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Submit ReviewCH 223191
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)
Biological Activity for CH 223191
CH 223191 is a 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 for CH 223191
CH 223191 is also offered as part of the Tocriscreen Stem Cell Library. Find out more about compound libraries available from Tocris.
Technical Data for CH 223191
| 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.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for CH 223191
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 33.34 | 100 | |
| ethanol | 3.33 | 10 |
Preparing Stock Solutions for CH 223191
The following data is based on the product molecular weight 333.39. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| 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 for CH 223191
References for CH 223191
References are publications that support the biological activity of the product.
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
If you know of a relevant reference for CH 223191, please let us know.
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13 Citations for CH 223191
Citations are publications that use Tocris products. Selected citations for CH 223191 include:
Gimenez-Gomez et al (2018) Increasing kynurenine brain levels reduces ethanol consumption in mice by inhibiting dopamine release in nucleus accumbens. Neuropharmacology 135 581 PMID: 29705534
Nicholas C et al (2018) Gut Microbiota-Produced Tryptamine Activates an Epithelial G-Protein-Coupled Receptor to Increase Colonic Secretion. Cell Host Microbe 23 775-785.e5 PMID: 29902441
Matino et al (2015) IDO1 suppresses inhibitor development in hemophilia A treated with factor VIII. Br J Pharmacol 125 3766 PMID: 26426076
Sergio Costa et al (2022) STING is an intrinsic checkpoint inhibitor that restrains the TH17 cell pathogenic program. Cell Rep 39 110838 PMID: 35613599
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
Liu et al (2014) Regulation of plasmacytoid dendritic cell development in mice by aryl hydrocarbon receptor. Immunol Cell Biol 92 200 PMID: 24165981
Alexandra E et al (2017) Mechanisms of Skin Toxicity Associated with Metabotropic Glutamate Receptor 5 Negative Allosteric Modulators. Cell Chem Biol 24 858-869.e5 PMID: 28669525
Rao et al (2016) Effects of Cigarette Smoke Condensate on Oxidative Stress, Apoptotic Cell Death, and HIV Replication in Human Monocytic Cells. PLoS One 11 e0155791 PMID: 27203850
Stephen et al (2015) Aryl Hydrocarbon Receptor Activity of Tryptophan Metabolites in Young Adult Mouse Colonocytes. Drug Metab Dispos 43 1536-43 PMID: 25873348
Howard L et al (2019) Control of tumor-associated macrophages and T cells in glioblastoma via AHR and CD39. Nat Neurosci 22 729-740 PMID: 30962630
Beom K et al (2020) Targeting Actomyosin Contractility Suppresses Malignant Phenotypes of Acute Myeloid Leukemia Cells. Int J Mol Sci 21 PMID: 32422910
Yuecheng et al (2021) Hypoxia-Inducible Factor 1α (HIF1α) Suppresses Virus Replication in Human Cytomegalovirus Infection by Limiting Kynurenine Synthesis. MBio 12 PMID: 33758082
Brian T et al (2021) Vitamin D Inhibits IL-22 Production Through a Repressive Vitamin D Response Element in the il22 Promoter. Front Immunol 12 715059 PMID: 34408754
Do you know of a great paper that uses CH 223191 from Tocris? Please let us know.
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