G9893

Gliotoxin

from Gliocladium fimbriatum, ≥98% (HPLC), powder, immunomodulating agent

• Synonym(s): Aspergillin
• Empirical Formula (Hill Notation): C₁₃H₁₄N₂O₄S₂
• CAS Number: 67-99-2
• Molecular Weight: 326.39
• UNSPSC Code: 12352200
• PubChem Substance ID: 24895384
• NACRES: NA.77
• Beilstein/REAXYS Number: 50675
• MDL number: MFCD00058534

Properties

• Product Name: Gliotoxin from Gliocladium fimbriatum,
• Quality Segment: 200
• antibiotic activity spectrum: viruses
• mode of action: DNA synthesis | interferes, enzyme | inhibits
• storage temp.: 2-8°C
• SMILES string: CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3
• InChI: 1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1
• InChI key: FIVPIPIDMRVLAY-RBJBARPLSA-N

Description

General description

Gliotoxin is the mycotoxin produced by Aspergillus fumigatus (AF). It is a hydrophobic metabolite of 326 Da.

Chemical structure: epipolythiodioxopiperazine

Application

Gliotoxin has been used for performing cytotoxicity tests in adenocarcinomic human alveolar basal epithelial (A549) cell lines.

Noncompetitive inhibitor of the chymotrypsin-like activity of the 20S proteasome in vitro.

Biochem/physiol Actions

Gliotoxin is associated with immunosuppression. It is an antiphagocytic and immunomodulating agent that acts by blocking membrane thiol groups. It is implicated in the pathophysiology of invasive aspergillosis (IA) and impacts functional T-cell responses. Gliotoxin in observed in the sera of cancer patients with IA infection.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges