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Chemical Compound Review

Resorufin     7-hydroxyphenoxazin-3-one

Synonyms: Resorufine, SureCN8066, AG-G-36231, CHEBI:51602, ANW-43856, ...
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Disease relevance of Resorufin


High impact information on Resorufin

  • Additionally, we report a better refined structure of the HslVU complex crystallized along with resorufin-labeled casein [6].
  • Staining of fresh liver slices with resorufin beta-glucoside revealed that cytosolic beta-glucosidase is expressed in all hepatocytes, with no significant portal-central gradient [7].
  • Determination of specific activity of beta-galactosidase using resorufin-beta-galactopyranoside as substrate in homogenates of whole embryos heterozygous for the human c-myc/lac Z transgene demonstrates significantly elevated beta-galactosidase activity over control embryos in day 11 and day 14 embryos [8].
  • The principle of this method is based on the resorufin reductase activity of NQO1 [9].
  • Both CYPIA1 and CYPIIB6 P450 isozymes were determined to be functional with the fluorescent resorufin assay [10].

Biological context of Resorufin

  • In the absence of cofactor, the rate-limiting step in the hydrolysis of resorufin acetate and of PNP acetate is hydrolysis of the common acetyl-enzyme, as shown by the observation of bursts of chromophoric product and very similar values of kcat [11].
  • Reaction kinetics were obtained by varying the concentration of substrate on-chip and monitoring the production of resorufin using laser-induced fluorescence [12].
  • In the presence of NAD+ or NADH, however, the deacylation step with resorufin acetate is greatly accelerated until acylation seems to become rate-limiting, because no burst is seen under these conditions [11].
  • Resorufin derivatives dealkylation specific activities were higher in brain microsomal fractions than in hepatic ones in all the six regions examined when results were expressed per cytochrome P450 content [13].
  • In contrast, resorufin and 4-hydroxy-ifosfamide assays revealed that CYP2B1 activity was up to 10-fold reduced in CPR/CYP2B1 cotransfected HEK293 cells as compared to cells transfected with the CYP2B1 expression plasmid alone [14].

Anatomical context of Resorufin


Associations of Resorufin with other chemical compounds

  • The first reaction involved the horseradish peroxidase-catalyzed reaction between hydrogen peroxide and N-acetyl-3,7-dihydroxyphenoxazine (amplex red) to yield fluorescent resorufin, and the second the beta-galactosidase-catalyzed reaction of nonfluorescent resorufin-beta-D-galactopyranoside to yield D-galactose and fluorescent resorufin [19].
  • Cells were at least 99.9% pure as assessed by cell counting using specific markers for hepatocytes (resorufin O-glucoside) and Kupffer cells (FITC-labelled latex beads) [20].
  • The kinetics of NADPH consumption, PRF utilization, NADP and resorufin formation was monitored at lambda(max) of 338, 484, 260 and 572 nm, respectively [21].
  • Lipase activity was indicated by the hydrolysis of the artificial triglyceride 1,2-O-dilauryl-rac-glycero-3-glutaric acid resorufin ester [22].
  • At 1-5 microM concentrations at physiological pH, the redox cycling of ethoxy- and pentoxyresorufin was shown to be far more efficient than the redox cycling of their product from the cytochrome P-450 dependent O-dealkylation, resorufin (7-hydroxyphenoxazone) [23].

Gene context of Resorufin

  • Activity of cytochrome CYP1A1 was analysed by conversion of hydroxyresorufin to resorufin [24].
  • E. purpurea demonstrated mild inhibition of CYP3A4 activity with 7- benzyloxy-4-trifluoromethylcoumarin (BFC) as the model substrate, but mild inducing effects in the presence of the model substrate resorufin benzyl ether (BzRes) [25].
  • For the O-alkyl ethers of resorufin, rates of metabolism (per nmol P450) were affected differently in B6 and D2 by BeP pretreatment [26].
  • The O-deethylation of ethoxyresorufin to resorufin was used to measure CYP1B1 activity in RCC [27].
  • Increased CYPOR activity impaired the CYP1A2-dependent fluorometric resorufin assay, presumably by conversion of the 7-alkoxyresorufins and resorufin to their one-electron-reduced semiquinoneimine forms [28].

