Photochemical reaction of 9-nitro-substituted anthracene-like molecules 9-methyl-10-nitroanthracene and 12-methyl-7-nitrobenz[a]anthracene

Journal of Photochemistry and Photobiology A: Chemistry

Volumn 201, Issue 1, 2009, Pages 39-44

  Stewart, Gernerique ^a   Jiao, Yuguo ^a,b   Valente, Edward J ^c   Fu, Peter P ^d   Li, Tianqiao ^b   Hu, Zhenzhong ^b   Yu, Hongtao ^a  

^a JACKSON STATE UNIVERSITY   (United States)

^b MINZU UNIVERSITY OF CHINA   (China)

^c MISSISSIPPI COLLEGE   (United States)

^d NATIONAL CENTER FOR TOXICOLOGICAL RESEARCH   (United States)

Author keywords

7 Nitrobenz a anthracene, 12 Methyl 7 nitrobenz a anthracene; 9 Methyl 10 nitroanthracene; Nitro rearrangement; Photoreaction

Indexed keywords

EID: 57749199300     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2008.09.016     Document Type: Article

References (36)

1. Pitts Jr. J.N., Lokensgard D.M., Harger W., Fisher T.S., Mejia V., Schuler J.J., Scorziell G.M., and Katzenstein Y.A. Mutagens in diesel exhaust particulate. Identification and direct activities of 6-nitrobenzo[a]pyrene, 9-nitroanthracene, 1-nitropyrene, and 5H-phenanthro[4,5-bcd]pyran-5-one. Mutat. Res. 103 (1982) 241-249
2. Fu P.P. Metabolism of nito-polycyclic aromatic hydrocarbons. Drug Metab. Rev. 22 (1990) 209-268
3. Löfroth G., Nilsson L., Agurell E., and Yasuhara A. Salmonella/microsome mutagenicity of 1-nitropyrene-2-ol, a nitropyrene phenol formed in the photolysis of 1-nitropyrene. Z. Naturforsch. 39 (1984) 193-195
4. Fu P.P., Heflich R.H., Unruh L.E., Shaikh A.U., Wu Y.-S., Lai C.-C., and Lai J.-S. Relationships among direct-acting mutagenicity, nitro group orientation and polarographic reduction potential of 6-nitrobenzo[a]pyrene, 7-nitrobenz[a]anthracene and their derivatives. Mutat. Res. 209 (1988) 115-122
5. Fu P.P., Ni Y.-C., Zhang Y.-M., Heflich R.H., Wang Y.-K., and Lai J.-S. Effect of the orientation of the nitro substituent on the bacterial mutagenicity of dinitrobenzo[e]pyrenes. Mutat. Res. 225 (1989) 121-125
6. Fu P.P., and Herrero-Saenz D. Nitro-polycyclic aromatic hydrocarbons: a class of genotoxic environmental pollutants. Environ. Carcinog. Ecotox. Rev. C17 (1999) 1-43
7. Heeb N.V., Schmid P., Kohler M., Gujer E., Zennegg M., Wenger D., Wichser A., Ulrich A., Gfeller U., Honegger P., Zeyer K., Emmenegger L., Petermann J.-L., Czerwinski J., Mosimann T., Kasper M., and Mayer A. Secondary effects of catalytic diesel particulate filters: conversion of PAHs versus formation of nitro-PAHs. Environ. Sci. Technol. 42 (2008) 3773-3779
8. Howsam M., and Jones K.C. Sources of PAHs in the environment. In: Neilson A.H. (Ed). PAHs and Related Compounds (1998), Springer-Verlag, Berlin, Germany 137-174
9. Srogi K. Monitoring of environmental exposure to polycyclic aromatic hydrocarbons: a review. Environ. Chem. Lett. 5 (2007) 169-195
10. Arey J., and Atkinson R. Photochemical reactions of PAHs in the atmosphere. In: Douben P.E.T. (Ed). PAHs: An Ecotoxicological Perspective (2003), Wiley & Sons Ltd., Chichester, England 47-63
11. Pitts Jr. J.N., Van Cauwenberghe K.A., Grosjean D., Schmid J.P., and Fitz D.R. Atmospheric reactions of polycyclic aromatic hydrocarbons: facile formation of mutagenic nitro derivatives. Science 202 (1978) 515-519
12. Reisen F., and Arey J. Atmospheric reactions influence seasonal PAH and Nitro-PAH concentrations in the Los Angeles basin. Environ. Sci. Technol. 39 (2005) 64-73
13. Fan Z., Chen D., Birla P., and Kamens R.M. Modeling of nitro-polycyclic aromatic hydrocarbon formation and decay in the atmosphere. Atmos. Environ. 29 (1995) 1171-1181
14. Atkinson R., and Arey J. Atmospheric chemistry of gas-phase polycyclic aromatic hydrocarbons: formation of atmospheric mutagens. Environ. Health Perspect. 102 Suppl. 4 (1994) 117-126
15. Arey J. Atmospheric reactions of PAHs including formation of nitroarenes. In: Neilson A.H. (Ed). PAHs and Related Compounds (1998), Springer-Verlag, Berlin, Germany 347-385
