Toxicological effects of polycyclic aromatic hydrocarbon quinones contaminated in diesel exhaust particles

Asian Journal of Atmospheric Environment

Volumn 1, Issue 1, 2007, Pages 28-35

  Kumagai, Yoshito ^a   Taguchi, Keiko ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Diesel exhaust particle; Oxidative stress; Polycyclic aromatic hydrocarbon; Quinone; Vascular dysfunction

Indexed keywords

EID: 84870014988     PISSN: 19766912     EISSN: 22871160     Source Type: Journal    
DOI: 10.5572/ajae.2007.1.1.028     Document Type: Article

References (53)

1. Allen, J.O., N.M. Dookeran, K. Taghizadeh, A.L. Lafleur, K.A. Smith, and A.F. Sarofim (1997) Measurement of oxygenated polycyclic aromatic hydrocarbons associated with a size-segregated urban aerosol. Environ. Sci. Technol., 31, 2064-2070.
2. Baulig, A., M. Garlatti, V. Bonvallot, A. Marchand, R. Barouki, F. Marano, and A. Baeza-Squiban (2003) Involvement of reactive oxygen species in the metabolic pathways triggered by diesel exhaust particles in human airway epithelial cells. Am. J. Physiol. Lung. Cell. Mol. Physiol., 285, L671-679.
3. Bolton, J.L., M.A. Trush, T.M. Penning, G. Dryhurst, and T.J. Monks (2000) Role of quinones in toxicology. Chem. Res. Toxicol., 13, 135-160.
4. Casillas, A.M., T. Hiura, N. Li, and A.E. Nel (1999) Enhancement of allergic inflammation by diesel exhaust particles: permissive role of reactive oxygen species. Ann. Allergy. Asthma. Immunol., 83, 624-629.
5. Cho, A.K., D.A. Schmitz, Y. You, C.E. Rodriquez, E.D. Stefano, Y. Kumagai, A.H. Miguel, A. Eiguren, T. Kobayashi, E. Avol, and J.R. Froines (2004) Determination of four quinones in diesel exhaust particles, SRM 1649a and atmospheric PM2.5. Aerosol Science & Technology, 38, 1-14.
6. Cho, A.K., C. Sioutas, A.H. Miguel, Y. Kumagai, D.A. Schmitz, M. Singh, A. Eiguren-Fernandez, and J.R. Froines (2005) Redox activity of airborne particulate matter at different sites in the Los Angeles Basin. Environ. Res., 99, 40-47.
7. Diaz-Sanchez, D., AR. Dotson, H. Takenaka, and A. Saxon (1994) Diesel exhaust particles induce local IgE production in vivo and alter the pattern of IgE messenger RNA isoforms. J. Clin. Invest., 94, 1417-1425.
8. Dockery, D.W., C.A. Pope 3rd., X. Xu. J.D. Spengler, J.H. Ware, M.E. Fay, B.G. Jr. Ferris, and F.E. Speizer (1993) An association between air pollution and mortality in six U.S. cities. N. Engl. J. Med., 329, 1753-1759.
9. 22 nonpolar and semipolar aromatic compounds. Environ. Sci. & Technol., 32, 1760-1770.
10. Gavett, S.H. and H.S. Koren (2001) The role of particulate matter in exacerbation of atopic asthma. Int. Arch. Allergy. Immunol., 124, 109-112.
11. Hiura. T.S., M.P. Kaszubowski, N. Li, and A.E. Nel (1999) Chemicals in diesel exhaust particles generate reactive oxygen radicals and induce apoptosis in macrophages. J. Immunol., 163, 5582-5591.
12. Hiyoshi, K., H. Takano, K. Inoue, T. Ichinose, R. Yanagisawa, S. Tomura, A.K. Cho, J.R. Froines, and Y. Kumagai (2005a) Effects of a single intratracheal administration of phenanthraquinone on murine lung. J. Appl. Toxicol., 25, 47-51.
13. Hiyoshi, K., H. Takano, K.I. Inoue, T. Ichinose, R. Yanagisawa, S. Tomura, and Y. Kumagai (2005b) Effects of phenanthraquinone on allergic airway inflammation in mice. Clin. Exp. Allergy., 35, 1243-1248.
14. Ichinose, T., H. Takano, Y. Miyabara, and M. Sagai (1998) Long-term exposure to diesel exhaust enhances antigen-induced eosinophilic inflammation and epithelial damage in the murine airway. Toxicol. Sci., 44, 70-79.
15. Ikeda, M., M. Suzuki, K. Watarai, M. Sagai, and T. Tomita (1995) Impairment of endothelium-dependent relaxation by diesel exhaust particles in rat thoracic aorta. Jpn. J. Pharmacol., 68, 183-189.
16. Inoue, K.I., H. Takano, K. Hiyoshi, T. Ichinose, K. Sadakane, R. Yanagisawa, S. Tomura, and Y. Kumagai (2007) Naphthoquinone enhances antigen-related airway inflammation in mice. Eur Respir J. in press.
