Gliotoxin

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Cat.No. 2637 - Gliotoxin | C13H14N2O4S2 | CAS No. 67-99-2
Description: Inhibitor of 20S proteasome; immunosuppressant
Alternative Names: Aspergillin
Chemical Name: (3R,5aS,6S,10aR)-2,3,5a,6-Tetrahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3,10a-epidithiopyrazino[1,2-a]indole-1,4-dione
Datasheet
Citations
Literature

Biological Activity

Immunosuppressive agent; blocks phagocytosis, cytokine production and proliferation of T and B cells. Non-competitively inhibits chymotrypsin-like activity of 20S proteasome; prevents degradation of IκBα, an endogenous blocker of NF-κB. Also inhibits farnesyltransferase and geranylgeranyltransferase I (IC50 values are 80 and 17 μM respectively) and displays antitumor activity against breast cancer in vivo.

Technical Data

M. Wt 326.38
Formula C13H14N2O4S2
Storage Desiccate at -20°C
CAS Number 67-99-2
PubChem ID 6223
InChI Key FIVPIPIDMRVLAY-RBJBARPLSA-N
Smiles O=C([C@@]2(SS4)N(C([C@@]43CO)=O)[C@@H]1[C@@H](O)C=CC=C1C2)N3C

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

SolubilitySoluble in DMSO and in ethanol

Preparing Stock Solutions

The following data is based on the product molecular weight 326.38. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

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Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3.06 mL 15.32 mL 30.64 mL
5 mM 0.61 mL 3.06 mL 6.13 mL
10 mM 0.31 mL 1.53 mL 3.06 mL
50 mM 0.06 mL 0.31 mL 0.61 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Waring and Beaver (1996) Gliotoxin and related epipolythiodioxopiperazines. Gen.Pharmacol. 27 1311 PMID: 9304400

Fitzpatrick et al (2000) In vitro and in vivo effects of gliotoxin, a fungal metabolite: efficacy against dextran sodium sulfate-induced colitis in rats. Dig.Dis.Sci. 45 2327 PMID: 11258552

Vigushin et al (2004) Gliotoxin is a dual inhibitor of farnesyltransferase and geranylgeranyltransferase I with antitumour activity against breast cancer in vivo. Med.Oncol. 21 21 PMID: 15034210


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Keywords: Gliotoxin, supplier, inhibitors, 20S, proteasome, immunosuppressant, inhibits, NF-κB, NF-kappaB, NF-kB, cytokine, production, Farnesyltransferase, geranylgeranyltransferase, I, Proteinases, Proteases, Nuclear, Factor, Kappa, B, Cytokine, Signaling, Signalling, Post-translational, Modification, Aspergillin, Proteasome, Tocris Bioscience

Citations for Gliotoxin

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Literature in this Area

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Pathways for Gliotoxin

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