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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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Angela Rico de Souza et al.
Frontiers in immunology, 12, 630427-630427 (2021-03-05)
Cigarette smoke is a prevalent respiratory toxicant that remains a leading cause of death worldwide. Cigarette smoke induces inflammation in the lungs and airways that contributes to the development of diseases such as lung cancer and chronic obstructive pulmonary disease
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
Down-regulation of the expression of alcohol dehydrogenase 4 and CYP2E1 by the combination of alpha-endosulfan and dioxin in HepaRG human cells
Attignon E, et al.
Toxicology in vitro, 45, 309-317 (2017)
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
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