17. Kasai, H. and S. Nishimura (1984) Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic. Acids. Res., 12, 2137-2145.
18. Kelly, R.A., J.L. Balligand, and T.W. Smith (1996) Nitric oxide and cardiac function. Circ. Res., 79. 363-380.
19. Kikuno. S., K. Taguchi, N. Iwamoto, S. Yamano, A.K. Cho, J.R. Froines, and Y. Kumagai (2006) 1,2-Naphthoquinone activates vanilloid receptor 1 through increased protein tyrosine phosphorylation, leading to contraction of guinea pig trachea. Toxicol. Appl. Pharmacol., 210, 47-54.
20. Kumagai, Y., T. Arimoto, M. Shinyashiki, N. Shimojo, Y. Nakai, T. Yoshikawa, and M. Sagai (1997) Generation of reactive oxygen species during interaction of diesel exhaust particle components with NADPHcytochrome P450 reductase and involvement of the bioactivation in the DNA damage. Free Radic. Biol. Med., 22, 479-487.
21. Kumagai, Y., T. Hayashi, T. Miyauchi, A. Endo, A. Iguchi, M. Kiriya-Sakai, S. Sakai, K. Yuki, M. Kikushima, and N. Shimojo (2001) Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation. Am. J. Physiol. Regul. Integr. Comp. Physiol., 281, R25-30.
22. Kumagai, Y., S. Koide, K. Taguchi, A. Endo, Y. Nakai, T. Yoshikawa, and N. Shimojo (2002) Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles. Chem. Res. Toxicol., 15, 483-489.
23. Kumagai, Y., H. Nakajima, K. Midorikawa, S. Homma-Takeda, and N. Shimojo (1998b) Inhibition of nitric oxide formation by neuronal nitric oxide synthase by quinones: nitric oxide synthase as a quinone reductase. Chem. Res. Toxicol., 11, 608-613.
24. Leotz-Gartziandia, E., V. Tatry, and P. Carlier (2000) Sampling and Analysis of Polycyclic Aromatic Hydrocarbons (PAHs) and Oxygenated PAH in Diesel Exhaust and Ambient Air. Polycyclic Aromatic Compounds, 20, 245-258.
25. Li, N., M.I. Venkatesan, A. Miguel, R. Kaplan, C. Gujuluva, J. Alam, and A. Nel (2000) Induction of heme oxygenase-1 expression in macrophages by diesel exhaust particle chemicals and quinones via the antioxidant-responsive element. J. Immunol., 165, 3393-3401.
26. Lim, H.B., T. Ichinose, Y. Miyabara, H. Takano, Y. Kumagai, N. Shimojyo, J.L. Devalia, and M. Sagai (1998) Involvement of superoxide and nitric oxide on airway inflammation and hyperresponsiveness induced by diesel exhaust particles in mice. Free Radic. Biol. Med., 25, 635-44.
27. McClellan, R.O. (1987) Health effects of exposure to diesel exhaust particles. Annu. Rev. Pharmacol. Toxicol., 27, 279-300.
28. Moncada, S., R.M. Palmer, and E.A. Higgs (1991) Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev., 43, 109-142.
29. Monks, T.J., R.P. Hanzlik, G.M. Cohen, D. Ross, and D.G. Graham (1992) Quinone chemistry and toxicity. Toxicol. Appl. Pharmacol., 112, 2-16.
30. Nagashima, M., H. Kasai, J. Yokota, Y. Nagamachi, T. Ichinose, and M. Sagai (1995) Formation of an oxidative DNA damage, 8-hydroxydeoxyguanosine, in mouse lung DNA after intratracheal instillation of diesel exhaust particles and effects of high dietary fat and beta-carotene on this process. Carcinogenesis, 16, 1441-1445.
31. Nel, A.E., D. Diaz-Sanchez, and N. Li (2001) The role of particulate pollutants in pulmonary inflammation and asthma: evidence for the involvement of organic chemicals and oxidative stress. Curr. Opin. Pulm. Med., 7, 20-26.
32. Nel, A.E., D. Diaz-Sanchez, D. Ng, T. Hiura, and A. Saxon (1998) Enhancement of allergic inflammation by the interaction between diesel exhaust particles and the immune system. J. Allergy. Clin. Immunol., 102, 539-554.
33. O'Brien, P.J. (1991) Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact., 80, 1-41.
34. Penning, T.M., S.T. Ohnishi, T. Ohnishi, and R.G. Harvey (1996) Generation of reactive oxygen species during the enzymatic oxidation of polycyclic aromatic hydrocarbon trans-dihydrodiols catalyzed by dihydrodiol dehydrogenase. Chem. Res. Toxicol., 9, 84-92.
35. Pope, C.A., 3rd, R.T. Burnett, M.J. Thun, E.E. Calle, D. Krewski, K. Ito, and G.D. Thurston (2002) Lung cancer, cardiopulmonary mortality, and long-term exposure to fine particulate air pollution. Jama, 287, 1132-1141.
