The chemical biology of naphthoquinones and its environmental implications

Annual Review of Pharmacology and Toxicology

Volumn 52, Issue , 2012, Pages 221-247

  Kumagai, Yoshito ^a   Shinkai, Yasuhiro ^a   Miura, Takashi ^a   Cho, Arthur K ^b  

^a UNIVERSITY OF TSUKUBA   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Covalent bond; Electrophile; Oxidative stress; Prooxidant; Quinone; Redox cycling

Indexed keywords

1,2 NAPHTHOQUINONE DERIVATIVE; 1,4 NAPHTHOQUINONE DERIVATIVE; 2 (3,3 DICHLOROALLYL) 3 HYDROXY 1,4 NAPHTHOQUINONE; 2,3 DIMETHOXY 1,4 NAPHTHOQUINONE; BETA LAPACHONE; CAULIBUGULONE A; GLYCERALDEHYDE 3 PHOSPHATE DEHYDROGENASE; JUGLONE; KELCH LIKE ECH ASSOCIATED PROTEIN 1; LAPACHOL; MENADIONE; MENAQUINONE; NAPHTHALENE; NAPHTHOQUINONE; NITROGEN; PHYTOMENADIONE; PLUMBAGIN; POLYCYCLIC AROMATIC HYDROCARBON; PPM 18; PROTEIN TYROSINE PHOSPHATASE; QUINONE DERIVATIVE; TRANSCRIPTION FACTOR NF E2; UNCLASSIFIED DRUG;

AIR POLLUTION; ARTICLE; BIOCHEMISTRY; CHEMICAL REACTION; CYTOLOGY; DRUG EFFECT; DRUG TARGETING; EXPOSURE; HUMAN; NONHUMAN; PRIORITY JOURNAL; PROTEIN INTERACTION; SIGNAL TRANSDUCTION;

AIR POLLUTANTS; ANIMALS; ANTI-INFLAMMATORY AGENTS; CARCINOGENS; CELLS, CULTURED; CYSTEINE; ENVIRONMENT; ENVIRONMENTAL EXPOSURE; GLYCERALDEHYDE-3-PHOSPHATE DEHYDROGENASES; HUMANS; NAPHTHALENES; NAPHTHOQUINONES; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; QUINONES; REACTIVE OXYGEN SPECIES;

NICOTIANA TABACUM;

EID: 81755188279     PISSN: 03621642     EISSN: 15454304     Source Type: Book Series    
DOI: 10.1146/annurev-pharmtox-010611-134517     Document Type: Article

References (151)

1. Bolton JL, Trush MA, Penning TM, Dryhurst G, Monks TJ. 2000. Role of quinones in toxicology. Chem. Res. Toxicol. 13:135-60 (Pubitemid 30169958)
2. Cadenas E, Hochstein P, Ernster L. 1992. Pro-and antioxidant functions of quinones and quinone reductases in mammalian cells. Adv. Enzymol. Relat. Areas Mol. Biol. 65:97-146
3. Monks TJ, Jones DC. 2002. The metabolism and toxicity of quinones, quinonimines, quinone methides, and quinone-thioethers. Curr. Drug Metab. 3:425-38 (Pubitemid 34778005)
4. O'Brien PJ. 1991. Molecular mechanisms of quinone cytotoxicity. Chem. Biol. Interact.80:1-41.
5. Erratum. 1992. Chem. Biol. Interact. 81(1-2):219
6. Penning TM, Burczynski ME, Hung CF, McCoull KD, Palackal NT, Tsuruda LS. 1999. Dihydrodiol dehydrogenases and polycyclic aromatic hydrocarbon activation: generation of reactive and redox active o-quinones. Chem. Res. Toxicol. 12:1-18 (Pubitemid 29048827)
7. PintoAV, de Castro SL. 2009. The trypanocidal activity of naphthoquinones: a review. Molecules 14:4570-90
8. Abdelmohsen K, Patak P, von Montfort C, Melchheier I, Sies H, Klotz LO. 2004. Signaling effects of menadione: from tyrosine phosphatase inactivation to connexin phosphorylation. Methods Enzymol. 378:258-72
9. Shearer MJ, Newman P. 2008. Metabolism and cell biology of vitamin K. Thromb. Haemost. 100:530-47
10. Eiguren-Fernandez A, MiguelA,Di Stefano E, SchmitzD,Cho AK, et al. 2008. Atmospheric distribution of gas-and particle-phase quinones in Southern California. Aerosol Sci. Technol. 42:854-61
11. Chung MY, Lazaro RA, Lim D, Jackson J, Lyon J, et al. 2006. Aerosol-borne quinones and reactive oxygen species generation by particulate matter extracts. Environ. Sci. Technol. 40:4880-86 (Pubitemid 44257448)
12. Jakober CA, Riddle SG, Robert MA, Destaillats H, Charles MJ, et al. 2007. Quinone emissions from gasoline and diesel motor vehicles. Environ. Sci. Technol. 41:4548-54 (Pubitemid 47047387)
13. Shinyashiki M, Eiguren-Fernandez A, Schmitz DA, Di Stefano E, Li N, et al. 2009. Electrophilic and redox properties of diesel exhaust particles. Environ. Res. 109:239-44
14. Kautzman KE, Surratt JD, Chan MN, Chan AWH, Hersey SP, et al. 2010. Chemical composition of gas-and aerosol-phase products from the photooxidation of naphthalene. J. Phys. Chem. A 114:913-34
