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C8124

Sigma-Aldrich

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:
301326-22-7
Molecular Weight:
333.39
MDL number:
MFCD00377884
UNSPSC Code:
12352200
PubChem Substance ID:
329775161
NACRES:
NA.77

product name

CH-223191,

Assay

≥98% (HPLC)

Quality Level

100

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. 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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Ping Gong et al.
Molecular and cellular endocrinology, 437, 190-200 (2016-08-21)
Botanical estrogen (BE) dietary supplements are consumed by women as substitutes for loss of endogenous estrogens at menopause. To examine the roles of estrogen receptor α (ERα) and aryl hydrocarbon receptor (AhR) and their crosstalk in the actions of BEs
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(-/-) )
Lei Dong et al.
Scientific reports, 6, 36598-36598 (2016-11-04)
Understanding of T helper 17 lineage (T
Qin Wang et al.
Environmental health perspectives, 121(11-12), 1334-1343 (2013-09-24)
The aryl hydrocarbon receptor (AHR) is a ligand-activated transcription factor that regulates the expression of xenobiotic detoxification genes and is a critical mediator of gene-environment interactions. Many AHR target genes identified by genome-wide gene expression profiling have morphogenetic functions, suggesting
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