A flavone that modulates xenobiotic metabolism
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Isomer(s)
34040β-Naphthoflavone
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α-Naphthoflavone

Item No. 16924

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-phenyl-4H-naphtho[1,2-b]pyran-4-one
CAS Number
604-59-1
Synonyms
  • 7,8-Benzoflavone
  • NSC 407011
Molecular Formula
C19H12O2
Formula Weight
272.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:4): 0.1 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
225, 280, 344 nm
SMILES
O=C1C2=C(C(C=CC=C3)=C3C=C2)OC(C4=CC=CC=C4)=C1
InChi Code
InChI=1S/C19H12O2/c20-17-12-18(14-7-2-1-3-8-14)21-19-15-9-5-4-6-13(15)10-11-16(17)19/h1-12H
InChi Key
VFMMPHCGEFXGIP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $32

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    5 g

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    10 g

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    25 g

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    Product Description

    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 CYP1A2.1 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).2,3 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).4,5,6 Dietary α-naphthoflavone can contribute to carcinogenesis in the presence of synthetic estrogens.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Denison, M.S., and Nagy, S.R. Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 43, 309-334 (2003).

    2. Smith, K.J., Murray, I.A., Tanos, R., et al. Identification of a high-affinity ligand that exhibits complete aryl hydrocarbon receptor antagonism. J. Pharmacol. Exp. Ther. 338(1), 318-327 (2011).

    3. Wilhelmsson, A., Whitelaw, M.L., Gustafsson, J.A., et al. Agonistic and antagonistic effects of α-naphthoflavone on dioxin receptor function. Role of the basic region helix-loop-helix dioxin receptor partner factor Arnt. The Journal of Biological Chemisty 269(29), 19028-19033 (1994).

    4. Bruno, R.D., and Njar, V.C.O. Targeting cytochrome P450 enzymes: A new approach in anti-cancer drug development. Bioorg. Med. Chem. 15(15), 5047-5060 (2007).

    5. Campbell, D.R., and Kurzer, M.S. Flavonoid inhibition of aromatase enzyme activity in human preadipocytes. J. Steroid Biochem. Mol. Biol. 46(3), 381-388 (1993).

    6. Sineva, E.V., Rumfeldt, J.A.O., Halpert, J.R., et al. A large-scale allosteric transition in cytochrome P450 3A4 revealed by luminescence resonance energy transfer (LRET). PLoS One 8(12), 1-13 (2013).

    7. Metzler, M., Blaich, G., and Tritscher, A.M. Role of metabolic activation in the carcinogenicity of estrogens: Studies in an animal liver tumor model. Environ. Health Perspect. 88, 117-121 (1990).