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Chemical Compound Review

PEITC     2-isothiocyanatoethylbenzene

Synonyms: AGN-PC-00BDZX, CHEMBL151649, ACMC-1CLKQ, CCRIS 3146, AG-B-42723, ...
 
 
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Disease relevance of beta-Phenylethyl isothiocyanate

 

High impact information on beta-Phenylethyl isothiocyanate

 

Chemical compound and disease context of beta-Phenylethyl isothiocyanate

 

Biological context of beta-Phenylethyl isothiocyanate

 

Anatomical context of beta-Phenylethyl isothiocyanate

 

Associations of beta-Phenylethyl isothiocyanate with other chemical compounds

 

Gene context of beta-Phenylethyl isothiocyanate

 

Analytical, diagnostic and therapeutic context of beta-Phenylethyl isothiocyanate

  • Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers [29].
  • Several isothiocyanates, including phenethyl isothiocyanate (PEITC), found naturally in cruciferous vegetables, induced growth arrest and apoptosis in prostate cancer cells in culture and xenografts [30].
  • Concurrently PEITC demethylated the promoter and restored the unmethylated GSTP1 in both androgen-dependent and -independent LNCaP cancer cells to the level found in normal prostatic cells, as quantified by methylation-specific PCR and pyrosequencing [30].
  • Although total tumor incidence was marginally decreased, PEIT inhibited significantly the tumor frequency and tumor burden by 79% and 74%, respectively [11].
  • In the present study, a transcriptional profile of liver of the wild-type (Nrf2+/+) and knock-out (Nrf2-/-) mice after treatments with vehicle or PEITC at 3 h and at 12 h was generated using the Affymetrix Mouse Genome 430 2.0 Array [31].