15. Chu SN, Sands S, Tomasik MR, Lee PS, McNeill VF. 2010. Ozone oxidation of surface-adsorbed polycyclic aromatic hydrocarbons: role of PAH-surface interaction. J. Am. Chem. Soc. 132:15968-75
16. MurrayR, Singh M. 1997. Activation ofPAHby ozone derived oxidants: results using fly ash as particulate [I]. Polycycl. Aromat. Compd. 12:51-60
17. Finlayson-Pitts B, Pitts J. 2000. Chemistry of the Upper and Lower Atmosphere: Theory, Experiments, and Applications. San Diego, CA: Academic
18. Nadal M, Mari M, Schuhmacher M, Domingo JL. 2009. Multi-compartmental environmental surveillance of a petrochemical area: levels of micropollutants. Environ. Int. 35:227-35
19. Preuss R, Koch HM, Wilhelm M, Pischetsrieder M, Angerer J. 2004. Pilot study on the naphthalene exposure of German adults and children by means of urinary 1-and 2-naphthol levels. Int. J. Hyg. Environ. Health 207:441-45 (Pubitemid 39468905)
20. Eiguren-Fernandez A, Miguel AH, Froines JR, Thurairatnam S, Avol EL. 2004. Seasonal and spatial variation of polycyclic aromatic hydrocarbons in vapor-phase and PM2.5 in Southern California urban and rural communities. Aerosol Sci. Technol. 38:447-55 (Pubitemid 38879982)
21. Lu H, Zhu L. 2007. Pollution patterns of polycyclic aromatic hydrocarbons in tobacco smoke. J. Hazard. Mater. 139:193-98 (Pubitemid 44909308)
22. Lin CY, Isbell MA, Morin D, Boland BC, Salemi MR, et al. 2005. Characterization of a structurally intact in situ lung model and comparison of naphthalene protein adducts generated in this model versus lung microsomes. Chem. Res. Toxicol. 18:802-13 (Pubitemid 40705446)
23. Gram TE. 1997. Chemically reactive intermediates and pulmonary xenobiotic toxicity. Pharmacol. Rev. 49:297-341 (Pubitemid 28030943)
24. DeStefano-Shields C, Morin D, Buckpitt A. 2010. Formation of covalently bound protein adducts from the cytotoxicant naphthalene in nasal epithelium: species comparisons. Environ.Health Perspect. 118:647-52
25. Lin PH, Chen DR, Wang TW, Lin CH, Chuang MC. 2009. Investigation of the cumulative tissue doses of naphthoquinones in human serum using protein adducts as biomarker of exposure. Chem. Biol. Interact. 181:107-14
26. Preuss R, Angerer J, Drexler H. 2003. Naphthalene-an environmental and occupational toxicant. Int. Arch. Occup. Environ. Health 76:556-76
27. Zheng J, Cho M, Jones AD, Hammock BD. 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. 10:1008-14 (Pubitemid 27418017)
28. Penning TM, Ohnishi ST, Ohnishi T, Harvey RG. 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 (Pubitemid 26041277)
29. Brunmark A, Cadenas E. 1989. Redox and addition chemistry of quinoid compounds and its biological implications. Free Radic. Biol. Med. 7:435-77 (Pubitemid 19273369)
30. Sugimoto R, Kumagai Y, Nakai Y, Ishii T. 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 Radic. Biol. Med. 38:388-95 (Pubitemid 40075580)
31. Wardman P. 1990. Bioreductive activation of quinones: redox properties and thiol reactivity. Free Radic. Res. Commun. 8:219-29 (Pubitemid 20262564)
32. Goin J, Gibson DD, McCay PB, Cadenas E. 1991. Glutathionyl-and hydroxyl radical formation coupled to the redox transitions of 1,4-naphthoquinone bioreductive alkylating agents during glutathione twoelectron reductive addition. Arch. Biochem. Biophys. 288:386-96
33. Taguchi K, Fujii S, Yamano S, Cho AK, Kamisuki S, et al. 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. 43:789-99 (Pubitemid 47102127)
34. Kumagai Y,NakajimaH,Midorikawa K,Homma-Takeda S, 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. 11:608-13 (Pubitemid 28285585)
35. Rodriguez CE, Shinyashiki M, Froines J, Yu RC, Fukuto JM, Cho AK. 2004. An examination of quinone toxicity using the yeast Saccharomyces cerevisiae model system. Toxicology 201:185-96 (Pubitemid 39023945)
