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

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

Product ID A0910
Cas No.
Purity ≥98%
Product Unit SizeCostQuantityStock
10 mg $100.70 In stock
25 mg $201.20 In stock
100 mg $591.00 In stock
Bulk Quote

Quicklinks

  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Description
  • Product Info
  • Shipping and Storage
  • Downloads
  • References
  • Custom Order

Description

N-Acetyl-S-(N’-phenylthiocarbamoyl)-L-cysteine (PITC) is a cysteine conjugate of N-acetyl-phenylisothiocyanate. 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. PITC also exhibits vasodilatory properties that are linked to its release of H2S, causing membrane depolarization of vascular smooth muscle cells. PITC inhibits lipid peroxidation, scavenges hydroxyl radicals, and decreases nitrite production in vivo, inhibiting tumor development and increasing life span in animal models of cancer. Additionally, PITC decreases expression of VEGF, IL-1β, IL-6, GM-CSF, and TNF-α and increases expression of IL-2 and tissue inhibitor of metalloproteinase 1 (TIMP1), inhibiting cell proliferation in vitro; these anti-angiogenic effects also occur in vivo, as PITC decreases capillary formation and vessel outgrowth in animal models. PITC exhibits antibacterial activity against species of Bacillus, Staphylococcus, Enterococcus, Salmonella, and Enterobacter, altering surface charge and hydrophilicity, resulting in membrane depolarization and cell death; it also displays anti-parasitic activity against nematodes of the genus Heterodera. This compound shows immunomodulatory activity as well, increasing total white blood cell count, antibody titer, and number of plaque-forming cells in animal models.

Product Info

Purity

≥98%

Formula

C12H14N2O3S2

Formula Wt.

298.38

Chemical Name

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

Synonym

Phenylisothiocyanate N-acetyl-L-cysteine

Appearance

White to off white powder

Shipping and Storage

Store Temp

-20°C

Ship Temp

Ambient

Downloads

MSDS

A0910 MSDS PDF

Info Sheet

A0910 Info Sheet PDF

References

Martelli A, Testai L, Citi V, et al. Pharmacological characterization of the vascular effects of aryl isothiocyanates: Is hydrogen sulfide the real player? Vascul Pharmacol. 2013 Nov 25. pii: S1537-1891(13)00138-9. PMID: 24287004.

Abreu AC, Borges A, Simões LC, et al. Antibacterial activity of phenyl isothiocyanate on Escherichia coli and Staphylococcus aureus. Med Chem. 2013 Aug;9(5):756-61. PMID: 22974327.

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.

Thejass P, Kuttan G. Inhibition of endothelial cell differentiation and proinflammatory cytokine production during angiogenesis by allyl isothiocyanate and phenyl isothiocyanate. Integr Cancer Ther. 2007 Dec;6(4):389-99. PMID: 18048887.

Thejass P, Kuttan G. Allyl isothiocyanate (AITC) and phenyl isothiocyanate (PITC) inhibit tumour-specific angiogenesis by downregulating nitric oxide (NO) and tumour necrosis factor-alpha (TNF-alpha) production. Nitric Oxide. 2007 Mar;16(2):247-57. PMID: 17097904.

Manesh C, Kuttan G. Effect of naturally occurring isothiocyanates on the immune system. Immunopharmacol Immunotoxicol. 2003 Aug;25(3):451-9. PMID: 19180807.

Manesh C, Kuttan G. Anti-tumour and anti-oxidant activity of naturally occurring isothiocyanates. J Exp Clin Cancer Res. 2003 Jun;22(2):193-9. PMID: 12866569.

Custom Order

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