The difference between 14-epi-previtamin D3 and 14-epi-19-norprevitamin D3: their synthesis and binding affinity for human VDR

Anticancer Res. 2012 Jan;32(1):319-26.

Abstract

The synthesis of 14-epi-1α,25(OH)(2)previtamin D(3), 14-epi-19-nor-1α,25(OH)(2)previtamin D(3), and their 2-substituted analogs is described. The vitamin D receptor (VDR) binding affinity was further evaluated and 2α-methyl substituted 14-epi-1α,25(OH)(2)previtamin D(3) had 17-fold more potent affinity than 14-epi-1α,25(OH)(2)previtamin D(3).In the comparison of these compounds, the effects of thermal equilibrium, with or without 19-carbon at the A-ring, and their CD-ring structures are discussed.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cholecalciferol / analogs & derivatives*
  • Cholecalciferol / chemical synthesis
  • Cholecalciferol / chemistry
  • Cholecalciferol / metabolism
  • Humans
  • Molecular Structure
  • Protein Binding
  • Receptors, Calcitriol / metabolism*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Receptors, Calcitriol
  • Cholecalciferol
  • previtamin D(3)