Requirements for cytochrome b5 in the oxidation of 7-ethoxycoumarin, chlorzoxazone, aniline, and N-nitrosodimethylamine by recombinant cytochrome P450 2E1 and by human liver microsomes

Biochem Pharmacol. 1996 Jul 26;52(2):301-9. doi: 10.1016/0006-2952(96)00208-0.

Abstract

NADH-dependent 7-ethoxycoumarin O-deethylation activities could be reconstituted in systems containing cytochrome b5 (b5), NADH-b5 reductase, and bacterial recombinant P450 2E1 in 100 mM potassium phosphate buffer (pH 7.4) containing a synthetic phospholipid mixture and cholate. Replacement of NADH-b5 reductase with NADPH-P450 reductase yielded a 4-fold increase in 7-ethoxycoumarin O-deethylation activity, and further stimulation (approximately 1.5-fold) could be obtained when NADPH was used as an electron donor. Removal of b5 from the NADH- and NADPH-supported systems caused a 90% loss of 7-ethoxycoumarin O-deethylation activities in the presence of NADPH-P450 reductase, but resulted in complete loss of the activities in the absence of NADPH-P450 reductase. Km values were increased and Vmax values were decreased for 7-ethoxycoumarin O-deethylation when b5 was omitted from the NADPH-supported P450 2E1-reconstituted systems. Requirements for b5 in P450 2E1 systems were also observed in chlorzoxazone 6-hydroxylation, aniline p-hydroxylation, and N-nitrosodimethylamine N-demethylation. In human liver microsomes, NADH-dependent 7-ethoxycoumarin O-deethylation, chlorzoxazone 6-hydroxylation, aniline p-hydroxylation, and N-nitrosodimethylamine N-demethylation activities were found to be about 55, 41, 33, and 50%, respectively, of those catalyzed by NADPH-supported systems. Anti-rat NADPH-P450 reductase immunoglobulin G inhibited 7-ethoxycoumarin O-deethylation activity catalyzed by human liver microsomes more strongly in NADPH- than NADH-supported reactions, while anti-human b5 immunoglobulin G inhibited microsomal activities in both NADH- and NADPH-supported systems to similar extents. These results suggest that b5 is an essential component in P450 2E1-catalyzed oxidations of several substrates used, that about 10% of the activities occur via P450 2E1 reduction by NADPH-P450 reductase in the absence of b5, and that the NADH-supported system contributes, in part, to some reactions catalyzed by P450 2E1 in human liver microsomes.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aniline Compounds / metabolism*
  • Chlorzoxazone / metabolism*
  • Coumarins / metabolism*
  • Cytochrome P-450 CYP1A2
  • Cytochrome P-450 CYP2E1
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Enzyme System / metabolism*
  • Cytochromes b5 / antagonists & inhibitors
  • Cytochromes b5 / metabolism*
  • Dimethylnitrosamine / metabolism*
  • Humans
  • Kinetics
  • Microsomes, Liver / metabolism*
  • NADH, NADPH Oxidoreductases / metabolism
  • NADPH-Ferrihemoprotein Reductase
  • Oxidation-Reduction
  • Oxidoreductases / metabolism
  • Oxidoreductases, N-Demethylating / antagonists & inhibitors
  • Oxidoreductases, N-Demethylating / metabolism*
  • Recombinant Proteins / metabolism

Substances

  • Aniline Compounds
  • Coumarins
  • Cytochrome P-450 Enzyme Inhibitors
  • Recombinant Proteins
  • 7-ethoxycoumarin
  • Cytochromes b5
  • Cytochrome P-450 Enzyme System
  • Oxidoreductases
  • Cytochrome P-450 CYP2E1
  • Cytochrome P-450 CYP1A2
  • Oxidoreductases, N-Demethylating
  • NADH, NADPH Oxidoreductases
  • NADPH-Ferrihemoprotein Reductase
  • Chlorzoxazone
  • Dimethylnitrosamine
  • aniline