Analytical, diagnostic and therapeutic context of Resorufin


  1. Directed evolution of an esterase from Pseudomonas fluorescens. Random mutagenesis by error-prone PCR or a mutator strain and identification of mutants showing enhanced enantioselectivity by a resorufin-based fluorescence assay. Henke, E., Bornscheuer, U.T. Biol. Chem. (1999) [Pubmed]
  2. Use of resorufin-labelled N-glycopeptide in a high-performance liquid chromatography assay to monitor endoglycosidase activities during cultivation of Flavobacterium meningosepticum. Bourgerie, S., Karamanos, Y., Berger, S., Julien, R. Glycoconj. J. (1992) [Pubmed]
  3. Assessment of the potential irritation and photoirritation of novel amino acid-based surfactants by in vitro methods as alternative to the animal tests. Benavides, T., Martínez, V., Mitjans, M., Infante, M.R., Moran, C., Clapés, P., Clothier, R., Vinardell, M.P. Toxicology (2004) [Pubmed]
  4. Assessment of primary eye and skin irritants by in vitro cytotoxicity and phototoxicity models: an in vitro approach of new arginine-based surfactant-induced irritation. Benavides, T., Mitjans, M., Martínez, V., Clapés, P., Infante, M.R., Clothier, R.H., Vinardell, M.P. Toxicology (2004) [Pubmed]
  5. Isolation, partial purification, and characterization of the cytochrome P-450-dependent monooxygenase system from the midgut of the earthworm Lumbricus terrestris. Berghout, A.G., Wenzel, E., Büld, J., Netter, K.J. Comp. Biochem. Physiol. C, Comp. Pharmacol. Toxicol. (1991) [Pubmed]
  6. Mutational studies on HslU and its docking mode with HslV. Song, H.K., Hartmann, C., Ramachandran, R., Bochtler, M., Behrendt, R., Moroder, L., Huber, R. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  7. Expression of cytosolic beta-glucosidase in guinea pig liver cells. Hays, W.S., Wheeler, D.E., Eghtesad, B., Glew, R.H., Johnston, D.E. Hepatology (1998) [Pubmed]
  8. Expression of beta-galactosidase under the control of the human c-myc promoter in transgenic mice is inhibited by mithramycin. Jones, D.E., Cui, D.M., Miller, D.M. Oncogene (1995) [Pubmed]
  9. Human NAD(P)H:quinone oxidoreductase inhibition by flavonoids in living cells. Lee, Y.Y., Westphal, A.H., de Haan, L.H., Aarts, J.M., Rietjens, I.M., van Berkel, W.J. Free Radic. Biol. Med. (2005) [Pubmed]
  10. Characterization of the A549 cell line as a type II pulmonary epithelial cell model for drug metabolism. Foster, K.A., Oster, C.G., Mayer, M.M., Avery, M.L., Audus, K.L. Exp. Cell Res. (1998) [Pubmed]
  11. Studies of the esterase activity of cytosolic aldehyde dehydrogenase with resorufin acetate as substrate. Kitson, T.M., Kitson, K.E. Biochem. J. (1997) [Pubmed]
  12. Microchip device for performing enzyme assays. Hadd, A.G., Raymond, D.E., Halliwell, J.W., Jacobson, S.C., Ramsey, J.M. Anal. Chem. (1997) [Pubmed]
  13. Distribution of cytochrome P450 activities towards alkoxyresorufin derivatives in rat brain regions, subcellular fractions and isolated cerebral microvessels. Perrin, R., Minn, A., Ghersi-Egea, J.F., Grassiot, M.C., Siest, G. Biochem. Pharmacol. (1990) [Pubmed]
  14. Cytochrome P450 reductase dependent inhibition of cytochrome P450 2B1 activity: Implications for gene directed enzyme prodrug therapy. Lengler, J., Omann, M., Düvier, D., Holzmüller, H., Gregor, W., Salmons, B., Günzburg, W.H., Renner, M. Biochem. Pharmacol. (2006) [Pubmed]
  15. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Burke, M.D., Thompson, S., Weaver, R.J., Wolf, C.R., Mayer, R.T. Biochem. Pharmacol. (1994) [Pubmed]
  16. NAD(P)H: quinone oxidoreductase (DT-diaphorase) in chick embryo liver. Comparison to activity in rat and guinea pig liver and differences in co-induction with 7-ethoxyresorufin deethylase by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Spencer, C.B., Rifkind, A.B. Biochem. Pharmacol. (1990) [Pubmed]
