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Chemical Compound Review

SureCN345862     5-prop-1-enylbenzo[1,3]dioxole

Synonyms: AG-E-26684, AG-F-43375, KBioGR_001735, KBioSS_001767, DSSTox_CID_767, ...
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Disease relevance of C10472


High impact information on C10472

  • Cytochrome P-450 isoform d was induced by TCDD, isosafrole, phenothiazine, and AAF, while cytochrome P-450 isoform b was induced by phenobarbital, and to a lesser extent by isosafrole [4].
  • In contrast, comparison of isozyme 4 with rat cytochrome P-450d, which is also induced by isosafrole and for which the sequence has recently been deduced from cDNA [Kawajiri, K., Gotoh, O., Sogawa, K., Tagashira, Y., Muramatsu, M. & Fujii-Kuriyama, Y. (1984) Proc. Natl. Acad. Sci. USA 81, 1649-1653], showed about 70% homology [5].
  • In contrast, phenobarbital- and isosafrole-induced microsomes had Vmax values of 2.5 and 1.2 nmol/min/mg protein and Km values of 590 and 134 microM, respectively [6].
  • The sensitivity of the P2-450 induction process to isosafrole is inherited as an autosomal additive trait; studies of offspring from the C57BL/6N(DBA/N)F1 X DBA/2N backcross confirm involvement of the Ah locus or s closely segregating gene [7].
  • Mouse "cytochrome P2-450" is defined as that form of isosafrole-induced P-450 in DBA/2N liver most specifically correlated with isosafrole metabolism [7].

Biological context of C10472

  • The transformation kinetics of SO-ABZ to SO2-ABZ in microsomes from rats treated with ABZ, 3-methylcholanthrene, Aroclor and isosafrole were biphasic [8].
  • The rates of dealkylation of the alkoxyphenoxazones by ISF-treated microsomes occurred in the following order: methoxy > ethoxy > propoxy > benzxyloxy > butoxy > pentoxy [9].
  • Musk xylene and isosafrole increased more efficiently the metabolic activation of 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1) to mutagen than that of benzo(a)pyrene [10].
  • In order to elucidate the isozyme specificity of complex formation between cytochrome P-450 and the isosafrole metabolite the effect of complex dissociation on different steroid hydroxylation pathways was studied in hepatic microsomal fractions [11].
  • Mouse liver cytochrome P2-450 is defined as the major isosafrole-inducible form of P-450 which is most specific for isosafrole metabolism. lambda AhP-1 represents a 15.5 X 10(3)-base-pair segment of mouse genomic DNA having the cytochrome P1-450 gene (approximately equal to 4600 base pairs) located in the middle portion [12].

Anatomical context of C10472


Associations of C10472 with other chemical compounds

  • Utilizing the RIAs, both forms of cytochrome P-448 were found in significant quantities in liver microsomes of rats treated with 3-MC, 3,4,5-HCB, isosafrole, and Aroclor 1254 but only in minute concentrations in untreated and phenobarbital-treated rats [16].
  • Aroclor 1254 completely inhibited the cytochrome P-450d-dependent estradiol 2-hydroxylase activity of butanol-treated microsomes from isosafrole-treated rats [1].
  • DEX treatment resulted in a significant elevation of pentoxyphenoxazone metabolism (about a 144-fold increase) compared with microsomes induced by beta-NF (11-fold) and ISF (37-fold) [9].
  • By use of 2-naphthylamine, whose N-oxidation was known to be selectively catalyzed by rat cytochrome P-450ISF-G (P-450IA2), and hepatic microsomes from isosafrole-treated rats, each of these ethynyl derivatives was found to be strongly inhibitory at concentrations of 1 and 10 microM [17].
  • Identical results were obtained by in-vivo treatment of rats with four inducers of P450 1A enzymes, namely, beta-naphthoflavone, isosafrole, Arochlor 1254, and 3-methylcholanthrene [18].

