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Chemical Structure| 301326-22-7 Chemical Structure| 301326-22-7

Structure of CH-223191
CAS No.: 301326-22-7

Chemical Structure| 301326-22-7

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CH-223191 is a potent and specific antagonist of the aryl hydrocarbon receptor (AhR). It inhibits TCDD-mediated nuclear translocation and DNA binding of AhR, and suppresses TCDD-induced luciferase activity with an IC50 of 0.03 μM.

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Product Details of CH-223191

CAS No. :301326-22-7
Formula : C19H19N5O
M.W : 333.39
SMILES Code : O=C(C1=CC=NN1C)NC2=CC=C(N=NC3=CC=CC=C3C)C=C2C
MDL No. :MFCD00377884
InChI Key :LKTNEXPODAWWFM-UHFFFAOYSA-N
Pubchem ID :3091786

Safety of CH-223191

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330-P501

Isoform Comparison

Biological Activity

Target
  • AhR

    AhR, IC50:30 nM

In Vitro:

Cell Line
Concentration Treated Time Description References
DLD1 colon cancer cells 10 µM 2 days Reduced the proliferation of colon cancer cells Genes Dev. 2019 Sep 1;33(17-18):1236-1251.
EL-4 cells 10 μM 24 h CH223191 almost offset alpinetin-mediated increase of CYP1A1 expression Cell Death Dis. 2018 Aug 30;9(9):890.
Hs578T cells 10 μM 48 h Reduced ALDH1 activity and decreased the percentage of ALDHhigh cells BMC Biol. 2016 Mar 16;14:20.
SUM149 cells 10 μM 48 h Reduced ALDH1 activity and decreased the percentage of ALDHhigh cells BMC Biol. 2016 Mar 16;14:20.
Caco-2 cells 10 μM 24 h Inhibit AHR activity to study its effect on IL10R1 expression Mucosal Immunol. 2017 Sep;10(5):1133-1144.
CD8 T cells 30 μM 72 h To evaluate the effect of CH-223191 on IFN γ production in CD8 T cells. Results showed that CH-223191 significantly suppressed IFN γ production. Cell Host Microbe. 2022 Jul 13;30(7):1003-1019.e10.
H4G1.1c3 cells 10 µM 12 h CH-223191 suppressed the GFP expression induced by BaP and FICZ, indicating that CH-223191 is an AHR antagonist. Int J Mol Sci. 2023 Oct 12;24(20):15116.
CD4+ T cells 10 μM 72 h CH223191 almost completely abolished alpinetin-promoted Treg differentiation Cell Death Dis. 2018 Aug 30;9(9):890.

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
C57BL/6 mice Obesity model Oral 10 mg/kg Once daily, starting 1 week before administration of vehicle or PCB-77 and continued throughout the study To investigate the effect of CH-223191 on PCB-77-induced glucose and insulin intolerance, results showed that CH-223191 blocked these effects of PCB-77. Environ Health Perspect. 2013 Jan;121(1):105-10.
Mice Tiparp-/- or WT mice Intraperitoneal injection 10 mg/kg Days 1 and 3 CH223191 cotreatment reduced 3MC-induced ALT activity and epididymal adipose tissue loss, but did not completely prevent 3MC-induced chylous ascites. Int J Mol Sci. 2019 May 10;20(9):2312
Mice Tet2ΔV A V mice Intraperitoneal injection 300 μg/mouse 5 days per week for 5 weeks To evaluate the effect of CH-223191 on AIH-like pathology. Results showed that CH-223191 significantly suppressed the development of AIH-like pathology. Cell Host Microbe. 2022 Jul 13;30(7):1003-1019.e10.
Mice ApoE −/− mice Intraperitoneal injection 5 mg/kg Weekly for 60 days To test the inhibitory effect of CH-223191 on TCDD-induced atherosclerotic plaque formation, results showed that CH-223191 significantly reduced TCDD-induced atherosclerotic plaque formation. Arterioscler Thromb Vasc Biol. 2011 Jun;31(6):1260-7.
Mice B6. AhRfl/f LysM- Cre+/− mice Intraperitoneal injection 100μg/mouse Single injection To detect the effect of AhR on tolerance induced by apoptotic cells in vivo, results showed that AhR deletion led to enhanced immune responses. Nat Immunol. 2018 Jun;19(6):571-582
Mice DSS-induced colitis model Intraperitoneal injection 10 mg/kg Once daily for 10 days CH223191 almost reversed alpinetin-alleviated UC symptoms and prevented alpinetin-induced Treg cells and regulation of miR-302/DNMT-1/CREB signals Cell Death Dis. 2018 Aug 30;9(9):890.

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