GliotoxinA toxic epipolythiodioxopiperazine metabolite that induces apoptosis and inhibits NF-κB

Gliotoxin (CAS 67-99-2)

Gliotoxin | CAS 67-99-2 is rated 5.0 out of 5 by 1.
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Application: A toxic epipolythiodioxopiperazine metabolite that induces apoptosis and inhibits NF-κB
CAS Number: 67-99-2
Purity: ≥97%
Molecular Weight: 326.4
Molecular Formula: C13H14N2O4S2
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Gliotoxin, a toxic epipolythiodioxopiperazine metabolite, has been shown to be an immunosuppressive mycotoxin. This agent displays a capacity to induce macrophagocytic, thymocytic, splenocytic, and mesenteric lymph node cell apoptosis and inhibit transcription factor NF-κB activation. Mechanistic studies suggest that this inhibition is done via a suppression of proteasome-mediated degradation of IκB-α. Additional research reports that Gliotoxin is capable of down-regulating inflammation and suppressing TNFα IL-1α and mRNA expression. Gliotoxin is an inhibitor of Farnesyl Transferase and GGTase. Gliotoxin is an inhibitor of 20S Proteasome. Gliotoxin exhibits inhibitory activities against histone H3K9 methyltransferase, a key enzyme in the regulation of transcriptional activity by writing epigenetic marks.


References

1. Pahl, H.L., et al. 1996. J. Exp. Med. 183: 1829-1840. PMID: 8666939
2. Kroll, M., et al. 1999. Chem. Biol. 6: 689-698. PMID: 10508680
3. Ward, C., et al. 1999. J. Biol. Chem. 274: 4309-4318. PMID: 9933632
4. Herfarth, H., et al. 2000. Clin. Exp. Immunol. 120: 59-65. PMID: 10759764
5. Sugui, J.A., et al. 2007. Eukaryotic Cell. 6: 1562-1569. PMID: 17601876

Physical State :
Solid
Derived From :
Gladiocladium fimbriatum
Solubility :
Soluble in DMSO (10 mg/ml), methanol (10 mg/ml), chloroform (10 mg/ml), DMF, and Pyridine.
Storage :
Store at -20° C
Boiling Point :
699.72° C at 760 mmHg
Density :
1.75 g/cm3
Refractive Index :
n20D 1.81
IC50 :
geranylgeranyltransferase I: IC50 = 17 µM; farnesyltransferase: IC50 = 80 µM; FTase: IC50 = 1.1 µM; A549 (Lung carcinoma cells): IC50 = 3 nM (Homo sapiens); Trypanosoma brucei brucei: IC50 = 10 nM (Trypanosoma brucei brucei); HUVEC50 (Umbilical vein endothelial cells): IC50 = 123 nM (Homo sapiens); CEM (T-cell leukemia): IC50 = 150 nM (Homo sapiens); Acetolactate synthase catalytic subunit, mitochondrial: IC50 = 200 nM (Saccharomyces cerevisiae S288c); Protein farnesyltransferase/geranylgeranyltransferase type I alpha subunit: IC50 = 1100 nM (Homo sapiens); HeLa (Cervical adenocarcinoma cells): IC50 = 2450 nM (Homo sapiens); Candida albicans: IC50 = 3100 nM (Candida albicans); Plasmodium falciparum (isolate K1 / Thailand): IC50 = 3600 nM (Plasmodium falciparum K1); Protein farnesyltransferase/geranylgeranyltransferase type I alpha subunit: IC50 = 17000 nM (Homo sapiens); Mycothiol S-conjugate amidase: IC50 = 50000 nM (Mycobacterium tuberculosis); Protein farnesyltransferase
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
KB4725000
PubChem CID :
6223
Merck Index :
14: 4441
MDL Number :
MFCD00058534
Beilstein Registry :
50675
SMILES :
CN1C(=O)C23CC4=CC=C[C@H](O)C4N2C(=O)C1(CO)SS3

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Gliotoxin  Product Citations

See how others have used Gliotoxin. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 31540008  Toxins (Basel). 11:

Citations 1 to 1 of 1 total
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Rated 5 out of 5 by from Sugui et al Sugui et al. (PubMed ID 17601876) found that gliotoxin, a suppressive mycotoxin, is a virulence determinant of A. fumigatus via gliP. -SCBT Publication Review
Date published: 2015-07-12
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