Resorufin 7-O-methyl ether

Product ID: M1166



Unit SizePriceQuantity 
5mg
$138.95
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Description

One of the most popular substrates for analysis of microsomal dealkylase and cytochrome P450 enzymes.

This CYP450 substrate produces the red fluorescent dye resorufin (EX/EM 571/585 nm) upon enzyme activity. This substrate, along with other alkyl resorufins such as the ethyl and benzyl ethers (Product M1209) has also been extensively used to differentiate the various isozymes of the Cytochrome P450 system. O-Dealkylations of resorufin and coumarin ethers are mediated by microsomal cytochrome P450 mono-oxygenases from animals, plants and microorganisms.

Technical Data
SKU M1166
CAS Number 5725-89-3
Unit Size 5mg
Alternative Names 7-Methoxyresorufin; Resorufin methyl ether
Detection Method Fluorescence
Molecular Formula C₁₃H₉O₃N
Molecular Weight 227.22
Soluble In DMSO
Storage Conditions 2-8C, Protect From Light
Notes The cytochome P450's are a large group of monooxygenase enzymes responsible for the metabolism of toxins in the body. These enzymes, requiring NADPH as a cofactor and O2 as co-substrate, are located in the endoplasmic reticulum and are highly concentrated in the liver and small intestine. Additionally, Cytochrome P450's are also found in the mitochondrial membrane. P450 enzymes encompass a highly diverse "superfamily" of hemoproteins, and metabolic oxidation of chemical compounds is the main function of the cytochrome-mediated monooxygenase or mixed-function oxidase system. Cytochrome P450 is also used as a marker for the endoplasmic reticulum. The active site of cytochrome P450 contains the catalyst heme (iron-porphyrin) with a sulfur of cysteine serving as the fifth iron ligand. Although these enzymes typically have a low turnover rate, their intracellular activity can be monitored using fluorogenic alkyl ether derivatives of fluorophores including resorufin. Ex = 463 nm [EX/EM 571/585 nm of resorufin enzymatic product]

References and Citations

References:

  • "Evaluation of alkoxyresorufins as fluorescent substrates for cytochrome P450 BM3 and site-directed mutants." Lussenburg, Barbara M. A.; Babel, Lloyd C.; Vermeulen, Nico P. E.; Commandeur, Jan N. M. Analytical Biochemistry 341(1): 148-155 (2005).
  • "In vivo induction for enhanced function of isolated hepatocytes." Sullivan, Susan J.; Gregory, Paul G.; Dimilla, Paul A. PCT Int. Appl. : 18pp (2002).
  • "In vivo O-dealkylation of resorufin and coumarin ethers by the green alga Chlorella fusca analyzed by a rapid and sensitive high-performance liquid chromatographic assay." Thies, Frank; Grimme, L. Horst. Journal of Chromatography 684(1): 168-73 (1994).
  • "7-Alkoxyquinolines: new fluorescent substrates for cytochrome P450 monooxygenases." Mayer, Richard T.; Netter, Karl J.; Heubel, Friedrich; Hahnemann, Birger; Buchheister, Armin; Mayer, G. Klitschka; Burke, M. D. Biochemical Pharmacology. 40(7): 1645-55 (1990).
  • "Methoxyresorufin as a substrate for the fluorometric assay of insect microsomal O-dealkylases." Mayer, Richard T.; Jermyn, John W.; Burke, M. Danny; Prough, Russell A. Pesticide Biochemistry and Physiology 7(4): 349-54 (1977).
  • Sugihara K., Kitamura S., Yamada T., Okayama T., Ohta S., Yamashita K., Yasuda M., Fujii-Kuriyama Y., Saeki K., Matsui S., Matsuda T., (2004) "Aryl hydrocarbon receptor-mediated induction of microsomal drug-metabolizing enzyme activity by indirubin and indigo." Biochem Biophys Res Commun. 318(2): 571-578.
  • Haasch M.L., Graf W.K., Quardokus E.M., Mayer R.T., Lech J.J (1994) "Use of 7-alkoxyphenoxazones, 7-alkoxycoumarins and 7-alkoxyquinolines as fluorescent substrates for rainbow trout hepatic microsomes after treatment with various inducers." Biochem Pharmacol 47: 893-903.
  • Nerurkar P.V., Park S.S. Thomas P.E., Nims R.W., Lubet R.A., (1993) "Methoxyresorufin and benzyloxyresorufin: substrates preferentially metabolized by cytochromes P4501A2 and 2B, respectively, in the rat and mouse." Biochem. Pharmacol. 46: 933-943.
  • Wolf C.R., Seilman S., Oesch F., Mayer R.T., Burke M.D., (1986) "Multiple forms of cytochrome P-450 related to forms induced marginally by phenobarbital. Differences in structure and in the metabolism of alkoxyresorufins." Biochem. J. 240: 27-33.
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