BIS(METHYLTHIO)GLIOTOXIN Chemical Properties

Boiling point:

669.6±55.0 °C(Predicted)

Density 

1.49±0.1 g/cm3(Predicted)

storage temp. 

−20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

White solid.

pka

12.69±0.60(Predicted)

color 

Off-White to Yellow

biological source

natural

Water Solubility 

water: soluble

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36

RIDADR 

1544

HazardClass 

6.1(b)

PackingGroup 

III

BIS(METHYLTHIO)GLIOTOXIN Usage And Synthesis

Description

Bis(methylthio)gliotoxin is a fungal metabolite originally isolated from G. deliquescens that has diverse biological activities. 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). Bis(methylthio)gliotoxin inhibits growth of HCT116 colon cancer cells (IC₅₀ = 23.56 μM). 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 . Bis(methylthio)gliotoxin has been used as a serum biomarker in patients infected with invasive aspergillosis.

Uses

Bis(methylthio)gliotoxin (FR-49175) is an antiphagocytic metabolite.

Enzyme inhibitor

This naturally occurring indole derivative (FW = 356.47 g/mol; CAS 74149- 38-5), also known as bis(methylthio)gliotoxin and dimethylgliotoxin, is a platelet-acivating factor (PAF) antagonist that inhibits PAF-induced platelet aggregation. The parent compound, gliotoxin is a dual inhibitor of famesyltransferase and geranylgeranyl-transferase. Bisdethiobis(methylthio)gliotoxin is a minor metabolite of Gliocladium deliquescens, Radiocarbon tracer experiments showed it is formed, apparently irreversibly, from gliotoxin. It has also been synthesized from gliotoxin by reduction and methylation. Bisdethio-bis(methylthio)gliotoxin also binds Cu+ and Ag+ ions.

References

[1] G. W. KIRBY. Biosynthesis of bisdethiobis(methylthio)gliotoxin, a new metabolite of Gliocladium deliquescens[J]. Journal of The Chemical Society-perkin Transactions 1, 1980, 31 1: 119-121. DOI: 10.1039/p19800000119
[2] M OKAMOTO. Studies of platelet activating factor (PAF) antagonists from microbial products. I. Bisdethiobis(methylthio)gliotoxin and its derivatives.[J]. Chemical & pharmaceutical bulletin, 1986, 34 1: 340-344. DOI: 10.1248/cpb.34.340
[3] BáRBARA S. F. RODRIGUES. Bioprospection of Cytotoxic Compounds in Fungal Strains Recovered from Sediments of the Brazilian Coast[J]. Chemistry & Biodiversity, 2015, 12 3: 432-442. DOI: 10.1002/cbdv.201400193
[4] M OKAMOTO. Studies of platelet activating factor (PAF) antagonists from microbial products. II. Pharmacological studies of FR-49175 in animal models.[J]. Chemical & pharmaceutical bulletin, 1986, 34 1: 345-348. DOI: 10.1248/cpb.34.345
[5] MARIA P. DOMINGO . Bis(methyl)gliotoxin proves to be a more stable and reliable marker for invasive aspergillosis than gliotoxin and suitable for use in diagnosis[J]. Diagnostic microbiology and infectious disease, 2012, 73 1: Pages 57-64. DOI: 10.1016/j.diagmicrobio.2012.01.012

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