Bis(methylthio)gliotoxin (FR-49175) Bis(methylthio)gliotoxin (FR-49175) is analog of gliotoxin shown to inhibit PAF-induced platelet aggregation and speed up PAF hydrolysis.

Bis(methylthio)gliotoxin (FR-49175)  (CAS 74149-38-5)

Bis(methylthio)gliotoxin (FR-49175) is rated 5.0 out of 5 by 1.
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| See 5 Citations
Application: An antiphagocytic metabolite
CAS Number: 74149-38-5
Purity: 99%
Molecular Weight: 356.5
Molecular Formula: C15H20N2O4S2
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ordering Information

PRODUCT NAME CATALOG # UNIT PRICE QTY FAVORITES
Bis(methylthio)gliotoxin (FR-49175) sc-201027 1 mg $86.00
Bis(methylthio)gliotoxin (FR-49175) sc-201027A 5 mg $341.00

Bis(methylthio)gliotoxin (FR-49175) is a toxic metabolite with anthiphagocytic and immunosuppressive properties synthesized by pathogenic fungi such as Aspergillus fumigatus. Bis(methylthio)gliotoxin (FR-49175) is an analog of gliotoxin known to inhibit PAF-induced platelet aggregation and collagen-aggregation, but has no activity with arachidonic or ADP induced aggregation. Shown to speed up PAF hydrolysis and inhibit PAF-mediated caspase 3 activation. From guinea-pig experiments, reported to Inhibit PAF-induced bronchoconstriction.


References

1. Pahl, H.L., et al. 1996. J. Exp. Med. 183: 1829-1840. PMID: 8666939
2. Bonin, F., et al. 2004. J. Biol. Chem. 279: 52425-52436. PMID: 15456758
3. Zhao, W.Y., et al. 2009. Nat. Prod. Res. 23: 203-207. PMID: 19235019

Appearance :
Oil
Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/ml), ethanol (25 mg/ml), and water (Partly miscible).
Storage :
Store at -20° C
Melting Point :
70° C
Boiling Point :
669.62° C at 760 mmHg (Predicted)
Density :
1.50 g/cm3 (Predicted)
Refractive Index :
n20D 1.70
IC50 :
P388 cells : IC50 = 110 nM (mouse); HUVEC50: IC50 = 1120 nM (human); PAF: IC50 = 8400 nM; PAF-induced platelet aggregation: IC50 = 8.4 µM; collagen-induced aggregation: IC50 = 84.2 µM
pK Values :
pKa: 12.7 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
Transport :
UN 3462, Class 6.1, Packing group III
PubChem CID :
194564
MDL Number :
MFCD00133146
SMILES :
CN1C(=O)C2(CC3=CC=CC(C3N2C(=O)C1(CO)SC)O)SC

Download SDS (MSDS)

Certificate of Analysis

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Bis(methylthio)gliotoxin (FR-49175) Product Citations

See how others have used Bis(methylthio)gliotoxin (FR-49175). Click on the entry to view the PubMed entry .

Citations 1 to 5 of 5 total

PMID: # 16830893
Li, X. et al. 2006. A new antibacterial dioxopiperazine alkaloid related to gliotoxin from a marine isolate of the fungus Pseudallescheria. J. Antibiot.. 59: 248-250.

PMID: # 11374585
Woodcock, JC. et al. 2001. Metal complexes of sporidesmin D and dimethylgliotoxin, investigated by electrospray ionisation mass spectrometry. J. Inorg. Biochem.. 84: 225-232.

PMID: # 9933632
Ward, C. et al. 1999. NF-kappaB activation is a critical regulator of human granulocyte apoptosis in vitro. J. Biol. Chem.. 274: 4309-4318.

PMID: # 2457219
Yoshida, K. et al. 1988. PAF inhibitors of microbial origin. Studies on diketopiperazine derivatives. Prog Biochem Pharmacol. 22: 66-80.

PMID: # 2421924
Okamoto, M. et al. 1986. Studies of platelet activating factor (PAF) antagonists from microbial products. II. Pharmacological studies of FR-49175 in animal models. Chem. Pharm. Bull.. 34: 345-348.

Citations 1 to 5 of 5 total
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Rated 5 out of 5 by from Bonin et al Bonin et al. (PubMed ID 15456758) used the PAF antagonist, Bis(methylthio)gliotoxin (FR-49175), to block the PAF receptor-independent death pathway. -SCBT Publication Review
Date published: 2015-02-21
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