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

Zongtao Lin, Srinivasa R. Marepally, Dejian Ma, Tae Kang Kim, Allen Sw Oak, Linda Myers, Robert C. Tuckey, Andrzej T. Slominski, Duane Miller, Wei Li

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

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 (US)
Pages (from-to)5102-5108
Number of pages7
JournalJournal of Medicinal Chemistry
Volume59
Issue number10
DOIs
StatePublished - May 26 2016

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Cholecalciferol
25-Hydroxyvitamin D3 1-alpha-Hydroxylase
Calcitriol Receptors
Esters
Anti-Inflammatory Agents
dihydroxy-vitamin D3

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Drug Discovery

Cite this

Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer. / Lin, Zongtao; Marepally, Srinivasa R.; Ma, Dejian; Kim, Tae Kang; Oak, Allen Sw; Myers, Linda; Tuckey, Robert C.; Slominski, Andrzej T.; Miller, Duane; Li, Wei.

In: Journal of Medicinal Chemistry, Vol. 59, No. 10, 26.05.2016, p. 5102-5108.

Research output: Contribution to journalArticle

Lin, Zongtao ; Marepally, Srinivasa R. ; Ma, Dejian ; Kim, Tae Kang ; Oak, Allen Sw ; Myers, Linda ; Tuckey, Robert C. ; Slominski, Andrzej T. ; Miller, Duane ; Li, Wei. / Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer. In: Journal of Medicinal Chemistry. 2016 ; Vol. 59, No. 10. pp. 5102-5108.
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AU - Myers, Linda

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