Mechanism of biochemical action of substituted 4-methylbenzopyran-2-ones. Part 4: hyperbolic activation of rat liver microsomal NADPH-cytochrome C reductase by the novel acetylator 7,8-diacetoxy-4-methylcoumarin

Bioorg Med Chem. 1999 Feb;7(2):369-73. doi: 10.1016/s0968-0896(98)00228-4.

Abstract

The effect of 7,8-diacetoxy-4-methylcoumarin (DAMC) has been studied on hepatic NADPH cytochrome C reductase-- an enzyme participating in the microsomal electron transport. The preincubation of liver microsomes with DAMC resulted in a time-dependent activation of NADPH cytochrome C reductase. The catalytic activity of the enzyme enhanced nearly 600% by 25 microM concentration of DAMC after 10 min of preincubation. The action of DAMC on the reductase resulted in enhanced v(max) while Km remained constant. A plot of 1/v(max) as a function of DAMC concentration resulted in a non-linear, but rectangular hyperbola indicative of hyperbolic activation. DAMC was also proved to be effective in significantly enhancing the activity of NADPH cytochrome C reductase in vivo. 7,8-Dihydroxy-4-methylcoumarin (DHMC), the deacetylated product of DAMC failed to irreversibly activate the enzyme. The activation effect of DAMC upon the enzyme was abolished by p-hydroxymercury benzoate. The role of a transacetylase in transferring the acetyl group of DAMC to the amino acid(s) of the active site of NADPH cytochrome C reductase causing irreversible enzyme activation is enunciated.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Animals
  • Coumarins / metabolism*
  • Dose-Response Relationship, Drug
  • Hydroxymercuribenzoates / metabolism
  • Kinetics
  • Male
  • Microsomes, Liver / metabolism*
  • Models, Chemical
  • NADPH-Ferrihemoprotein Reductase / metabolism*
  • Rats
  • Rats, Wistar
  • Time Factors

Substances

  • 7,8-diacetoxy-4-methylcoumarin
  • Coumarins
  • Hydroxymercuribenzoates
  • 4-hydroxymercuribenzoate
  • NADPH-Ferrihemoprotein Reductase