γ-Tocopheryl quinone, not α-tocopheryl quinone, induces adaptive response through up-regulation of cellular glutathione and cysteine availability via activation of ATF4

Free Radical Research

Volumn 42, Issue 7, 2008, Pages 674-687

  Ogawa, Yoko ^a,b   Saito, Yoshiro ^a,c   Nishio, Keiko ^a   Yoshida, Yasukazu ^a   Ashida, Hitoshi ^b   Niki, Etsuo ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b KOBE UNIVERSITY   (Japan)

^c DOSHISHA UNIVERSITY   (Japan)

Author keywords

Tocopheryl quinine; Activating transcription factor 4; Adaptive response; Amino acid response element; Cystine transporter; Electrophile response element; Glutathione

Indexed keywords

ACTIVATING TRANSCRIPTION FACTOR 4; ALPHA TOCOPHERYLQUINONE; AMINO ACID TRANSPORTER; CYSTEINE; GAMMA TOCOPHERYLQUINONE; GLUTAMATE CYSTEINE LIGASE; GLUTATHIONE; MESSENGER RNA; REACTIVE OXYGEN METABOLITE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE DEHYDROGENASE (UBIQUINONE); SMALL INTERFERING RNA; THIOREDOXIN REDUCTASE; TOCOPHEROL; TRANSCRIPTION FACTOR NRF2;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; BRAIN CELL; CELL PROTECTION; CELL STRAIN; CONTROLLED STUDY; ENZYME ACTIVITY; GLUTATHIONE METABOLISM; NONHUMAN; OXIDATIVE STRESS; RAT; SIGNAL TRANSDUCTION; TRANSCRIPTION INITIATION; UPREGULATION;

ACTIVATING TRANSCRIPTION FACTOR 4; ADAPTATION, PHYSIOLOGICAL; AMINO ACID TRANSPORT SYSTEM Y+; ANIMALS; ANTIOXIDANTS; CEREBRAL CORTEX; CYSTEINE; CYTOPROTECTION; FETUS; GLUTAMATE-CYSTEINE LIGASE; GLUTATHIONE; NEURONS; NF-E2-RELATED FACTOR 2; OXIDATIVE STRESS; PC12 CELLS; RATS; RATS, SPRAGUE-DAWLEY; RNA INTERFERENCE; RNA, SMALL INTERFERING; SIGNAL TRANSDUCTION; TRANSCRIPTION, GENETIC; UP-REGULATION; VITAMIN E;

EID: 48449096699     PISSN: 10715762     EISSN: 10292470     Source Type: Journal    
DOI: 10.1080/10715760802277396     Document Type: Article

References (51)

