WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406631
CAS#: 301326-22-7
Description: CH223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. CH223191 can prevent 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor. 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is a widespread environmental pollutant with many toxic effects, including endocrine disruption, reproductive dysfunction, immunotoxicity, liver damage, and cancer. CH223191 potently inhibits TCDD-induced AhR-dependent transcription. In addition, CH-223191 blocked the binding of TCDD to AhR and inhibited TCDD-mediated nuclear translocation and DNA binding of AhR. These inhibitory effects of CH-223191 prevented the expression of cytochrome P450 enzymes, target genes of the AhR. CH-223191, may be a useful agent for the study of AhR-mediated signal transduction and the prevention of TCDD-associated pathology.
MedKoo Cat#: 406631
Name: CH223191
CAS#: 301326-22-7
Chemical Formula: C19H19N5O
Exact Mass: 333.15896
Molecular Weight: 333.39
Elemental Analysis: C, 68.45; H, 5.74; N, 21.01; O, 4.80
Synonym: CH223191; CH-223191; CH 223191.
IUPAC/Chemical Name: (E)-1-methyl-N-(2-methyl-4-(o-tolyldiazenyl)phenyl)-1H-pyrazole-5-carboxamide
InChi Key: LKTNEXPODAWWFM-GHVJWSGMSA-N
InChi Code: 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+
SMILES Code: O=C(C1=CC=NN1C)NC2=CC=C(/N=N/C3=CC=CC=C3C)C=C2C
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
| Biological target: | CH-223191 is an antagonist of aryl hydrocarbon receptor (AhR) that also inhibits TCDD-mediated nuclear translocation and inhibits TCDD-induced luciferase activity with an IC50 of 0.03 μM. |
| In vitro activity: | To explore the role of AHR during decidualization, tryptophan-treated stromal cells were co-treated with CH223191, a specific AHR inhibitor. The tryptophan induction of IGFBP1 and prolactin was abrogated by CH223191 (Fig. 4A and B). The AHR stimulation by tryptophan was also obviously suppressed by CH223191 (Fig. 4C). Furthermore, tryptophan-induced CYP1A1 and CYP1B1 expression was down-regulated by CH223191 (Figs. 4D and E). These results indicated that tryptophan stimulated IGFBP1 and prolactin expression through activating AHR and its target genes. Reference: Reprod Toxicol. 2020 Aug 8;96:282-292. https://www.sciencedirect.com/science/article/pii/S0890623820301854?via%3Dihub |
| In vivo activity: | To confirm that the regulatory effect of NPD-0414-2 and NPD-0414-24 on cytokine expression was strictly dependent on the activation of AhR, anti-CD3/CD28-activated IBD LPMC were treated with Ficz, NPD-0414-2 or NPD-0414-24 in the presence or absence of CH223191, a specific inhibitor of the interaction between AhR and its ligands. Pre-incubation of IBD LPMC with CH223191 fully abolished the regulatory effect of Ficz, NPD-0414-2, and NPD-0414-24 on IFN-γ and IL-22 expression (Figure 3). Reference: Front Pharmacol. 2019; 10: 380. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6473199/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 40.09 | 120.25 | |
| DMF | 30.0 | 89.98 | |
| Ethanol | 2.14 | 6.42 |
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 | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Kulas J, Tucovic D, Zeljkovic M, Popovic D, Popov Aleksandrov A, Kataranovski M, Mirkov I. Aryl Hydrocarbon Receptor is Involved in the Proinflammatory Cytokine Response to Cadmium. Biomed Environ Sci. 2021 Mar 20;34(3):192-202. doi: 10.3967/bes2021.025. PMID: 33766215. 2. Wang PC, Chen ST, Hong ZK, Li SY, Yang ZS, Quan S, Yang ZM. Tryptophan and kynurenine stimulate human decidualization via activating Aryl hydrocarbon receptor: Short title: Kynurenine action on human decidualization. Reprod Toxicol. 2020 Aug 8;96:282-292. doi: 10.1016/j.reprotox.2020.07.011. Epub ahead of print. PMID: 32781018. 3. Wang Y, Chen S, Tan J, Gao Y, Yan H, Liu Y, Yi S, Xiao Z, Wu H. Tryptophan in the diet ameliorates motor deficits in a rotenone-induced rat Parkinson's disease model via activating the aromatic hydrocarbon receptor pathway. Brain Behav. 2021 Jun 9. doi: 10.1002/brb3.2226. Epub ahead of print. PMID: 34105899. 4. Marafini I, Di Fusco D, Dinallo V, Franzè E, Stolfi C, Sica G, Monteleone G, Monteleone I. NPD-0414-2 and NPD-0414-24, Two Chemical Entities Designed as Aryl Hydrocarbon Receptor (AhR) Ligands, Inhibit Gut Inflammatory Signals. Front Pharmacol. 2019 Apr 12;10:380. doi: 10.3389/fphar.2019.00380. PMID: 31031628; PMCID: PMC6473199. |
| In vitro protocol: | 1. Kulas J, Tucovic D, Zeljkovic M, Popovic D, Popov Aleksandrov A, Kataranovski M, Mirkov I. Aryl Hydrocarbon Receptor is Involved in the Proinflammatory Cytokine Response to Cadmium. Biomed Environ Sci. 2021 Mar 20;34(3):192-202. doi: 10.3967/bes2021.025. PMID: 33766215. 2. Wang PC, Chen ST, Hong ZK, Li SY, Yang ZS, Quan S, Yang ZM. Tryptophan and kynurenine stimulate human decidualization via activating Aryl hydrocarbon receptor: Short title: Kynurenine action on human decidualization. Reprod Toxicol. 2020 Aug 8;96:282-292. doi: 10.1016/j.reprotox.2020.07.011. Epub ahead of print. PMID: 32781018. |
| In vivo protocol: | 1. Wang Y, Chen S, Tan J, Gao Y, Yan H, Liu Y, Yi S, Xiao Z, Wu H. Tryptophan in the diet ameliorates motor deficits in a rotenone-induced rat Parkinson's disease model via activating the aromatic hydrocarbon receptor pathway. Brain Behav. 2021 Jun 9. doi: 10.1002/brb3.2226. Epub ahead of print. PMID: 34105899. 2. Marafini I, Di Fusco D, Dinallo V, Franzè E, Stolfi C, Sica G, Monteleone G, Monteleone I. NPD-0414-2 and NPD-0414-24, Two Chemical Entities Designed as Aryl Hydrocarbon Receptor (AhR) Ligands, Inhibit Gut Inflammatory Signals. Front Pharmacol. 2019 Apr 12;10:380. doi: 10.3389/fphar.2019.00380. PMID: 31031628; PMCID: PMC6473199. |
1: Kim SH, Henry EC, Kim DK, Kim YH, Shin KJ, Han MS, Lee TG, Kang JK, Gasiewicz TA, Ryu SH, Suh PG. 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. 2006 Jun;69(6):1871-8. Epub 2006 Mar 15. PubMed PMID: 16540597.