Gene context of C10472


Analytical, diagnostic and therapeutic context of C10472


  1. Inhibition of 2-aminofluorene mutagenesis in bacteria by inducers of cytochrome P-450d. Miller, D.M., Aust, A.E., Voorman, R., Aust, S.D. Carcinogenesis (1988) [Pubmed]
  2. Genotoxicity of safrole-related chemicals in microbial test systems. Sekizawa, J., Shibamoto, T. Mutat. Res. (1982) [Pubmed]
  3. Evidence for the involvement of CYP1A2 in the metabolism of bromodichloromethane in rat liver. Allis, J.W., Anderson, B.P., Zhao, G., Ross, T.M., Pegram, R.A. Toxicology (2002) [Pubmed]
  4. Coinduction of MDR-1 multidrug-resistance and cytochrome P-450 genes in rat liver by xenobiotics. Burt, R.K., Thorgeirsson, S.S. J. Natl. Cancer Inst. (1988) [Pubmed]
  5. On the amino acid sequence of cytochrome P-450 isozyme 4 from rabbit liver microsomes. Fujita, V.S., Black, S.D., Tarr, G.E., Koop, D.R., Coon, M.J. Proc. Natl. Acad. Sci. U.S.A. (1984) [Pubmed]
  6. Role of P450IIE1 in the metabolism of 3-hydroxypyridine, a constituent of tobacco smoke: redox cycling and DNA strand scission by the metabolite 2,5-dihydroxypyridine. Kim, S.G., Novak, R.F. Cancer Res. (1990) [Pubmed]
  7. Isosafrole-induced cytochrome P2-450 in DBA/2N mouse liver. Characterization and genetic control of induction. Ohyama, T., Nebert, D.W., Negishi, M. J. Biol. Chem. (1984) [Pubmed]
  8. Albendazole sulfonation by rat liver cytochrome P-450c. Souhaili-El Amri, H., Mothe, O., Totis, M., Masson, C., Batt, A.M., Delatour, P., Siest, G. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
  9. Use of 7-alkoxyphenoxazones, 7-alkoxycoumarins and 7-alkoxyquinolines as fluorescent substrates for rainbow trout hepatic microsomes after treatment with various inducers. Haasch, M.L., Graf, W.K., Quardokus, E.M., Mayer, R.T., Lech, J.J. Biochem. Pharmacol. (1994) [Pubmed]
  10. Induction of cytochrome P450 1A2 by musk analogues and other inducing agents in rat liver. Iwata, N., Suzuki, K., Minegishi, K., Kawanishi, T., Hara, S., Endo, T., Takahashi, A. Eur. J. Pharmacol. (1993) [Pubmed]
  11. Selective reactivation of steroid hydroxylases following dissociation of the isosafrole metabolite complex with rat hepatic cytochrome P-450. Murray, M., Zaluzny, L., Farrell, G.C. Arch. Biochem. Biophys. (1986) [Pubmed]
  12. Characterization of cytochrome P2-450 (20-S) mRNA. Association with the P1-450 genomic gene and differential response to the inducers 3-methylcholanthrene and isosafrole. Ikeda, T., Altieri, M., Chen, Y.T., Nakamura, M., Tukey, R.H., Nebert, D.W., Negishi, M. Eur. J. Biochem. (1983) [Pubmed]
  13. Induction of cytochrome P-450 in cultured rat hepatocytes. The heterogeneous localization of specific isoenzymes using immunocytochemistry. Bars, R.G., Mitchell, A.M., Wolf, C.R., Elcombe, C.R. Biochem. J. (1989) [Pubmed]
  14. Regulation of cytochrome P450IA1 gene expression in a human intestinal cell line, Caco-2. Boulenc, X., Bourrie, M., Fabre, I., Roque, C., Joyeux, H., Berger, Y., Fabre, G. J. Pharmacol. Exp. Ther. (1992) [Pubmed]
