Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name azobenzene
CAS diphenyldiazene

Reference List

PubMed Abstract RScore(About this table)
1912304 Zbaida S, Levine WG: A novel application of cyclic voltammetry for direct investigation of metabolic intermediates in microsomal azo reduction. Chem Res Toxicol. 1991 Jan-Feb;4(1):82-8.

We have established that reduction of azo dyes structurally related to 4-(dimethylamino)-azobenzene (DAB) by rat liver microsomal cytochrome P-450 requires a polar electron-donating substituent on one ring.
31(0,1,1,1) Details
3312182 Degawa M, Yamada H, Hishinuma T, Masuko T, Hashimoto Y: Organ selective induction of cytochrome P-448 isozymes in the rat by 2-methoxy-4-aminoazobenzene and 3-methylcholanthrene. J Biochem. 1987 Jun;101(6):1437-45.

Male Sprague Dawley rats were injected intraperitoneally with 2-methoxy-4-amino-azobenzene (2-MeO-AAB) or 3-methylcholanthrene (MC), and then the expression of microsomal cytochrome P-450 isozymes in liver and extrahepatic tissues was investigated by means of immunological methods and a bacterial mutation test.
6(0,0,1,1) Details
8521752 Zbaida S: The mechanism of microsomal azoreduction: predictions based on electronic aspects of structure-activity relationships. Drug Metab Rev. 1995;27(3):497-516.

Anaerobic cyclic voltammograms of azobenzene derivatives verify the following points: A nonsubstrate azo dye will not exhibit a positive potential. (Several nonsubstrate hydrazobenzenes exhibited positive potentials, but in a low range 0.41-0.48 V.
A comparison between the oxidative and the reductive pathway of microsomal cytochrome P450 indicates a similarity in the first two steps in the reaction cycle, for example, substrate binding and uptake of the first electron by the cytochrome [76, 109, 110].
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2914330 Zbaida S, Stoddart AM, Levine WG: Studies on the mechanism of reduction of azo dye carcinogens by rat liver microsomal cytochrome P-450. Chem Biol Interact. 1989;69(1):61-71.

In contrast, only negligible rates were obtained for unsubstituted azobenzene (1g), hydrazobenzene (2g), p-isopropylazobenzene (1e) and 1f, the benzoylamide derivative of 1b.
3(0,0,0,3) Details
2788017 Precious WY, Barrett J: The possible absence of cytochrome P-450 linked xenobiotic metabolism in helminths. Biochim Biophys Acta. 1989 Aug 18;992(2):215-22.

P. redivivus was able to reduce 1,2-dimethyl-4-(4-carboxyphenylazo)-5-hydroxybenzene and azobenzene, which is predominantly microsomal.
2(0,0,0,2) Details
6413856 Mori Y, Niwa T, Toyoshi K: Participation of cytochrome P450 in mutagenic activation of the carcinogen 3'-hydroxymethyl-N,N-dimethyl-4-aminoazobenzene and its N-demethylated compounds by rat liver. Mutat Res. 1983 Oct;122(1):13-22.

1(0,0,0,1) Details
6807533 Hino O, Nemoto N, Nagao M, Kosugi A, Kitagawa T: Induction of drug-metabolizing enzymes in the rat liver by 3'-methyl-4-(dimethylamino) azobenzene. Cancer Lett. 1982 Feb;15(2):131-6.

Feeding of 3-Me-DAB for 3 weeks at 10, 20 and 600 ppm increased the content of hepatic microsomal cytochrome P-450 slightly (up to 27% raise) but significantly.
1(0,0,0,1) Details
102518 Danz M, Klinger W, Muller D, Kleeberg U, Glockner R, Ziebarth D, Urban H: N,N-diethyl-4-aminoazobenzene (DEAB): acute actions with respect to possible carcinogenicity as well as the role of solvents. Exp Pathol. 1978;16(1-6):245-53.

Cytochrome P-450-DEPENDENT N-demethylation of ethylmorphine and dimethylnitrosamine are differentially altered depending on the solvent used.
The excretion of DEAB as well as of N,N-dimethyl-4-amino-azobenzene (DAB) is delayed and diminished if the substances are dissolved in DMSO.
1(0,0,0,1) Details
1970775 Stoddart AM, Levine WG: Azoreduction of dimethylaminoazobenzene (DAB) in primary cultures of rat hepatocytes. Drug Metab Dispos. 1990 Jan-Feb;18(1):36-41.


This laboratory has investigated the azoreduction of the hepatocarcinogen, N,N-dimethyl-4-aminoazobenzene (DAB), by hepatic microsomal cytochrome P-450 (P-450) and its specific induction by the hypolipidemic drug, clofibrate.
1(0,0,0,1) Details
11338675 Muhlenfeld K, Langner A: Cytochrome P450 1A1 and 4A activities in isolated rat spleen lymphocytes. . Pharmazie. 2001 Apr;56(4):329-31.

In this study the activity of Cytochrome P 450 (CYP) enzymes in isolated spleen lymphocytes of Wistar rats was estimated. 7-Ethoxyresorufin-O-deethylase was analysed to determine the activity of CYP 1A1/2.
To estimate reductive activities the azoreduction of 4-(N,N-dimethyl-amino) azobenzene was analysed.
1(0,0,0,1) Details
3929790 Levine WG: Studies on microsomal azoreduction. Biochem Pharmacol. 1985 Sep 15;34(18):3259-64.

These findings suggest that microsomal azoreduction of DAB and MAB may proceed via different mechanisms, possibly through different species of cytochrome P-450 which have selective dependence upon the sulfhydryl environment.
The azoreduction of N,N-dimethyl-4-aminoazobenzene (DAB) and N-methyl-4-amino-azobenzene (MAB) by rat liver microsomes was investigated.
1(0,0,0,1) Details