Gliotoxin

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Gliotoxin is a sulfur-containing antibiotic produced by some unrelated species of pathogenic fungi, such as Aspergillus, Trichoderma, and Penicillium, and by the yeast Candida. It was originally isolated from Gliocladium fimbriatum, and was named accordingly. It is an epipolythiodioxopiperazine metabilite.

Gliotoxin posesses immunosuppressive properties as it may suppress and cause apoptosis in certain types of cells of the immune system, including neutrophils, eosinophils, and granulocytes. Causes apoptosis in macrophages and thymocytes. It also acts as an inhibitor of farnesyl transferase. It noncompetitively inhibits the chymotrypsin-like activity of the 20S proteasome. In vivo it displays anti-inflammatory activity. [1] It acts by blocking thiol groups in the cell membranes.

[edit] Chemical and physical data

Formula: C₁₃H₁₄N₂O₄S₂

Molecular weight: 326.4

• Its CAS number is [67-99-2] [2] and its SMILES structure is O=C1N(C)C2 (CO)C(N(C3C(C4) =CC=C[C@@H]3O) C41SS2)=O.
• It is a white to light yellow solid
• soluble in DMSO.

[edit] External links

• ANUTECH: Gliotoxin Immunosuppresant for use in transplantation.
• Gliotoxin from Fermentek, a vendor's product page
• Gliotoxin MSDS

[edit] References

• Identification of an agent in cultures of Aspergillus fumigatus displaying anti-phagocytic and immunomodulating activity in vitro: A. Müllbacher, et al.; J. Gen. Microbiol. 131, 1251 (1985)
• R.J. Jones & J.G. Hancock; J. Gen. Microbiol. 134, 2067 (1988) Gliotoxin stimulates Ca²⁺ release from intact rat liver mitochondria: M. Schweizer & C. Richter; Biochemistry 33, 13401 (1994)
• Extracellular calcium is not required for gliotoxin or dexamethasone- induced DNA fragmentation: a reappraisal of the use of EGTA: P. Waring & A. Sjaarda; Int. J. Immunopharmacol. 17, 403 (1995)