  15. Cytochrome P450 1A1 cDNA from plaice (Pleuronectes platessa) and induction of P450 1A1 mRNA in various tissues by 3-methylcholanthrene and isosafrole. Leaver, M.J., Pirrit, L., George, S.G. Mol. Marine Biol. Biotechnol. (1993) [Pubmed]
  16. Immunochemical evidence for two 3-methylcholanthrene-inducible forms of cytochrome P-448 in rat liver microsomes using a double-antibody radioimmunoassay procedure. Luster, M.I., Lawson, L.D., Linko, P., Goldstein, J.A. Mol. Pharmacol. (1983) [Pubmed]
  17. 2-ethynylnaphthalene as a mechanism-based inactivator of the cytochrome P-450 catalyzed N-oxidation of 2-naphthylamine. Hammons, G.J., Alworth, W.L., Hopkins, N.E., Guengerich, F.P., Kadlubar, F.F. Chem. Res. Toxicol. (1989) [Pubmed]
  18. Both cytochromes P450 2E1 and 1A1 are involved in the metabolism of chlorzoxazone. Carriere, V., Goasduff, T., Ratanasavanh, D., Morel, F., Gautier, J.C., Guillouzo, A., Beaune, P., Berthou, F. Chem. Res. Toxicol. (1993) [Pubmed]
  19. 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]
  20. Identification of cytochrome P450 isoform involved in the metabolism of YM992, a novel selective serotonin re-uptake inhibitor, in human liver microsomes. Noguchi, K., Mera, A., Watanabe, T., Higuchi, S., Chiba, K. Xenobiotica (2000) [Pubmed]
  21. Amino-terminal and carboxy-terminal sequence of hepatic microsomal cytochrome P-450d, a unique hemoprotein from rats treated with isosafrole. Botelho, L.H., Ryan, D.E., Yuan, P.M., Kutny, R., Shively, J.E., Levin, W. Biochemistry (1982) [Pubmed]
  22. Complementary DNA sequence of 3-methylcholanthrene-inducible P-450 from the rat lung. Kikuchi, H., Sagami, I., Fujii, H., Ohmachi, T., Watanabe, M. Tohoku J. Exp. Med. (1990) [Pubmed]
  23. Cytochrome P450 mediated bioactivation of methyleugenol to 1'-hydroxymethyleugenol in Fischer 344 rat and human liver microsomes. Gardner, I., Wakazono, H., Bergin, P., de Waziers, I., Beaune, P., Kenna, J.G., Caldwell, J. Carcinogenesis (1997) [Pubmed]
  24. Comparison of primary structures deduced from cDNA nucleotide sequences for various forms of liver microsomal cytochrome P-450 from phenobarbital-treated rabbits. Imai, Y., Komori, M., Sato, R. Biochemistry (1988) [Pubmed]
  25. Polypeptide patterns of hepatic microsomes from Long-Evans rats treated with different xenobiotics. Vlasuk, G.P., Ryan, D.E., Thomas, P.E., Levin, W., Walz, F.G. Biochemistry (1982) [Pubmed]
  26. Use of monoclonal antibody probes against rat hepatic cytochromes P-450c and P-450d to detect immunochemically related isozymes in liver microsomes from different species. Thomas, P.E., Reidy, J., Reik, L.M., Ryan, D.E., Koop, D.R., Levin, W. Arch. Biochem. Biophys. (1984) [Pubmed]
  27. The influence of age on the inducibility of rat liver cytochrome P450IA1 (CYPIA1) and P450IA2 (CYPIA2) mRNAs. Horbach, G.J., Van Asten, J.G., Van Bezooijen, C.F. Mutat. Res. (1990) [Pubmed]
  28. The primary structure of cytochrome P-450d purified from rat liver microsomes: prediction of helical regions and domain analysis. Haniu, M., Ryan, D.E., Levin, W., Shively, J.E. Arch. Biochem. Biophys. (1986) [Pubmed]
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