Combating oxidative/nitrosative stress with electrophilic counterattack strategies

Oxidative Stress and Redox Regulation

Volumn , Issue , 2013, Pages 277-307

  Satoh, Takumi ^a,b   Akhtar, Mohd Waseem ^a   Lipton, Stuart A ^a  

^a BURNHAM INSTITUTE   (United States)

^b IWATE UNIVERSITY   (Japan)

Author keywords

Electrophile; HSF 1; HSP90; Keap1; Nrf2; Pathologically activated therapeutic; Pro electrophilic drug

Indexed keywords

EID: 84932085573     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-94-007-5787-5_10     Document Type: Chapter

References (102)

1. Ahlgren-Beckendorf JA, Reising AM, Schander MA, Herdler JW, Johnson JA (1999) Coordinate regulation of NAD(P)H:quinone oxidoreductase and glutathione-S-transferase in primary cultures of rat neurons and glias: role of the antioxidant/electrophile responsive element. Glia 15:131-142
2. Ahmad A, Khan MM, Hoda MN, Raza SS, Khan MB, Javed H, Ishrat T, Ashafaq M, Ahmad ME, Safhi MM, Islam F (2011) Quercetin protects against oxidative stress associated damages in a rat model of transient focal cerebral ischemia and reperfusion. Neurochem Res 36:1360-1371
3. Akaike T, Fujii S, Sawa T, Ihara H (2010) Cell signaling mediated by nitrated cyclic guanine nucleotide. Nitric Oxide 23:166-174
4. Alfieri A, Srivastava S, Siow RC, Modo M, Fraser PA, Mann GE (2011) Targeting the Nrf2-Keap1 antioxidant defence pathway for neurovascular protection in stroke. J Physiol 589:4125-4136
5. Arteel GE, Sies H (2001) The biochemistry of selenium and the glutathione system. Environ Toxicol Pharmacol 10:153-158
6. Bredesen DE (2008) Programmed cell death mechanism in neurological diseases. Curr Mol Med 8:173-186
7. Bukau B, Weisman J, Horwich A (2006) Molecular chaperones and protein quality control. Cell 125:443-451
8. Burdo J, Schubert D, Maher P (2008) Glutathione production is regulated via distinct pathways in stressed and non-stressed cortical neurons. Brain Res 1189:12-22
9. Bureau G, Longpré F, Martinoli MG (2008) Resveratrol and quercetin, two natural polyphenols, reduce apoptotic neuronal cell death induced by neuroinflammation. J Neurosci Res 86: 403-410
10. Butterfield DA, Reed T, Sultana R (2011) Roles of 3-nitrotyrosine-and 4-hydroxynonenalmodified brain proteins in the progression and pathogenesis of Alzheimer's disease. Free Radic Res 45:59-72
11. Catalá A (2009) Lipid peroxidation of membrane phospholipids generates hydroxy-alkenals and oxidized phospholipids active in physiological and/or pathological conditions. Chem Phys Lipids 157:1-11
12. Chang TS, Jeong W, Woo HA, Lee SM, Park S, Rhee SG (2004) Characterization of mammalian sulfiredoxin and its reactivation of hyperoxidized peroxiredoxin through reduction of cysteine sulfinic acid in the active site to cysteine. J Biol Chem 279:50994-51001
13. Cho DH, Nakamura T, Fang J, Cieplak P, Godzik A, Gu Z, Lipton SA (2009) S-Nitrosylation of Drp1 mediates beta-amyloid-related mitochondrial fission and neuronal injury. Science 324:102-105
14. Chung KK, Thomas B, Li X, Pletnikova O, Troncoso JC, Marsh L, Dawson VL, Dawson TM (2004) S-Nitrosylation of parkin regulates ubiquitination and compromises parkin's protective function. Science 304:1328-1331
15. Clement AM, Nguyen MD, Roberts EA, Garcia ML, Boillée S, Rule M, McMahon AP, Doucette W, Siwek D, Ferrante RJ, Brown RH Jr, Julien JP, Goldstein LS, Cleveland DW (2003) Wildtype nonneuronal cells extend survival of SOD1 mutant motor neurons in ALS mice. Science 302:113-117
