Design, synthesis, and biological action of 20R-hydroxyvitamin D3

J Med Chem. 2012 Apr 12;55(7):3573-7. doi: 10.1021/jm201478e. Epub 2012 Mar 20.

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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 25-Hydroxyvitamin D3 1-alpha-Hydroxylase / chemistry
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Calcifediol / analogs & derivatives*
  • Calcifediol / chemical synthesis
  • Calcifediol / chemistry
  • Calcifediol / pharmacology
  • Cell Differentiation / drug effects
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Cholesterol Side-Chain Cleavage Enzyme / chemistry
  • Drug Design
  • Humans
  • Keratinocytes / cytology
  • Keratinocytes / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 20-hydroxyvitamin D3
  • Antineoplastic Agents
  • 25-Hydroxyvitamin D3 1-alpha-Hydroxylase
  • Cholesterol Side-Chain Cleavage Enzyme
  • Calcifediol