A fluorogenic substrate for, and inhibitor of, CYP1A1
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7-Ethoxyresorufin

Item No. 16122

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-ethoxy-3H-phenoxazin-3-one
CAS Number
5725-91-7
Synonyms
  • 7-ER
  • 7-Ethoxyphenoxazone
  • Resorufin ethyl ether
Molecular Formula
C14H11NO3
Formula Weight
241.2
Purity
≥95%
Emission
570 nm
Excitation
580 nm
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMF: SolubleDMSO: Soluble
SMILES
O=C1C=CC2=NC(C=CC(OCC)=C3)=C3OC2=C1
InChi Code
InChI=1S/C14H11NO3/c1-2-17-10-4-6-12-14(8-10)18-13-7-9(16)3-5-11(13)15-12/h3-8H,2H2,1H3
InChi Key
CRCWUBLTFGOMDD-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    10 mg

    $190

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    Product Description

    7-Ethoxyresorufin (7-ER) is a fluorogenic substrate for, and competitive inhibitor of, the cytochrome P450 (CYP) isoform CYP1A1 (IC50 = 0.1 µM).1,2,3 Upon enzymatic cleavage by CYP1A1, resorufin is released and its fluorescence can be used to quantify CYP1A1 activity. Resorufin displays excitation/emission maxima of 570/580 nm, respectively.4 7-ER has been used in the study of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) metabolism and the mechanisms of vasodilation.5,6 7-ER is a noncompetitive inhibitor of neuronal nitric oxide synthase (nNOS; Ki = 0.76 µM).7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dutton, D.R., Reed, G.A., and Parkinson, A. Redox cycling of resorufin catalyzed by rat liver microsomal NADPH-cytochrome P450 reductase. Arch. Biochem. Biophys. 268(2), 605-616 (1989).

    2. Bourrié, M., Meunier, V., Berger, Y., et al. Cytochrome P450 isoform inhibitors as a tool for the investigation of metabolic reactions catalyzed by human liver microsomes. J. Pharmacol. Exp. Ther. 277(1), 321-332 (1996).

    3. Tassaneeyakul, W., Birkett, D.J., Veronese, M.E., et al. Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J. Pharmacol. Exp. Ther. 265(1), 401-407 (1993).

    4. Hofmann, J., and Sernetz, M. Immobilized enzyme kinetics analyzed by flow-through microfluorimetry: Resorufin-β-D-galactopyranoside as a new fluorogenic substrate for β-galactosidase. Anal. Chim. Acta 163, 67-72 (1984).

    5. Labitzke, E.M., Diani-Moore, S., and Rifkind, A.B. Mitochondrial P450-dependent arachidonic acid metabolism by TCDD-induced hepatic CYP1A5; conversion of EETs to DHETs by mitochondrial soluble epoxide hydrolase. Arch. Biochem. Biophys. 468(1), 70-81 (2007).

    6. Imig, J.D., Zou, A.P., de Montellano, P.R.O., et al. Cytochrome P-450 inhibitors alter afferent arteriolar responses to elevations in pressure. Am. J. Physiol. 266(5 Pt 2), H1879-H1885 (1994).

    7. Li, C.G., and Rand, M.J. Inhibition of NO-medicate responses by 7-ethoxyresorufin, a substrate and competitive inhibitor of cytochrome P450. Br. J. Pharmacol. 118(1), 57-62 (1996).

    8. Jiang, H.B., and Ichikawa, Y. Neuronal nitric oxide synthase catalyzes the reduction of 7-ethoxyresorufin. Life Sci. 65(12), 1257-1264 (1999).