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  • Title: Chemical synthesis of dioxygen-18 labelled omega-/beta-oxidized cysteinyl leukotrienes: analysis by gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry.
    Author: Tsikas D, Fauler J, Frölich JC.
    Journal: J Chromatogr B Biomed Appl; 1995 May 19; 667(2):209-21. PubMed ID: 7663693.
    Abstract:
    Cysteinyl leukotrienes (LT) C4, LTD4 and LTE4 are potent mediators of anaphylaxis and inflammation. LTE4 is extensively metabolized in man mainly by omega-oxidation followed by subsequent beta-oxidation to more polar and biologically inactive metabolites. This paper describes a method for the synthesis of [1,20-18O2]-carboxy-LTE4, [1,18-18O2]-carboxy-dinor-LTE4, and [1,16-18O2]-carboxy-14,15-dihydro-tetranor-LTE4 starting from the unlabelled dimethyl esters of 20-carboxy-LTA4, 18-carboxy-dinor-LTA4 and 16-carboxy-14,15-dihydro-tetranor-LTA4, respectively, by separate chemical conjugation with cysteine hydrochloride in H2-18O-methanol followed by alkaline hydrolysis with Li18OH. The isotopic purity of the isolated reaction products was 94% at 18O for all three preparations while only 0.3% remained unlabelled as confirmed by negative-ion chemical-ionization gas chromatography-mass spectrometry (GC-NICI-MS) after their catalytical reduction/desulphurization and derivatization. The 18O2-labelled compounds are demonstrated to be suitable internal standards for quantification by GC-NICI-MS and GC-NICI-tandem MS. We found by GC-NICI-tandem MS that the excretion rate of 20-carboxy-LTE4 is comparable to that of LTE4 (both in nmol/mol creatinine, mean +/- S.E.) in healthy children (26.7 +/- 4.7 vs. 32.0 +/- 6.0, n = 9) and adults (13.9 +/- 1.1 vs. 27.2 +/- 5.4, n = 3).
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