16. Coyle JT, Puttfarcken P (1993) Oxidative stress, glutamate and neurodegenerative disorders. Science 262:689-695
17. Dalle-Donne I, Rossi R, Colombo G, Giustarini D, Milzani A (2009) Protein S-glutathionylation: a regulatory device from bacteria to humans. Trends Biochem Sci 34:85-96
18. Dinkova-Kostova AT, Holtzclaw WD, Cole RN, Itoh K, Wakabayashi N, Katoh Y, Yamamoto M, Talalay P (2002) Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc Natl Acad Sci USA 99:11908-11913
19. Fang J, Nakamura T, Cho DH, Gu Z, Lipton SA (2007) S-Nitrosylation of peroxiredoxin 2 promotes oxidative stress-induced neuronal cell death in Parkinson's disease. Proc Natl Acad Sci USA 104:18742-18747
20. Fourquet S, Guerois R, Biard D, Toledano MB (2010) Activation of NRF2 by nitrosative agents and H2O2 involves KEAP1 disulfide formation. J Biol Chem 285:8463-8471
21. Fujii S, Sawa T, Ihara H, Tong KI, Ida T, Okamoto T, Ahtesham AK, Ishima Y, Motohashi H, Yamamoto M, Akaike T (2010) The critical role of nitric oxide signaling, via protein S-guanylation and nitrated cyclic GMP, in the antioxidant adaptive response. J Biol Chem 285:23970-23984
22. Garden GA, La Spada AR (2012) Intercellular (Mis)communication in neurodegenerative disease. Neuron 73:886-901
23. Groeger AL, Freeman BA (2010) Signaling actions of electrophiles: anti-inflammatory therapeutic candidates. Mol Interv 10:39-50
24. Gu Z, Kaul M, Yan B, Kridel SJ, Cui J, Strongin A, Smith JW, Liddington RC, Lipton SA (2002) S-nitrosylation of matrix metalloproteinases: signaling pathway to neuronal cell death. Science 297:1186-1190
25. Halliwell B, Gutteridge JMC (1999) Free radicals in biology and medicine. Oxford University Press, Oxford
26. Hanneken A, Lin FF, Johnson J, Maher P (2006) Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death. Invest Ophthalmol Vis Sci 47:3164-3177
27. Hara MR, Snyder SH (2007) Cell signaling and neuronal death. Annu Rev Pharmacol Toxicol 47:117-141
28. Hardingham GE, Lipton SA (2011) Regulation of neuronal oxidative and nitrosative stress by endogenous protective pathways and disease processes. Antioxid Redox Signal 14:1421-1424
29. Hastings TG (2009) The role of dopamine oxidation in mitochondrial dysfunction: implications for Parkinson's disease. J Bioenerg Biomembr 41:469-472
30. Hess DT, Matsumoto A, Kim SO, Marshall HE, Stamler JS (2005) Protein S-nitrosylation: purview and parameters. Nat Rev Mol Cell Biol 6:150-166
31. Holmgren A, Lu J (2010) Thioredoxin and thioredoxin reductase: current research with special reference to human disease. Biochem Biophys Res Commun 396:120-124
32. Hong F, Freeman ML, Lieber DC (2005) Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane. Chem Res Toxicol 18:1917-1926
33. Immenschuh S, Baumgart-Vogt E (2005) Peroxiredoxin, oxidative stress and cell proliferation. Antioxid Redox Signal 7:768-777
34. Ishige K, Schubert D, Sagara Y (2001) Flavonoids protect neuronal cells from oxidative stress by three distinct mechanisms. Free Radic Biol Med 30:433-446
35. Itoh K, Tong KI, Yamamoto M (2004) Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. Free Radic Biol Med 36:1208-1213
36. Jakel RJ, Townsend JA, Kraft AD, Johnson JA (2007) Nrf2-mediated protection against 6-hydroxydopamine. Brain Res 1144:192-201
