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G9893

Gliotoxin

Name: Gliotoxin
Brand: SIGMA

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

UNSPSC Code:

12352200

PubChem Substance ID:

24895384

NACRES:

NA.77

Beilstein/REAXYS Number:

50675

MDL number:

MFCD00058534

Quality level:

200

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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

Related Categories

Bioactive Small Molecule Toxins

Bioactive Small Molecules

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.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

0000492560

0000465977

0000445734

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Detection of gliotoxin in experimental and human aspergillosis

Lewis RE, et al.

Infection and Immunity, 73(1), 635 -6637 (2005)

Aspergillus fumigatus suppresses the human cellular immune response via gliotoxin-mediated apoptosis of monocytes

Stanzani M, et al.

Blood, 105(6), 2258 -22265 (2005)

Gliotoxin and related epipolythiodioxopiperazines

Waring P and Beaver J

General Pharmacology, 27(8), 1311-1316 (1996)

On the cytotoxicity of some microbial volatile organic compounds as studied in the human lung cell line A549

Kreja L and Seidel HJ

Chemosphere, 49(1), 105 -1110 (2002)

Aspergillus mycotoxins and their effect on the host

Kamei K and Watanabe A

Medical Mycology, 43(sup1), 95 -999 (2005)

View All Related Papers

Articles

Bioactive Molecules for Immunology Research

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

Global Trade Item Number

SKU	GTIN
G9893-25MG	04061832632100
G9893-5MG	04061833651339

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