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2006 | 53 | 3 | 547-552
Article title

Tocopherol esters inhibit human glutathione S-transferase omega

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EN
Abstracts
EN
Human glutathione S-transferase omega 1-1 (hGSTO1-1) is a newly identified member of the glutathione S-transferase (GST) family of genes, which also contains alpha, mu, pi, sigma, theta, and zeta members. hGSTO1-1 catalyzes the reduction of arsenate, monomethylarsenate (MMA(V)), and dimethylarsenate (DMA(V)) and exhibits thioltransferase and dehydroascorbate reductase activities. Recent evidence has show that cytokine release inhibitory drugs, which specifically inhibit interleukin-1b (IL-1b), directly target hGSTO1-1. We found that (+)-α-tocopherol phosphate and (+)-α-tocopherol succinate inhibit hGSTO1-1 in a concentration-dependent manner with IC50 values of 2 µM and 4 µM, respectively. A Lineweaver-Burk plot demonstrated the uncompetitive nature of this inhibition. The molecular mechanism behind the inhibition of hGSTO1-1 by α-tocopherol esters (vitamin E) is important for understanding neurodegenerative diseases, which are also influenced by vitamin E.
Publisher

Year
Volume
53
Issue
3
Pages
547-552
Physical description
Dates
published
2006
received
2006-02-02
revised
2006-06-23
accepted
2006-08-09
(unknown)
2006-10-01
Contributors
  • División de Farmacología y Toxicología, Centro de Investigación Biomédica del Noreste, Instituto Mexicano del Seguro Social, Monterrey, Nuevo León, México
  • Department of Molecular and Cellular Biology; The University of Arizona, Tucson, Arizona, USA
References
  • Anatol K, Svetlana S (2004) Vitamin E in neurodegenerative disorders Alzheimer's disease. Ann NY Acad Sci 1031: 249-262.
  • Aposhian HV, Zakharyan RA, Avram MD, Sampayo-Reyes A, Wollenberg ML (2004) A review of the enzymology of arsenic metabolism and a new potential role of hydrogen peroxide in the detoxication of the trivalent arsenic species. Toxicol Appl Pharmacol 198: 327-335.
  • Azzi A, Stocker A (2000) Vitamin E: non-antioxidant roles. Prog Lipid Res 39: 231-255.
  • Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254.
  • Board PG, Coggan M, Chelvanayagam G, Easteal S, Jermiin LS, Schulte GK, Danley DE, Hoth LR, Griffor MC, Kamath AV, Rosner MH, Chrunyk BA, Perregaux DE, Gabel CA, Geoghegan KF, Pandit J (2000) Identification, characterization, and crystal structure of the Omega class glutathione transferases. J Biol Chem 275: 24798-24806.
  • Burg D, Hameetman L, Filippov DV, van der Marel GA, Mulder GJ (2002) Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl-GSH analogue. Bioorg Med Chem Lett 12: 1579-1582.
  • Clare MM, Evans DA, Tangney CC, Bienias JL, Wilson RS, Aggarwal NT, Scherr PA (2005) Relation of the tocopherol forms to incident Alzheimer disease and to cognitive change 1-3. Am J Clin Nutr 81: 508-514.
  • Dirr H, Reinemer P, Huber R (1994) X-ray crystal structures of cytosolic glutathione S-transferases. Implications for protein architecture, substrate recognition and catalytic function. Eur J Biochem 220: 645-661.
  • Dulhunty A, Gage P, Curtis S, Chelvanayagam G, Board P (2001) The glutathione transferase structural family includes a nuclear chloride channel and a ryanodine receptor calcium release channel modulator. J Biol Chem 276: 3319-3323.
  • Gianello R, Libinaki R, Azzi A, Gavin PD, Negis Y, Zingg JM, Holt P, Keah HH, Griffey A, Smallridge A, West SM, Ogru E (2005) Alpha-tocopheryl phosphate: a novel, natural form of vitamin E. Free Radic Biol Med 39: 970-976.
  • Giri U, Terry NH, Kala SV, Lieberman MW, Story MD (2005) Elimination of the differential chemoresistance between the murine B-cell lymphoma LY-ar and LY-as cell lines after arsenic (As2o3) exposure via overexpression of GSTO1(p28) Cancer Chemother Pharmacol 55: 511-521.