37. Johnson J, Maher P, Hanneken A (2009) The flavonoid, eriodictyol, induces long-term protection in ARPE-19 cells through its effects on Nrf2 activation and phase 2 gene expression. Invest Ophthalmol Vis Sci 50:2398-2406
38. Kansanen E, Bonacci G, Schopfer FJ, Kuosmanen SM, Tong KI, Leinonen H, Woodcock SR, Yamamoto M, Carlberg C, Ylä-Herttuala S, Freeman BA, Levonen AL (2011) Electrophilic nitro-fatty acids activate NRF2 by a KEAP1 cysteine 151-independent mechanism. J Biol Chem 286:14019-14027
39. Kim W-K, Choi Y-B, Rayudu PV, Das P, Asaad W, Arnelle DR, Stamler JS, Lipton SA (1999) Attenuation of NMDA receptor activity and neurotoxicity by nitroxyl (NO-). Neuron 24: 461-469
40. Kim I, Xu W, Reed JC (2008) Cell death and endoplasmic reticulum stress: disease relevance and therapeutic opportunities. Nat Rev Drug Discov 7:1013-1030
41. Kobayashi M, Li L, Iwamoto N, Nakajima-Takagi Y, Kaneko H, Nakayama Y, Eguchi M, Wada Y, Kumagai Y, Yamamoto M (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
42. Kraft AD, Johnson DA, Johnson JA (2004) Nuclear factor E2-related factor 2-dependent antioxidant response element activation by tert-butylhydroquinone and sulforaphane occurring preferentially in astrocytes conditions neurons against oxidative insult. J Neurosci 24: 1101-1112
43. Lee JM, Calkins MJ, Chan K, Kan YW, Johonson JA (2003) Identification of the NF-E2-related factor-2-dependent genes conferring protection against oxidative stress in primary cortical astrocytes using oligonucleotide microarray analysis. J Biol Chem 278:12029-12038
44. Lewerenz J, Dargusch R, Maher P (2010) Lactacidosis modulates glutathione metabolism and oxidative glutamate toxicity. J Neurochem 113:502-514
45. Linder MC, Hazegh-Azam M (1996) Copper biochemistry and molecular biology. Am J Clin Nutr 63:797S-811S
46. Lioy DT, Garg SK, Monaghan CE, Raber J, Foust KD, Kaspar BK, Hirrlinger PG, Kirchhoff F, Bissonnette JM, Ballas N, Mandel G (2011) A role for glia in the progression of Rett's syndrome. Nature 475:497-500
47. Lipton SA (2004) Concepts: turning down but not off-neuroprotection requires a paradigm shift in drug development. Nature 428:473
48. Lipton SA (2006) Paradigm shift in neuroprotection by NMDA receptor blockade: memantine and beyond. Nat Rev Drug Discov 5:160-170
49. Lipton SA (2007) Pathologically-activated therapeutics. Nat Rev Neurosci 8:803-808
50. Lipton SA, Stamler JS (1994) Actions of redox-related congeners of nitric oxide at the NMDA receptor. Neuropharmacology 33:1229-1233
51. Lipton SA, Choi Y-B, Pan Z-H, Lei SZ, Chen H-SV, Sucher NJ, Singel DJ, Loscalzo J, Stamler JS (1993) A redox-based mechanism for the neuroprotective and neurodestructive effects of nitric oxide and related nitroso-compounds. Nature 364:626-632
52. Long EK, Picklo MJ Sr (2010) Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE. Free Radic Biol Med 49:1-8
53. Maher P (2008) The flavonoid fisetin promotes nerve cell survival from trophic factor withdrawal by enhancement of proteasome activity. Arch Biochem Biophys 476:139-144
54. Maher P, Dargusch R, Bodai L, Gerard PE, Purcell JM, Marsh JL (2011) ERK activation by the polyphenols fisetin and resveratrol provides neuroprotection in multiple models of Huntington's disease. Hum Mol Genet 20:261-270
