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

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.

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