  • Hayes D, Flanagan JU, Jowsey IR (2005) Glutathione transferases. Annu Rev Pharmacol Toxicol 45: 51-88.
  • Johansson A, Ridderstrom M, Mannervik B (2000) The human glutathione transferase P1-1 specific inhibitor ter 117 designed for overcoming cytostatic-drug resistance is also a strong inhibitor of glyoxalase I. Mol Pharmacol 57: 619-624.
  • Laliberte RE, Perregaux DG, Hoth LR, Rosner PJ, Jordan CK, Peese KM, Eggler JF, Dombroski MA, Geoghegan KF, Gabel CA (2003) Glutathione S-transferase omega 1-1 is a target of cytokine release inhibitory drugs and may be responsible for their effect on interleukin-1β posttranslational processing. J Biol Chem 278: 16567-16578.
  • Nakayama S, Katoh EM, Tsuzuki T, Kobayashi S (2003) Protective effect of alpha-tocopherol-6-O-phosphate against ultraviolet B-induced damage in cultured mouse skin. J Invest Dermatol 121: 406-411.
  • Ogru E, Libinaki R, Gianello R, West S, Munteanu A, Zingg J, Azzi A (2004) Modulation of cell proliferation and gene expression by α-tocopheryl phosphates relevance to atherosclerosis and inflammation. Ann NY Acad Sci 1031: 405-411.
  • Rota C, Rimbach G, Minihane AM, Stoecklin E, Barella L (2005) Dietary vitamin E modulates differential gene expression in the rat hippocampus: potential implications for its neuroprotective properties. Nutr Neurosci 8: 21-29.
  • Sano M, Ernesto C, Thomas RG, Klauber MR, Schafer K, Grundam M, Woodbury P, Growdon J, Cotman CW, Pfeiffer E, Schneider LS, Thal LJ (1997) A controlled trial of selegiline, alpha-tocopherol, or both as treatment for Alzheimer's disease. The Alzheimer's disease cooperative study. N Engl J Med 336: 1216-1222.
  • Schmuck EM, Board PG, Whitbread AK, Tetlow N, Cavanaugh JA, Blackburn AC, Masoumi A (2005) Characterization of the monomethylarsonate reductase and dehydroascorbate reductase activities of Omega class glutathione transferase variants: implications for arsenic metabolism and the age-at-onset of Alzheimer's and Parkinson's diseases. Pharmacogenet Genomics 15: 493-501.
  • Serrano-Sanchez T, Diaz-Armesto I (2001) Participation of interleukin 1 and interleukin 6 in the aetiopathogenesis of Alzheimer's disease. Rev Neurol 33: 648-652.
  • Sinning I, Kleywegt GJ, Cowan SW, Reinemer P, Dirr HW, Huber R, Gilliland GL, Armstrong RN, Ji X, Board PG, Olin B, Mannervik B, Jones TA (1993) Structure determination and refinement of human alpha class glutathione transferase A1-1, and a comparison with the Mu and Pi class enzymes. J Mol Biol 232: 192-212.
  • Traber MG, Packer L (1995) Vitamin E: beyond antioxidant function. Am J Clin Nutr 62 (Suppl): 1501S-1509S.
  • van Haaften RI, Evelo CT, Haenen GR, Bast A (2001) Alfa-tocopherol inhibits human glutathione S-transferase. Biochem Biophys Res Commun 280: 631-633.
  • van Haaften RI, Haenen GR, Evelo CT, Bast A (2002) Tocotrienols inhibit human glutathione S-transferase P1-1. IUBMB Life 54: 81-84.
  • Wang L, Xu J, Ji C, Gu S, Lv Y, Li S, Xu Y, Xie Y, Mao Y (2005) Cloning, expression and characterization of human glutathione S-transferase Omega-2. Int J Mol Med 16: 19-27.
  • Yin ZL, Dahlstrom JE, Le Couteur DG, Board PG (2001) Immunohistochemistry of omega class glutathione S-transferase in human tissues. J Histochem Cytochem 49: 983-988.
  • Zakharyan RA, Aposhian HV (1999) Enzymatic reduction of arsenic compounds in mammalian systems: the rate-limiting enzyme of rabbit liver arsenic biotransformation is MMA(V) reductase. Chem Res Toxicol 12: 1278-1283.
  • Zakharyan RA, Sampayo-Reyes A, Healy SM, Tsaprailis G, Board PG, Liebler DC, Aposhian HV (2001) Human monomethylarsonic acid (MMA(V)) reductase is a member of the glutathione-S-transferase superfamily. Chem Res Toxicol 14: 1051-1057.
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.bwnjournal-article-abpv53p547kz
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