A fungal metabolite with diverse biological activities
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Bis(methylthio)gliotoxin

Item No. 26271

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R,5aS,6S,10aR)-2,3,5a,6,10,10a-hexahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylthio)-pyrazino[1,2-a]indole-1,4-dione
CAS Number
74149-38-5
Synonyms
  • Bisdethiobis(methylthio)gliotoxin
  • FR 49175
Molecular Formula
C15H20N2O4S2
Formula Weight
356.5
Purity
≥90%
Formulation (Request formulation change)
A semi-solid
Solubility(Learn about Variance in Solubility)
DMSO: 25 mg/mlEthanol: 25 mg/ml
SMILES
O=C1N(C)[C@](CO)(SC)C(N2[C@]3([H])[C@@H](O)C=CC=C3C[C@]21SC)=O
InChi Code
InChI=1S/C15H20N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,10-11,18-19H,7-8H2,1-3H3/t10-,11-,14+,15+/m0/s1
InChi Key
OVBAGMZLGLXSBN-UOVKNHIHSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Bis(methylthio)gliotoxin is a fungal metabolite originally isolated from G. deliquescens that has diverse biological activities.1 It inhibits PAF- and collagen-induced platelet aggregation in rabbit platelet-rich plasma (IC50s = 8.4 and 84.2 µM, respectively) but has no effect on arachidonic acid- or ADP-induced platelet aggregation (IC50s = >400 µM).2 Bis(methylthio)gliotoxin inhibits growth of HCT116 colon cancer cells (IC50 = 23.56 µM).3 It inhibits PAF-induced bronchoconstriction in guinea pigs when administered at a dose of 0.1 mg/kg and is less toxic to mice (LD50 = >500 mg/kg) than gliotoxin (Item No. 11433).2,4 Bis(methylthio)gliotoxin has been used as a serum biomarker in patients infected with invasive aspergillosis.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kirby, G.W., Robins, D.J., Sefton, M.A., et al. Biosynthesis of bisdethiobis (methylthio) gliotoxin, a new metabolite of Gliocladium deliquescens. J. Chem. Soc. Perkin 1 1(1), 119-121 (1980).

    2. Okamoto, M., Yoshida, K., Uchida, I., et al. Studies of platelet activating factor (PAF) antagonists from microbial products. I. Bisdethiobis(methylthio)gliotoxin and its derivatives. Chem. Pharm. Bull. (Tokyo) 34(1), 340-344 (1986).

    3. Rodrigues, B.S., Sahm, B.D., Jimenez, P.C., et al. Bioprospection of cytotoxic compounds in fungal strains recovered from sediments of the Brazilian coast. Chem. Biodivers. 12(3), 432-442 (2015).

    4. Okamoto, M., Yoshida, K., Uchida, I., et al. Studies of platelet activating factor (PAF) antagonists from microbial products. II. Pharmacological studies of FR-49175 in animal models. Chem. Pharm. Bull. (Tokyo) 34(1), 345-348 (1986).

    5. Domingo, M.P., Colmenarejo, C., Martínez-Lostao, L., et al. Bis(methyl)gliotoxin proves to be a more stable and reliable marker for invasive aspergillosis than gliotoxin and suitable for use in diagnosis. Diagn. Microbiol. Infect. Dis. 73(1), 57-64 (2012).