Direct and simultaneous profiling of epoxyeicosatrienoic acid enantiomers by capillary tandem column chiral-phase liquid chromatography with dual online photodiode array and tandem mass spectrometric detection

Analytical and Bioanalytical Chemistry
L KissWerner Seeger

Abstract

Despite first evidence for the cytochrome P450-mediated enantioselective biosynthesis and activity of cis-epoxyeicosatrienoic acids (EETs), as yet little is known about the stereospecifity of EET generation and physiology, because the existing chiral methods are time consuming, labor intensive, and not sensitive enough. We present a method for highly sensitive, direct, and simultaneous chiral analysis of all eight EET enantiomers consisting of (i) solid-phase extraction, (ii) reversed-phase high-performance liquid chromatographic purification followed by (iii) consecutive regio- and enantiomeric separation of the four underivatized EET regioisomers within one chromatographic run employing capillary tandem column chiral-phase liquid chromatography with (iv) reliable dual online photodiode array and gentle electrospray ionization tandem mass spectrometric identification and quantitation of the eluting optical antipodes. This one-step, simple, expeditious, and highly sensitive measurement allows profiling of all eight EET enantiomers at once, thus avoiding substance loss and enabling high sample throughput. Limits of quantification in the low picogram range were achieved by the use of capillary columns with typical high quantitati...Continue Reading

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Citations

Oct 20, 2011·Cancer Metastasis Reviews·Ingrid Fleming
Oct 30, 2013·Proceedings of the National Academy of Sciences of the United States of America·Daniela WenzelBernd K Fleischmann
Oct 6, 2017·Antioxidants & Redox Signaling·Ana Carolina AraújoJesper Z Haeggström
Feb 28, 2021·Signal Transduction and Targeted Therapy·Bei WangDao Wen Wang

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