Glutamate dehydrogenase covalently binds to a reactive metabolite of acetaminophen

Chem Res Toxicol. 1996 Mar;9(2):541-6. doi: 10.1021/tx950158a.

Abstract

The mechanism of the hepatotoxicity of the analgesic acetaminophen is believed to be mediated by covalent binding to protein; however, critical targets which effect the toxicity are unknown. It has been shown that mitochondrial respiration in vivo is inhibited in mice as early as 1 h following a hepatotoxic dose of acetaminophen, and it is postulated that covalent binding to critical mitochondrial proteins may be important. A time course of mitochondrial proteins stained with anti-acetaminophen in an immunoblot detected two major adducts of 50 and 67 kDa as early as 30 min after a hepatotoxic dose of acetaminophen in mice. To further understand the role of covalent binding to mitochondrial proteins and acetaminophen hepatotoxicity, we have purified and identified a 50 kDa mitochondrial protein which becomes covalently bound to a reactive metabolite of acetaminophen. An N-terminal sequence of the 50 kDa adduct was 100% homologous with the deduced amino acid sequence of glutamate dehydrogenase. In addition, the purified protein was immunochemically reactive with rat liver anti-glutamate dehydrogenase. Enzyme activity of glutamate dehydrogenase was significantly decreased in mice 1 h following hepatotoxic treatment with acetaminophen. These data suggest that acetaminophen hepatotoxicity may in part be mediated by covalent binding to glutamate dehydrogenase.

Publication types

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

MeSH terms

  • Acetaminophen / metabolism*
  • Amino Acid Sequence
  • Animals
  • DNA Adducts / pharmacology*
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / metabolism*
  • Glutamate Dehydrogenase / metabolism*
  • Histones / metabolism*
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Mitochondria, Liver / enzymology
  • Molecular Sequence Data
  • Nickel / metabolism*
  • Oxidation-Reduction / drug effects
  • Phosphates / pharmacology
  • Protein Binding

Substances

  • DNA Adducts
  • Histones
  • Phosphates
  • Acetaminophen
  • Nickel
  • Glutamate Dehydrogenase
  • Deoxyguanosine