Comprehensive kinetic analysis and influence of reaction components for chlorzoxazone 6-hydroxylation in human liver microsomes with CYP antibodies

Xenobiotica. 2015 Apr;45(4):353-60. doi: 10.3109/00498254.2014.985760. Epub 2014 Nov 19.

Abstract

1. Chlorzoxazone (CLZ) is currently being used as a marker substrate in vitro/vivo studies to quantify cytochrome P450 2E1 (CYP2E1) activity in humans. Although in CLZ 6-hydroxylation several CYPs are responsible, previous studies have presented the monophasicity of the reaction in human liver microsomes (HLMs). Furthermore, the Km values of CYP2E1 for the 6-hydroxylation in HLMs were reported to be lower than those of its recombinant enzymes. 2. This study aimed to provide the comprehensive Km values for the CLZ 6-hydroxylation in HLMs using CYP antibodies. The Eadie-Hofstee plots revealed a biphasic profile and indicate that the reaction was mainly mediated by CYP1A2 as well as CYP2E1. The formation of 6-hydroxychlorzoxazone was more specific for CYP2E1 activity at higher substrate concentration in HLMs. 3. Moreover, KOH as a vehicle for substrate or sucrose included in HLMs preparation had some effect on the activity of CLZ 6-hydroxylase. These constituents seemed to be casually related to the apparent monophasic kinetics and variability in Km values for the CLZ 6-hydroxylation in HLMs. 4. The Km of CYP1A2 and CYP2E1 in HLMs was 3.8 µmol/L and 410 µmol/L, respectively, and the value of CYP2E1 was close to that of recombinant CYP2E1.

Keywords: CYP1A2; CYP2E1; Chlorzoxazone; HLMs; KOH; kinetics; sucrose.

MeSH terms

  • Chlorzoxazone / analogs & derivatives*
  • Chlorzoxazone / pharmacokinetics
  • Chromatography, Liquid
  • Cytochrome P-450 CYP1A2 / metabolism*
  • Cytochrome P-450 CYP2E1 / metabolism*
  • Humans
  • Hydroxylation
  • Microsomes, Liver / drug effects*
  • Microsomes, Liver / metabolism
  • Recombinant Proteins / metabolism
  • Tandem Mass Spectrometry

Substances

  • Recombinant Proteins
  • 6-hydroxychlorzoxazone
  • Cytochrome P-450 CYP2E1
  • CYP1A2 protein, human
  • Cytochrome P-450 CYP1A2
  • Chlorzoxazone