55. Mandel MN, Patlolla JM, Zheng L, Agbaga MP, Tran JT, Wicker L, Kasus-Jacobi A, Elliott MH, Rao CV, Anderson RE (2009) Curcumin protects retinal cells from light-and oxidant stressinduced cell death. Free Radic Biol Med 46:672-679
56. Mangialasche F, Polidori MC, Monastero R, Ercolani S, Camarda C, Cecchetti R, Mecocci P (2009) Biomarkers of oxidative and nitrosative damage in Alzheimer's disease and mild cognitive impairment. Ageing Res Rev 8:285-305
57. MattsonMP, Cheng A (2006) Neurohormetic phytochemicals: low-dose toxins that induce adaptive neuronal stress response. Trends Neurosci 29:632-639
58. Milioli EM, Cologni P, Santos CC, Marcos TD, Yunes VM, Fernandes MS, Schoenfelder T, Costa-Campos L (2007) Effect of acute administration of hydroalcohol extract of Ilex paraguariensis St Hilaire (Aquifoliaceae) in animal models of Parkinson's disease. Phytother Res 21:771-776
59. Morimoto RI (2008) Proteotoxic stress and inducible chaperone networks in neurodegenerative disease and aging. Genes Dev 22:1427-1438
60. Murphy TH, De Long MJ, Coyle JT (1991) Enhanced NAD(P)H:quinone reductase activity prevents glutamate toxicity produced by oxidative stress. J Neurochem 56:990-995
61. Nakamura Y, Kumagai T, Yoshida C, Naito Y, Miyamoto M, Ohigashi H, Osawa T, Uchida K (2003) Pivotal role of electrophilicity in glutathione S-transferase induction by tertbutylhydroquinone. Biochemistry 15:4300-4309
62. Nakamuara T, Lipton SA (2009) Cell death: protein misfolding and neurodegenerative diseases. Apoptosis 14:455-468
63. Nakamura T, Wang L, Wong CC, Scott FL, Eckelman BP, Han X, Tzitzilonis C, Meng F, Gu Z, Holland EA, Clemente AT, Okamoto S, Salvesen GS, Riek R, Yates JR 3rd, Lipton SA (2010) Transnitrosylation of XIAP regulates caspase-dependent neuronal cell death. Mol Cell 39:184-195
64. Nakamura T, Lipton SA (2011) Redox modulation by S-nitrosylation contributes to protein misfolding, mitochondrial dynamics, and neuronal synaptic damage in neurodegenerative diseases. Cell Death Differ 18:1478-1486
65. Nakamura T, Wang L, Wong CC, Scott FL, Eckelman BP, Han X, Tzitzilonis C, Meng F, Gu Z, Holland EA, Clemente AT, Okamoto S, Salvesen GS, Riek R, Yates JR III, Lipton SA (2011) Transnitrosylation of XIAP regulates caspase-dependent neuronal cell death. Mol Cell 39:184-195
66. Niles JC, Wishnok JS, Tannenbaum SR (2006) Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation. Nitric Oxide 14:109-121
67. Numajiri N, Takasawa K, Nishiya T, Hayakawa W, Asada M, Matsuda H, Azumi K, Tanaka H, Hyakkoku K, Kamata H, Nakamura T, Hara H, Minami M, Lipton SA, Uehara T (2011) Onoff system for PI3-kinase-Akt signaling through S-nitrosylation of phosphatase with sequence homology to tensin (PTEN). Proc Natl Acad Sci USA 108:10349-10354
68. Pacher P, Beckman JS, Liaudet L (2007) Nitric oxide and peroxynitrite in health and disease. Physiol Rev 87:315-424
69. Padmanabhan B, Tong KI, Ohta T, Nakamura Y, Scharlock M, Ohtsuji M, Kang MI, Kobayashi A, Yokoyama S, Yamamoto M (2006) Structural basis for defects of Keap1 activity provoked by its point mutations in lung cancer. Mol Cell 21:689-700
70. Qu J, Nakamura T, Cao G, Holland EA, McKercher SR, Lipton SA (2011) S-Nitrosylation activates Cdk5 and contributes to synaptic spine loss induced by "-amyloid peptide. Proc Natl Acad Sci USA 108:14330-14335
71. Radi R (2004) Nitric oxide, oxidants, and protein tyrosine nitration. Proc Natl Acad Sci USA 101:4003-4008
