh, D. Z., Schantz, M. M., Wise, S. A. and Baker, J. E. (2003) Determination and comparison of nitrated-polycyclic hydrocarbons measured in air and diesel particulate reference materials. Chemosphere, 50, 575-587.
5. Bezabeh, D. Z., Bamford, H. A., Schantz, M.M. and Wise, S. A. (2003) Determination of nitrated polycyclic aromatic hydrocarbons in diesel particulaterelated standard reference materials by using gas chromatography/mass spectrometry with negative ion chemical ionization. Anal. Bioanal. Chem., 375, 381-388.
6. Zielinska, B., Arey, J., Atkinson, R., Ramdahl, T. and Winer, A. M. (1989) The nitroarenes of molecular weight 247 in ambient particulate samples collected in southern California. Atmos. Environ., 23, 223-229.
7. 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, 19567-19581.
8. Reisen, F. and Arey, J. (2005) Atmospheric reactions influence seasonal PAH and nitro-PAH concentrations in the Los Angeles basin. Environ. Sci. Technol., 39, 64-73.
9. Atkinson, R. and Arey, J. (1994) Atmospheric chemistry of gas-phase polycyclic aromatic hydrocarbons: Formation of atmospheric mutagens. Environ. Health Perspect., 102, 117-126.
10. Sasaki, J., Aschmann, S. M., Kwok, E. S. C., Atkinson, R. and Arey, J. (1997) Products of the gas-phase OH and NO3 radical-initiated reactions of naphthalene. Environ. Sci. Technol., 31, 3173-3179.
11. Cvrčeková, O., Ciganek, M. and Šimek, Z. (2006) Anthracene, chrysene, their nitro- and methylderivatives photostability in isooctane. Polycycl. Aromat. Compd., 26, 331-344.
12. Warner, S. D., Farant, J.-P. and Butler, I. S. (2004) Photochemical degradation of selected nitropolycyclic aromatic hydrocarbons in solution and adsorbed to solid particles. Chemosphere, 54, 1207-1215.
13. Ishii, S., Hisamatsu, Y., Inazu, K. and Aika, K. (2000) Ambient measurement of nitrotriphenylenes and possibility of nitrotriphenylene formation by atmospheric reaction. Environ. Sci. Technol., 34, 1893-1899.
14. Ishii, S., Hisamatsu, Y., Inazu, K. and Aika, K. (2001) Environmental occurrence of nitrotriphenylene observed in airborne particulatematter. Chemosphere, 44, 681-690.
15. Kameda, T., Inazu, K., Hisamatsu, Y., Takenaka, N. and Bandow, H. (2004) Determination of atmospheric nitro-polycyclic aromatic hydrocarbons and their precursors at a heavy traffic roadside and at a residential area in Osaka, Japan. Polycycl. Aromat. Compd., 24, 657-666.
16. Kawanaka, Y., Sakamoto, K., Wang, N. and Yun, S. (2005) Determination of nitroarenes and 3-nitrobenzanthrone in atmospheric particulate matter by gas chromatography/tandem mass spectrometry with negative ion chemical ionization. Bunseki Kagaku, 54, 685-691.
17. Kameda, T., Inazu, K., Hisamatsu, Y., Takenaka, N. and Bandow, H. (2006) Isomer distribution of nitrotriphenylenes in airborne particles, diesel exhaust particles, and the products of gas-phase radicalinitiated nitration of triphenylene. Atmos. Environ., 40, 7742-7751.
18. Phousongphouang, P. T. and Arey, J. (2003) Sources of the atmospheric contaminants, 2-nitrobenzanthrone and 3-nitrobenzanthrone. Atmos. Environ., 37, 3189-3199.
19. Zielinska, B., Arey, J., Atkinson, R., Ramdahl, T., Winer, A. M. and Pitts, J. N., Jr. (1986) Reaction of dinitrogen pentoxide with fluoranthene. J. Am. Chem. Soc., 108, 4126-4132.
20. Barker, C. C., Emmerson, R. G. and Periam, J. D. (1955) The monosubstitution of triphenylene. J. Chem. Soc., 4482-4485.
21. Radner, F. (1983) Nitration of polycyclic aromatic hydrocarbons with dinitrogen tetroxide. A simple and selective synthesis of mononitroderivatives. Acta Chem.Scand. B, 37, 65-67.
22. Kameda, T., Inazu, K., Asano, K., Murota, M., Takenaka, N., Sadanaga, Y., Hisamatsu, Y. and Bandow, H. Atmospheric occurrence of particleassociated nitrotriphenylenes via gas-phase radicalinitiated reactions observed in south Osaka, Japan. Atmos. Environ., submitted.
