SML1489
FICZ
≥95% (HPLC), lyophilized powder, AhR agonist
Synonym(s):
5,11-Dihydro-indolo[3,2-b]carbazole-6-carboxaldehyde, 6-Formylindolo[3,2-b]carbazole
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About This Item
Empirical Formula (Hill Notation):
C19H12N2O
CAS Number:
Molecular Weight:
284.31
UNSPSC Code:
12352200
NACRES:
NA.77
Product Name
FICZ, ≥95% (HPLC)
Quality Level
assay
≥95% (HPLC)
form
lyophilized powder
color
yellow
solubility
DMSO: 0.5 mg/mL, clear (warmed)
storage temp.
−20°C
SMILES string
[nH]1c2c(c5c1cccc5)cc3[nH]c4c(c3c2C=O)cccc4
InChI
1S/C19H12N2O/c22-10-14-18-12-6-2-4-8-16(12)20-17(18)9-13-11-5-1-3-7-15(11)21-19(13)14/h1-10,20-21H
InChI key
ZUDXFBWDXVNRKF-UHFFFAOYSA-N
Biochem/physiol Actions
FICZ (6-formylindolo(3,2b)carbazole) being a photooxidation product of tryptophan, might serve as a chemical messenger of light.
FICZ is a potent high affinity ligand of the aryl hydrocarbon receptor (AhR), which is a ligand-activated transcription factor that activates the expression of aromatic hydrocarbon metabolizing enzyme genes such as the CYP1A1 gene and has also been shown to have multiple additional roles in cell-cycle regulation, development and maturation of many tissues, control of inflammation, and immune response. FICZ is a photoproduct of tryptophan and is believed to be an endogenous AhR ligand. It is extremely potent, with a Kd value of 0.07 nM.
FICZ is a potent high affinity ligand of the aryl hydrocarbon receptor (AhR).
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
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Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals.
Denison M S and Nagy S R
Annual Review of Pharmacology, 43(1), 309-334 (2003)
Hui Li et al.
FEBS letters, 593(9), 952-961 (2019-04-07)
Interleukin (IL)-17 plays a critical role in the pathogenesis of inflammation and autoimmune diseases. The aryl hydrocarbon receptor (AHR) is a transcription factor responsible for the elimination of xenobiotic chemicals. However, it remains unknown whether AHR is involved in IL-17
Barbora Vyhlídalová et al.
International journal of molecular sciences, 21(7) (2020-04-15)
We examined the effects of gut microbial catabolites of tryptophan on the aryl hydrocarbon receptor (AhR). Using a reporter gene assay, we show that all studied catabolites are low-potency agonists of human AhR. The efficacy of catabolites differed substantially, comprising
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML1489-1MG | 04061826274651 |
| SML1489-5MG | 04061832649382 |