36. SlaughterDE, Hanzlik RP. 1991. Identification of epoxide-and quinone-derived bromobenzene adducts to protein sulfur nucleophiles. Chem. Res. Toxicol. 4:349-59
37. Smithgall TE, Harvey RG, Penning TM. 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 (Pubitemid 18052134)
38. Monks TJ. 1995. Modulation of quinol/quinone-thioether toxicity by intramolecular detoxication. Drug Metab. Rev. 27:93-106
39. Monks TJ, Hanzlik RP, Cohen GM, Ross D, Graham DG. 1992. Quinone chemistry and toxicity. Toxicol. Appl. Pharmacol. 112:2-16
40. Schafer FQ, Buettner GR. 2001. Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radic. Biol. Med. 30:1191-212 (Pubitemid 32463931)
41. SegalHL, Boyer PD. 1953. The role of sulfhydryl groups in the activity of D-glyceraldehyde 3-phosphate dehydrogenase. J. Biol. Chem. 204:265-81
42. Talfournier F, Colloc'h N, Mornon JP, Branlant G. 1998. Comparative study of the catalytic domain of phosphorylating glyceraldehyde-3-phosphate dehydrogenases from bacteria and archaea via essential cysteine probes and site-directed mutagenesis. Eur. J. Biochem. 252:447-57 (Pubitemid 28156868)
43. Barford D, Flint AJ, Tonks NK. 1994. Crystal structure of human protein tyrosine phosphatase 1B. Science 263:1397-404 (Pubitemid 24137822)
44. Guan KL, Dixon JE. 1991. Evidence for protein-tyrosine-phosphatase catalysis proceeding via a cysteine-phosphate intermediate. J. Biol. Chem. 266:17026-30 (Pubitemid 21907901)
45. Jones DP. 2008. Radical-free biology of oxidative stress. Am. J. Physiol. Cell Physiol. 295:849-68
46. Forman HJ, Maiorino M, Ursini F. 2010. Signaling functions of reactive oxygen species. Biochemistry 49:835-42
47. Poole LB, Nelson KJ. 2008. Discovering mechanisms of signaling-mediated cysteine oxidation. Curr. Opin. Chem. Biol. 12:18-24
48. Saurin AT, Neubert H, Brennan JP, Eaton P. 2004. Widespread sulfenic acid formation in tissues in response to hydrogen peroxide. Proc. Natl. Acad. Sci. USA 101:17982-87 (Pubitemid 40054061)
49. Claiborne A, Yeh JI, Mallett TC, Luba J, Crane EJ III, et al. 1999. Protein-sulfenic acids: diverse roles for an unlikely player in enzyme catalysis and redox regulation. Biochemistry 38:15407-16
50. Shinyashiki M, Rodriguez CE, Di Stefano EW, Sioutas C, Delfino RJ, et al. 2008. On the interaction between glyceraldehyde-3-phosphate dehydrogenase and airborne particles: evidence for electrophilic species. Atmos. Environ. 42:517-29
51. PooleLB, Karplus PA, Claiborne A. 2004. Protein sulfenic acids in redox signaling. Annu. Rev. Pharmacol. Toxicol. 44:325-47 (Pubitemid 38263844)
52. Jacob C, Holme AL, Fry FH. 2004. The sulfinic acid switch in proteins. Org. Biomol. Chem. 2:1953-56
53. Jacobs AT, Marnett LJ. 2010. Systems analysis of protein modification and cellular responses induced by electrophile stress. Acc. Chem. Res. 43:673-83
54. Labenski MT, Fisher AA, Lo HH, MonksTJ, Lau SS. 2009. Protein electrophile-binding motifs:Lysinerich proteins are preferential targets of quinones. Drug Metab. Dispos. 37:1211-18
55. Iwamoto N, Sumi D, Ishii T, Uchida K, Cho AK, et al. 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. 282:33396-404 (Pubitemid 350159512)
56. Fisher AA, LabenskiMT,Malladi S,Gokhale V, BowenME, et al. 2007. Quinone electrophiles selectively adduct "electrophile binding motifs" within cytochrome c. Biochemistry 46:11090-100 (Pubitemid 47502775)
57. Wardman P. 1989. Reduction potentials of one-electron couples involving free radicals in aqueous solution. J. Phys. Chem. Ref. Data 18:1637-756
58. O'Connor T, Ireland LS, Harrison DJ, Hayes JD. 1999. Major differences exist in the function and tissue-specific expression of human aflatoxin B1 aldehyde reductase and the principal human aldo-keto reductase AKR1 family members. Biochem. J. 343(Pt. 2):487-504 (Pubitemid 29511786)
