Structural influence of isothiocyanates on the antioxidant response element (ARE)-mediated heme oxygenase-1 (HO-1) expression

Pharmaceutical Research

Volumn 25, Issue 4, 2008, Pages 836-844

  Prawan, Auemduan ^a,b   Keum, Young Sam ^b   Khor, Tin Oo ^b   Yu, Siwang ^b   Nair, Sujit ^b   Li, Wenge ^b   Hu, Longqin ^b   Kong, Ah Ng Tony ^b  

^a KHON KAEN UNIVERSITY   (Thailand)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

Heme oxygenase 1 (HO 1); Isothiocyanates (ITCs); Nrf2; Phase II drug metabolism; Structure activity relationship

Indexed keywords

2 (4 MORPHOLINO)ETHYL ISOTHIOCYANATE; 2 METHOXYETHYL ISOTHIOCYANATE; 3 (4 MORPHOLINO)PROPYL ISOTHIOCYANATE; 3 (DIETHYLAMINO)PROPYL ISOTHIOCYANATE; 3 METHOXYPROPYL ISOTHIOCYANATE; 3,4 METHYELENEDIOXYBENZYL ISOTHIOCYANATE; 4 CYANOPHENYL ISOTHIOCYANATE; FURFURYL ISOTHIOCYANATE; GLUTATHIONE; HEME OXYGENASE 1; ISOTHIOCYANIC ACID DERIVATIVE; LUCIFERASE; MESSENGER RNA; METHYL 3 ISOTHIOCYANATOPROPIONATE; TETRAHYDROFURFURYL ISOTHIOCYANATE; TRANSCRIPTION FACTOR NRF2;

ANTIOXIDANT RESPONSIVE ELEMENT; ARTICLE; CELL VIABILITY; CHEMICAL STRUCTURE; CHEMOPROPHYLAXIS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INDUCTION; FIBROBLAST; GENETIC TRANSCRIPTION; GENETIC TRANSFECTION; HEPATOMA CELL; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION; REAL TIME POLYMERASE CHAIN REACTION; WESTERN BLOTTING;

ANIMALS; ANTICARCINOGENIC AGENTS; ANTIOXIDANTS; BLOTTING, WESTERN; CELL LINE, TUMOR; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; GENES, REPORTER; GLUTATHIONE; HEME OXYGENASE-1; HUMANS; ISOTHIOCYANATES; MEMBRANE PROTEINS; MICE; MICE, INBRED C57BL; MICE, KNOCKOUT; MOLECULAR STRUCTURE; NF-E2-RELATED FACTOR 2; RESPONSE ELEMENTS; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; RNA, MESSENGER; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION, GENETIC; TRANSFECTION; UP-REGULATION;

EID: 43349098881     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-007-9370-9     Document Type: Article

References (24)

