1,2-Naphthoquinone suppresses lipopolysaccharidedependent activation of IKKβ/NF-κB/NO signaling: An alternative mechanism for the disturbance of inducible NO synthase-catalyzed NO formation

Journal of Toxicological Sciences

Volumn 35, Issue 6, 2010, Pages 891-898

  Sumi, Daigo ^a   Akimori, Masako ^a   Inoue, Ken Ichiro ^b   Takano, Hirohisa ^b   Kumagai, Yoshito ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b NATIONAL INSTITUTE FOR ENVIRONMENTAL STUDIES   (Japan)

Author keywords

Electrophile; IKK ; NF B

Indexed keywords

1,2 NAPHTHOQUINONE; I KAPPA B KINASE ALPHA; I KAPPA B KINASE BETA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; NITRIC OXIDE; NITRITE; RECOMBINANT PROTEIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATALYSIS; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME PHOSPHORYLATION; ENZYME SYNTHESIS; GENETIC TRANSFECTION; LUNG; MOUSE; NONHUMAN; SIGNAL TRANSDUCTION;

MUS;

EID: 78649864044     PISSN: 03881350     EISSN: 18803989     Source Type: Journal    
DOI: 10.2131/jts.35.891     Document Type: Article

References (26)

1. Bredt, D.S., Hwang, P.M., Glatt, C.E., Lowenstein, C., Reed, R.R. and Snyder, S.H. (1991): Cloned and expressed nitric oxide synthase structurally resembles cytochrome P-450 reductase. Nature, 351, 714-718.
2. Cho, A.K., Stefano, E.D., You, Y., Rodriguez, C.E., Schmitz, D.A., Kumagai, Y., Miguel, A.H., Eiguren-Fernandez, A., Kobayashi, T., Avol, E. and Froines, J.R. (2004): Determination of Four Quinones in Diesel Exhaust Particles, SRM 1649a, and Atmospheric PM2.5 Special Issue of Aerosol Science and Technology on Findings from the Fine Particulate Matter Supersites Program. Aerosol. Sci. Technol., 38, 68-81.
3. Chung, M.Y., Lazaro, R.A., Lim, D., Jackson, J., Lyon, J., Rendulic, D. and Hasson, A.S. (2006): Aerosol-borne quinones and reactive oxygen species generation by particulate matter extracts. Environ. Sci. Technol., 40, 4880-4886.
4. 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.
5. Hayden, M.S. and Ghosh, S. (2004): Signaling to NF-kappaB. Genes Dev., 18, 2195-2224.
6. Iwamoto, N., Sumi, D., Ishii, T., Uchida, K., Cho, A.K., Froines, J.R. and Kumagai, Y. (2007): Chemical knockdown of proteintyrosine phosphatase 1B by 1,2-naphthoquinone through covalent modification causes persistent transactivation of epidermal growth factor receptor. J. Biol. Chem., 282, 33396-33404.
7. Kapahi, P., Takahashi, T., Natoli, G., Adams, S.R., Chen, Y., Tsien, R.Y. and Karin, M. (2000): Inhibition of NF-kappa B activation by arsenite through reaction with a critical cysteine in the activation loop of Ikappa B kinase. J. Biol. Chem., 275, 36062-36066.
8. 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. Regul. Integr. Comp. Physiol., 281, R25-30.
9. 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.
10. Nakano, H., Shindo, M., Sakon, S., Nishinaka, S., Mihara, M., Yagita, H. and Okumura, K. (1998): Differential regulation of IkappaB kinase alpha and beta by two upstream kinases, NFkappaB- inducing kinase and mitogen-activated protein kinase/ ERK kinase kinase-1. Proc. Natl. Acad. Sci. USA, 95, 3537-3542.
11. Nathan, C. (1992): Nitric oxide as a secretory product of mammalian cells. FASEB J., 6, 3051-3064.
12. Niwa, M., Nakamura, N., Kitajima, K., Ueda, M., Tsutsumishita, Y., Futaki, S. and Takaishi, Y. (1997): Benzoquinones inhibit the expression of inducible nitric oxide synthase gene. Biochem. Biophys. Res. Commun., 239, 367-371.
13. Niwa, M., Tsutsumishita, Y., Kawai, Y., Takahara, H., Nakamura, N., Futaki, S., Takaishi, Y., Kondoh, W. and Moritoki, H. (1996): Suppression of inducible nitric oxide synthase mRNA expression by tryptoquinone A. Biochem. Biophys. Res. Commun., 224, 579-585.
14. Pandey, M.K., Sandur, S.K., Sung, B., Sethi, G., Kunnumakkara, A.B. and Aggarwal, B.B. (2007): Butein, a tetrahydroxychalcone, inhibits nuclear factor (NF)-kappaB and NF-kappaB-regulated gene expression through direct inhibition of IkappaBalpha kinase beta on cysteine 179 residue. J. Biol. Chem., 282, 17340-17350.
15. Rossi, A., Kapahi, P., Natoli, G., Takahashi, T., Chen, Y., Karin, M. and Santoro, M.G. (2000): Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IkappaB kinase. Nature, 403, 103-108.
16. Sandur, S.K., Ichikawa, H., Sethi, G., Ahn, K.S. and Aggarwal, B.B. (2006): Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) suppresses NF-kappaB activation and NF-kappaB-regulated gene products through modulation of p65 and IkappaBalpha kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents. J. Biol. Chem., 281, 17023-17033.
17. Schmidt, H.H. and Walter, U. (1994): NO at work. Cell, 78, 919-925.
18. Snyder, S.H. and Bredt, D.S. (1991): Nitric oxide as a neuronal messenger. Trends Pharmacol. Sci., 12, 125-128.
19. Speyer, C.L., Neff, T.A., Warner, R.L., Guo, R.F., Sarma, J.V., Riedemann, N.C., Murphy, M.E., Murphy, H.S. and Ward, P.A. (2003): Regulatory effects of iNOS on acute lung inflammatory responses in mice. Am. J. Pathol., 163, 2319-2328.
20. 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.
21. Takano, H., Yanagisawa, R., Ichinose, T., Sadakane, K., Yoshino, S., Yoshikawa, T. and Morita, M. (2002): Diesel exhaust particles enhance lung injury related to bacterial endotoxin through expression of proinflammatory cytokines, chemokines, and intercellular adhesion molecule-1. Am. J. Respir. Crit. Care Med., 165, 1329-1335.
22. Valavanidis, A., Fiotakis, K., Vlahogianni, T., Papadimitriou, V. and Pantikaki, V. (2006): Determination of Selective Quinones and Quinoid Radicals in Airborne Particulate Matter and Vehicular Exhaust Particles. Environ. Chem., 3, 118-123.
23. Wardman, P. (1989): Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data, 18, 1637-1755.
24. Xie, Q.W., Kashiwabara, Y. and Nathan, C. (1994): Role of transcription factor NF-kappa B/Rel in induction of nitric oxide synthase. J. Biol. Chem., 269, 4705-4708.
25. Yamamoto, Y. and Gaynor, R.B. (2004): IkappaB kinases: key regulators of the NF-kappaB pathway. Trends Biochem. Sci., 29, 72-79.
26. Zhang, J. and Snyder, S.H. (1995): Nitric oxide in the nervous system. Annu. Rev. Pharmacol. Toxicol., 35, 213-233.