  17. Phase I and II biotransformations in living CaCo 2 cells cultivated under serum-free conditions. Selective apical excretion of reaction products. Sergent-Engelen, T., Delistrie, V., Schneider, Y.J. Biochem. Pharmacol. (1993) [Pubmed]
  18. Hormone stimulated steroid biosynthesis in granulosa cells studied with a fluorogenic probe for cytochrome P-450SCC. Asem, E.K., Simpson, D.J., Marrone, B.L. J. Steroid Biochem. Mol. Biol. (1992) [Pubmed]
  19. Measurement of enzyme kinetics using a continuous-flow microfluidic system. Seong, G.H., Heo, J., Crooks, R.M. Anal. Chem. (2003) [Pubmed]
  20. Peroxisome proliferators do not increase DNA synthesis in purified rat hepatocytes. Parzefall, W., Berger, W., Kainzbauer, E., Teufelhofer, O., Schulte-Hermann, R., Thurman, R.G. Carcinogenesis (2001) [Pubmed]
  21. A novel approach to study the activity and stoichiometry simultaneously for microsomal pentoxyresorufin-O-dealkylase reaction. Rastogi, S., Das, M., Khanna, S.K. FEBS Lett. (2002) [Pubmed]
  22. Mycoplasma hyopneumoniae p65 surface lipoprotein is a lipolytic enzyme with a preference for shorter-chain fatty acids. Schmidt, J.A., Browning, G.F., Markham, P.F. J. Bacteriol. (2004) [Pubmed]
  23. Experimental and theoretical study on the redox cycling of resorufin by solubilized and membrane-bound NADPH-cytochrome reductase. Balvers, W.G., Boersma, M.G., Vervoort, J., Rietjens, I.M. Chem. Res. Toxicol. (1992) [Pubmed]
  24. The use of Yarrowia lipolytica for the expression of human cytochrome P450 CYP1A1. Nthangeni, M.B., Urban, P., Pompon, D., Smit, M.S., Nicaud, J.M. Yeast (2004) [Pubmed]
  25. Analysis of the inhibitory potential of Ginkgo biloba, Echinacea purpurea, and Serenoa repens on the metabolic activity of cytochrome P450 3A4, 2D6, and 2C9. Yale, S.H., Glurich, I. Journal of alternative and complementary medicine (New York, N.Y.) (2005) [Pubmed]
  26. Benzo[e]pyrene elicits changes in the biochemical activities and chromatographic behavior of murine hepatic cytochromes P-450 that are distinct from those induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Gibbons, J.A., Babish, J.G. Chem. Biol. Interact. (1992) [Pubmed]
  27. Cytochrome P450 CYP1B1 activity in renal cell carcinoma. McFadyen, M.C., Melvin, W.T., Murray, G.I. Br. J. Cancer (2004) [Pubmed]
  28. Stable expression and coexpression of human cytochrome P450 oxidoreductase and cytochrome P450 1A2 in V79 Chinese hamster cells: sensitivity to quinones and biotransformation of 7-alkoxyresorufins and triazines. Schmalix, W.A., Lang, D., Schneider, A., Bocker, R., Greim, H., Doehmer, J. Drug Metab. Dispos. (1996) [Pubmed]
  29. O2 delivery and redox state are determinants of compartment-specific reactive O2 species in myocardial reperfusion. Stoner, J.D., Clanton, T.L., Aune, S.E., Angelos, M.G. Am. J. Physiol. Heart Circ. Physiol. (2007) [Pubmed]
  30. Evidence of two enzymes performing the de-N-glycosylation of proteins in barley: expression during germination, localization within the grain and set-up during grain formation. Vuylsteker, C., Cuvellier, G., Berger, S., Faugeron, C., Karamanos, Y. J. Exp. Bot. (2000) [Pubmed]
  31. Enhanced cytochrome P450 IA1 activity of self-assembled rat hepatocyte spheroids. Wu, F.J., Friend, J.R., Remmel, R.P., Cerra, F.B., Hu, W.S. Cell transplantation. (1999) [Pubmed]
  32. Effect of oral administration of clinically relevant doses of dexamethasone on regulation of cytochrome P450 subfamilies in hepatic microsomes from dogs and rats. Zhang, K., Kuroha, M., Shibata, Y., Kokue, E., Shimoda, M. Am. J. Vet. Res. (2006) [Pubmed]
  33. Real-time fluorescence analysis on molecular mechanisms for regulation of cytochrome P450scc activity upon steroidogenic stimulation in adrenocortical cells. Homma, R., Kimoto, T., Niimura, Y., Krivosheev, A., Hara, T., Ohta, Y., Kawato, S. J. Inorg. Biochem. (2000) [Pubmed]
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