Induction of hepatic CYP1A2 by the oral administration of caffeine to rats: lack of association with the Ah locus

Biochim Biophys Acta. 1995 Oct 17;1272(2):89-94. doi: 10.1016/0925-4439(95)00071-b.

Abstract

Caffeine was administered to male Wistar albino rats for two weeks at three concentrations, namely 0.1, 0.2 and 0.3%, and hepatic cytochrome P450-dependent mixed-function oxidase determined. Caffeine administration gave rise to a marked, dose-dependent increase in the O-deethylation of ethoxyresorufin and, to a lesser extent, in the O-depentylation of pentoxyresorufin. Erythromycin N-demethylase, p-nitrophenol hydroxylase and lauric acid hydroxylase activities, as well as total cytochrome P450 content were unaffected by this treatment. Immunoblot analysis revealed that caffeine gave rise to a dose-dependent increase in the hepatic CYP1A2, and at the highest dose only, CYP2B apoprotein levels. Apoprotein levels of CYP3A and CYP2E1 were not modulated by the treatment with caffeine at all dose levels studied. Caffeine could not displace [3H]TCDD from the rat hepatic cytosolic Ah receptor. Computer analysis showed that caffeine is essentially a planar molecule with an area/depth ratio 4.8, characteristic of CYP1A substrates/inducers. Molecular modelling revealed that the caffeine molecule could orientate itself within the putative CYP1A2 active site so as to facilitate demethylation of the N-1, N-3 and N-7 positions. However, at physiological pH, the N-9 nitrogen atom is likely to be partially protonated, allowing it to participate in an electrostatic interaction with the negatively-charged glutamate 318-residue, favouring N-3 demethylation, the major pathway of metabolism in both humans and animals. In conclusion caffeine, being essentially planar, is an inducer of CYP1A2 in rat liver.

MeSH terms

  • Administration, Oral
  • Animals
  • Caffeine / administration & dosage
  • Caffeine / pharmacology*
  • Cytochrome P-450 CYP1A2
  • Cytochrome P-450 Enzyme System / biosynthesis*
  • Enzyme Induction
  • Immunoblotting
  • Liver / drug effects*
  • Liver / enzymology
  • Male
  • Oxidoreductases / biosynthesis*
  • Rats
  • Rats, Wistar
  • Receptors, Aryl Hydrocarbon / drug effects

Substances

  • Receptors, Aryl Hydrocarbon
  • Caffeine
  • Cytochrome P-450 Enzyme System
  • Oxidoreductases
  • Cytochrome P-450 CYP1A2