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371715

Gliotoxin, Gladiocladium fimbriatum

Name: Gliotoxin, <i>Gladiocladium fimbriatum</i>
Brand: MM

An immunosuppressive secondary metabolite produced by several pathogenic fungi.

Synonym(s):

Gliotoxin, Gladiocladium fimbriatum, 2,3,5a,6-Tetrahydro-6-hydroxy-3(hyroxymethyl)-2-methyl-10H-3a,10a-epidithio-pyrazinol[1,2α]indole-1,4-dione

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About This Item

Empirical Formula (Hill Notation):

C₁₃H₁₄N₂O₄S₂

CAS Number:

67-99-2

Molecular Weight:

326.39

MDL number:

MFCD00058534

UNSPSC Code:

12352200

Quality Level

100

Assay

≥98% (TLC)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze

color

white

solubility

DMSO: 10 mg/mL
ethanol: 2 mg/mL

shipped in

ambient

storage temp.

2-8°C

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

General description

An immunosuppressive mycotoxin secondary metabolite produced by several pathogenic fungi. Reported to increase ryanodine Ca²⁺ channel activity possibly by oxidizing cysteine residues located on the ryanodine receptor. Immunosuppressive effect is caused by the blocking of membrane thiol groups. Causes apoptosis in a variety of cell types, including macrophages and thymocytes. Inactivates alcohol dehydrogenase by either covalent modification of thiol groups or free radical damage. Protein farnesyltransferase (PFT) inhibitor (IC50 = 1.1 µM). Also inhibits Ras protein in a noncompetitive manner.

An immunosuppressive secondary metabolite produced by several pathogenic fungi. Immunosuppressive effects are caused by blocking of membrane thiol groups. Causes apoptotic cell death in a variety of cell types including macrophages and thymocytes. Farnesyltransferase (FTase) inhibitor (IC₅₀ = 1.1 µM). Reported to increase ryanodine Ca²⁺ channel activity possibly by oxidizing cysteine residues located on the ryanodine receptor. Specifically inhibits NF-κB activation in B and T cells at nanomolar concentrations.

Biochem/physiol Actions

Cell permeable: no

Primary Target
FTase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 1.1 µM against Farnesyltransferase (FTase)

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Green, D., et al. 2000. J. Membr. Biol. 175, 223.
Sutton, P., et al. 1995. Transplantation60, 900.
Waring, P., et al. 1995. Biochem. Pharmacol. 49, 1195.
Waring, P., and Sjaarda, A. 1995. Int. J. Immunopharmacol.17, 403.
Van der Pyl, D., et al. 1992. J. Antibiot. 45, 1802.
Jones, R.J., and Hancock, J.G. 1988. J. Gen. Microbiol.134, 2067.
Waring, P., et al. 1988. J. Biol. Chem. 263, 18493.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Toxic (F)

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P264 - P270 - P301 + P310 - P405 - P501

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)