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SML0287

Sigma-Aldrich

680C91

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C15H11FN2
CAS-Nummer:
163239-22-3
Molekulargewicht:
238.26
MDL-Nummer:
MFCD20926361
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825295
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to beige

Löslichkeit

DMSO: ≥10 mg/mL

Lagertemp.

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+

InChIKey

YBSDQTBCNYWBMX-ONEGZZNKSA-N

Anwendung

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. Wirkung

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.

Piktogramme

Corrosion
GHS05

Signalwort

Danger

H-Sätze

H318

Gefahreneinstufungen

Eye Dam. 1

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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
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
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)
Vasco Rodrigues et al.
Frontiers in cellular and infection microbiology, 9, 338-338 (2019-10-23)
Disease manifestation after infection with cutaneous Leishmania species is the result of a complex interplay of diverse factors, including the immune status of the host, the infecting parasite species, or the parasite load at the lesion site. Understanding how these
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