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Chemical Compound Review

SureCN563335     7-phenylmethoxyphenoxazin-3- one

Synonyms: AG-H-53965, B1532_SIGMA, AC1L3GBQ, CTK8D9518, STK299141, ...
 
 
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Disease relevance of Resorufin benzyl ether

 

High impact information on Resorufin benzyl ether

 

Biological context of Resorufin benzyl ether

  • Lower IC50 values for both inhibitory phases were obtained in the case of benzyloxyresorufin O-dealkylase activity than in the case of ethoxyresorufin O-dealkylase activity, suggesting a differential susceptibility to inhibition by NO for the two O-dealkylase activities [9].
  • PB-induction of hepatic microsomes significantly increased the rate of dealkylation of long alkyl chain alkoxyresorufin ethers, benzyloxyresorufin and pentoxyresorufin 47-fold and 17-fold, respectively, but had little or no effect on short alkyl chains [10].
 

Anatomical context of Resorufin benzyl ether

  • Liver and lung microsomes from control rats differed in their activity profiles (rate of resorufin production plotted against side-chain length), showing highest activity with ethoxy- and benzyloxyresorufin respectively [11].
  • Human recombinant interleukin 6 (rhIL-6) caused a dose dependent decrease in the phenobarbital induction of benzyloxyresorufin O-deethylase activity in cultured rat hepatocytes [12].
  • Significant negative correlations between the patterns of P450-dependent 7-benzyloxyresorufin metabolism activity and cell line chemosensitivity were observed for 10 standard anticancer agents (including 6 alkylating agents) and 55 investigational compounds, suggesting a role for P450 metabolism in the inactivation of these agents [13].
  • The O-dealkylase activity measured towards 7-benzoxyresorufin, a substrate for the main cytochrome P-450 isoforms involved in the metabolism of xenobiotics, was 5 times higher in the pituitary gland than in the brain cortex [14].
  • Testosterone, ethoxyresorufin, benzyloxyresorufin and verapamil were used as substrates for cytochrome P450-catalysed oxidations and cultured cells were found to be differentiated as well as metabolically competent during cultivation [15].
 

Associations of Resorufin benzyl ether with other chemical compounds

 

Gene context of Resorufin benzyl ether

  • Benzyloxyresorufin O-dealkylase activity catalyzed by CYP2B6 was most strongly and noncompetitively inhibited (K(i) = 1.5 +/- 0.0 microM) [21].
  • In largha seals, both levels of alkoxyresorufin- (methoxy-, ethoxy-, pentoxy-, and benzyloxyresorufin) O-dealkylase (AROD) activities and proteins detected by polyclonal antibodies against rat CYP1A1 were significantly correlated with the concentrations of individual coplanar PCB congeners, total TEQs, and total PCBs [22].
  • For CYP3A4 inhibition studies, two substrates, 7-benzyloxyresorufin (BzRes) and 7-benzyloxy-4-trifluoromethyl-coumarin (BFC), were used [23].
  • However, the activities of other P450-dependent monooxygenases, namely 7-ethoxyresorufin O-deethylase (EROD), 7-benzyloxyresorufin O-debenzylase (BROD), aminopyrine N-demethylase (APND), erythromycin N-demethylase (EMND), lauric acid omega-hydroxylase (LAOH), and testosterone 7alpha-hydroxylase (T7AH) were not affected by 1,1-DCE at any dose [24].
  • 3. Phenobarbitone induced (2-6-fold) coumarin 7-hydroxylase, cortisol 6beta-hydroxylase, S-mephenytoin N-demethylase, phenoxazone hydroxylase and benzyloxyresorufin O-dealkylase activities, but not the O-dealkylations of pentoxyresorufin or other alkoxyresorufins, in monkey [25].
 

Analytical, diagnostic and therapeutic context of Resorufin benzyl ether

  • A slice perfusion chamber that mounts on the cytometer stage was developed to allow for successive measurement of region-specific P450-dependent O-dealkylation of 7-ethoxy-, 7-pentoxy-, and 7-benzyloxyresorufin (EROD, PROD, and BROD activity, respectively) in the same liver slice [26].

References

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  3. Lack of evidence for induction of CYP2B1, CYP3A23, and CYP1A2 gene expression by Panax ginseng and Panax quinquefolius extracts in adult rats and primary cultures of rat hepatocytes. Yu, C.T., Chen, J., Teng, X.W., Tong, V., Chang, T.K. Drug Metab. Dispos. (2005) [Pubmed]
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  9. Inhibition of cytochromes P450 by nitric oxide and a nitric oxide-releasing agent. Wink, D.A., Osawa, Y., Darbyshire, J.F., Jones, C.R., Eshenaur, S.C., Nims, R.W. Arch. Biochem. Biophys. (1993) [Pubmed]
  10. Effects of feeding Artemisia filifolia and Helenium flexuosum on rabbit cytochrome P450 isozymes. Eissa, F.Z., Qualls, C.W., Burrows, G.E., Lish, J.W. Veterinary and human toxicology. (1996) [Pubmed]
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  12. Effect of interleukin 6 on phenobarbital induction of cytochrome P-450IIB in cultured rat hepatocytes. Williams, J.F., Bement, W.J., Sinclair, J.F., Sinclair, P.R. Biochem. Biophys. Res. Commun. (1991) [Pubmed]
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  14. Drug metabolizing enzymes in the rat pituitary gland. Ghersi-Egea, J.F., Leininger-Muller, B., Minn, A., Siest, G. Prog. Brain Res. (1992) [Pubmed]
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  20. Substrate-dependent modulation of CYP3A4 catalytic activity: analysis of 27 test compounds with four fluorometric substrates. Stresser, D.M., Blanchard, A.P., Turner, S.D., Erve, J.C., Dandeneau, A.A., Miller, V.P., Crespi, C.L. Drug Metab. Dispos. (2000) [Pubmed]
  21. Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. Nakajima, M., Yoshida, R., Shimada, N., Yamazaki, H., Yokoi, T. Drug Metab. Dispos. (2001) [Pubmed]
  22. Hepatic microsomal cytochrome p450s and chlorinated hydrocarbons in largha and ribbon seals from Hokkaido, Japan: differential response of seal species to Ah receptor agonist exposure. Chiba, I., Sakakibara, A., Iwata, T.H., Ishizuka, M., Tanabe, S., Akahori, F., Kazusaka, A., Fujita, S. Environ. Toxicol. Chem. (2002) [Pubmed]
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