Endocannabinoid Metabolomics: a Novel Liquid Chromatography-mass Spectrometry Reagent for Fatty Acid Analysis

Overview

Journal AAPS J

Specialty Pharmacology

Date 2007 Jan 20

PMID 17233529

Citations 9

Authors

John Williams

Lakshmipathi Pandarinathan

JodiAnne Wood

Paul Vouros

Alexandros Makriyannis

Affiliations

Soon will be listed here.

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.

Citing Articles

Inhibition of triple negative breast cancer-associated inflammation and progression by N- acylethanolamine acid amide hydrolase (NAAA).

Benchama O, Malamas M, Praveen K, Ethier E, Williams M, Makriyannis A Sci Rep. 2022; 12(1):22255.

PMID: 36564457 PMC: 9789040. DOI: 10.1038/s41598-022-26564-6.

Liquid Chromatography-Mass Spectrometry (LC-MS) Derivatization-Based Methods for the Determination of Fatty Acids in Biological Samples.

Mantzourani C, Kokotou M Molecules. 2022; 27(17).

PMID: 36080484 PMC: 9458108. DOI: 10.3390/molecules27175717.

Rapid quantification of fatty acids in plant oils and biological samples by LC-MS.

Koch E, Wiebel M, Hopmann C, Kampschulte N, Schebb N Anal Bioanal Chem. 2021; 413(21):5439-5451.

PMID: 34296318 PMC: 8405509. DOI: 10.1007/s00216-021-03525-y.

Endocannabinoid Metabolome Characterization of Transitional and Mature Human Milk.

Gaitan A, Wood J, Zhang F, Makriyannis A, Lammi-Keefe C Nutrients. 2018; 10(9).

PMID: 30213124 PMC: 6165354. DOI: 10.3390/nu10091294.

2012 Division of medicinal chemistry award address. Trekking the cannabinoid road: a personal perspective.

Makriyannis A J Med Chem. 2014; 57(10):3891-911.

PMID: 24707904 PMC: 4064474. DOI: 10.1021/jm500220s.

References

Di Marzo V, Breivogel C, Tao Q, Bridgen D, Razdan R, Zimmer A . Levels, metabolism, and pharmacological activity of anandamide in CB(1) cannabinoid receptor knockout mice: evidence for non-CB(1), non-CB(2) receptor-mediated actions of anandamide in mouse brain. J Neurochem. 2000; 75(6):2434-44. DOI: 10.1046/j.1471-4159.2000.0752434.x. View

Byrdwell W . Atmospheric pressure chemical ionization mass spectrometry for analysis of lipids. Lipids. 2001; 36(4):327-46. DOI: 10.1007/s11745-001-0725-5. View

Bazinet R, Lee H, Felder C, Porter A, Rapoport S, Rosenberger T . Rapid high-energy microwave fixation is required to determine the anandamide (N-arachidonoylethanolamine) concentration of rat brain. Neurochem Res. 2005; 30(5):597-601. DOI: 10.1007/s11064-005-2746-5. View

Spitzer V . Structure analysis of fatty acids by gas chromatography--low resolution electron impact mass spectrometry of their 4,4-dimethyloxazoline derivatives--a review. Prog Lipid Res. 1996; 35(4):387-408. DOI: 10.1016/s0163-7827(96)00011-2. View

RYHAGE R, STENHAGEN E . Mass spectrometry in lipid research. J Lipid Res. 1960; 1:361-90. View