Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer

Z. Lin, S.R. Marepally, D. Ma, T.K. Kim, A.S. Oak, L.K. Myers, Robert Tuckey, A.T. Slominski, D.D. Miller, W. Li

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

© 2016 American Chemical Society.The vitamin D3 metabolite, 20S,23S-dihydroxyvitamin D3, was chemically synthesized for the first time and identified to be the same as the enzymatically produced metabolite. The C23 absolute configurations of both 20S,23S/R-dihydroxyvitamin D3 epimers were unambiguously assigned by NMR and Mosher ester analysis. Their kinetics of CYP27B1 metabolism were investigated during the production of their 1α-hydroxylated derivatives. Bioactivities of these products were compared in terms of vitamin D3 receptor activation, anti-inflammatory, and antiproliferative activities.
Original languageEnglish
Pages (from-to)5102-5108
JournalJournal of Medicinal Chemistry
Volume59
Issue number10
DOIs
Publication statusPublished - 2016

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