59. Lind C, CadenasE,Hochstein P, ErnsterL. 1990. DT-diaphorase: purification, properties, and function. Methods Enzymol. 186:287-301 (Pubitemid 20279970)
60. Kumagai Y, Arimoto T, Shinyashiki M, Shimojo N, Nakai Y, et al. 1997. Generation of reactive oxygen species during interaction of diesel exhaust particle components with NADPH-cytochrome P450 reductase and involvement of the bioactivation in the DNA damage. Free Radic. Biol. Med. 22:479-87 (Pubitemid 27020122)
61. Rodriguez CE, Fukuto JM, Taguchi K, Froines J, Cho AK. 2005. The interactions of 9,10-phenanthrenequinone with glyceraldehyde-3-phosphate dehydrogenase (GAPDH), a potential site for toxic actions. Chem. Biol. Interact. 155:97-110 (Pubitemid 40835993)
62. Gant TW, RaoDN, Mason RP, CohenGM. 1988. Redox cycling and sulphydryl arylation; their relative importance in the mechanism of quinone cytotoxicity to isolated hepatocytes. Chem. Biol. Interact. 65:157-73
63. Eiguren-Fernandez A, Shinyashiki M, Schmitz DA, Di Stefano E, Hinds W, et al. 2010. Redox and electrophilic properties of vapor-and particle-phase components of ambient aerosols. Environ. Res. 110:207-12
64. Kumagai Y, Midorikawa K, Nakai Y, Yoshikawa T, Kushida K, et al. 1998. Inhibition of nitric oxide formation and superoxide generation during reduction of LY83583 by neuronal nitric oxide synthase. Eur. J. Pharmacol. 360:213-18 (Pubitemid 28529188)
65. Kumagai Y, Hayashi T, Miyauchi T, Endo A, Iguchi A, et al. 2001. Phenanthraquinone inhibits eNOS activity and suppresses vasorelaxation. Am. J. Physiol. Regul. Integr. Comp. Physiol. 281:25-30
66. Sun Y, Taguchi K, Sumi D, Yamano S, 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. 80:280-85
67. Brisson M, Foster C, Wipf P, Joo B, Tomko RJ Jr, et al. 2007. Independent mechanistic inhibition of Cdc25 phosphatases by a natural product caulibugulone. Mol. Pharmacol. 71:184-92 (Pubitemid 46020988)
68. Brisson M, Nguyen T, Wipf P, Joo B, Day BW, et al. 2005. Redox regulation of Cdc25B by cell-active quinolinediones. Mol. Pharmacol. 68:1810-20 (Pubitemid 41656028)
69. Bhatnagar A, Liu SQ, Petrash JM, Srivastava SK. 1992. Mechanism of inhibition of aldose reductase by menadione (vitamin K3). Mol. Pharmacol. 42:917-21 (Pubitemid 23021497)
70. Otsuka M, Kato N, Ichimura T, Abe S, Tanaka Y, et al. 2005. Vitamin K2 binds 17β-hydroxysteroid dehydrogenase 4 and modulates estrogen metabolism. Life Sci. 76:2473-82 (Pubitemid 40341963)
71. Lame MW, Jones AD, Wilson DW, Segall HJ. 2003. Protein targets of 1,4-benzoquinone and 1,4-naphthoquinone in human bronchial epithelial cells. Proteomics 3:479-95 (Pubitemid 36428300)
72. Inbaraj JJ, Chignell CF. 2004. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Chem. Res. Toxicol. 17:55-62 (Pubitemid 38134060)
73. Hennig L, Christner C, Kipping M, Schelbert B, Rucknagel KP, et al. 1998. Selective inactivation of parvulin-like peptidyl-prolyl cis/trans isomerases by juglone. Biochemistry 37:5953-60 (Pubitemid 28196748)
74. Ravindra KC, Selvi BR, Arif M, Reddy BA, Thanuja GR, et al. 2009. Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin. J. Biol. Chem. 284:24453-64
75. Kar S, Lefterov IM, Wang M, Lazo JS, Scott CN, et al. 2003. Binding and inhibition of Cdc25 phosphatases by vitamin K analogues. Biochemistry 42:10490-97 (Pubitemid 37071449)
76. Samet JM, Tal TL. 2010. Toxicological disruption of signaling homeostasis: tyrosine phosphatases as targets. Annu. Rev. Pharmacol. Toxicol. 50:215-35
77. Tabernero L, Aricescu AR, Jones EY, Szedlacsek SE. 2008. Protein tyrosine phosphatases: structurefunction relationships. FEBS J. 275:867-82 (Pubitemid 351230204)
78. AbdelmohsenK,Gerber PA, vonMontfort C, Sies H, Klotz LO. 2003. Epidermal growth factor receptor is a common mediator of quinone-induced signaling leading to phosphorylation of connexin-43: role of glutathione and tyrosine phosphatases. J. Biol. Chem. 278:38360-67 (Pubitemid 37221728)
