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N-Acetyl-S-(N′-benzylthiocarbamoyl)-L-cysteine

N-Acetyl-S-(N′-benzylthiocarbamoyl)-L-cysteine

Product ID A0820
Cas No.
Purity ≥98%
Product Unit SizeCostQuantityStock
10 mg $95.70 In stock
25 mg $188.70 In stock
100 mg $566.10 In stock
Bulk Quote

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  • Product Info
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  • References
  • Description
  • Product Info
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  • Downloads
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Description

N-Acetyl-S-(N’-benzylthiocarbamoyl)-L-cysteine (ABITC) is a cysteine conjugate of N-acetyl-benzylisothiocyanate; acetylbenzyl isothiocyanate-L-cysteine is a derivative of benzyl isothiocyanate-L-cysteine (BITC). 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, BITC increases caspase-mediated apoptosis in Jurkat T cells. BITC also induces oxidative stress in glioma cells, inhibiting expression of superoxide dismutase and glutathione-S-transferase, resulting in cell cycle arrest and apoptosis. BITC downregulates expression of protein Ron, preventing growth of breast cancer stem cells in vitro and in vivo. Additionally, this compound inhibits mTOR activity, inducing autophagy in prostate cancer cells. In other in vitro models, BITC inhibits phosphorylation of VEGFR2 and downregulates expression of VEGF, HIF-1α, STAT3, and matrix metalloproteinase 2 (MMP2). BITC exhibits antibacterial activity against species of Bacillus, Staphylococcus, Enterococcus, Salmonella, and Enterobacter; it also displays anti-parasitic activity against nematodes of the genus Heterodera.

Product Info

Purity

≥98%

Formula

C13H16N2O3S2

Formula Wt.

312.41

IUPAC Name

(2R)-2-acetamido-3-(benzylcarbamothioylsulfanyl)propanoic acid

Synonym

Acetyl-benzylisothiocyanate-L-cysteine

Appearance

White to off white powder

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

MSDS

A0820 MSDS PDF

Info Sheet

A0820 Info Sheet PDF

References

Dufour V, Stahl M, Rosenfeld E, et al. Insights into the mode of action of benzyl isothiocyanate on Campylobacter jejuni. Appl Environ Microbiol. 2013 Nov;79(22):6958-68. PMID: 24014524.

Ni WY, Hsiao YP, Hsu SC, et al. Oral administration of benzyl-isothiocyanate inhibits in vivo growth of subcutaneous xenograft tumors of human malignant melanoma A375.S2 cells. In Vivo. 2013 Sep-Oct;27(5):623-6. PMID: 23988897.

Zhu Y, Zhuang JX, Wang Q, et al. Inhibitory effect of benzyl isothiocyanate on proliferation in vitro of human glioma cells. Asian Pac J Cancer Prev. 2013;14(4):2607-10. PMID: 23725183.

Kim SH, Sehrawat A, Singh SV. Dietary chemopreventative benzyl isothiocyanate inhibits breast cancer stem cells in vitro and in vivo. Cancer Prev Res (Phila). 2013 Aug;6(8):782-90. PMID: 23661606.

Lin JF, Tsai TF, Liao PC, et al. Benzyl isothiocyanate induces protective autophagy in human prostate cancer cells via inhibition of mTOR signaling. Carcinogenesis. 2013 Feb;34(2):406-14. PMID: 23172666.

Boreddy SR, Sahu RP, Srivastava SK. Benzyl isothiocyanate suppresses pancreatic tumor angiogenesis and invasion by inhibiting HIF-α/VEGF/Rho-GTPases: pivotal role of STAT-3. PLoS One. 2011;6(10):e25799. PMID: 22016776.

Schroeder NE, Macguidwin AE. Mortality and behavior in Heterodera glycines juveniles following exposure to isothiocyanate compounds. J Nematol. 2010 Sep;42(3):194-200. PMID: 22736856.

Beevi SS, Mangamoori LN, Dhand V, et al. Isothiocyanate profile and selective antibacterial activity of root, stem, and leaf extracts derived from Raphanus sativus L. Foodborne Pathog Dis. 2009 Jan-Feb;6(1):129-36. PMID: 19182965.

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