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Chemical Compound Review

MTBHQ     2-tert-butylbenzene-1,4-diol

Synonyms: TBHQ, t-BHQ, PubChem14585, TBHQ(i), CHEMBL242080, ...
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Disease relevance of T-BUTYLHYDROQUINONE


High impact information on T-BUTYLHYDROQUINONE


Chemical compound and disease context of T-BUTYLHYDROQUINONE

  • When the antimutagenic activity of five antioxidants against MeIQx- or activated MeIQx-induced mutagenesis was compared in the Ames assay using the Salmonella strain TA 98, HTHQ showed the greatest effect, followed by BHA, BHT, PG and TBHQ, in that order [11].

Biological context of T-BUTYLHYDROQUINONE


Anatomical context of T-BUTYLHYDROQUINONE


Associations of T-BUTYLHYDROQUINONE with other chemical compounds



  • Overexpression of Nrf3 in Hep-G2 cells led to a concentration-dependent decrease in transfected and endogenous NQO1 gene expression and induction in response to antioxidant tert-butylhydroquinone (t-BHQ) [25].
  • Inhibition of MAPK kinase with its inhibitor, PD98059, abolished ERK2 activation and impaired the induction of quinone reductase, a phase II detoxifying enzyme, and antioxidant response element (ARE)-linked reporter gene by tBHQ and SUL [26].
  • To examine the contribution of oxidants toward the regulation of human UGT1A1 in vivo, transgenic mice bearing the human UGT1 locus (Tg-UGT1) were treated with tert-butylhydroquinone [27].
  • Transfectants of the point-mutated ARE-like motif showed marginally reduced response to tBHQ, but surprisingly, loss of response to TCDD, suggesting interference of flanking proteins with the AhR/Arnt complex [28].
  • Therefore, it was investigated whether antioxidant response elements (AREs) are involved in tBHQ induction of UGT1A6 [28].

