Electrophilic tuning of the chemoprotective natural product sulforaphane

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 21, 2010, Pages 9590-9595

  Ahn, Young Hoon ^a   Hwang, Yousang ^a   Liu, Hua ^a   Wang, Xiu Jun ^b   Zhang, Ying ^b   Stephenson, Katherine K ^a   Boronina, Tatiana N ^a   Cole, Robert N ^a   Dinkova Kostova, Albena T ^a,b   Talalay, Paul ^a   Cole, Philip A ^a  

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

^b UNIVERSITY OF DUNDEE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; ISOTHIOCYANIC ACID; KELCH LIKE ECH ASSOCIATED PROTEIN 1; LIPOPOLYSACCHARIDE; NITRIC OXIDE; SULFORAPHANE; SULFOXYTHIOCARBAMATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER CELL CULTURE; DRUG MECHANISM; ELECTROPHILICITY; FEMALE; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ADAPTOR PROTEINS, SIGNAL TRANSDUCING; ANIMALS; BIOLOGICAL PRODUCTS; CELL LINE; CELL SURVIVAL; CYTOSKELETAL PROTEINS; ELECTRONS; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NITRIC OXIDE; SKIN; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; THIOCYANATES;

EID: 77953100764     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1004104107     Document Type: Article

References (47)