72. Rhee SG, Jeong W, Chang TS, Woo HA (2007) Sulfiredoxin, the cysteine sulfinic acid reductase specific to 2-Cys peroxiredoxin: its discovery, mechanism of action, and biological significance. Kidney Int Suppl 106:S3-S8
73. Sasaki S, Tozawa T, VanWagoner RM, Ireland CM, HarperMK, Satoh T (2011) Strongylophorine-8, a pro-electrophilic compound from the marine sponge Petrosia (Strongylophora) corticata, provides neuroprotection through Nrf2/ARE pathway. Biochem Biophys Res Commun 415: 6-10
74. Satoh T, Lipton SA (2007) Redox regulation of neuronal survival by electrophilic compounds. Trends Neurosci 30:38-45
75. Satoh T, Furuta K, Tomokiyo K, Nakatsuka D, Tanikawa M, Nakanishi M, Miura M, Tanaka S, Koike T, Hatanaka H, Ikuta K, Suzuki M, Watanabe Y (2000) Facilitatory roles of novel compounds designed from cyclopentenone prostaglandins on neurite outgrowth-promoting activities of nerve growth factor. J Neurochem 75:1092-1102
76. Satoh T, Furuta K, Tomokiyo K, Namura S, Nakatsuka D, Sugie Y, Ishikawa Y, Hatanaka H, Suzuki M, Watanabe Y (2001) Neurotrophic actions of novel compounds designed from cyclopentenone prostaglandins. J Neurochem 77:50-62
77. Satoh T, Baba M, Nakatsuka D, Ishikawa Y, Aburatani H, Furuta K, Ishikawa T, Hatanaka H, Suzuki M, Watanabe Y (2003) Role of heme oxygenase-1 protein in the neuroprotective effects by cyclopentenone prostaglandin derivatives as a sustained phase of neuronal survival promoting mechanism under oxidative stress. Eur J Neurosci 17:2249-2255
78. Satoh T, Okamoto S, Cui J, Watanabe Y, Furuta K, Suzuki M, Tohyama K, Lipton SA (2006) Activation of the Keap1/Nrf2 pathway for neuroprotection by electrophilic phase II inducers. Proc Natl Acad Sci USA 103:768-773
79. Satoh T, Kosaka K, Itoh K, Kobayashi A, Yamamoto M, Shimojo Y, Kitajima C, Cui J, Kamins J, Okamoto S, Shirasawa T, Lipton SA (2008a) Carnosic acid, a catechol-type electrophilic compound, protects neurons both in vitro and in vivo through activation of the Keap1/Nrf2 pathway via S-alkylation of specific cysteines. J Neurochem 104:1116-1131
80. Satoh T, Izumi M, Inukai Y, Tsutumi Y, Nakayama N, Kosaka K, Kitajima C, Itoh K, Yokoi T, Shirasawa T (2008b) Carnosic acid protects neuronal HT22 cells through activation of the antioxidant-responsive element in free carboxylic acid-and catechol hydroxyl moietiesdependent manners. Neurosci Lett 434:260-265
81. Satoh T, Saitoh S, Hosaka H, Kosaka K (2009a) Simple ortho-and para-hydroquinones as neuroprotective compounds against oxidative stress associated with a specific transcriptional activation. Biochem Biophys Res Commun 379:537-541
82. Satoh T, Harada N, Hosoya T, Tohyama K, Yamamoto M, Itoh K (2009b) Keap1/Nrf2 system regulates neuronal survival as revealed through study of keap1 gene knockout mice. Biochem Biophys Res Commun 380:298-302
83. Satoh T, Rezaie T, Seki M, Sunico CR, Tabuchi T, Kitagawa T, Yanagitai M, Senzaki M, Kosegawa C, Taira H, McKercher SR, Hoffman JK, Roth GP, Lipton SA (2011) Dual neuroprotective pathways of a pro-electrophilic compound via HSF-1-activated heat-shock proteins and Nrf2-activated phase 2 antioxidant response enzymes. J Neurochem 119:569-578
84. Shih AY, Li P, Murphy TH (2005) A small-molecule-inducible Nrf2-mediated antioxidant response provides effective prophylaxis against cerebral ischemia in vivo. J Neurosci 25:10321-10335
