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SML0287

Sigma-Aldrich

680C91

≥98% (HPLC)

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C15H11FN2
Číslo CAS:
163239-22-3
Molekulová hmotnost:
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

Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

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
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)
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)
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
Giuseppina Bonanno et al.
Journal of translational medicine, 10, 247-247 (2012-12-13)
Multiple myeloma (MM) is a plasma cell malignancy with a multifaceted immune dysfunction. Indoleamine 2,3-dioxygenase 1 (IDO1) degrades tryptophan into kynurenine (KYN), which inhibits effector T cells and promote regulatory T-cell (Treg) differentiation. It is presently unknown whether MM cells
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