1. Talalay P, Fahey JW (2001) Phytochemicals from cruciferous plants protect against cancer by modulating carcinogen metabolism. J Nutr 131:3027S-3033S.
2. Surh YJ (2003) Cancer chemoprevention with dietary phytochemicals. Nat Rev Cancer 3:768-780.
3. Zhang Y, Talalay P, Cho CG, Posner GH (1992) A major inducer of anticarcinogenic protective enzymes from broccoli-isolation and elucidation of structure. Proc Natl Acad Sci USA 89:2399-2403.
4. Juge N, Mithen RF, Traka M (2007) Molecular basis for chemoprevention by sulforaphane: A comprehensive review. Cell Mol Life Sci 64:1105-1127.
5. Zhang Y, et al. (1994) Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. Proc Natl Acad Sci USA 91:3147-3150. (Pubitemid 24130192)
6. Kensler TW, et al. (2005) Effects of glucosinolate-rich broccoli sprouts on urinary levels of aflatoxin-DNA adducts and phenanthrene tetraols in a randomized clinical trial in He Zuo township, Qidong, People's Republic of China. Cancer Epidem Biomar 14:2605-2613.
7. Cornblatt BS, et al. (2007) Preclinical and clinical evaluation of sulforaphane for chemoprevention in the breast. Carcinogenesis 28:1485-1490.
8. Conaway CC, et al. (2005) Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. Cancer Res 65:8548-8557.
9. Kong L, et al. (2007) Delay of photoreceptor degeneration in tubby mouse by sulforaphane. J Neurochem 101:1041-1052.
10. Talalay P, et al. (2007) Sulforaphane mobilizes cellular defenses that protect skin against damage by UV radiation. Proc Natl Acad Sci USA 104:17500-17505.
11. Dinkova-Kostova AT, et al. (2006) Protection against UV-light-induced skin carcinogenesis in SKH-1 high-risk mice by sulforaphane-containing broccoli sprout extracts. Cancer Lett 240:243-252.
12. Dinkova-Kostova AT, et al. (2007) Induction of the phase 2 response in mouse and human skin by sulforaphane-containing broccoli sprout extracts. Cancer Epidem Biomar 16:847-851.
13. Kong L, et al. (2009) Molecular mechanisms underlying cochlear degeneration in the tubby mouse and the therapeutic effect of sulforaphane. Neurochem Int 54:172-179.
14. Dinkova-Kostova AT, Fahey JW, Talalay P (2004) Chemical structures of inducers of nicotinamide quinone oxidoreductase 1 (NQO1). Method Enzymol 382:423-448.
15. Dinkova-Kostova AT, et al. (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.
16. Dinkova-Kostova AT, et al. (2001) Potency of Michael reaction accepters as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. Proc Natl Acad Sci USA 98:3404-3409.
17. Wakabayashi N, 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 101:2040-2045.
18. Heiss E, et al. (2001) Nuclear factor kappa B is a molecular target for sulforaphane-mediated anti-inflammatory mechanisms. J Biol Chem 276:32008-32015.
19. Hong F, Freeman ML, Liebler DC (2005) Identification of sensor cysteines in human Keap1 modified by the cancer chemopreventive agent sulforaphane. Chem Res Toxicol 18:1917-1926.
20. Zipper LM, Mulcahy RT (2002) The Keap1 BTB/POZ dimerization function is required to sequester Nrf2 in cytoplasm. J Biol Chem 277:36544-36552.
21. Li XC, Zhang D, Hannink M, Beamer LJ (2004) Crystal structure of the Kelch domain of human Keap1. J Biol Chem 279:54750-54758.
22. Zhang Y, Kolm RH, Mannervik B, Talalay P (1995) Reversible conjugation of isothiocyanates with glutathione catalyzed by human glutathione transferases. Biochem Biophys Res Commun 206:748-755.
23. Zhang Y, Talalay P (1994) Anticarcinogenic activities of organic isothiocyanates - chemistry and mechanisms. Cancer Res 54:S1976-S1981.
24. Hwang Y, et al. (2007) A selective chemical probe for coenzyme A - Requiring enzymes. Angew Chem Int Edit 46:7621-7624.
25. Prochaska HJ, Santamaria AB (1988) Direct measurement of NAD(P)H - quinone reductase from cells cultured in microtiter wells - a screening assay for anticarcinogenic enzyme inducers. Anal Biochem 169:328-336.
26. Fahey JW, Dinkova-Kostova AT, Stephenson KK, Talalay P (2004) The "Prochaska" microtiter plate bioassay for inducers of NQO1. Method Enzymol 382:243-258.
27. Posner GH, et al. (1994) Design and synthesis of bifunctional isothiocyanate analogs of sulforaphane - correlation between structure and potency as inducers of anticarcinogenic detoxication enzymes. J Med Chem 37:170-176.
28. Dinkova-Kostova AT, et al. (2005) Extremely potent triterpenoid inducers of the phase 2 response: Correlations of protection against oxidant and inflammatory stress. Proc Natl Acad Sci USA 102:4584-4589.
29. Prochaska HJ, Santamaria AB, Talalay P (1992) Rapid detection of inducers of enzymes that protect against carcinogens. Proc Natl Acad Sci USA 89:2394-2398.
30. Gerhauser C, et al. (1997) Cancer chemopreventive potential of sulforamate, a novel analogue of sulforaphane that induces phase 2 drug-metabolizing enzymes. Cancer Res 57:272-278. (Pubitemid 27036605)
31. Gao X, Talalay P (2004) Induction of phase 2 genes by sulforaphane protects retinal pigment epithelial cells against photooxidative damage. Proc Natl Acad Sci USA 101:10446-10451.
32. Yuspa SH, et al. (1986) Cultivation and characterization of cells derived from mouse skin papillomas induced by an initiation promotion protocol. Carcinogenesis 7:949-958.
33. Wang XJ, Hayes JD, Wolf CR (2006) Generation of a stable antioxidant response element-driven reporter gene cell line and its use to show redox-dependent activation of Nrf2 by cancer chemotherapeutic agents. Cancer Res 66:10983-10994.
34. Liu H, Dinkova-Kostova AT, Talalay P (2008) Coordinate regulation of enzyme markers for inflammation and for protection against oxidants and electrophiles. Proc Natl Acad Sci USA 105:15926-15931.
35. Wang Q, et al. (2003) Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. J Am Chem Soc 125:3192-3193.
36. Sun XL, Stabler CL, Cazalis CS, Chaikof EL (2006) Carbohydrate and protein immobilization onto solid surfaces by sequential Diels-Alder and azide-alkyne cycloadditions. Bioconjugate Chem 17:52-57.
37. Zhang DD, Hannink M (2003) Distinct cysteine residues in Keap1 are required for Keap1-dependent ubiquitination of Nrf2 and for stabilization of Nrf2 by chemopreventive agents and oxidative stress. Mol Cell Biol 23:8137-8151.
38. Yamamoto T, et al. (2008) Physiological significance of reactive cysteine residues of keap1 in determining Nrf2 activity. Mol Cell Biol 28:2758-2770.
39. Kobayashi M, 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.
40. Eggler AL, et al. (2005) Modifying specific cysteines of the electrophile-sensing human Keap1 disrupt binding to the protein is insufficient to Nrf2 domain Neh2. Proc Natl Acad Sci USA 102:10070-10075.
41. Hong F, Sekhar KR, Freeman ML, Liebler DC (2005) Specific patterns of electrophile adduction trigger Keap1 ubiquitination and Nrf2 activation. J Biol Chem 280:31768-31775.
42. Rachakonda G, et al. (2008) Covalent modification at Cys151 dissociates the electrophile sensor Keap1 from the ubiquitin ligase CUL3. Chem Res Toxicol 21:705-710.
43. Eggler AL, Luo Y, van Breemen RB, Mesecar AD (2007) Identification of the highly reactive cysteine 151 in the chemopreventive agent-sensor Keap1 protein is method- dependent. Chem Res Toxicol 20:1878-1884.
44. Luo Y, et al. (2007) Sites of alkylation of human Keap1 by natural chemoprevention agents. J Am Soc Mass Spectr 18:2226-2232.
45. Snyder GH, Cennerazzo MJ, Karalis AJ, Field D (1981) Electrostatic influence of local cysteine environments on disulfide exchange kinetics. Biochemistry 20:6509-6519.
46. Cooke G, Armstrong ME, Donnelly SC (2009) Macrophage migration inhibitory factor (MIF), enzymatic activity and the inflammatory response. Biofactors 35:165-168.
47. Brown KK, et al. (2009) Direct Modification of the Proinflammatory Cytokine Macrophage Migration Inhibitory Factor by Dietary Isothiocyanates. J Biol Chem 284:32425-32433.