79. Beier JI, vonMontfort C, Sies H, Klotz LO. 2006. Activation of ErbB2 by 2-methyl-1,4-naphthoquinone (menadione) in human keratinocytes: role of EGFR and protein tyrosine phosphatases. FEBS Lett. 580:1859-64
80. Klotz LO, Patak P, Ale-Agha N, Buchczyk DP, Abdelmohsen K, et al. 2002. 2-Methyl-1,4-naphthoquinone, vitamin K3, decreases gap-junctional intercellular communication via activation of the epidermal growth factor receptor/ extracellular signal-regulated kinase cascade. Cancer Res. 62:4922-28 (Pubitemid 34984415)
81. Kikuno S, Taguchi K, IwamotoN, Yamano S, Cho AK, et al. 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 (Pubitemid 41790550)
82. Tonks NK. 2003. PTP1B: from the sidelines to the front lines! FEBS Lett. 546:140-48 (Pubitemid 36782295)
83. Kumagai Y, Koide S, Taguchi K, Endo A, Nakai Y, et al. 2002. Oxidation of proximal protein sulfhydryls by phenanthraquinone, a component of diesel exhaust particles. Chem. Res. Toxicol. 15:483-89 (Pubitemid 34326929)
84. Kobayashi A, Kang MI, Watai Y, Tong KI, Shibata T, et al. 2006. Oxidative and electrophilic stresses activate Nrf2 through inhibition of ubiquitination activity of Keap1. Mol. Cell. Biol. 26:221-29
85. Wakabayashi N, Dinkova-Kostova AT, Holtzclaw WD, Kang MI, Kobayashi A, et al. 2004. Protection against electrophile and oxidant stress by induction of the phase 2 response: fate of cysteines of the Keap1 sensor modified by inducers. Proc. Natl. Acad. Sci. USA 101:2040-45 (Pubitemid 38229011)
86. Taguchi K, Motohashi H, Yamamoto M. 2011. Molecular mechanisms of the Keap1-Nrf2 pathway in stress response and cancer evolution. Genes Cells 16:123-40
87. Sumi D, Numasawa Y, Endo A, Iwamoto N, Kumagai Y. 2009. Catechol estrogens mediated activation of Nrf2 through covalent modification of its quinone metabolite to Keap1. J. Toxicol. Sci. 34:627-35
88. Kobayashi M, Li L, Iwamoto N, Nakajima-Takagi Y, Kaneko H, et al. 2009. The antioxidant defense system Keap1-Nrf2 comprises a multiple sensing mechanism for responding to a wide range of chemical compounds. Mol. Cell. Biol. 29:493-502
89. Miura T, Shinkai Y, Jiang HY, Iwamoto N, Sumi D, et al. 2011. Initial response and cellular protection through the Keap1/Nrf2 system during the exposure of primary mouse hepatocytes to 1,2-naphthoquinone. Chem. Res. Toxicol. 24(4):559-67
90. NakayamaWongLS,LameMW,Jones AD, WilsonDW.2010. Differential cellular responses to protein adducts of naphthoquinone and monocrotaline pyrrole. Chem. Res. Toxicol. 23:1504-13
91. Son TG, Camandola S, Arumugam TV, Cutler RG, Telljohann RS, et al. 2010. Plumbagin, a novel Nrf2/ARE activator, protects against cerebral ischemia. J. Neurochem. 112:1316-26
92. Ishii T, Itoh K, Takahashi S, Sato H, Yanagawa T, et al. 2000. Transcription factor Nrf2 coordinately regulates a group of oxidative stress-inducible genes in macrophages. J. Biol. Chem. 275:16023-29 (Pubitemid 30366908)
93. Abiko Y, Miura T, Phuc BH, Shinkai Y, Kumagai Y. 2011. Participation of covalent modification of Keap1 in the activation of Nrf2 by tert- butylbenzoquinone, an electrophilic metabolite of butylated hydroxyanisole. Toxicol. Appl. Pharmacol. 255:32-39
94. Fourquet S, Guerois R, Biard D, Toledano MB. 2010. Activation of NRF2 by nitrosative agents and H2O2 involves KEAP1 disulfide formation. J. Biol. Chem. 285:8463-71
95. Sawa T, Zaki MH, Okamoto T, Akuta T, Tokutomi Y, et al. 2007. Protein S-guanylation by the biological signal 8-nitroguanosine 3′,5′-cyclic monophosphate. Nat. Chem. Biol. 3:727-35 (Pubitemid 47609113)
96. Tsujita T, Li L, Nakajima H, Iwamoto N, Nakajima-Takagi Y, et al. 2011. Nitro-fatty acids and cyclopentenone prostaglandins share strategies to activate the Keap1-Nrf2 system: a study using green fluorescent protein transgenic zebrafish. Genes Cells 16:46-57
