1alpha,25-dihydroxyvitamin D3-24-hydroxylase (CYP24) hydroxylates the carbon at the end of the side chain (C-26) of the C-24-fluorinated analog of 1alpha,25-dihydroxyvitamin D3.

The Journal of Biological Chemistry
Y MiyamotoT Suda

Abstract

The sequential oxidation and cleavage of the side chain of 1alpha, 25-dihydroxyvitamin D3 (1alpha,25(OH)2D3) initiated by the hydroxylation at C-24 is considered to be the major pathway of this hormone in the target cell metabolism. In this study, we examined renal metabolism of a synthetic analog of 1alpha,25(OH)2D3, 24, 24-difluoro-1alpha,25-dihydroxyvitamin D3 (F2-1alpha,25(OH)2D3), C-24 of which was designed to resist metabolic hydroxylation. When kidney homogenates prepared from 1alpha,25(OH)2D3-supplemented rats were incubated with F2-1alpha,25(OH)2D3, it was mainly converted to a more polar metabolite. We isolated and unequivocally identified the metabolite as 24,24-difluoro-1alpha,25,26-trihydroxyvitamin D3 (F2-1alpha,25,26(OH)3D3) by ultraviolet absorption spectrometry, frit-fast atom bombardment liquid chromatography/mass spectroscopy analysis, and direct comparison with chemically synthesized F2-1alpha,25,26(OH)3D3. Metabolism of F2-1alpha,25(OH)2D3 into F2-1alpha,25,26(OH)3D3 by kidney homogenates was induced by the prior administration of 1alpha,25(OH)2D3 into rats. The C-24 oxidation of 1alpha,25(OH)2D3 in renal homogenates was inhibited by F2-1alpha,25(OH)2D3 in a concentration-dependent manner. Moreover, F2-1alp...Continue Reading

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Citations

May 26, 2011·Current Opinion in Nephrology and Hypertension·Martin Petkovich, Glenville Jones
Feb 23, 2002·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Hiroaki Takayama
Oct 7, 2003·Environmental Health Perspectives·Erin N HaynesBruce P Lanphear
Dec 16, 1997·Proceedings of the National Academy of Sciences of the United States of America·T ShinkiT Suda
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Aug 12, 1999·Archives of Biochemistry and Biophysics·D S RaoG S Reddy
Feb 23, 2011·Archives of Biochemistry and Biophysics·Steve Y RhieuG Satyanarayana Reddy

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