Journal of Lipid Research, Vol 17, 231-238, Copyright © 1976 by Lipid Research, Inc.
Synthesis of 11, 12-2H2- and 11, 12-3H2-labeled chenodeoxycholic and lithocholic acids
AE Cowen, AF Hofmann, DL Hachey, PJ Thomas, DT Belobaba, PD Klein and L Tokes
Deuterium- and tritium-labeled chenodeoxycholic acid and lithocholic were
prepared by catalytic reduction of their respective delta11 derivatives.
Structures of the intermediates and their isotopic purity were verified by
chemical ionization and electron impact mass spectrometry and by nuclear
magnetic resonance spectroscopy. Experimental conditions for reductive
deuteration were defined which gave complete reduction of the olefin and a
product of high isotopic purity. Conditions for optimal tritiation were
developed with which little exchange of protons with the solvent occurred;
the product had high specific activity. To test biological stability of the
label, the 3H-labeled chenodeoxycholic acid was administered simultaneously
with 14C-labeled chenodeoxycholic acid to two healthy subjects and the
3H/14C ratio in bile was determined daily for several days. The ratio
remained identical to that administered, suggesting that the 11,12- 3Hlabel
in chenodeoxycholic acid is stable during enterohepatic cycling and can be
used for valid estimates fo bile acid kinetics in many by the isotope
dilution technique.
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