Analytical, diagnostic and therapeutic context of T-BUTYLHYDROQUINONE


  1. Phosphatidylinositol 3-kinase, not extracellular signal-regulated kinase, regulates activation of the antioxidant-responsive element in IMR-32 human neuroblastoma cells. Lee, J.M., Hanson, J.M., Chu, W.A., Johnson, J.A. J. Biol. Chem. (2001) [Pubmed]
  2. p38 mitogen-activated protein kinase negatively regulates the induction of phase II drug-metabolizing enzymes that detoxify carcinogens. Yu, R., Mandlekar, S., Lei, W., Fahl, W.E., Tan, T.H., Kong, A.T. J. Biol. Chem. (2000) [Pubmed]
  3. Enhanced NAD(P)H:quinone reductase activity prevents glutamate toxicity produced by oxidative stress. Murphy, T.H., De Long, M.J., Coyle, J.T. J. Neurochem. (1991) [Pubmed]
  4. Increase of antioxidative potential by tert-butylhydroquinone protects against cell death associated with 6-hydroxydopamine-induced oxidative stress in neuroblastoma SH-SY5Y cells. Hara, H., Ohta, M., Ohta, K., Kuno, S., Adachi, T. Brain Res. Mol. Brain Res. (2003) [Pubmed]
  5. Allergic contact dermatitis from tertiary-butylhydroquinone and Laureth 12 in a hair dye. Field, S., Hazelwood, E., Bourke, B., Bourke, J.F. Contact Derm. (2007) [Pubmed]
  6. Activation of the Keap1/Nrf2 pathway for neuroprotection by electrophilic [correction of electrophillic] phase II inducers. Satoh, T., Okamoto, S.I., Cui, J., Watanabe, Y., Furuta, K., Suzuki, M., Tohyama, K., Lipton, S.A. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  7. Regulation of the antioxidant response element by protein kinase C-mediated phosphorylation of NF-E2-related factor 2. Huang, H.C., Nguyen, T., Pickett, C.B. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  8. Antitumor promotion by phenolic antioxidants: inhibition of AP-1 activity through induction of Fra expression. Yoshioka, K., Deng, T., Cavigelli, M., Karin, M. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
  9. Glucocorticoid receptor (GR)-associated SMRT binding to C/EBPbeta TAD and Nrf2 Neh4/5: role of SMRT recruited to GR in GSTA2 gene repression. Ki, S.H., Cho, I.J., Choi, D.W., Kim, S.G. Mol. Cell. Biol. (2005) [Pubmed]
  10. Metabolism of 3-tert-butyl-4-hydroxyanisole by microsomal fractions and isolated rat hepatocytes. Cummings, S.W., Ansari, G.A., Guengerich, F.P., Crouch, L.S., Prough, R.A. Cancer Res. (1985) [Pubmed]
  11. Prevention by synthetic phenolic antioxidants of 2-amino-3, 8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)- or activated MeIQx-induced mutagenesis and MeIQx-induced rat hepatocarcinogenesis, and role of antioxidant activity in the prevention of carcinogenesis. Hirose, M., Ito, T., Takahashi, S., Ozaki, M., Ogiso, T., Nihro, Y., Miki, T., Shirai, T. Eur. J. Cancer Prev. (1998) [Pubmed]
  12. Two adjacent AP-1-like binding sites form the electrophile-responsive element of the murine glutathione S-transferase Ya subunit gene. Friling, R.S., Bergelson, S., Daniel, V. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  13. Phosphorylation of Nrf2 at Ser40 by protein kinase C in response to antioxidants leads to the release of Nrf2 from INrf2, but is not required for Nrf2 stabilization/accumulation in the nucleus and transcriptional activation of antioxidant response element-mediated NAD(P)H:quinone oxidoreductase-1 gene expression. Bloom, D.A., Jaiswal, A.K. J. Biol. Chem. (2003) [Pubmed]
  14. Transcriptional activation of the human Galphai2 gene promoter through nuclear factor-kappaB and antioxidant response elements. Arinze, I.J., Kawai, Y. J. Biol. Chem. (2005) [Pubmed]
  15. Transcriptional regulation of the rat glutathione S-transferase Ya subunit gene. Characterization of a xenobiotic-responsive element controlling inducible expression by phenolic antioxidants. Rushmore, T.H., Pickett, C.B. J. Biol. Chem. (1990) [Pubmed]
  16. Cyclopentenone prostaglandins as potential inducers of phase II detoxification enzymes. 15-deoxy-delta(12,14)-prostaglandin j2-induced expression of glutathione S-transferases. Kawamoto, Y., Nakamura, Y., Naito, Y., Torii, Y., Kumagai, T., Osawa, T., Ohigashi, H., Satoh, K., Imagawa, M., Uchida, K. J. Biol. Chem. (2000) [Pubmed]
  17. Cellular uptake of lead is activated by depletion of intracellular calcium stores. Kerper, L.E., Hinkle, P.M. J. Biol. Chem. (1997) [Pubmed]
  18. Transcriptional regulation of the antioxidant response element. Activation by Nrf2 and repression by MafK. Nguyen, T., Huang, H.C., Pickett, C.B. J. Biol. Chem. (2000) [Pubmed]
  19. Troglitazone selectively inhibits glyoxalase I gene expression. Wu, L., Eftekharpour, E., Davies, G.F., Roesler, W.J., Juurlink, B.H. Diabetologia (2001) [Pubmed]
  20. Nrf2 Possesses a Redox-sensitive Nuclear Exporting Signal in the Neh5 Transactivation Domain. Li, W., Yu, S.W., Kong, A.N. J. Biol. Chem. (2006) [Pubmed]
  21. Nrf2, a Cap'n'Collar transcription factor, regulates induction of the heme oxygenase-1 gene. Alam, J., Stewart, D., Touchard, C., Boinapally, S., Choi, A.M., Cook, J.L. J. Biol. Chem. (1999) [Pubmed]
  22. Microarray analysis reveals an antioxidant responsive element-driven gene set involved in conferring protection from an oxidative stress-induced apoptosis in IMR-32 cells. Li, J., Lee, J.M., Johnson, J.A. J. Biol. Chem. (2002) [Pubmed]
  23. Site-selective modification of hyperreactive cysteines of ryanodine receptor complex by quinones. Feng, W., Liu, G., Xia, R., Abramson, J.J., Pessah, I.N. Mol. Pharmacol. (1999) [Pubmed]
  24. Steady state relation between cytoplasmic free Ca2+ concentration and force in intact frog skeletal muscle fibers. Konishi, M., Watanabe, M. J. Gen. Physiol. (1998) [Pubmed]
  25. Nrf3 negatively regulates antioxidant-response element-mediated expression and antioxidant induction of NAD(P)H:quinone oxidoreductase1 gene. Sankaranarayanan, K., Jaiswal, A.K. J. Biol. Chem. (2004) [Pubmed]
  26. Role of a mitogen-activated protein kinase pathway in the induction of phase II detoxifying enzymes by chemicals. Yu, R., Lei, W., Mandlekar, S., Weber, M.J., Der, C.J., Wu, J., Kong, A.T. J. Biol. Chem. (1999) [Pubmed]
  27. Nrf2-Keap1 Signaling Pathway Regulates Human UGT1A1 Expression in Vitro and in Transgenic UGT1 Mice. Yueh, M.F., Tukey, R.H. J. Biol. Chem. (2007) [Pubmed]
  28. Contribution of the Ah receptor to the phenolic antioxidant-mediated expression of human and rat UDP-glucuronosyltransferase UGT1A6 in Caco-2 and rat hepatoma 5L cells. Münzel, P.A., Schmohl, S., Buckler, F., Jaehrling, J., Raschko, F.T., Köhle, C., Bock, K.W. Biochem. Pharmacol. (2003) [Pubmed]
  29. Oxidative stress activates metal-responsive transcription factor-1 binding activity. Occupancy in vivo of metal response elements in the metallothionein-I gene promoter. Dalton, T.P., Li, Q., Bittel, D., Liang, L., Andrews, G.K. J. Biol. Chem. (1996) [Pubmed]
  30. JunD activates transcription of the human ferritin H gene through an antioxidant response element during oxidative stress. Tsuji, Y. Oncogene (2005) [Pubmed]
  31. Pivotal role of electrophilicity in glutathione S-transferase induction by tert-butylhydroquinone. Nakamura, Y., Kumagai, T., Yoshida, C., Naito, Y., Miyamoto, M., Ohigashi, H., Osawa, T., Uchida, K. Biochemistry (2003) [Pubmed]
  32. Stabilization of Nrf2 by tBHQ confers protection against oxidative stress-induced cell death in human neural stem cells. Li, J., Johnson, D., Calkins, M., Wright, L., Svendsen, C., Johnson, J. Toxicol. Sci. (2005) [Pubmed]
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