References

  1. Phenethyl isothiocyanate-induced apoptosis in p53-deficient PC-3 human prostate cancer cell line is mediated by extracellular signal-regulated kinases. Xiao, D., Singh, S.V. Cancer Res. (2002) [Pubmed]
  2. Phenethyl isothiocyanate and sulforaphane and their N-acetylcysteine conjugates inhibit malignant progression of lung adenomas induced by tobacco carcinogens in A/J mice. Conaway, C.C., Wang, C.X., Pittman, B., Yang, Y.M., Schwartz, J.E., Tian, D., McIntee, E.J., Hecht, S.S., Chung, F.L. Cancer Res. (2005) [Pubmed]
  3. New potential chemopreventive agents for lung carcinogenesis of tobacco-specific nitrosamine. Chung, F.L., Morse, M.A., Eklind, K.I. Cancer Res. (1992) [Pubmed]
  4. Metabolic activation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone as measured by DNA alkylation in vitro and its inhibition by isothiocyanates. Guo, Z., Smith, T.J., Thomas, P.E., Yang, C.S. Cancer Res. (1991) [Pubmed]
  5. Inhibition of carcinogenic effects of polycyclic hydrocarbons by benzyl isothiocyanate and related compounds. Wattenberg, L.W. J. Natl. Cancer Inst. (1977) [Pubmed]
  6. Phenethyl isothiocyanate triggers apoptosis in Jurkat cells made resistant by the overexpression of Bcl-2. Thomson, S.J., Brown, K.K., Pullar, J.M., Hampton, M.B. Cancer Res. (2006) [Pubmed]
  7. N-acetylcysteine conjugate of phenethyl isothiocyanate enhances apoptosis in growth-stimulated human lung cells. Yang, Y.M., Jhanwar-Uniyal, M., Schwartz, J., Conaway, C.C., Halicka, H.D., Traganos, F., Chung, F.L. Cancer Res. (2005) [Pubmed]
  8. Dietary indoles and isothiocyanates that are generated from cruciferous vegetables can both stimulate apoptosis and confer protection against DNA damage in human colon cell lines. Bonnesen, C., Eggleston, I.M., Hayes, J.D. Cancer Res. (2001) [Pubmed]
  9. Suppression of NF-kappaB and NF-kappaB-regulated gene expression by sulforaphane and PEITC through IkappaBalpha, IKK pathway in human prostate cancer PC-3 cells. Xu, C., Shen, G., Chen, C., Gélinas, C., Kong, A.N. Oncogene (2005) [Pubmed]
  10. Selective toxicity of compounds naturally present in food toward the transformed phenotype of human colorectal cell line HT29. Musk, S.R., Stephenson, P., Smith, T.K., Stening, P., Fyfe, D., Johnson, I.T. Nutrition and cancer. (1995) [Pubmed]
  11. Rapid in vivo assay for topical oral cancer chemopreventive agents. Shabany, K., Chiu, P.C., Raghian, A., Chang, K.W., Solt, D.B. Int. J. Oncol. (2002) [Pubmed]
  12. Involvement of toxicity as an early event in urinary bladder carcinogenesis induced by phenethyl isothiocyanate, benzyl isothiocyanate, and analogues in F344 rats. Akagi, K., Sano, M., Ogawa, K., Hirose, M., Goshima, H., Shirai, T. Toxicologic pathology. (2003) [Pubmed]
  13. Genotoxic effects of allyl isothiocyanate (AITC) and phenethyl isothiocyanate (PEITC). Kassie, F., Knasmüller, S. Chem. Biol. Interact. (2000) [Pubmed]
  14. Modulation of experimental alcohol-induced liver disease by cytochrome P450 2E1 inhibitors. Morimoto, M., Hagbjörk, A.L., Wan, Y.J., Fu, P.C., Clot, P., Albano, E., Ingelman-Sundberg, M., French, S.W. Hepatology (1995) [Pubmed]
  15. Enzymes involved in the bioactivation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in patas monkey lung and liver microsomes. Smith, T.J., Liao, A.M., Liu, Y., Jones, A.B., Anderson, L.M., Yang, C.S. Carcinogenesis (1997) [Pubmed]
  16. The roles of JNK and apoptotic signaling pathways in PEITC-mediated responses in human HT-29 colon adenocarcinoma cells. Hu, R., Kim, B.R., Chen, C., Hebbar, V., Kong, A.N. Carcinogenesis (2003) [Pubmed]
  17. Phenethyl isothiocyanate-induced apoptosis in PC-3 human prostate cancer cells is mediated by reactive oxygen species-dependent disruption of the mitochondrial membrane potential. Xiao, D., Lew, K.L., Zeng, Y., Xiao, H., Marynowski, S.W., Dhir, R., Singh, S.V. Carcinogenesis (2006) [Pubmed]
  18. Dietary isothiocyanates inhibit Caco-2 cell proliferation and induce G2/M phase cell cycle arrest, DNA damage, and G2/M checkpoint activation. Visanji, J.M., Duthie, S.J., Pirie, L., Thompson, D.G., Padfield, P.J. J. Nutr. (2004) [Pubmed]
  19. Effects of watercress consumption on urinary metabolites of nicotine in smokers. Hecht, S.S., Carmella, S.G., Murphy, S.E. Cancer Epidemiol. Biomarkers Prev. (1999) [Pubmed]
  20. Inhibition by allyl sulfides and phenethyl isothiocyanate of methyl-n-pentylnitrosamine depentylation by rat esophageal microsomes, human and rat CYP2E1, and Rat CYP2A3. Morris, C.R., Chen, S.C., Zhou, L., Schopfer, L.M., Ding, X., Mirvish, S.S. Nutrition and cancer. (2004) [Pubmed]
  21. Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation and tumorigenicity in the lung of F344 rats by dietary phenethyl isothiocyanate. Morse, M.A., Wang, C.X., Stoner, G.D., Mandal, S., Conran, P.B., Amin, S.G., Hecht, S.S., Chung, F.L. Cancer Res. (1989) [Pubmed]
  22. Differential induction of mafF, mafG and mafK expression by electrophile-response-element activators. Moran, J.A., Dahl, E.L., Mulcahy, R.T. Biochem. J. (2002) [Pubmed]
  23. Inhibition of N'-nitrosonornicotine-induced esophageal tumorigenesis by 3-phenylpropyl isothiocyanate. Stoner, G.D., Adams, C., Kresty, L.A., Amin, S.G., Desai, D., Hecht, S.S., Murphy, S.E., Morse, M.A. Carcinogenesis (1998) [Pubmed]
  24. Effects of dietary indoles and isothiocyanates on N-nitrosodimethylamine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone alpha-hydroxylation and DNA methylation in rat liver. Chung, F.L., Wang, M.Y., Hecht, S.S. Carcinogenesis (1985) [Pubmed]
  25. Transport of dietary phenethyl isothiocyanate is mediated by multidrug resistance protein 2 but not P-glycoprotein. Ji, Y., Morris, M.E. Biochem. Pharmacol. (2005) [Pubmed]
  26. Differential activation of MAPK and ICE/Ced-3 protease in chemical-induced apoptosis. The role of oxidative stress in the regulation of mitogen-activated protein kinases (MAPKs) leading to gene expression and survival or activation of caspases leading to apoptosis. Kong, A.N., Yu, R., Lei, W., Mandlekar, S., Tan, T.H., Ucker, D.S. Restorative neurology and neuroscience. (1998) [Pubmed]
  27. Membrane transport of dietary phenethyl isothiocyanate by ABCG2 (breast cancer resistance protein). Ji, Y., Morris, M.E. Mol. Pharm. (2005) [Pubmed]
  28. Mechanism of action of isothiocyanates: the induction of ARE-regulated genes is associated with activation of ERK and JNK and the phosphorylation and nuclear translocation of Nrf2. Xu, C., Yuan, X., Pan, Z., Shen, G., Kim, J.H., Yu, S., Khor, T.O., Li, W., Ma, J., Kong, A.N. Mol. Cancer Ther. (2006) [Pubmed]
  29. Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. von Weymarn, L.B., Chun, J.A., Hollenberg, P.F. Carcinogenesis (2006) [Pubmed]
  30. Dual action on promoter demethylation and chromatin by an isothiocyanate restored GSTP1 silenced in prostate cancer. Wang, L.G., Beklemisheva, A., Liu, X.M., Ferrari, A.C., Feng, J., Chiao, J.W. Mol. Carcinog. (2007) [Pubmed]
  31. Identification of Nrf2-regulated genes induced by chemopreventive isothiocyanate PEITC by oligonucleotide microarray. Hu, R., Xu, C., Shen, G., Jain, M.R., Khor, T.O., Gopalkrishnan, A., Lin, W., Reddy, B., Chan, J.Y., Kong, A.N. Life Sci. (2006) [Pubmed]
 
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