16. Fu P.P., Chou M.W., and Beland F.A. Effects of nitro substitution on the in vitro metabolic activation of polycyclic aromatic hydrocarbons. In: Yang S.K., and Silverman B.D. (Eds). Polycyclic Aromatic Hydrocarbon Carcinogenesis: Structure-Activity Relationships Vol. II (1988), CRC Press, Boca Raton, Florida 37-65
17. Yu H. Environmental carcinogenic polycyclic aromatic hydrocarbons: photochemistry and phototoxicity. J. Environ. Sci. Health C C20 (2002) 149-183
18. Fu P.P., and Herrero-Saenz D. Nitro-polycyclic aromatic hydrocarbons: a class of genotoxic environmental pollutants. J. Environ. Sci. Health: Environ. Carcinog. Ecotox. Rev. C17 (1999) 1-43
19. Phousongphouang P.T., and Arey J. Rate constants for the photolysis of the nitronaphthalenes and methylnitronaphthalenes. J. Photochem. Photobiol. A: Chem. 157 (2003) 301-309
20. Chapman O.L., Heckert D.C., Reasoner J.W., and Thackaberry S.P. Photochemical studies on 9-nitroanthracene. J. Am. Chem. Soc. 88 (1966) 5550-5554
21. Galiani G., and Rindone B. The photolysis of 9-nitroanthracene derivatives. Gazz. Chim. Ital. 107 (1977) 435-436
22. Ioki Y. Aryloxyl radicals by photorearrangement of nitro-compounds. J. Chem. Soc., Perkin Trans. 2 (1977) 1240-1242
23. Hamanoue K., Amano M., Kimoto M., Kajiwara Y., Nakayama T., and Teranishi H. Photochemical reactions of nitroanthracene derivatives in fluid solutions. J. Am. Chem. Soc. 106 (1984) 5993-5997
24. Hamanoue K., Nakayama T., Amijima Y., and Ibuki K. A rapid decay channel of the lowest excited singlet state of 9-benzoyl-10-nitroanthracene generating 9-benzoyl-10-anthryloxy radical and nitrogen(II)oxide. Chem. Phys. Lett. 267 (1997) 165-170
25. Umbuzeiro G.A., Franco A., Martins M.H., Kummrow F., Carvalho L., Schmeiser H.H., Leykauf J., Stiborova M., and Claxton L.D. Mutagenicity and DNA adduct formation of PAH, nitro-PAH, and oxy-PAH fractions of atmospheric particulate matter from Sao Paulo, Brazil. Mutat. Res. 652 (2008) 72-80
26. Holloway M.P., Biaglow M.C., McCoy E.C., Anders M., Rosenkranz H.S., and Howard P.C. Photochemical instability of 1-nitropyrene, 3-nitrofluoranthene, 1,8-dinitropyrene and their parent polycyclic aromatic hydrocarbons. Mutat. Res. 187 (1987) 199-207
27. Stärk G., Stauff J., Miltenburger H.G., and Stumm-Fischer I. Photodecomposition of 1-nitropyrene and other direct-acting mutagens extracted from diesel-exhaust particulates. Mutat. Res. 155 (1985) 27-33
28. Iversen B., and Greibrokk T. Identification of the decomposition products of nitrobenzanthracenes in solution. Anal. Chim. Acta 174 (1985) 317-322
29. Fukuhara K., Kurihara M., and Miyata N. Photochemical generation of nitric oxide from 6-nitrobenzo[a]pyrene. J. Am. Chem. Soc. 123 (2001) 8662-8666
30. Crespo-Hernandez C., Burdzinski G., and Arce R. Environmental photochemistry of nitro-PAHs: direct observation of ultrafast intersystem crossing in 1-nitropyrene. J. Phys. Chem. A 112 (2008) 6313-6319
31. Hamanoue K., Nakayama T., Ushida K., Kajiwara K., and Yamanaka S. Photophysics and photochemistry of nitroanthracenes. Part 1. Primary processes in the photochemical reactions of 9-benzoyl-10-nitroanthracene and 9-cyano-10-nitroanthracene by steady-state photolysis and nanosecond laser photolysis. J. Chem. Soc., Faraday Trans. 87 (1991) 3365-3371
32. Iversen B., Sydnes L.K., and Greibrokk T. Characterization of nitrobenzanthracenes and nitrodibenzanthracenes. Acta Chem. Scandin. B: Org. Chem. Biochem. 39 (1985) 837-847
33. Newman M.S., and Lilje K.C. Synthesis of 7-fluorobenz[a]anthracene. J. Org. Chem. 44 (1979) 1347-1348
34. Armillotta N., Bartoli G., Bosco M., and Dalpozzo R. Conjugate addition of Grignard reagents to nitroarenes: a new synthesis of 9-alkylanthracenes, 9-nitro-10-alkylanthracenes, and 10,10-dialkylanthrones. Synthesis (1982) 836-839
35. Hamanoue K., Nakayama T., Kajiwara K., Yamanaka S., and Ushida K. Photophysics and photochemistry of nitroanthracenes. Part 2. Primary process in the photochemical reaction of 9-nitroanthracene studied by steady-state photolysis and laser photolysis. J. Chem. Soc., Faraday Trans. 88 (1992) 3145-3151
36. Kornblum N., Blackwood R.K., and Mooberry D.D. The reaction of aliphatic nitro compounds with nitrite esters. J. Am. Chem. Soc. 78 (1956) 1502-1504