C8124
CH-223191
≥98% (HPLC), powder, AhR antagonist
Synonym(s):
1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phen yl-1H-pyrazole-5-carboxamide, 2-Methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide
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About This Item
Empirical Formula (Hill Notation):
C19H19N5O
CAS Number:
Molecular Weight:
333.39
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
CH-223191,
assay
≥98% (HPLC)
Quality Level
form
powder
color
orange-brown
solubility
DMSO: ≥20 mg/mL
storage temp.
2-8°C
SMILES string
Cc1cc(ccc1NC(=O)c2ccnn2C)\N=N\c3ccccc3C
InChI
1S/C19H19N5O/c1-13-6-4-5-7-17(13)23-22-15-8-9-16(14(2)12-15)21-19(25)18-10-11-20-24(18)3/h4-12H,1-3H3,(H,21,25)/b23-22+
InChI key
LKTNEXPODAWWFM-GHVJWSGMSA-N
Application
CH-223191 has been used as aryl hydrocarbon receptor (AHR) antagonist in HepaRG cells, TH17-IL-10+ cells and organoids.
Biochem/physiol Actions
CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist.
CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. It inhibited TCDD-mediated nuclear translocation and DNA binding of AhR, and inhibited TCDD-induced luciferase activity with an IC50 of 30nM. Unlike some other AhR antagonists which display agonist activity at high concentrations, CH-223191 did not stimulate AhR-dependent transcription even at 100 micromolar. It is also specific for AhR, displaying no affinity for the estrogen receptor, as some other antagonists do.
Features and Benefits
This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
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Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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An immunoregulatory and tissue-residency program modulated by c-MAF in human TH 17 cells
Aschenbrenner D, et al.
Nature Immunology, 19(10), 1126-1126 (2018)
Lei Dong et al.
Scientific reports, 6, 36598-36598 (2016-11-04)
Understanding of T helper 17 lineage (T
Michela Zago et al.
PloS one, 8(9), e74953-e74953 (2013-10-03)
The aryl hydrocarbon receptor (AhR), a ligand-activated transcription factor that responds to man-made environmental toxicants, has emerged as an endogenous regulator of cyclooxygenase-2 (Cox-2) by a mechanism that is poorly understood. In this study, we first used AhR-deficient (AhR(-/-) )