36. Pope, CA., 3rd, M.J. Thun, M.M. Namboodiri, D.W. Dockery, J.S. Evans, F.E. Speizer, and C.W. Jr. Heath (1995) Particulate air pollution as a predictor of mortality in a prospective study of U.S. adults. Am. J. Respir. Crit. Care. Med., 151, 669-674.
37. Ramdahl, T. (1985) Characterization of Polar Compounds Such as Polycyclic Aromatic Ketones in Air-Pollution Including Wood Smoke. Environ. Int., 11, 197-203.
38. Sagai, M., H. Saito, T. Ichinose, M. Kodama, and Y. Mori (1993) Biological effects of diesel exhaust particles. I. In vitro production of superoxide and in vivo toxicity in mouse. Free Radic. Biol. Med., 14, 37-47.
39. Schuetzle, D. (1983) Sampling of vehicle emissions for chemical analysis and biological testing. Environ Health Perspect, 47, 65-80.
40. Schuetzle, D., FS. Lee, and T.J. Prater (1981) The identification of polynuclear aromatic hydrocarbon (PAH) derivatives in mutagenic fractions of diesel particulate extracts. Int. J. Environ. Anal. Chem., 9, 93-144.
41. Simoneit, B.R.T., G.Y. Sheng, X.J. Chen, J.M. Fu, J. Zhang, and Y.P. Xu (1991) Molecular Marker Study of Extractable Organic-Matter in Aerosols from Urban Areas of China. Atmos. Environ., A-25, 2111-2129.
42. Smithgall, T.E., R.G. Harvey, and T.M. Penning (1988) Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. A potential route of proximate carcinogen metabolism. J. Biol. Chem., 263, 1814-20.
43. Squadrito, G.L., R. Cueto, B. Dellinger, and W.A. Pryor (2001) Quinoid redox cycling as a mechanism for sustained free radical generation by inhaled airborne particulate matter. Free Radic. Biol. Med., 31, 1132-8.
44. Sugimoto, R., Y. Kumagai, Y. Nakai, and T. Ishii (2005) 9,10-phenanthraquinone in diesel exhaust particles downregulates Cu, Zn-SOD and HO-1 in human pulmonary epithelial cells: intracellular iron scavenger 1,10-phenanthroline affords protection against apoptosis. Free Rad. Biol. Med., 38, 388-395.
45. Sun, Y., K. Taguchi, D. Sumi, S. Yamano, and Y. Kumagai (2006) Inhibition of endothelial nitric oxide synthase activity and suppression of endotheliumdependent vasorelaxation by 1,2-naphthoquinone, a component of diesel exhaust particles. Arch. Toxicol., 80, 280-285.
46. Takano, H., T. Ichinose, Y. Miyabara, T. Yoshikawa, and M. Sagai (1998) Diesel exhaust particles enhance airway responsiveness following allergen exposure in mice. Immunopharmacol. Immunotoxicol., 20, 329-336.
47. Takano, H., T. Yoshikawa, T. Ichinose, Y. Miyabara, K. Imaoka, and M. Sagai (1997) Diesel exhaust particles enhance antigen-induced airway inflammation and local cytokine expression in mice. Am. J. Respir. Crit. Care. Med., 156, 36-42.
48. Takizawa, H., T. Ohtoshi, S. Kawasaki, S. Abe, I. Sugawara, K. Nakahara, K. Matsushima, and S. Kudoh (2000) Diesel exhaust particles activate human bronchial epithelial cells to express inflammatory mediators in the airways: a review. Respirology, 5, 197-203.
49. Umans, J.G. and R. Levi (1995) Nitric oxide in the regulation of blood flow and arterial pressure. Annu. Rev. Physiol., 57, 771-90.
50. Wise, S.A., B.A. Benner, M.J.L. De Alda, B.J. Porter, D.L. Poster, L.C. Sander, and M.M. Schantz (2000) Recent Developments in NIST Standard Reference Materials for Polycyclic Aromatic Hydrocarbons in Environmental Matrices. Polycyclic Aromatic Compounds, 19, 297-313.
51. Xiao, G.G., M. Wang, N. Li, J.A. Loo, and A.E. Nel (2003) Use of proteomics to demonstrate a hierarchical oxidative stress response to diesel exhaust particle chemicals in a macrophage cell line. J. Biol. Chem., 278, 50781-50790.
52. Yu, M.L. and R.A. Hites (1981) Identification of organic compounds on diesel engine soot. Anal. Chem., 53, 951-954.
53. Zheng, J., M. Cho, A.D. Jones, and B.D. Hammock (1997) Evidence of quinone metabolites of naphthalene covalently bound to sulfur nucleophiles of proteins of murine Clara cells after exposure to naphthalene. Chem. Res. Toxicol., 10, 1008-1014.