Abstract
The non-naturally occurring 20R epimer of 20-hydroxyvitamin D3 is synthesized based on chemical design and hypothesis. The 20R isomer is separated by semipreparative HPLC, and its structure is characterized. A comparison of 20R isomer to its 20S counterpart in biological evaluation demonstrates that they have different behaviors in antiproliferative and metabolic studies.
© 2012 American Chemical Society
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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25-Hydroxyvitamin D3 1-alpha-Hydroxylase / chemistry
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Antineoplastic Agents / chemical synthesis
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Calcifediol / analogs & derivatives*
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Calcifediol / chemical synthesis
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Calcifediol / chemistry
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Calcifediol / pharmacology
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Cell Differentiation / drug effects
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Cell Proliferation / drug effects
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Cells, Cultured
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Cholesterol Side-Chain Cleavage Enzyme / chemistry
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Drug Design
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Humans
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Keratinocytes / cytology
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Keratinocytes / drug effects
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Stereoisomerism
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Structure-Activity Relationship
Substances
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20-hydroxyvitamin D3
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Antineoplastic Agents
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25-Hydroxyvitamin D3 1-alpha-Hydroxylase
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Cholesterol Side-Chain Cleavage Enzyme
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Calcifediol