| Identification | Back Directory | [Name]
BIS(METHYLTHIO)GLIOTOXIN | [CAS]
74149-38-5 | [Synonyms]
FR-49175
BIS(METHYLTHIO)GLIOTOXIN
bis-dethio-bis(methylthio)gliotoxin
Bis(methylthio)gliotoxin (FR-49175)
gliotoxin, bis-dethio-bis(methylthio)-
2,3,5aβ,6,10,10a-Hexahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-3,10aα-bis(methylthio)pyrazino[1,2-a]indole-1,4-dione
(3R)-2,3,5aβ,6,10,10a-Hexahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-3α,10aα-bis(methylthio)pyrazino[1,2-a]indole-1,4-dione
Pyrazino[1,2-a]indole-1,4-dione, 2,3,5a,6,10,10a-hexahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylthio)-, (3R,5aS,6S,10aR)- | [Molecular Formula]
C15H20N2O4S2 | [MDL Number]
MFCD00133146 | [MOL File]
74149-38-5.mol | [Molecular Weight]
356.46 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. | [storage]
Store at -20°C | [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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