Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc.

The FEBS Journal
R C TuckeyAndrzej T Slominski

Abstract

Cytochrome P450scc (CYP11A1) can hydroxylate vitamin D3 to produce 20-hydroxyvitamin D3 and other poorly characterized hydroxylated products. The present study aimed to identify all the products of vitamin D3 metabolism by P450scc, as well as the pathways leading to their formation. Besides 20-hydroxyvitamin D3, other major metabolites of vitamin D3 were a dihydroxyvitamin D3 and a trihydroxyvitamin D3 product. The dihydroxyvitamin D3 was clearly identified as 20,23-dihydroxyvitamin D3 by NMR, in contrast to previous reports that postulated hydroxyl groups in positions 20 and 22. NMR of the trihydroxy product identified it as 17alpha,20,23-trihydroxyvitamin D3. This product could be directly produced by P450scc acting on 20,23-dihydroxyvitamin D3, confirming that hydroxyl groups are present at positions 20 and 23. Three minor products of D3 metabolism by P450scc were identified by MS and by examining their subsequent metabolism by P450scc. These products were 23-hydroxyvitamin D3, 17alpha-hydroxyvitamin D3 and 17alpha,20-dihydroxyvitamin D3 and arise from the three P450scc-catalysed hydroxylations occurring in a different order. We conclude that the major pathway of vitamin D3 metabolism by P450scc is: vitamin D3 --> 20-hydroxy...Continue Reading

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Citations

Mar 13, 2012·Journal of Medicinal Chemistry·Yan LuDuane D Miller
Jun 4, 2011·Proceedings of the National Academy of Sciences of the United States of America·Natallia StrushkevichHee-Won Park
Jun 12, 2012·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Andrzej T SlominskiRobert C Tuckey
Jan 1, 2009·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Minh N NguyenRobert C Tuckey
Jun 18, 2010·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Edith K Y TangRobert C Tuckey
Jun 17, 2011·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Robert C TuckeyAndrzej Slominski
Nov 23, 2011·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Robert C TuckeyWei Li
Jan 9, 2013·The Journal of Clinical Endocrinology and Metabolism·Andrzej SlominskiArnold E Postlethwaite
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Dec 3, 2014·The Journal of Steroid Biochemistry and Molecular Biology·Andrzej T SlominskiRobert C Tuckey
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Jul 23, 2019·Cell Biochemistry and Function·Carl Jenkinson

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