CH 223191

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Cat.No. 3858 - CH 223191 | C19H19N5O | CAS No. 301326-22-7
Description: Potent aryl hydrocarbon receptor (AhR) antagonist
Chemical Name: 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide
Purity: ≥98% (HPLC)
Datasheet
Citations (3)
Literature

Biological Activity

Potent aryl hydrocarbon receptor (AhR) antagonist (IC50 = 30 nM). Exhibits no AhR agonist-like activity (at concentrations up to 100 μM). Inhibits 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD)-induced AhR-dependent transcription in vitro and reduces TCDD-induced toxicity in vivo. Attenuates Th17 differentiation of naive CD4 T cells and promotes expansion of hematopoietic stem cells in vitro.

Compound Libraries

CH 223191 is also offered as part of the Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 333.39
Formula C19H19N5O
Storage Store at +4°C
Purity ≥98% (HPLC)
CAS Number 301326-22-7
PubChem ID 3091786
InChI Key LKTNEXPODAWWFM-UHFFFAOYSA-N
Smiles CC1=C(/N=N/C2=CC=C(NC(C3=CC=NN3C)=O)C(C)=C2)C=CC=C1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 33.34 100
ethanol 3.33 10

Preparing Stock Solutions

The following data is based on the product molecular weight 333.39. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 3 mL 15 mL 29.99 mL
5 mM 0.6 mL 3 mL 6 mL
10 mM 0.3 mL 1.5 mL 3 mL
50 mM 0.06 mL 0.3 mL 0.6 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Kim et al (2006) Novel compound 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide (CH-223191) prevents 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor. Mol.Pharmacol. 69 1871 PMID: 16540597

Veldhoen et al (2009) Natural agonists for aryl hydrocarbon receptor in culture medium are essential for optimal differentiation of TH17 T cells. J.Exp.Med. 206 43 PMID: 19114668

Dubrovska et al (2012) CXCR4 activation maintains a stem cell population in tamoxifen-resistant breast cancer cells through AhR signalling. Br.J.Cancer. 107 43 PMID: 22644306

Boitano et al (2010) Aryl hydrocarbon receptor antagonists promote the expansion of human hematopoietic stem cells. Science 329 1345 PMID: 20688981


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3 Citations for CH 223191

Citations are publications that use Tocris products. Selected citations for CH 223191 include:

D'Amato et al (2015) A TDO2-AhR Signaling Axis Facilitates Anoikis Resistance and Metastasis in Triple-Negative Breast Cancer. Cancer Res 75 4651 PMID: 26363006

Matino et al (2015) IDO1 suppresses inhibitor development in hemophilia A treated with factor VIII. Br J Pharmacol 125 3766 PMID: 26426076

Liu et al (2014) Regulation of plasmacytoid dendritic cell development in mice by aryl hydrocarbon receptor. Immunol Cell Biol 92 200 PMID: 24165981


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