Measurement of urinary free cortisol by stable isotope dilution mass spectrometry using a new cortisol derivative

The reaction of the bismethylenedioxy derivative of cortisol (cortisol-BMD) with heptafluorobutyric anhydride to give the corresponding 3,5-dienol heptafluorobutyrate (cortisol-BMD-HFB) has been shown to proceed with dehydration. Acid-promoted dehydration of either cortisol-BMD or cortisol-BMD-HFB,...

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Bibliographic Details
Published in:Journal of chromatography. B, Biomedical applications Biomedical applications, 1994-10, Vol.660 (1), p.151-157
Main Authors: Varelis, P., Smythe, G.A., Hodgson, D., Lazarus, L.
Format: Article
Language:English
Subjects:
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Fluorocarbons - chemistry
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Humans
Hydrocortisone - analogs & derivatives
Hydrocortisone - urine
Other biological molecules
Radioisotope Dilution Technique
Terpenes, steroids. Hormones
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Summary:The reaction of the bismethylenedioxy derivative of cortisol (cortisol-BMD) with heptafluorobutyric anhydride to give the corresponding 3,5-dienol heptafluorobutyrate (cortisol-BMD-HFB) has been shown to proceed with dehydration. Acid-promoted dehydration of either cortisol-BMD or cortisol-BMD-HFB, or concurrent dehydration of both, is the proposed reaction mechanism leading to a trienol heptafluorobutyrate, whose chromatographic properties and mass spectral data are consistent with the additional double bond in the C 9C 11 position. Forming the 3,5-dienol heptafluorobutyrate of cortisol-BMD in benzene rather than acetone gave a compound whose chromatographic properties and mass spectral data were different to that of the 3,5,9(11)-trienol heptafluorobutyrate but consistent with that of a cortisol-BMD-HFB. The mass fragmentometry of this new cortisol derivative was found to be more suited to the technique of isotope dilution mass spectrometry than the 3,5,9(11)-trienol heptafluorobutyrate, and thus was applied to our intended goal of measuring urinary free cortisol by gas chromatography—mass spectrometry. An efficient and convenient solid-phase extraction technique is employed in our assay to isolate cortisol from 5 ml of urine.
ISSN:0378-4347
1572-6495
DOI:10.1016/0378-4347(94)00281-9