680C91

Product Name680C91
CAS163239-22-3
MFC15H11FN2
MW238.26
EINECS
MOL File163239-22-3.mol

Chemical Properties

Boiling point	431.2±35.0 °C(Predicted)
Density	1.305±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: ≥10mg/mL
pka	15.92±0.30(Predicted)
form	powder
color	white to beige
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChI	1S/C15H11FN2/c16-13-5-6-14-12(10-18-15(14)8-13)4-3-11-2-1-7-17-9-11/h1-10,18H/b4-3+
InChIKey	YBSDQTBCNYWBMX-ONEGZZNKSA-N
SMILES	Fc1ccc2c(\C=C\c3cccnc3)c[nH]c2c1

Safety Information

Hazard Codes	Xi
Risk Statements	41
Safety Statements	26-39
WGK Germany	3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Dam. 1

Usage And Synthesis

Description

680C91 (163239-22-3) is a potent and selective inhibitor of tryptophan 2,3-dioxygenase (TDO) Ki=42 nM).1,2Displays no activity against indoleamine 2,3-dioxygenase, MAO-A and B and does not effect serotonin uptake. Elevates CSF tryptophan by up to 260% and CSF serotonin by 170% of basal.2TDO inhibition by 680C91 in glioma cells blocked the release of kynurenine (Cat.# 10-2666), an endogenous tumor promoting AHR ligand.4

Uses

680C91 has been used:

as a tryptophan 2,3 dioxygenase (TDO) inhibitor to study its effects on the pigmentation in Doryteuthis pealeii embryos
as a TDO inhibitor to study its effects on esophageal squamous cell carcinoma in xenograft tumor assay
as a tryptophan 2,3 dioxygenase 2 (TDO2) inhibitor to study its effects on toxic fragment formation in human embryonic kidney cells

Definition

ChEBI: A fluoroindole that is 6-fluoroindole in which the hydrogen at position 3 has been replaced by a 2-(pyridin-3-yl)vinyl group (trans configuration). It is a selective inhibitor of tryptophan 2,3-dioxygenase (TDO), which directs the conversi n of trypophan to kynurenin.

Biochem/physiol Actions

680C91 is a potent inhibitor of the enzyme tryptophan 2,3-dioxygenase (TDO), which directs the conversion of trypophan to kynurenin. Kynurenin has recently been identified as an endogenous lignd of the arylhydrocarbon receptor (AHR). TDO is highly expressed in glioma cells, and contributes to AHR-mediated glioma cell survival and suppression of anti-tumor immune responses.

storage

Store at +4°C

References

[1] ROBERT SCHWARCZ R P. Manipulation of brain kynurenines: glial targets, neuronal effects, and clinical opportunities.[J]. Journal of Pharmacology and Experimental Therapeutics, 2002, 303 1: 1-10. DOI:10.1124/jpet.102.034439
[2] MARK SALTER. The effects of a novel and selective inhibitor of tryptophan 2,3-dioxygenase on tryptophan and serotonin metabolism in the rat[J]. Biochemical pharmacology, 1995, 49 10: Pages 1435-1442. DOI:10.1016/0006-2952(95)00006-l
[3] M. SALTER . The Effects of an inhibitor of tryptophan 2,3-dioxygenase and a combined inhibitor of tryptophan 2,3-dioxygenase and 5-HT reuptake in the rat[J]. Neuropharmacology, 1995, 34 2: Pages 217-227. DOI:10.1016/0028-3908(94)00147-k
[4] CHRISTIANE A. OPITZ. An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor[J]. Nature, 2011, 478 7368: 197-203. DOI:10.1038/nature10491

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