S-(N-Phenethylthiocarbamoyl)-L-cysteine
S-(N-Phenethylthiocarbamoyl)-L-cysteine is a conjugate of a phenethylisothiocyanate (PEITC) compound and cysteine. Isothiocyanates are typically found in plants of the Brassicaceae family, including broccoli, cabbage, and radish. Isothiocyanates are best known for their antioxidative, anticancer chemotherapeutic, chemopreventive, anti-angiogenic, and antibiotic properties. In vitro, PEITC increases caspase 3 activity and cleavage of poly(ADP)-ribose polymerase (PARP), inducing caspase-mediated apoptosis in Jurkat T cells and other cellular models. PEITC increases activation of JNK1, one potential mechanism behind its regulation of phase II detoxifying enzyme gene expression. Additionally, PEITC decreases levels of Bcl-xl and increases levels of Bax, also decreasing the mitochondrial membrane potential and inducing intracellular influx of free Ca2+, resulting in cell death. This compound decreases oxidation of carcinogen NNK and increases activity of NADPH:quinone oxidoreductase and glutathione-S-transferase in vitro and in vivo. In glioma cells, PEITC alters PI3K/MAPK signaling to inhibit accumulation of HIF-1α and secretion of VEGF during hypoxia.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18971091/
| Purity |
≥98% |
|---|---|
| Formula |
C12H16N2O2S2 |
| Formula Wt. |
284.40 |
| Synonym |
Phenethylisothiocyanate-L-cysteine |
| Appearance |
White to off white powder |
Tusskorn O, Senggunprai L, Prawan A, et al Phenethyl isothiocyanate induces calcium mobilization and mitochondrial cell death pathway in cholangiocarcinoma KKU-M214 cells. BMC Cancer. 2013 Dec 5;13(1):571. PMID: 24304591.
Stan SD, Singh SV, Whitcomb DC, et al. Phenethyl Isothiocyanate Inhibits Proliferation and Induces Apoptosis in Pancreatic Cancer Cells In Vitro and in a MIAPaca2 Xenograft Animal Model. Nutr Cancer. 2013 Nov 6. [Epub ahead of print]. PMID: 24195616.
Gupta B, Chiang L, Chae K, et al. Phenethyl isothiocyanate inhibits hypoxia-induced accumulation of HIF-1α and VEGF expression in human glioma cells. Food Chem. 2013 Dec 1;141(3):1841-6. PMID: 23870899.
Thomson SJ, Brown KK, Pullar JM, et al. Phenethyl isothiocyanate triggers apoptosis in Jurkat cells made resistant by the overexpression of Bcl-2. Cancer Res. 2006 Jul 1;66(13):6772-7. PMID: 16818653.
Yu R, Mandlekar S, Harvey KJ, et al. Chemopreventive isothiocyanates induce apoptosis and caspase-3-like protease activity. Cancer Res. 1998 Feb 1;58(3):402-8. PMID: 9458080.
Yu R, Jiao JJ, Duh JL, et al. Phenethyl isothiocyanate, a natural chemopreventive agent, activates c-Jun N-terminal kinase 1. Cancer Res. 1996 Jul 1;56(13):2954-9. PMID: 8674048.
Guo Z, Smith TJ, Wang E, et al. Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis. 1993 Jun;14(6):1167-73. PMID: 8508504.
