Molecular Weight: 227.22
Storage: C, L
[C=Cold D=Desiccated F=Frozen L=Light Sensitive RT=Room Temperature]
Soluble: DMSO
Molecular Formula: C13H9O3N
CAS Number: [5725-89-3]
Alternative Name: 7-Methoxyresorufin
Unit Price (USD):
5 mg $112.88
Bulk Price/unit (when you buy 5 or more): $90.30
Description:
One of the most popular substrates for analysis of microsomal dealkylase and cytochrome P450 enzymes.
Note:
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]
Application:
It produces the red fluorescent dye resorufin (EX/EM 571/585 nm) upon enzyme activity. This substrate has also been extensively used to differentiate the various isozymes of the Cytochrome P450 system.
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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