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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Anti-Inflammatory Agents, Non-Steroidal / chemistry*
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Anti-Inflammatory Agents, Non-Steroidal / metabolism
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Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / metabolism
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Antineoplastic Agents / pharmacology*
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Cell Proliferation / drug effects
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Cholecalciferol / analogs & derivatives
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Cholecalciferol / chemistry
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Cholecalciferol / metabolism*
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Dihydroxycholecalciferols / chemistry
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Dihydroxycholecalciferols / metabolism
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Dihydroxycholecalciferols / pharmacology*
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Dose-Response Relationship, Drug
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Drug Screening Assays, Antitumor
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Humans
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Models, Molecular
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Molecular Structure
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Receptors, Immunologic / antagonists & inhibitors*
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Receptors, Immunologic / immunology
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Stereoisomerism
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Structure-Activity Relationship
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Tumor Cells, Cultured
Substances
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20,23-dihydroxyvitamin D3
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Anti-Inflammatory Agents, Non-Steroidal
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Antineoplastic Agents
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Dihydroxycholecalciferols
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Receptors, Immunologic
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leukocyte-associated immunoglobulin-like receptor 1
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Cholecalciferol