A stereospecific phosphotriesterase in hen liver and brain

Chem Biol Interact. 1998 Jan 30;108(3):187-96. doi: 10.1016/s0009-2797(97)00106-3.

Abstract

O-Hexyl, O-2,5-dichlorophenyl phosphoramidate (HDCP) is a chiral compound that induces delayed neuropathy in hens. This compound is hydrolyzed by a phosphotriesterase known as HDCPase in hen and rat plasma, liver and brain. We studied the stereospecificity of HDCPase in hen tissues and in human and rabbit plasma employing a chromatographic method for analysis and quantification of HDCP stereoisomers. Hen and human plasma HDCPases were not stereospecific. However, rabbit plasma showed a remarkable stereospecificity to S-(-)-HDCP. High levels of stereospecific HDCPase were found in the particulate fraction of hen liver, where S-(-)-HDCP is hydrolyzed faster than R-(+)-HDCP. However, in hen brain the stereospecificity was found in the soluble fraction, where R-(+)-HDCP is hydrolyzed faster than S-(-)-HDCP. It is concluded that liver particulate fraction must be the main tissue responsible for the HDCP stereospecific biotransformation in hens. In an oral administration, the steroisomer R-(+)-HDCP would survive after passing through the liver and would interact with acetylcholinesterase and neuropathy target esterase in the nervous system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aryldialkylphosphatase
  • Brain / enzymology*
  • Chickens
  • Cholinesterase Inhibitors / metabolism
  • Esterases / chemistry
  • Esterases / metabolism*
  • Female
  • Humans
  • Hydrolysis
  • Liver / enzymology*
  • Organophosphorus Compounds / metabolism
  • Plasma / enzymology
  • Rabbits
  • Stereoisomerism

Substances

  • Cholinesterase Inhibitors
  • Organophosphorus Compounds
  • hexyl 2,5-dichlorophenylphosphoroamidate
  • Esterases
  • Aryldialkylphosphatase