Polycyclic aromatic hydrocarbon quinones as redox and electrophilic chemicals contaminated in the atmosphere

Journal of Health Science

Volumn 55, Issue 6, 2009, Pages 887-894

  Kumagai, Yoshito ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

Covalent modification; Diesel exhaust particles; Electrophile; Oxidative stress; Quinone; Redox cycling

Indexed keywords

CELL PROTEIN; ELECTROPHILE; GASOLINE; OXYGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE;

AIR POLLUTION; ATMOSPHERIC DISPERSION; CHEMICAL MODIFICATION; COMBUSTION; COVALENT BOND; ELECTRON TRANSPORT; EXHAUST GAS; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; SHORT SURVEY; SIGNAL TRANSDUCTION;

EID: 74549121525     PISSN: 13449702     EISSN: 13475207     Source Type: Journal    
DOI: 10.1248/jhs.55.887     Document Type: Short Survey

References (27)

1. Sagai, M., Saito, H., Ichinose, T., Kodama, M. and Mori, Y. (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.
2. Nagashima, M., Kasai, H., Yokota, J., Nagamachi, Y., Ichinose, T. and Sagai, M. (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 betacarotene on this process. Carcinogenesis, 16, 1441-1445.
3. Kumagai, Y., Arimoto, T., Shinyashiki, M., Shimojo, N., Nakai, Y., Yoshikawa, T. and Sagai, M. (1997) Generation of reactive oxygen species during interaction of diesel exhaust particles components with NADPH-cytochrome P450 reductase and involvement of the bioactivation in the DNA damage. Free Radic. Biol. Med., 22, 479-487.
4. Cho, A. K., Schmitz, D. A., Ying, Y., Rodriguez, C. E., Di Stefano, E. W., Kumagai, Y., Miguel, A., Eiguren, A., Kobayashi, T., Avol, E. and Froines, J. R. (2004) Determination of four quinones in diesel exhaust particles, SRM1649a and, atmospheric PM2.5. Aerosol Sci. Technol., 38, 68-81.
5. Bolton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G. and Monks, T. J. (2000) Role of quinones in toxicology. Chem. Res. Toxicol., 13, 135-160.
6. Kumagai, Y., Nakajima, H., Midorikawa, K., Homma-Takeda, S. and Shimojo, N. (1998) 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.
7. Kumagai, Y., Hayashi, T., Miyauchi, T., Endo, A., Iguchi, A., Kiriya-Sakai, M., Sakai, S., Yuki, K., Kikushima, M. and Shimojo, N. (2001) Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation. Am. J. Physiol., 281, R25-R30.
8. Taguchi, K., Kumagai, Y., Endo, A., Kikushima, M., Ishii, Y. and Shimojo, N. (2001) Phenanthraquinone affects endothelial nitric oxide synthase activity throughmodification of the thiol groups: An alternative inhibition mechanism. J. Health Sci., 47, 571-574.
9. Kumagai, Y., Koide, S., Taguchi, K., Endo, A., Nakai, Y., Yoshikawa, T. and Shimojo, N. (2002) Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles. Chem. Res. Toxicol., 15, 483-489.
10. Motoyama, Y., Bekki, K., Chung, S. W., Tang, N., Kameda, T., Toriba, A., Taguchi, K. and Hayakawa, K. (2009) Oxidative stress more strongly induced by ortho- than para-quinoid polycyclic aromatic hydrocarbons in A549 cells. J. Health Sci., 55, 845-850.
11. Sugimoto, R., Kumagai, Y., Nakai, Y. and Ishii, T. (2005) 9,10-phenanthraquinone in diesel exhaust downregulates HO-1 and Cu,Zn-SOD in human pulmonary epithelial cells: intracellular iron scavenger 1, 10-phenanthroline affords protection against apoptosis. Free Radic. Biol. Med., 38, 388-397.
12. Taguchi, K., Fujii, S., Yamano, S., Cho, A. K., Kamisuki, S., Nakai, Y., Sugawara, F., Froines, J. R. and Kumagai, Y. (2007) An approach to evaluate two-electron reduction of 9,10-phenanthraquinone and redox activity of the hydroquinone associated with oxidative stress. Free Radic. Biol. Med., 43, 789-799.
