title: Endocannabinoid metabolomics: a novel liquid chromatography-mass spectrometry reagent for fatty acid analysis.
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.
authors.affiliation: Center for Drug Discovery, Northeastern University, Boston, MA, USA.
authors.forename: John
authors.initials: J
authors.lastname: Williams
authors.forename: Lakshmipathi
authors.initials: L
authors.lastname: Pandarinathan
authors.forename: JodiAnne
authors.initials: J
authors.lastname: Wood
authors.forename: Paul
authors.initials: P
authors.lastname: Vouros
authors.forename: Alexandros
authors.initials: A
authors.lastname: Makriyannis
mesh_terms: D063385:Cannabinoid Receptor Modulators / Q000737:chemistry / Q000378:metabolism*; D002853:Chromatography, Liquid / Q000379:methods; D063388:Endocannabinoids; D005227:Fatty Acids / Q000032:analysis / Q000737:chemistry / Q000378:metabolism*; D013058:Mass Spectrometry / Q000379:methods
chemical_list: D063385:Cannabinoid Receptor Modulators; D063388:Endocannabinoids; D005227:Fatty Acids