Skip to Content
Merck

Key Documents

View All Documentation

371715

Gliotoxin, Gladiocladium fimbriatum

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

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):
C13H14N2O4S2
CAS Number:
67-99-2
Molecular Weight:
326.39
UNSPSC Code:
12352200
MDL number:
MFCD00058534
Assay:
≥98% (TLC)
Form:
solid
Storage condition:
OK to freeze
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Segment

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

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library