Importance of phase 2 gene regulation in protection against electrophile and reactive oxygen toxicity and carcinogenesis

Advances in Enzyme Regulation

Volumn 43, Issue 1, 2003, Pages 121-134

  Talalay, Paul ^a   Dinkova Kostova, Albena T ^a   Holtzclaw, W David ^a  

^a JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMALIA; MURINAE;

EID: 0038378322     PISSN: 00652571     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0065-2571(02)00038-9     Document Type: Conference Paper

References (61)

1. Alberts DS, Colvin OM, Conney AH, Ernster VL, Garber JE, Greenwalt P, Gudas LJ, Hong KH, Kelloff GJ, Kramer RA, Lerman CE, Mangelsdorf DJ, Matter A, Minna JD, Nelson VWG, Pezzuto JM, Prendergast F, Rusch VW, Sporn MB, Wattenberg LW, Weinstein IB. Prevention of cancer in the next millennium: report of the chemoprevention working group to the American Association for Cancer Research. Cancer Res 1999;59:4743-58.
2. Benson AM, Batzinger RP, Ou S-YL, Bueding E, Cha Y-N, Talalay P. Elevation of hepatic glutathione S-transferase activities and protection against mutagenic metabolites of benzo(a)pyrene by dietary antioxidants. Cancer Res 1978;38:4486-95.
3. Benson AM, Cha Y-N, Bueding E, Heine HS, Talalay P. Elevation of extrahepatic glutathione S-transferase and epoxide hydratase activities by 2(3)-tert-butyl-4-hydroxyanisole. Cancer Res 1979;39:2971-7.
4. Benson AM, Hunkeler MJ, Talalay P. Increase of NAD(P)H:quinone reductase by dietary antioxidants: possible role in protection against carcinogenesis and toxicity. Proc Natl Acad Sci USA 1980;77:5216-20.
5. Benson AM, Hunkeler MJ, Morrow JF. Kinetics of glutathione transferase, glutathione transferase messenger RNA, and reduced nicotinamide adenine dinucleotide (phosphate): quinone reductase induction by 2(3)-tert-butyl-4-hydroxyanisole in mice. Cancer Res 1984;44:5256-61.
6. Chang LC, Gerhäuser C, Song L, Farnsworth NR, Pezzuto JM, Kinghorn AD. Activity-guided constituents of Tephrosia purpurea with the potential to induce the phase II enzyme, quinone reductase. J Nat Prod 1997;60:869-73.
7. Conney AH, Mueller GC, Miller JA. The metabolism of methylated aminoazo dyes. V. Evidence for induction of enzyme synthesis in the rat by methylcholanthrene. Cancer Res 1956;16:450-9.
8. De Long MJ, Dolan P, Santamaria AB, Bueding E. 1,2-Dithiol-3-thione analogs: effects on NAD(P)H:quinone reductase and glutathione levels in murine hepatoma cells. Carcinogenesis 1986a;7:977-80.
9. De Long MJ, Prochaska HJ, Talalay P. Induction of NAD(P)H:quinone reductase in murine hepatoma cells by phenolic antioxidants, azo dyes and other chemoprotectors: a model system for the study of anticarcinogens. Proc Natl Acad Sci USA 1986b;83:787-91.
10. 1-450 in the induction of NAD(P)H: quinone reductase in a murine hepatoma cell line and its mutants. Carcinogenesis 1987;8:1549-53.
11. Dinkova-Kostova AT, Talalay P. Relation of structure of curcumin analogs to their potencies as inducers of phase 2 detoxication enzymes. Carcinogenesis 1999;20:911-4.
12. Dinkova-Kostova AT, Abeygunawardana C, Talalay P. Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers. J Med Chem 1998;41:5287-96.
13. Dinkova-Kostova AT, Massiah MA, Bozak RE, Hicks RJ, Talalay P. Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc Natl Acad Sci USA 2001;98:3404-9.
14. Dinkova-Kostova AT, Holtzclaw WD, Cole RN, Wakabayashi N, Katoh Y, Yamamoto Y, Talalay P. 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 2002;99:11908-13.
15. Egner PA, Kensler TW, Prestera T, Talalay P, Libby AH, Joyner HH, Curphey TJ. Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones. Carcinogenesis 1994;15:177-81.
16. Fahey JW, Stephenson KK. Pinostrobin from honey and Thai ginger (Boesenbergia pandurata): a potent flavonoid inducer of mammalian phase 2 chemoprotective and antioxidant enzymes. J Agric Food Chem 2002;50:7472-6.
17. Fahey JW, Zhang Y, Talalay P. Broccoli sprouts: an exceptionally rich source of inducers of enzymes that protect against chemical carcinogens. Proc Natl Acad Sci USA 1997;94:10367-72.
