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Merck
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Key Documents

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SML0287

Sigma-Aldrich

680C91

≥98% (HPLC)

Sinónimos:

6-Fluoro-3-[(1E)-2-(3-pyridinyl)ethenyl)-1H-indole

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About This Item

Fórmula empírica (notación de Hill):
C15H11FN2
Número de CAS:
163239-22-3
Peso molecular:
238.26
MDL number:
MFCD20926361
UNSPSC Code:
12352200
PubChem Substance ID:
329825295
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥10 mg/mL

storage temp.

2-8°C

SMILES string

Fc1ccc2c(\C=C\c3cccnc3)c[nH]c2c1

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+

InChI key

YBSDQTBCNYWBMX-ONEGZZNKSA-N

Application

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

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.
680C91 shows no inhibitory effects against monoamine oxidase A and B, indoleamine 2,3-dioxygenase and serotonin (5-HT) uptake, and 5-HT1A,1D,2A, and 2C receptors.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Carlo Breda et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(19), 5435-5440 (2016-04-27)
Metabolites of the kynurenine pathway (KP) of tryptophan (TRP) degradation have been closely linked to the pathogenesis of several neurodegenerative disorders. Recent work has highlighted the therapeutic potential of inhibiting two critical regulatory enzymes in this pathway-kynurenine-3-monooxygenase (KMO) and tryptophan-2,3-dioxygenase
Tryptophan 2, 3-dioxygenase 2 controls M2 macrophages polarization to promote esophageal squamous cell carcinoma progression via AKT/GSK3 beta IL-8 signaling pathway
Zhao Y, et al.
Acta pharmaceutica Sinica. B (2021)
Karthyayani Rajamani et al.
Neuropharmacology, 117, 434-446 (2017-02-23)
Spinocerebellar ataxia type 3 or Machado-Joseph disease (SCA3/MJD) is characterized by the repetition of a CAG codon in the ataxin-3 gene (ATXN3), which leads to the formation of an elongated mutant ATXN3 protein that can neither be denatured nor undergo
Sara Paccosi et al.
Journal of cancer research and clinical oncology, 146(12), 3155-3163 (2020-08-11)
Indoleamine 2,3-dioxygenase-1 (IDO1) and more recently, tryptophan 2,3-dioxygenase (TDO), are tryptophan-catabolizing enzymes with immunoregulatory properties in cancer. IDO1 is more expressed than TDO in many tumours including melanomas; however, IDO inhibitors did not give expected results in clinical trials, highlighting
M Salter et al.
Biochemical pharmacology, 49(10), 1435-1442 (1995-05-17)
The effects of a novel inhibitor 680C91 ((E)-6-fluoro-3-[2-(3- pyridyl)vinyl]-1H-indole) of the key enzyme of tryptophan catabolism tryptophan 2,3-dioxygenase (TDO) (EC 1.13.11.11), were examined on tryptophan catabolism in vitro and in vivo and on brain levels of tryptophan, serotonin (5-HT) and
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