A flavone that modulates xenobiotic metabolism; antagonizes AhR at nanomolar concentrations

α-Naphthoflavone – 10 g

Brand:
Cayman
CAS:
604-59-1
Storage:
-20
UN-No:
Non-Hazardous - /

The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that promotes the expression of phase I and II xenobiotic chemical metabolizing enzyme genes, including the cytochrome P450 (CYP) isoforms CYP1A1 and CYP1A2.{12907} α-Naphthoflavone is a flavone that modulates xenobiotic metabolism at several points. It antagonizes AhR, blocking the expression of phase I and II genes at nanomolar concentrations, although it can agonize AhR at higher concentrations (10 µM).{27487,27488} α-Naphthoflavone inhibits CYP19 (aromatase), CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 µM).{27489,27484,27486} Dietary α-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.{27485}  

 

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Description

A flavone that modulates xenobiotic metabolism; antagonizes AhR at nanomolar concentrations, although it agonizes AhR at higher concentrations (10 µM); inhibits CYP19, CYP1A1, CYP1A2, and CYP1B1 (IC50s = 500, 60, 6, and 5 nM, respectively), whereas it activates CYP3A4 (Kd = 7.4 µM)

Formal name: 2-phenyl-4H-naphtho[1,2-b]pyran-4-one

Synonyms:  7,8-Benzoflavone|NSC 407011

Molecular weight: 272.3

CAS: 604-59-1

Purity: ≥98%

Formulation: A crystalline solid

Product Type|Biochemicals|Natural Products|Flavonoids||Product Type|Biochemicals|Small Molecule Inhibitors|Cytochrome P450||Product Type|Biochemicals|Small Molecule Inhibitors|MMPs||Research Area|Toxicology|Drug Metabolism|Cytochrome P450||Research Area|Toxicology|Drug Metabolism|Xenobiotic Sensing

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