1. Cornwell, DG, Kim, S., Mazzer, PA, Jones, KH and Hatcher, PG. (2003) Electrophile tocopheryl quinones in apoptosis and mutagenesis: thermochemolysis of thiol adducts with proteins and in cells. 38, pp. 973-979.
2. Bolton, JL, Trush, MA, Penning, TM, Dryhurst, G. and Monks, TJ. (2000) Role of quinones in toxicology. 13, pp. 135-160.
3. O'Brien, PJ. (1991) Molecular mechanisms of quinone cytotoxicity. 80, pp. 1-41.
4. Brunmark, A. and Cadenas, E. (1989) Redox and addition chemistry of quinoid compounds and its biological implications. 7, pp. 435-477.
5. Wang, X., Thomas, B., Sachdeva, R., Arterburn, L., Frye, L., Hatcher, PG, Cornwell, DG and Ma, J. (2006) Mechanism of arylating quinone toxicity involving Michael adduct formation and induction of endoplasmic reticulum stress. 103, pp. 3604-3609.
6. Brigelius-Flohe, R. and Traber, MG. (1999) Vitamin E: Function and metabolism. 13, pp. 1145-1155.
7. Packer, L., Weber, SU and Rimbach, G. (2001) Molecular aspects of alpha-tocotrienol antioxidant action and cell signalling. 131, pp. 369S-373S.
8. Saito, Y., Yoshida, Y., Nishio, K., Hayakawa, M. and Niki, E. (2004) Characterization of cellular uptake and distribution of vitamin E. 1031, pp. 368-375.
9. Shi, H., Noguchi, N. and Niki, E. (1999) Comparative study on dynamics of antioxidative action of alpha-tocopheryl hydroquinone, ubiquinol, and alpha-tocopherol against lipid peroxidation. 27, pp. 334-346.
10. Liepkalns, VA, Icard-Liepkalns, C. and Cornwell, DG. (1982) Regulation of cell division in a human glioma cell clone by arachidonic acid and alpha-tocopherolquinone. 15, pp. 173-178.
11. Calviello, G., Di Nicuolo, F, Piccioni, E., Marcocci, ME, Serini, S., Maggiano, N., Jones, KH, Cornwell, DG and Palozza, P. (2003) gamma-Tocopheryl quinone induces apoptosis in cancer cells via caspase-9 activation and cytochrome c release. 24, pp. 427-433.
12. Levonen, AL, Dickinson, DA, Moellering, DR, Mulcahy, RT, Forman, HJ and Darley-Usmar, VM. (2001) Biphasic effects of 15-deoxy-delta(12,14)-prostaglandin J(2) on glutathione induction and apoptosis in human endothelial cells. 21, pp. 1846-1851.
13. Saito, Y., Nishio, K., Numakawa, Y., Ogawa, Y., Yoshida, Y., Noguchi, N. and Niki, E. (2007) Protective effects of 15-deoxy-Delta12,14-prostaglandin J2 against glutamate-induced cell death in primary cortical neuron cultures: Induction of adaptive response and enhancement of cell tolerance primarily through up-regulation of cellular glutathione. 102, pp. 1625-1634.
14. Itoh, K., Tong, KI and Yamamoto, M. (2004) Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. 36, pp. 1208-1213.
15. Jaiswal, AK. (2000) Regulation of genes encoding NAD(P)H: Quinone oxidoreductases. 29, pp. 254-262.
16. Myhrstad, MC, Husberg, C., Murphy, P., Nordstrom, O., Blomhoff, R., Moskaug, JO and Kolsto, AB. (2001) TCF11/Nrf1 overexpression increases the intracellular glutathione level and can transactivate the gamma-glutamylcysteine synthetase (GCS) heavy subunit promoter. 1517, pp. 212-219.
17. Sies, H. (1999) Glutathione and its role in cellular functions. 27, pp. 916-921.
18. Lu, SC. (2000) Regulation of glutathione synthesis. 36, pp. 95-116.
19. Dickinson, DA, Levonen, AL, Moellering, DR, Arnold, EK, Zhang, H., Darley-Usmar, VM and Forman, HJ. (2004) Human glutamate cysteine ligase gene regulation through the electrophile response element. 37, pp. 1152-1159.
20. Yan, N. and Meister, A. (1990) Amino acid sequence of rat kidney gamma-glutamylcysteine synthetase. 265, pp. 1588-1593.
21. Bannai, S. and Tateishi, N. (1986) Role of membrane transport in metabolism and function of glutathione in mammals. 89, pp. 1-8.
22. Sato, H., Tamba, M., Ishii, T. and Bannai, S. (1999) Cloning and expression of a plasma membrane cystine/glutamate exchange transporter composed of two distinct proteins. 274, pp. 11455-11458.
23. Bea, F., Hudson, FN, Chait, A., Kavanagh, TJ and Rosenfeld, ME. (2003) Induction of glutathione synthesis in macrophages by oxidized low-density lipoproteins is mediated by consensus antioxidant response elements. 92, pp. 386-393.
24. Suh, JH, Shenvi, SV, Dixon, BM, Liu, H., Jaiswal, AK, Liu, RM and Hagen, TM. (2004) Decline in transcriptional activity of Nrf2 causes age-related loss of glutathione synthesis, which is reversible with lipoic acid. 101, pp. 3381-3386.
25. Sasaki, H., Sato, H., Kuriyama-Matsumura, K., Sato, K., Maebara, K., Wang, H., Tamba, M., Itoh, K., Yamamoto, M. and Bannai, S. (2002) Electrophile response element-mediated induction of the cystine/ glutamate exchange transporter gene expression. 277, pp. 44765-44771.
26. Sato, H., Nomura, S., Maebara, K., Sato, K., Tamba, M. and Bannai, S. (2004) Transcriptional control of cystine/glutamate transporter gene by amino acid deprivation. 325, pp. 109-116.
27. Hai, T. and Hartman, MG. (2001) The molecular biology and nomenclature of the activating transcription factor/cAMP responsive element binding family of transcription factors: Activating transcription factor proteins and homeostasis. 273, pp. 1-11.
28. Wek, RC, Jiang, HY and Anthony, TG. (2006) Coping with stress: EIF2 kinases and translational control. 34, pp. 7-11.
29. Thornton, DE, Jones, KH, Jiang, Z., Zhang, H., Liu, G. and Cornwell, DG. (1995) Antioxidant and cytotoxic tocopheryl quinones in normal and cancer cells. 18, pp. 963-976.
30. Chen, ZH, Saito, Y., Yoshida, Y., Sekine, A., Noguchi, N. and Niki, E. (2005) 4-Hydroxynonenal induces adaptive response and enhances PC12 cell tolerance primarily through induction of thioredoxin reductase 1 via activation of Nrf2. 280, pp. 41921-41927.
31. Chen, ZH, Yoshida, Y., Saito, Y., Sekine, A., Noguchi, N. and Niki, E. (2006) Induction of adaptive response and enhancement of PC12 cell tolerance by 7-hydroxycholesterol and 15-deoxy-delta(12,14)-prostaglandin J2 through up-regulation of cellular glutathione via different mechanisms. 281, pp. 14440-14445.
32. Saito, Y., Nishio, K., Ogawa, Y., Kinumi, T., Yoshida, Y., Masuo, Y. and Niki, E. (2007) Molecular mechanisms of 6-hydroxydopamine-induced cytotoxicity in PC12 cells: Involvement of hydrogen peroxide-dependent and -independent action. 42, pp. 675-685.
33. Piga, R., Saito, Y., Chen, Z., Yoshida, Y. and Niki, E. (2005) Characterization of monochloramine toxicity on PC12 cells and protective effect of tocopherol via antioxidative function. 436, pp. 101-109.
34. Jaiswal, AK. (2000) Characterization and partial purification of microsomal NAD(P)H: Quinone oxidoreductases. 375, pp. 62-68.
35. Hiraku, Y., Murata, M. and Kawanishi, S. (2002) Determination of intracellular glutathione and thiols by high performance liquid chromatography with a gold electrode at the femtomole level: Comparison with a spectroscopic assay. 1570, pp. 47-52.
36. Warabi, E., Takabe, W., Minami, T., Inoue, K., Itoh, K., Yamamoto, M., Ishii, T., Kodama, T. and Noguchi, N. (2007) Shear stress stabilizes NF-E2-related factor 2 and induces antioxidant genes in endothelial cells: Role of reactive oxygen/nitrogen species. 42, pp. 260-269.
37. Saito, Y., Yoshida, Y., Akazawa, T., Takahashi, K. and Niki, E. (2003) Cell death caused by selenium deficiency and protective effect of antioxidants. 278, pp. 39428-39434.
38. Saito, Y., Sato, N., Hirashima, M., Takebe, G., Nagasawa, S. and Takahashi, K. (2004) Domain structure of bi-functional selenoprotein P. 381, pp. 841-846.
39. Itoh, K., Chiba, T., Takahashi, S., Ishii, T., Igarashi, K., Katoh, Y., Oyake, T., Hayashi, N., Satoh, K., Hatayama, I., Yamamoto, M. and Nabeshima, Y. (1997) An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. 236, pp. 313-322.
40. Sachdeva, R., Thomas, B., Wang, X., Ma, J., Jones, KH, Hatcher, PG and Cornwell, DG. (2005) Tocopherol metabolism using thermochemolysis: chemical and biological properties of gamma-tocopherol, gamma-carboxyethyl-hydroxychroman, and their quinones. 18, pp. 1018-1025.
41. Cornwell, DG and Ma, J. (2007) Studies in vitamin E: Biochemistry and molecular biology of tocopherol quinones. 76, pp. 99-134.
42. Niki, E. (2007) Tocopherylquinone and tocopherylhydroquinone. 12, pp. 204-210.
43. Cullinan, SB and Diehl, JA. (2006) Coordination of ER and oxidative stress signaling: The PERK/Nrf2 signaling pathway. 38, pp. 317-332.
44. Boyce, M. and Yuan, J. (2006) Cellular response to endoplasmic reticulum stress: A matter of life or death. 13, pp. 363-373.
45. Levonen, AL, Landar, A., Ramachandran, A., Ceaser, EK, Dickinson, DA, Zanoni, G., Morrow, JD and Darley-Usmar, VM. (2004) Cellular mechanisms of redox cell signalling: Role of cysteine modification in controlling antioxidant defences in response to electrophilic lipid oxidation products. 378, pp. 373-382.
46. Cullinan, SB and Diehl, JA. (2004) PERK-dependent activation of Nrf2 contributes to redox homeostasis and cell survival following endoplasmic reticulum stress. 279, pp. 20108-20117.
47. He, CH, Gong, P., Hu, B., Stewart, D., Choi, ME, Choi, AM and Alam, J. (2001) Identification of activating transcription factor 4 (ATF4) as an Nrf2-interacting protein. Implication for heme oxygenase-1 gene regulation. 276, pp. 20858-20865.
48. Numazawa, S., Ishikawa, M., Yoshida, A., Tanaka, S. and Yoshida, T. (2003) Atypical protein kinase C mediates activation of NF-E2-related factor 2 in response to oxidative stress. 285, pp. C334-C342.
49. Martin, D., Rojo, AI, Salinas, M., Diaz, R., Gallardo, G., Alam, J., De Galarreta, CM and Cuadrado, A. (2004) Regulation of heme oxygenase-1 expression through the phosphatidylinositol 3-kinase/Akt pathway and the Nrf2 transcription factor in response to the antioxidant phytochemical carnosol. 279, pp. 8919-8929.
50. Kiyose, C., Saito, H., Ueda, T. and Igarashi, O. (2001) Simultaneous determination of alpha-, gamma-tocopherol and their quinones in rats plasma and tissues using reversed-phase high-performance liquid chromatography. 47, pp. 102-107.
51. Murphy, ME and Kehrer, JP. (1987) Simultaneous measurement of tocopherols and tocopheryl quinones in tissue fractions using high-performance liquid chromatography with redox-cycling electrochemical detection. 421, pp. 71-82.