23. Rosser, P. F., Ramachandran, P., Sangaiah, R., Austin, R. N., Gold, A. and Ball, L. M. (1996) Role of O-acetyltransferase in activation of oxidised metabolites of the genotoxic environmental pollutant 1-nitropyrene. Mutat. Res., 369, 209-220.
24. Gibson, T. L., Korsog, P. E. and Wolff, G. T. (1986) Evidence for the transformation of polycyclic organic matter in the atmosphere. Atmos. Environ., 20, 1575-1578.
25. Kameda, T., Akiyama, A., Toriba, A., Tang, N. and Hayakawa, K. (2010) Determination of particleassociated hydroxynitropyrenes with correction for chemical degradation on a quartz fibre filter during high volume air sampling. Int. J. Environ. Anal. Chem., 90, 976-987.
26. Schuetzle, D., Jensen, T. E. and Ball, J. C. (1985) Polar polynuclear aromatic hydrocarbon derivatives in extracts of particulates: Biological characterization and techniques for chemical analysis. Environ. Int., 11, 169-181.
27. Manabe, Y., Kinouchi, T. and Ohnishi, Y. (1985) Identification and quantification of highly mutagenic nitroacetoxypyrenes and nitrohydoroxypyrenes in diesel-exhaust particles. Mutat. Res., 158, 3-18.
28. Ball, L. M., Kohan, M. J., Claxton, L. D. and Lewtas, J. (1984) Mutagenicity of derivatives and metabolites of 1-nitropyrene: activation by rat liver S9 and bacterial enzymes. Mutat. Res., 138, 113-125.
29. Kameda, T., Akiyama, A., Toriba, A., Tachikawa, C., Yoshita, M., Tang, N. and Hayakawa, K. (2008) Evaluation of endocrine disrupting activities of monohydroxylated derivatives of 1-nitropyrene by yeast two-hybrid assay. J. Health Sci., 54, 118-122.
30. Kameda, T., Akiyama, A., Toriba, A., Tachikawa, C., Yoshita, M., Tang, N. and Hayakawa, K. (2011) Mutagenicities and endocrine-disrupting activities of 1-hydroxy-2-nitropyrene and 1-hydroxy-5-nitropyrene. J. Health Sci., 57, 372-377.
31. Kameda, T., Akiyama, A., Toriba, A., Tang, N. and Hayakawa, K. (2011) Atmospheric formation of hydroxynitropyrenes from a photochemical reaction of particle-associated 1-nitropyrene. Environ. Sci. Technol., 45, 3325-3332.
32. Finlayson-Pitts, B. J. and Pitts, J. N., Jr. (2000) Chemistry of the Upper and Lower Atmosphere, Academic Press, San Diego, CA.
33. Kamens, R. M., Guo, Z., Fulcher, J. and Bell, D. (1988) Influence of humidity, sunlight, and temperature on the daytime decay of polyaromatic hydrocarbons on atmospheric soot particles. Environ. Sci. Technol., 22, 103-108.
34. Chung, S. W., Chung, H. Y., Toriba, A., Kameda, T., Tang, N., Kizu, R. and Hayakawa, K. (2007) An environmental quinoid polycyclic aromatic hydrocarbon, acenaphthenequinone, modulates cyclooxygenase-2 expression through reactive oxygen species generation and nuclear factor kappa B activation in A549 cells. Toxicol. Sci., 95, 348-355.
35. Enya, T., Suzuki, H., Watanabe, T., Hirayama, T. and Hisamatsu, Y. (1997) 3-nitrobenzanthrone, a powerful bacterial mutagen and suspected human carcinogen found in diesel exhaust and airborne particulates. Environ. Sci. Technol., 31, 2772-2776.
36. Kameda, T., Nakayama, Y., Goto, T., Koyanagi, T., Bandow, H., Fujimori, K., Toriba, A., Tang, N. and Hayakawa, K. (2009) Airborne Particulates, Nova Science Publishers, NY, pp. 291-307.
37. Yang, D. T. C., Chou, A., Chen, E. and Chiu, L.-H. (1994) Photodecomposition of environmental nitropolycyclic aromatic hydrocarbons. Polycycl. Aromat. Compd., 5, 201-208.
38. Cvréková, O. and Ciganek, M. (2005) Photostability of polycyclic aromatic hydrocarbons (PAHs) and nitrated polycyclic aromatic hydrocarbons (NPAHs) in dichloromethane and isooctane solutions. Polycycl. Aromat. Compd., 25, 141-156.
39. Demerjian, K. L., Schere, K. L. and Peterson, J. T. (1980) Theoretical estimates of actinic (spherically integrated) flux and photolytic rate constants of atmospheric species in the lower troposphere. Advances in Environmental Science and Technology, 10, 369-459.