CH-223191 - AhR Antagonist

InvitroFit™ PRR inhibitor

ABOUT

AhR Antagonist

CH-223191 is a synthetic antagonist for the cytosolic aryl hydrocarborn receptor (AhR) transcription factor [1]. AhR is a ligand-dependent transcriptional factor able to sense a wide range of structurally different exogenous and endogenous molecules.

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Mode of action:

CH-223191 exerts a ligand-selective antagonism and appears to be more effective on halogenated aromatic hydrocarbons such as the xenobiotic 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD), than on polycyclic aromatic hydrocarbons and non-halogenated aromatic hydrocarbons such as FICZ and ITE, respectively [2].

Notably, CH-223191 is a pure AhR antagonist that does not stimulate AhR-dependent transcription even at concentrations up to 100 μM [1], unlike other AhR antagonists which display agonist activity at high concentrations. Moreover, CH-223191 is specific for AhR, displaying no affinity for the estrogen receptor, in contrast to other AhR antagonists [1].

InvivoGen's CH-223191 is of high quality, guaranteed free of bacterial contamination, and has been functionally tested on HepG2-Lucia™ AhR and HT29-Lucia™ AhR reporter cells.

Key features of CH-223191:

  • A potent and specific AhR antagonist
  • Ligand-selective antagonist activity
  • InvitroFit™: each lot is highly pure (≥95%) and functionally tested

 

More details Read our review on AhR's key role in the intestinal microbiota and immunity.

 

References

1. Kim, S.H. 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. 69:1871-78.
2. Zhao B. et al., 2010. CH223191 is a ligand-selective antagonist of the Ah (Dioxin) receptor. Toxicol. Sci. 117:393-403.

All products are for research use only, and not for human or veterinary use.

Inhibition of AhR signaling by CH-223191
Inhibition of AhR signaling by CH-223191

InvitroFit™

InvitroFit™ is a high-quality standard specifically adapted for in vitro studies of inhibitors. InvitroFit™ products are guaranteed free of bacterial contamination, as confirmed using HEK Blue™ TLR2 and HEK Blue™ TLR4 cellular assays. Each lot is rigorously tested for functional activity using validated (or proprietary) cellular models. This grade ensures reliability and reproducibility for your research applications.

SPECIFICATIONS

Specifications

Synonyms
2-methyl-2H-pyrazole-3-carboxylic acid
CAS number
301326-22-7
Chemical formula

C19H19N5O

Molecular weight
333.4 g/mol
Purity
≥ 95% (UHPLC)
Solubility

90 mM (30 mg/ml) in DMSO

Working concentration

1 µM (333 ng/ml) to 30 µM (10.1 μg/ml) for cell culture assays

Endotoxin

Negative (tested using EndotoxDetect™ assay)

Tested applications

In vitro cellular assays

Quality control

Each lot is functionally tested and validated using cellular assays.

CONTENTS

Contents

  • Product: 
    CH-223191
  • Cat code: 
    inh-ch22
  • Quantity: 
    10 mg
Notes:

CH-223191 is provided as a translucent film.

Shipping & Storage

  • Shipping method:  Room temperature

    • Storage:

    • -20°C
    Stability: The reconstituted product is stable at least 2 months at 4 °C.

    Caution:

    • Protect from light

Details

The aryl hydrocarbon receptor:

The aryl hydrocarbon receptor (AhR) is a ligand-dependent transcriptional factor able to sense a wide range of structurally different endogenous and exogenous molecules, including the prototypic AhR agonist 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) [1-3]. AhR resides in the cytoplasm within a Hsp90:XAP2:p23:Src chaperone protein complex. Upon ligand binding, the complex undergoes conformational changes and translocates into the nucleus. The chaperones are released and AhR heterodimerizes with AhR nuclear translocator (ARNT). The AhR:ligand:ARNT trimer binds to dioxin response elements (DREs) in the upstream regulatory regions of AhR target genes, which include the cytochrome P450-dependent monooxygenase Cyp1a1, the AhR repressor (AhRR), and the IL-22 interleukin.
 

1. Stockinger B. et al., 2014. The aryl hydrocarbon receptor: multitasking in the immune system. Annu. Rev. Immunol. 32:403-32.
2. Hubbard T.D. et al., 2015. Indole and tryptophan metabolism: endogenous and dietary routes to Ah receptor activation. Drug Metab. Dispos. 43:1522-35.
3. Murray I.A. et al., 2016. Expression of the aryl hydrocarbon receptor contributes to the establishment of intestinal microbial community structure in mice. Sci. Rep. 6:33969.

  

Chemical structure of CH-223191: 

Chemical structure of CH-223191 

DOCUMENTS

Documents

CH-223191

Technical Data Sheet

Validation Data Sheet

Safety Data Sheet

Certificate of analysis

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