97. Yu SM, Wu JF, Lin TL, Kuo SC. 1997. Inhibition of nitric oxide synthase expression by PPM-18, a novel anti-inflammatory agent, in vitro and in vivo. Biochem. J. 328(Pt. 2):363-69 (Pubitemid 27515574)
98. Ohsaki Y, Shirakawa H, Miura A, Giriwono PE, Sato S, et al. 2010. Vitamin K suppresses the lipopolysaccharide-induced expression of inflammatory cytokines in cultured macrophage-like cells via the inhibition of the activation of nuclear factor κB through the repression of IKKα/ βphosphorylation. J. Nutr. Biochem. 21:1120-26
99. Tanaka S, Nishiumi S, Nishida M, Mizushina Y, Kobayashi K, et al. 2010. Vitamin K3 attenuates lipopolysaccharide-induced acute lung injury through inhibition of nuclear factor-κB activation. Clin. Exp. Immunol. 160:283-92
100. CheckerR, SharmaD, Sandur SK,Khanam S,Poduval TB. 2009. Anti-inflammatory effects of plumbagin are mediated by inhibition of NF-κB activation in lymphocytes. Int. Immunopharmacol. 9:949-58
101. Luo P, Wong YF, Ge L, Zhang ZF, Liu Y, et al. 2010. Anti-inflammatory and analgesic effect of plumbagin through inhibition of nuclear factor-κB activation. J. Pharmacol. Exp. Ther. 335:735-42
102. Esnault S, Rosenthal LA, Shen ZJ, Sedgwick JB, Szakaly RJ, et al. 2007. A critical role for Pin1 in allergic pulmonary eosinophilia in rats. J. Allergy Clin. Immunol. 120:1082-88 (Pubitemid 350029884)
103. Moon DO, Choi YH, Kim ND, Park YM, Kim GY. 2007. Anti-inflammatory effects of β-lapachone in lipopolysaccharide-stimulated BV2 microglia. Int. Immunopharmacol. 7:506-14
104. Inoue K, Takano H, HiyoshiK, IchinoseT, SadakaneK, et al. 2007. Naphthoquinone enhances antigenrelated airway inflammation in mice. Eur. Respir. J. 29:259-67 (Pubitemid 46231902)
105. Inoue K, Takano H, Ichinose T, Tomura S, Yanagisawa R, et al. 2007. Effects of naphthoquinone on airway responsiveness in the presence or absence of antigen in mice. Arch. Toxicol. 81:575-81 (Pubitemid 47077062)
106. Speyer CL, Neff TA, Warner RL, Guo RF, Sarma JV, et al. 2003. Regulatory effects of iNOS on acute lung inflammatory responses in mice. Am. J. Pathol. 163:2319-28 (Pubitemid 37466475)
107. Sumi D, Akimori M, Inoue K, Takano H, Kumagai Y. 2010. 1,2-Naphthoquinone suppresses lipopolysaccharide-dependent activation of IKKβ/NF-κB/NO signaling: an alternative mechanism for the disturbance of inducible NO synthase-catalyzed NO formation. J. Toxicol. Sci. 35:891-98
108. Krishnan P, Bastow KF. 2000. Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives-eleutherin, αlapachone, and βlapachone. Biochem. Pharmacol. 60:1367-79
109. Li CJ, Averboukh L, Pardee AB. 1993. β-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J. Biol. Chem. 268:22463-68 (Pubitemid 23318296)
110. Choi BT, Cheong J, Choi YH. 2003. β-Lapachone-induced apoptosis is associated with activation of caspase-3 and inactivation ofNF-κB in human colon cancerHCT-116 cells. Anticancer Drugs 14:845-50 (Pubitemid 38339790)
111. Choi YH, Kang HS, Yoo MA. 2003. Suppression of human prostate cancer cell growth by β-lapachone via down-regulation of pRB phosphorylation and induction of Cdk inhibitor p21WAF1/CIP1. J. Biochem. Mol. Biol. 36:223-29 (Pubitemid 41200895)
112. Lee JI, Choi DY, Chung HS, Seo HG, Woo HJ, et al. 2006. β-Lapachone induces growth inhibition and apoptosis in bladder cancer cells by modulation of Bcl-2 family and activation of caspases. Exp. Oncol. 28:30-35
113. Li Y, Sun X, LaMont JT, Pardee AB, Li CJ. 2003. Selective killing of cancer cells by β-lapachone: direct checkpoint activation as a strategy against cancer. Proc. Natl. Acad. Sci. USA 100:2674-78 (Pubitemid 36297557)
114. Rao KV, McBride TJ, Oleson JJ. 1968. Recognition and evaluation of lapachol as an antitumor agent. Cancer Res. 28:1952-54