13. Taguchi, K., Shimada, M., Fujii, S., Sumi, D., Pan, X. Q., Yamano, S., Nishiyama, T., Hiratsuka, A., Yamamoto, M., Cho, A. K., Froines, J. R. and Kumagai, Y. (2008) Redox cycling of 9,10-phenanthraquinone to cause oxidative stress is terminated through its monoglucuronide conjugation in human pulmonary epithelial A549 cells. Free Radic. Biol. Med., 44, 1645-1655.
14. Motohashi, H. and Yamamoto, M. (2004) Nrf2-Keap1 defines a physiologically important stress response mechanism. Trends Mol. Med., 10, 549-557.
15. Hiyoshi, K., Takano, H., Inoue, K., Ichinose, T., Yanagisawa, R., Tomura, S., Cho, A. K., Froines, J. R. and Kumagai, Y. (2005) Effects of single intratracheal administration of phenanthraquinone on murine lung. J. Appl. Toxicol., 25, 47-51.
16. Hiyoshi, K., Takano, H., Inoue, K., Ichinose, T., Yanagisawa, R., Tomura, S. and Kumagai, Y. (2005) Effects of phenanthraquinone on allergic airway inflammation in mice. Clin. Exp. Allergy, 35, 1243-1248.
17. Sun, Y., Taguchi, K., Sumi, D., Yamano, S. and Kumagai, Y. (2006) Inhibition of endothelial nitric oxide synthase activity and suppression of endothelium-dependent vasorelaxation by 1,2-naphthoquinone, a component of diesel exhaust particles. Arch. Toxicol., 80, 280-285.
18. Iwamoto, N., Sumi, D., Ishii, T., Uchida, K., Cho, A. K., Froines, J. R. and Kumagai, Y. (2007) Chemical knockdown of protein tyrosine phosphatase 1B by 1,2-naphthoquinone through covalent modification causes persistent transactivation of epidermal growth factor receptor. J. Biol. Chem., 282, 33396-33404.
19. Jones, D. P. (2008) Radical-free biology of oxidative stress. Am. J. Physiol. Cell Physiol., 295, C849-C868.
20. Kikuno, S., Taguchi, K., Iwamoto, N., Yamano, S., Cho, A. K., Froines, J. R. and Kumagai, Y. (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.
21. Tonks, N. K. (2003) PTP1B: from the sidelines to the front lines! FEBS Lett., 546, 140-148.
22. Endo, A., Sumi, D. and Kumagai, Y. (2007) 1,2-Naphthoquinone disrupts the function of cAMP response element-binding protein through covalent modification. Biochem. Biophys. Res. Commun., 361, 243-248.
23. Kobayashi, M., Li, L., Iwamoto, N., Nakajima-Takagi, Y., Kaneko, H., Nakayama, Y., Eguchi, M., Wada, Y., Kumagai, Y. and Yamamoto, M. (2009) The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range chemical compounds. Mol. Cell. Biol., 29, 493-502.
24. Inoue, K., Takano, H., Hiyoshi, K., Ichinose, T., Sadakane, K., Yanagisawa, R., Tomura, S. and Kumagai, Y. (2007) Naphthoquinone enhances antigen-related airway inflammation in mice. Eur. Respir. J., 29, 259-267.
25. Inoue, K., Takano, H., Ichinose, T., Tomura, S., Yanagisawa, R., Sakurai, M., Sumi, D., Hiyoshi, K. and Kumagai, Y. (2007) Effects of naphthoquinone on airway responsiveness in the presence or absence of antigen in mice. Arch. Toxicol., 81, 575-581.
26. Cho, A. K., Sioutas, C., Miguel, A. H., Kumagai, Y., Schmitz, D. A., Singh, M., Eiguren-Fernandez, A. and Froines, J. R. (2005) Redox activity of airborne particulate matter at different sites in the Los Angeles Basin. Environ. Res., 99, 40-47.
27. Shinyashiki, M., Rodriguez, C. E., Di Stefano, E. W., Sioutas, C., Delfino, R. J., Kumagai, Y., Froines, J. R. and Cho, A. K. (2008) On the interaction between glyceraldehyde-3-phosphate dehydrogenase and airborne particles: Evidence for electrophilic species. Atmos. Environ., 42, 517-529.