85. Shih AY, Erb H, Murphy TH (2007) Dopamine activates Nrf2-regulated neuroprotective pathways in astrocytes and meningeal cells. J Neurochem 101:109-119
86. Soriano FX, Leveille F, Papadia S, Higgins LG, Varley J, Baxter P, Hayes JD, Hardingham GE (2008) Induction of sulfiredoxin expression and reduction of peroxiredoxin hyperoxidation by neuroprotective Nrf2 activator 3H-1, 2-dithiol-3-thione. J Neurochem 107:533-543
87. Soriano FX, Baxter P, Murray LM, Sporn MB, Gillingwater TH, Hardingham GE (2009) Transcriptional regulation of the AP-1 and Nrf2 target gene sulfiredoxin. Mol Cells 27: 279-282
88. Suematsu N, Hosoda M, Fujimori K (2011) Protective effects of quercetin against hydrogen peroxide-induced apoptosis in human neuronal SH-SY5Y cells. Neurosci Lett 504:223-227
89. Sun X, Erb H, Murphy TH (2005) Coordinate regulation of glutathione metabolism in astrocytes by Nrf2. Biochem Biophys Res Commun 326:371-377
90. Takahashi T, Tabuchi T, Tamaki Y, Kosaka K, Takikawa Y, Satoh T (2009) Carnosic acid and carnosol inhibit adipocyte differentiation in mouse 3 T3-L1 cells through induction of phase 2 enzymes and activation of glutathione metabolism. Biochem Biophys Res Commun 382: 549-554
91. Takahata Y, Takarada T, Iemata M, Yamamoto T, Nakamura Y, Kodama A, Yoneda Y (2009) Functional expression of beta2 adrenergic receptors responsible for protection against oxidative stress through promotion of glutathione synthesis after Nrf2 upregulation in undifferentiated mesenchymal C3H10T1/2 stem cells. J Cell Physiol 218:268-275
92. Talalay P (2000) Chemoprotection against cancer by induction of phase 2 enzymes. Biofactors 12:5-11
93. Tamaki Y, Tabuchi T, Takahashi T, Kosaka K, Satoh T (2010) Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells. Planta Med 76:683-688
94. Uchida K (2003) 4-Hydroxy-2-nonenal: a product and mediator of oxidative stress. Prog Lipid Res 42:318-343
95. Uehara T, Nakamura T, Yao D, Shi ZQ, Gu Z, Ma Y, Masliah E, Nomura Y, Lipton SA (2006) S-nitrosylated protein-disulphide isomerase links protein misfolding to neurodegeneration. Nature 441:513-517
96. Um HC, Jang JH, Kim DH, Lee C, Surh YJ (2011) Nitric oxide activates Nrf2 through Snitrosylation of Keap1 in PC12 cells. Nitric Oxide 25:161-168
97. Vargas MR, Johnson JA (2009) The Nrf2-ARE cytoprotective pathway in astrocytes. Expert Rev Mol Med 11:e17
98. Wang XJ, Hayes JD, Higgins LJ, Wolf CR, Dinkova-Kostova AT (2010) Activation of the NRF2 signaling pathway by copper-mediated redox cycling of para-and ortho-hydroquinones. Chem Biol 17:75-85
99. Winyard PG, Moody CJ, Jacob C (2005) Oxidative activation of antioxidant defence. Trends Biochem 30:453-461
100. Yao D, Gu Z, Nakamura T, Shi Z-Q, Ma Y, Gaston B, Palmer LA, Rockenstein EM, Zhang Z, Masliah E, Uehara T, Lipton SA (2004) Nitrosative stress linked to sporadic Parkinson's disease: S-Nitrosylation of parkin regulates it E3 ligase activity. Proc Natl Acad Sci USA 101:10810-10814
101. Zhang DD, Lo SC, Cross JV, Templeton DJ, Hannink M (2004) Keap1 is a redox-regulated substrate adaptor protein for a Cul3-dependent ubiquitin ligase complex. Mol Cell Biol 24:10941-10953
102. Zhang Y, Ahn YH, Benjamin IJ, Honda T, Hicks RJ, Calabrese V, Cole PA, Dinkova-Kostova AT (2011) HSF1-dependent upregulation of Hsp70 bysulfhydryl-reactive inducers of the KEAP1/NRF2/ARE pathway. Chem Biol 18:1355-1361