18. Fahey JW, Zalcmann AT, Talalay P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 2001;56:5-51.
19. Fahey JW, Haristoy X, Dolan PM, Kensler TW, Scholtus I, Stephenson KK, Talalay P, Lozniewski A. Sulforaphane inhibits extracellular, intracellular and antibiotic-resistant strains of Helicobacter pylori and prevents benzo[a]pyrene-induced stomach tumors. Proc Natl Acad Sci USA 2002;99:7610-5.
20. Gerhäuser C, You M, Liu J, Moriarty RM, Hawthorne M, Mehta RJ, Moon RC, Pezzuto JM. Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes. Cancer Res 1997;57:272-8.
21. Hayes JD, McMahon M. Molecular basis for the contribution of the antioxidant responsive element to cancer chemoprevention. Cancer Lett 2001;174:103-13.
22. Hayes JD, Ellis EM, Neal GE, Harrison DJ, Manson MM. Cellular response to cancer chemopreventive agents: contribution of the antioxidant responsive element to the adaptive response to oxidative and chemical stress. Biochem Soc Symp 1999;64:141-68.
23. Henderson CJ, Smith AG, Ure J, Brown K, Bacon EJ, Wolf CR. Increased skin tumorigenesis in mice lacking pi class glutathione S-transferases. Proc Natl Acad Sci USA 1998;95:5275-80.
24. Itoh K, Chiba T, Takahashi S, Ishii T, Igarashi K, Katoh Y, Oyake T, Hayashi N, Satoh K, Hatayama I, Yamamoto M. Nabeshima Y-i. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem Biophys Res Commun 1997;236:313-22.
25. Itoh K, Wakabayashi N, Katoh Y, Ishii T, Igarashi K, Engel JD, Yamamoto M. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain. Genes Dev 1999;13:76-86.
26. Jaiswal AK. Antioxidant response element. Biochem Pharmacol 1994;48:439-44.
27. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Mehta RJ, Moon RC, Pezzuto JM, Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997;275:218-20.
28. Kennelly EJ, Gerhäuser C, Song LL, Graham JG, Beecher CWW, Pezzuto JM, Kinghorn AD. Induction of quinone reductase by withanolides isolated from Physalia philadelphica (Tomatillos). J Agric Food Chem 1997;45:3771-7.
29. Kensler TW. Chemoprevention by inducers of carcinogen detoxication enzymes. Environ Health Perspect 1997;105(Suppl):965-70.
30. Kinghorn AD, Fong HHS, Farnsworth NR, Mehta RG, Moon RC, Moriarty RM, Pezzuto JM, Cancer chemopreventive agents discovered by activity-guided fractionation: a review. Curr Org Chem 1998;2:597-612.
31. Kosmeder II JW, Hirschelman WH, Song LS, Park EJ, Tan Y, Yu R, Hawthorne M, Mehta RJ, Grubbs CJ, Lubet RA, Moriarty RM, Pezzuto JM. Cancer chemopreventive activity of oxomate, a monofunctional inducer of Phase II detoxification enzymes. 224th American Chemical Society National Meet, Boston, August 18-22, 2002. Abstract MEDI 98.
32. Kwak M-K, Itoh K, Yamamoto M, Sutter TR, Kensler TW. Role of transcription factor Nrf2 in the induction of hepatic phase 2 and antioxidative enzymes in vivo by the cancer chemoprotective agent, 3H-1,2-dithiole-3-thione. Mol Med 2001;7:135-45.
33. Lam LKT, Sparnins VL, Wattenberg LW. Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance glutathione S-transferase activity in the mouse. Cancer Res 1982;42:1193-8.
34. Long II DJ, Waikel RL, Wang X-J, Perlaky L, Roop DR, Jaiswal AK. NAD(P)H: quinone oxidoreductase 1 deficiency increases susceptibility to benzo(a)pyrene-induced mouse skin carcinogenesis. Cancer Res 2000;60:5913-5.
35. Maxuitenko YY, Libby AH, Joyner HH, Curphey TJ, MacMillan DL, Kensler TW, Roebuck BD. Identification of dithiolethiones with better chemopreventive properties than oltipraz. Carcinogenesis 1998;19:1609-15.
36. McMahon M, Itoh K, Yamamoto M, Chanas SA, Henderson CJ, McLellan LI, Wolf CR, Cavin C, Hayes JD. The Cap "n" Collar basic leucine zipper transcription factor Nrf2 (NF-E2 p45-related Factor 2) controls both constitutive and inducible expression of intestinal detoxification and glutathione biosynthetic enzymes. Cancer Res 2001;61:3299-307.
37. Miller EC, Miller JA. Mechanisms of chemical carcinogenesis: nature of proximate carcinogens and interactions with macromolecules. Pharmacol Rev 1966;18:805-38.
38. Miyata M, Kudo G, Lee Y-H, Yang TJ, Gelboin HV, Fernandez-Salguero P, Kimura S, Gonzalez FJ. Targeted disruption of the microsomal epoxide hydrolase gene. J Biol Chem 1999;274:23963-8.
