| Identification | Back Directory | [Name]
680C91 | [CAS]
163239-22-3 | [Synonyms]
680C91
680C91 >=98% (HPLC)
6-fluoro-3-[(E)-2-(pyridin-3-yl)ethenyl]-1H-indole
6-Fluoro-3-[(1E)-2-(3-pyridinyl)ethenyl)-1H-indole
1H-Indole, 6-fluoro-3-[(1E)-2-(3-pyridinyl)ethenyl]- | [Molecular Formula]
C15H11FN2 | [MDL Number]
MFCD20926361 | [MOL File]
163239-22-3.mol | [Molecular Weight]
238.26 |
| Chemical Properties | Back Directory | [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 | [form ]
powder | [pka]
15.92±0.30(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
41 | [Safety Statements ]
26-39 | [WGK Germany ]
3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Dam. 1 |
| Hazard Information | Back Directory | [Description]
680C91 (163239-22-3) is a potent and selective inhibitor of tryptophan 2,3-dioxygenase (TDO) Ki=42 nM).1,2?Displays 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.2?TDO 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ChEBI: A fluoroindole that is 6-fluoroindole in which the hydrogen at position 3 has been replaced by a 2-(pyridin-3-yl)vinyl group (trans configuration).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) Schwarcz and Pellicciari (2002),?Manipulation of brain kynurenines: glial targets, neuronal effects, and clinical opportunities; J. Pharmacol. Exp. Therap.,?303?1
2) Salter?et al. (1995),?The effects of a novel and selective inhibitor of tryptophan 2,3-dioxygenase on tryptophan and serotonin metabolism; Biochem. Pharmacol,?49?1435
3) Salter?et al. (1995),?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; Neuropharmacology,?34?217
4) Opitz?et al. (2011),?An endogenous tumour-promoting ligand of the human aryl hydrocarbon receptor; Nature,?478197 |
|
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Bide Pharmatech Ltd.
|
| Telephone: |
400-1647117 13681763483 |
| Website: |
https://www.bidepharm.com/ |
|