1. M. Kapiszewska. A vegetable to meat consumption ratio as a relevant factor determining cancer preventive diet. The Mediterranean versus other European countries. Forum Nutr. 59:130-153 (2006).
2. M. Pavia, C. Pileggi, C. G. Nobile, and I. F. Angelillo. Association between fruit and vegetable consumption and oral cancer: a meta-analysis of observational studies. Am. J. Clin. Nutr. 83:1126-1134 (2006).
3. K. B. Michels, E. Giovannucci, A. T. Chan, R. Singhania, C. S. Fuchs, and W. C. Willett. Fruit and vegetable consumption and colorectal adenomas in the Nurses' Health Study. Cancer Res. 66:3942-3953 (2006).
4. S. C. Larsson, N. Hakansson, I. Naslund, L. Bergkvist, and A. Wolk. Fruit and vegetable consumption in relation to pancreatic cancer risk: a prospective study. Cancer Epidemiol. Biomarkers Prev. 15:301-305 (2006).
5. M. K. Kwak, P. A. Egner, P. M. Dolan, M. Ramos-Gomez, J. D. Groopman, K. Itoh, M. Yamamoto, and T. W. Kensler. Role of phase 2 enzyme induction in chemoprotection by dithiolethiones. Mutat. Res. 480-481:305-315 (2001).
6. A. T. Dinkova-Kostova, W. D. Holtzclaw, R. N. Cole, K. Itoh, N. Wakabayashi, Y. Katoh, M. Yamamoto, and P. Talalay. 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. U. S. A. 99:11908-11913 (2002).
7. H. Motohashi and M. Yamamoto. Nrf2-Keap1 defines a physiologically important stress response mechanism. Trends Mol. Med. 10:549-557 (2004).
8. W. S. Jeong, M. Jun, and A. N. Kong. Nrf2: a potential molecular target for cancer chemoprevention by natural compounds. Antioxid. Redox Signal. 8:99-106 (2006).
9. S. S. Hecht. Chemoprevention of cancer by isothiocyanates, modifiers of carcinogen metabolism. J. Nutr. 129:768S-774S (1999).
10. K. R. Sticha, M. E. Staretz, M. Wang, H. Liang, P. M. Kenney, and S. S. Hecht. Effects of benzyl isothiocyanate and phenethyl isothiocyanate on benzo[a]pyrene metabolism and DNA adduct formation in the A/J mouse. Carcinogenesis 21:1711-1719 (2000).
11. W. S. Jeong, Y. S. Keum, C. Chen, M. R. Jain, G. Shen, J. H. Kim, W. Li, and A. N. Kong. Differential expression and stability of endogenous nuclear factor E2-related factor 2 (Nrf2) by natural chemopreventive compounds in HepG2 human hepatoma cells. J. Biochem. Mol. Biol. 38:167-176 (2005).
12. L. Gamet-Payrastre, P. Li, S. Lumeau, G. Cassar, M. A. Dupont, S. Chevolleau, N. Gasc, J. Tulliez, and F. Terce. Sulforaphane, a naturally occurring isothiocyanate, induces cell cycle arrest and apoptosis in HT29 human colon cancer cells. Cancer Res. 60:1426-1433 (2000).
13. A. V. Singh, D. Xiao, K. L. Lew, R. Dhir, and S. V. Singh. Sulforaphane induces caspase-mediated apoptosis in cultured PC-3 human prostate cancer cells and retards growth of PC-3 xenografts in vivo. Carcinogenesis 25:83-90 (2004).
14. G. Shen, C. Xu, C. Chen, V. Hebbar, and A. N. Kong. p53-independent G1 cell cycle arrest of human colon carcinoma cells HT-29 by sulforaphane is associated with induction of p21CIP1 and inhibition of expression of cyclin D1. Cancer Chemother. Pharmacol. 57:317-327 (2006). Epub 2005 Sep 17.
15. C. Chen, R. Yu, E. D. Owuor, and A. N. Kong. Activation of antioxidant-response element (ARE), mitogen-activated protein kinases (MAPKs) and caspases by major green tea polyphenol components during cell survival and death. Arch. Pharm. Res. 23:605-612 (2000).
16. Y. S. Keum, S. Yu, P. P. Chang, X. Yuan, J. H. Kim, C. Xu, J. Han, A. Agarwal, and A. N. Kong. Mechanism of action of sulforaphane: inhibition of p38 mitogen-activated protein kinase isoforms contributing to the induction of antioxidant response element-mediated heme oxygenase-1 in human hepatoma HepG2 cells. Cancer Res. 66:8804-8813 (2006).
17. R. H. Kolm, U. H. Danielson, Y. Zhang, P. Talalay, and B. Mannervik. Isothiocyanates as substrates for human glutathione transferases: structure-activity studies. Biochem. J. 311:453-459 (1995).
18. Y. Zhang, P. Talalay, C. G. Cho, and G. H. Posner. A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. Proc. Natl. Acad. Sci. U. S. A. 89:2399-2403 (1992).
19. B. R. Kim, R. Hu, Y. S. Keum, V. Hebbar, G. Shen, S. S. Nair, and A. N. Kong. Effects of glutathione on antioxidant response element-mediated gene expression and apoptosis elicited by sulforaphane. Cancer Res. 63:7520-7525 (2003).
20. Y. Morimitsu, Y. Nakagawa, K. Hayashi, H. Fujii, T. Kumagai, Y. Nakamura, T. Osawa, F. Horio, K. Itoh, K. Iida, M. Yamamoto, and K. Uchida. A sulforaphane analogue that potently activates the Nrf2-dependent detoxification pathway. J. Biol. Chem. 277:3456-3463 (2002). Epub 2001 Nov 12.
21. P. Talalay, M. J. De Long, and H. J. Prochaska. Identification of a common chemical signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl. Acad. Sci. U. S. A. 85:8261-8265 (1988).
22. Y. S. Keum, E. D. Owuor, B. R. Kim, R. Hu, and A. N. Kong. Involvement of Nrf2 and JNK1 in the activation of antioxidant responsive element (ARE) by chemopreventive agent phenethyl isothiocyanate (PEITC). Pharm. Res. 20:1351-1356 (2003).
23. D. Lautier, P. Luscher, and R. M. Tyrrell. Endogenous glutathione levels modulate both constitutive and UVA radiation/hydrogen peroxide inducible expression of the human heme oxygenase gene. Carcinogenesis 13:227-332 (1992).
24. M. M. Shi, A. Kugelman, T. Iwamoto, L. Tian, and H. J. Forman. Quinone-induced oxidative stress elevates glutathione and induces gamma-glutamylcysteine synthetase activity in rat lung epithelial L2 cells. J. Biol. Chem. 269:26512-26517 (1994).