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Merck

G9893

Sigma-Aldrich

Gliotoxin

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

Synonym(s):

Aspergillin

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About This Item

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

Key Documents

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Product Name

Gliotoxin from Gliocladium fimbriatum,

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

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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.

Pictograms

Skull and crossbones
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

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Certificates of Analysis (COA)

Lot/Batch Number
099M4005V
088M4045V
116M4013V
094M4111V
075M4113V

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Aspergillus fumigatus suppresses the human cellular immune response via gliotoxin-mediated apoptosis of monocytes
Stanzani M, et al.
Blood, 105(6), 2258 -22265 (2005)
Detection of gliotoxin in experimental and human aspergillosis
Lewis RE, et al.
Infection and Immunity, 73(1), 635 -6637 (2005)
Gliotoxin and related epipolythiodioxopiperazines
Waring P and Beaver J
General Pharmacology, 27(8), 1311-1316 (1996)
Aspergillus mycotoxins and their effect on the host
Kamei K and Watanabe A
Medical Mycology, 43(sup1), 95 -999 (2005)
Jones, R.J. and Hancock, J.G.
Journal of General Microbiology, 134, 2067-2067 (1988)
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Articles

Bioactive Molecules for Immunology Research

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

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