Endocannabinoid metabolomics: a novel liquid chromatography-mass spectrometry reagent for fatty acid analysis

AAPS J. 2006 Oct 20;8(4):E655-60. doi: 10.1208/aapsj080474.

Abstract

We have synthesized 4,4-dimethoxyoxazoline derivatives of several fatty acids associated with the endocannabinoid metabolome using tris(hydroxymethyl)aminomethane in a 1-step reaction by microwave irradiation. The derivatization incorporates a nitrogen into the final product, which allows for improved detection by liquid chromatography-mass spectrometry in positive atmospheric pressure chemical ionization (APCI) mode. Palmitic and oleic acid derivatives show a 200-fold increase in sensitivity compared with the free acids when analyzed in negative-mode APCI. In addition to improving sensitivity, the oxazoline derivatization creates a similar ionization response for the fatty acids tested, which simplifies their quantitation. Fatty acid oxazoline derivatives can be detected using the same conditions optimized for the endocannabinoids, which allows for a simultaneous quantitation of the entire endocannabinoid metabolome.

MeSH terms

  • Cannabinoid Receptor Modulators / chemistry
  • Cannabinoid Receptor Modulators / metabolism*
  • Chromatography, Liquid / methods
  • Endocannabinoids*
  • Fatty Acids / analysis
  • Fatty Acids / chemistry
  • Fatty Acids / metabolism*
  • Mass Spectrometry / methods

Substances

  • Cannabinoid Receptor Modulators
  • Endocannabinoids
  • Fatty Acids