G9893

Gliotoxin from Gliocladium fimbriatum

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

Properties

• Quality Level: 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

Chemical structure: epipolythiodioxopiperazine

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

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
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves