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Gliotoxin

Gliotoxin

Product ID G4434
Cas No. 67-99-2
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $128.50 In stock
5 mg $462.70 In stock
10 mg $901.30 In stock
Bulk Quote

Quicklinks

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

Description

Gliotoxin was initially produced by the marine fungus Aspergillus and exhibits anticancer, immunosuppressive, and anti-fibrotic activities. In cervical cancer and chondrosarcoma cells, gliotoxin increases activation of caspases 3, 8, and 9, upregulates Bax, and downregulates Bcl-2, resulting in release of cytochrome c and apoptosis. In hepatoma cells, gliotoxin inhibits activation of NF-κB, p38, and Gadd45a, potentiating the effects of radiation and inhibiting cell proliferation. Gliotoxin also suppresses the adaptive immune response, decreasing ROS generation, inhibiting phagocytosis, and inducing apoptosis in leukocytes. Gliotoxin induces a thiol redox-dependent alteration in adenine nucleoside transporter (ANT) mobility and increases activation of caspase 3 and release of cytochrome c, resulting in mitochondria-mediated apoptosis in hepatic stellate cells. This compound also displays anti-parasitic and antimalarial activities against Plasmodium falciparum, inhibiting the proteasome.

Product Info

Cas No.

67-99-2

Purity

≥98%

Formula

C13H14N2O4S2

Formula Wt.

326.39

IUPAC Name

(1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione

Melting Point

200-202°C

Solubility

CHCl3, DMSO, Methanol, Ethanol, Ethyl acetate, Petrol-ether, Dichloromethane. Water insoluble

Appearance

White Powder

Shipping and Storage

Store Temp

4°C

Ship Temp

Ambient

Downloads

MSDS

G4434 MSDS PDF

Info Sheet

G4434 Info Sheet PDF

References

Nguyen VT, Lee JS, Qian ZJ, et al. Gliotoxin Isolated from Marine Fungus Aspergillus sp. Induces Apoptosis of Human Cervical Cancer and Chondrosarcoma Cells. Mar Drugs. 2013 Dec 24;12(1):69-87. PMID: 24368570.

Hur JM, Yun HJ, Yang SH, et al. Gliotoxin enhances radiotherapy via inhibition of radiation-induced GADD45a, p38, and NFkappaB activation. J Cell Biochem. 2008 Aug 15;104(6):2174-84. PMID: 18425744.

Orciuolo E, Stanzani M, Canestraro M, et al. Effects of Aspergillus fumigatus gliotoxin and methylprednisolone on human neutrophils: implications for the pathogenesis of invasive aspergillosis. J Leukoc Biol. 2007 Oct;82(4):839-48. PMID: 17626149.

Hatabu T, Hagiwara M, Taguchi N, et al. Plasmodium falciparum: the fungal metabolite gliotoxin inhibits proteasome proteolytic activity and exerts a plasmodicidal effect on P. falciparum. Exp Parasitol. 2006 Mar;112(3):179-83. PMID: 16384554.

Orr JG, Leel V, Cameron GA, et al. Mechanism of action of the antifibrogenic compound gliotoxin in rat liver cells. Hepatology. 2004 Jul;40(1):232-42. PMID: 15239107.

Kweon YO, Paik YH, Schnabl B, et al. Gliotoxin-mediated apoptosis of activated human hepatic stellate cells. J Hepatol. 2003 Jul;39(1):38-46. PMID: 12821042.

Custom Order

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