115. Preusch PC. 1986. Lapachol inhibition of DT-diaphorase (NAD(P)H:quinone dehydrogenase). Biochem. Biophys. Res. Commun. 137:781-87 (Pubitemid 16044456)
116. Kumagai Y, Tsurutani Y, Shinyashiki M, Homma-Takeda S, Yoshikawa T, et al. 1997. Bioactivation of lapachol responsible for DNA scission by NADPH-cytochrome P450 reductase. Environ. Toxicol. Pharmacol. 3:245-50 (Pubitemid 27390566)
117. Endo A, Sumi D, Kumagai Y. 2007. 1,2-Naphthoquinone disrupts the function of cAMP response element-binding protein through covalent modification. Biochem. Biophys. Res. Commun. 361:243-48 (Pubitemid 47102292)
118. Endo A, Sumi D, Iwamoto N, Kumagai Y. 2011. Inhibition of DNA binding activity of cAMP response element-binding protein by 1,2-naphthoquinone through chemical modification of Cys-286. Chem. Biol. Interact. 192(3):272-77
119. Bennett LL Jr, Smithers D, Rose LM, Adamson DJ, Thomas HJ. 1979. Inhibition of synthesis of pyrimidine nucleotides by 2-hydroxy-3-(3,3- dichloroallyl)-1,4-naphthoquinone. Cancer Res. 39:4868-74 (Pubitemid 10104858)
120. Kemp AJ, Lyons SD, Christopherson RI. 1986. Effects of acivicin and dichloroallyl lawsone upon pyrimidine biosynthesis in mouse L1210 leukemia cells. J. Biol. Chem. 261:14891-95 (Pubitemid 17218045)
121. KnechtW,LofflerM. 2000. Redoxal as a new lead structure for dihydroorotate dehydrogenase inhibitors: a kinetic study of the inhibition mechanism. FEBS Lett. 467:27-30 (Pubitemid 30069536)
122. Fila C, Metz C, van der Sluijs P. 2008. Juglone inactivates cysteine-rich proteins required for progression through mitosis. J. Biol. Chem. 283:21714-24
123. Hsu YL, Cho CY, Kuo PL, Huang YT, Lin CC. 2006. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) induces apoptosis and cell cycle arrest in A549 cells through p53 accumulation via c-Jun NH2-terminal kinase-mediated phosphorylation at serine 15 in vitro and in vivo. J. Pharmacol. Exp. Ther. 318:484-94
124. Kuo PL, Hsu YL, Cho CY. 2006. Plumbagin induces G2-M arrest and autophagy by inhibiting the AKT/mammalian target of rapamycin pathway in breast cancer cells. Mol. Cancer Ther. 5:3209-21
125. Luo Y, Mughal MR, Ouyang TG, Jiang H, Luo W, et al. 2010. Plumbagin promotes the generation of astrocytes from rat spinal cord neural progenitors via activation of the transcription factor STAT3. J. Neurochem. 115:1337-49
126. Taguchi K, Shimada M, Fujii S, Sumi D, Pan X, et al. 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. 44:1645-55
127. Batthyany C, Schopfer FJ, Baker PR, Duran R, Baker LM, et al. 2006. Reversible posttranslational modification of proteins by nitrated fatty acids in vivo. J. Biol. Chem. 281:20450-63 (Pubitemid 44065818)
128. Lin D, Saleh S, Liebler DC. 2008. Reversibility of covalent electrophile-protein adducts and chemical toxicity. Chem. Res. Toxicol. 21:2361-69
129. Rudolph TK, Freeman BA. 2009. Transduction of redox signaling by electrophile-protein reactions. Sci. Signal. 2:re7
130. Miura T, Kumagai Y. 2010. Immunochemical method to detect proteins that undergo selective modification by 1,2-naphthoquinone derived from naphthalene through metabolic activation. J. Toxicol. Sci. 35:843-52
131. Miura T, Kakehashi H, Shinkai Y, Egara Y, Hirose R, et al. 2011. GSH-mediated S-transarylation of a quinone glyceraldehyde-3-phosphate dehydrogenase conjugate. Chem. Res. Toxicol. In press
132. Song Y, Wagner BA, Witmer JR, Lehmler HJ, Buettner GR. 2009. Nonenzymatic displacement of chlorine and formation of free radicals upon the reaction of glutathione with PCB quinones. Proc. Natl. Acad. Sci. USA 106:9725-30
133. Baeza-Squiban A, Bonvallot V, Boland S, Marano F. 1999. Airborne particles evoke an inflammatory response in human airway epithelium. Activation of transcription factors. Cell Biol. Toxicol. 15:375-80 (Pubitemid 30233062)
