C8124

CH-223191

Name: CH-223191
Brand: SIGMA
Price: 129 USD
Availability: InStock

≥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

Key Documents

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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

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Bioactive Small Molecules

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This Item	SML2384	SML1061	SML1276
Sigma-Aldrich C8124 CH-223191	Sigma-Aldrich SML2384 BAY 87-2243	Sigma-Aldrich SML1061 PF-04856264	Sigma-Aldrich SML1276 BAZ2-ICR
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 100	Quality Level -	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: ≥20 mg/mL	solubility DMSO: 2 mg/mL, clear	solubility DMSO: 10 mg/mL, clear	solubility DMSO: 10 mg/mL, clear
color orange-brown	color white to beige	color white to light brown	color white to beige

Application

CH-223191 has been used as aryl hydrocarbon receptor (AHR) antagonist in HepaRG cells,[1] TH17-IL-10+ cells[2] and organoids.[3]

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.

Storage Class

11 - Combustible Solids

wgk_germany

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)

Aryl hydrocarbon receptor-dependent retention of nuclear HuR suppresses cigarette smoke-induced cyclooxygenase-2 expression independent of DNA-binding.

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(-/-) )

Surface-bound bovine serum albumin carrier protein as present in recombinant cytokine preparations amplifies T helper 17 cell polarization.

Lei Dong et al.

Scientific reports, 6, 36598-36598 (2016-11-04)

Understanding of T helper 17 lineage (T

Estrogen receptor-α and aryl hydrocarbon receptor involvement in the actions of botanical estrogens in target cells.

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

Disruption of aryl hydrocarbon receptor homeostatic levels during embryonic stem cell differentiation alters expression of homeobox transcription factors that control cardiomyogenesis.

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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CH-223191