39. Pearson WR, Windle JJ, Morrow JF, Benson AM, Talalay P. Increased synthesis of glutathione S-transferases in response to anticarcinogenic antioxidants. Cloning and measurement of messenger RNA. J Biol Chem 1983;258:2052-62.
40. Posner GH, Cho C-G, Green JV, Zhang Y, Talalay P. Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane: correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes. J Med Chem 1994;37:170-6.
41. Prestera T, Holtzclaw WD, Zhang Y, Talalay P. Chemical and molecular regulation of enzymes that detoxify carcinogens. Proc Natl Acad Sci USA 1993a;90;2965-9.
42. Prestera T, Zhang Y, Spencer SR, Wilczak CA, Talalay P. The electrophile counterattack response: protection against neoplasia and toxicity. Adv Enzyme Regul 1993b;33:281-96.
43. Prochaska H, Santamaria AB. Direct measurement of NAD(P)H:quinone reductase from cells cultured in microtiter wells: a screening assay for anticarcinogenic enzyme inducers. Anal Biochem 1988;169:328-36.
44. Prochaska HJ, Talalay P. Regulatory mechanisms of monofunctional and bifunctional anticarcinogenic enzyme inducers in murine liver. Cancer Res 1988;48:4776-82.
45. Prochaska HJ, De Long MJ, Talalay P. On the mechanisms of induction of cancer-protective enzymes: a unifying proposal. Proc Natl Acad Sci USA 1985;82:8232-6.
46. Prochaska HJ, Santamaria AB, Talalay P. Rapid detection of inducers of enzymes that protect against carcinogens. Proc Natl Acad Sci USA 1992;89:2394-8.
47. Ramos-Gomez M, Kwak M-K, Dolan PM, Itoh K, Yamamoto M, Talalay P, Kensler TW. Sensitivity to carcinogenesis is increased and chemoprotective efficacy of enzyme inducers is lost in Nrf2 transcription factor-deficient mice. Proc Natl Acad Sci USA 2001;98:3410-5.
48. Rushmore TH, Morton MR, Pickett CB. The antioxidant-responsive element. Activation by oxidative stress and identification of the DNA consensus sequence required for functional activity. J Biol Chem 1991;266:11632-9.
49. Shapiro TA, Fahey JW, Wade KL, Stephenson KK, Talalay P. Chemoprotective glucosinolates and isothiocyanates of broccoli sprouts: metabolism and excretion in humans. Cancer Epidemiol Biomark Prev 2001;10:501-8.
50. Song LL, Kosmeder II JW, Lee SK, Gerhäuser C, Lantvit D, Moon RC, Moriarty RM, Pezzuto JM. Cancer chemopreventive activity mediated by 4′-bromoflavone, a potent inducer of phase II detoxification enzymes. Cancer Res 1999;59:578-85.
51. Spencer SR, Xue L, Klenz EM, Talalay P. The potency of inducers of NAD(P)H: (quinone-acceptor) oxidoreductase parallels their efficiency as substrates for glutathione transferases. Structural and electronic correlations. Biochem J 1991;273:711-7.
52. Talalay P. The war against cancer: new hope. Proc Am Philos Soc 1999;143:52-72.
53. Talalay P. Chemoprotection against cancer by induction of phase 2 enzymes. BioFactors 2000;12:5-11.
54. Talalay P, De Long MJ, Prochaska HJ. Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc Natl Acad Sci USA 1988;85:8261-5.
55. Talalay P, Fahey JW, Holtzclaw WD, Prestera T, Zhang Y. Chemoprotection against cancer by phase 2 enzyme induction. Toxicol Lett 1995;82/83:173-9.
56. 1 gene. Proc Natl Acad Sci USA 1996;93:14960-5.
57. Wattenberg LW, Bueding E. Inhibitory effects of 5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione (oltipraz) on carcinogenesis induced by benzo[a]pyrene, diethylnitrosamine and uracil mustard. Carcinogenesis 1986;7:1379-81.
58. Yannai S, Day AJ, Williamson G, Rhodes MJC. Characterization of flavonoids as monofunctional or bifunctional inducers of quinone reductase in murine hepatoma cell lines. Food Chem Toxicol 1998;36:623-30.
59. Zhang Y, Talalay P, Cho C-G, Posner GH. A major inducer of anti-carcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc Natl Acad Sci USA 1992;89:2399-403.
60. Zhang Y, Kensler TW, Cho C-G, Posner GH, Talalay P. Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci USA 1994;91:3147-50.
61. Zipper LM, Mulcahy RT. The Keap1 BTB/POZ dimerization function is required to sequester Nrf2 in cytoplasm. J Biol Chem 2002;277:36544-52.