134. Donaldson K, Borm P, eds. 2007. Particle Toxicology. Boca Raton, FL: CRC. 424 pp.
135. Squadrito GL, Cueto R, Dellinger B, Pryor WA. 2001. Quinoid redox cycling as a mechanism for sustained free radical generation by inhaled airborne particulate matter. Free Radic. Biol. Med. 31:1132-38 (Pubitemid 33009320)
136. Blanchet S, Ramgolam K, Baulig A, Marano F, Baeza-Squiban A. 2004. Fine particulate matter induces amphiregulin secretion by bronchial epithelial cells. Am. J. Respir. Cell Mol. Biol. 30:421-27 (Pubitemid 38457174)
137. Davies DE, Wicks J, Powell RM, Puddicombe SM, Holgate ST. 2003. Airway remodeling in asthma: new insights. J. Allergy Clin. Immunol. 111:215-25; quiz 226
138. Amishima M, Munakata M, Nasuhara Y, Sato A, Takahashi T, et al. 1998. Expression of epidermal growth factor and epidermal growth factor receptor immunoreactivity in the asthmatic human airway. Am. J. Respir. Crit. CareMed. 157:1907-12
139. Casalino-Matsuda SM,MonzonME, Forteza RM. 2006. Epidermal growth factor receptor activation by epidermal growth factor mediates oxidant-induced goblet cell metaplasia in human airway epithelium. Am. J. Respir. Cell Mol. Biol. 34:581-91
140. Hamilton LM, Puddicombe SM, Dearman RJ, Kimber I, Sandstrom T, et al. 2005. Altered protein tyrosine phosphorylation in asthmatic bronchial epithelium. Eur. Respir. J. 25:978-85 (Pubitemid 40823771)
141. Puddicombe SM, Polosa R, Richter A, Krishna MT, Howarth PH, et al. 2000. Involvement of the epidermal growth factor receptor in epithelial repair in asthma. FASEB J. 14:1362-74 (Pubitemid 30439745)
142. Cho AK, Sioutas C, Miguel AH, Kumagai Y, Schmitz DA, et al. 2005. Redox activity of airborne particulate matter at different sites in the Los Angeles Basin. Environ. Res. 99:40-47
143. Iwamoto N, Nishiyama A, Eiguren-Fernandez A, Hinds W, Kumagai Y, et al. 2010. Biochemical and cellular effects of electrophiles present in ambient air samples. Atmos. Environ. 44:1483-89
144. Li N, Sioutas C, Cho A, Schmitz D, Misra C, et al. 2003. Ultrafine particulate pollutants induce oxidative stress and mitochondrial damage. Environ. Health Perspect. 111:455-60 (Pubitemid 36546522)
145. Shiraiwa M, Garland R, Poeschl U. 2009. Kinetic double-layer model of aerosol surface chemistry and gas-particle interactions (K2-SURF): Degradation of polycyclic aromatic hydrocarbons exposed to O3, NO2, H2O, OH and NO3. Atmos. Chem. Phys. 9:9571-86
146. Sun JD, Wolff RK, Kanapilly GM, McClellan RO. 1984. Lung retention and metabolic fate of inhaled benzo(a)pyrene associated with diesel exhaust particles. Toxicol. Appl. Pharmacol. 73:48-59 (Pubitemid 14131606)
147. Chao SH, Greenleaf AL, Price DH. 2001. Juglone, an inhibitor of the peptidyl-prolyl isomerase Pin1, also directly blocks transcription. Nucleic Acids Res. 29:767-73 (Pubitemid 32124389)
148. Jeong HG, Pokharel YR, Lim SC, Hwang YP, Han EH, et al. 2009. Novel role of Pin1 induction in type II collagen-mediated rheumatoid arthritis. J. Immunol. 183:6689-97
149. Sandur SK, Ichikawa H, Sethi G, Ahn KS, Aggarwal BB. 2006. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) suppresses NF-κB activation and NF-κB-regulated gene products through modulation of p65 and IκBα kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents. J. Biol. Chem. 281:17023-33
150. Shih YW, Lee YC,WuPF, Lee YB,ChiangTA. 2009. Plumbagin inhibits invasion andmigration of liver cancerHepG2 cells by decreasing productions ofmatrixmetalloproteinase-2 and urokinase-plasminogen activator. Hepatol. Res. 39:998-1009
151. Sandur SK, Pandey MK, Sung B, Aggarwal BB. 2010. 5-hydroxy-2-methyl-1,4- naphthoquinone, a vitamin K3 analogue, suppresses STAT3 activation pathway through induction of protein tyrosine phosphatase, SHP-1: potential role in chemosensitization. Mol. Cancer Res. 8:107-18