The aryl hydrocarbon receptor (AhR) is a ligand-dependent intracellular transcription factor whose ligands include some of the most infamous xenobiotics, including dioxin, benzo[a]pyrene, and numerous polyaromatics from soot and coal tar.1 PDM 11 is structurally very similar to several resveratrol analogs which act as a potent and selective AhR antagonists and agonists.2 One of these compounds, which contains fluorine in place of the 4'-chlorine of PDM11, acts as a AhR antagonist with a Ki of approximately 3 nM.2 This fluorine-containing compound is inactive as a ligand for the estrogen receptor even at 100 µM. As AhR knockout mice are insensitive to the carcinogenic effects of classical AhR ligands, antagonists of AhR could potentially serve as therapeutic agents for the treatment for dioxin and other aryl hydrocarbon poisonings.
1
Denison, M.S., and Nagy, S.R. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals.. Annu Rev Pharmacol Toxicol43309-334(2003).
2
de Medina, P., Casper, R., Savouret, J., et al. Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators. J Med Chem48287-291(2005).
Room temperature
in continental US; may vary elsewhere
SMILES
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ClC(C=C1)=CC=C1/C=C/C2=CC(OC)=CC(OC)=C2
Background Reading
de Medina, P., Casper, R., Savouret, J., et al. Synthesis and biological properties of new stilbene derivatives of resveratrol as new selective aryl hydrocarbon modulators. J Med Chem48287-291(2005).
Denison, M.S., and Nagy, S.R. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals.. Annu Rev Pharmacol Toxicol43309-334(2003).
PDM 11 is available in the following screening
library: