Chemical Synthesis and Biological Activities of 20S,24S/R-Dihydroxyvitamin D3 Epimers and Their 1α-Hydroxyl Derivatives

Academic Article

Abstract

  • Bioactive vitamin D3 metabolites 20S,24S-dihydroxyvitamin D3 [20S,24S(OH)2D3] and 20S,24R-dihydroxyvitamin D3 [20S,24R(OH)2D3] were chemically synthesized and confirmed to be identical to their enzymatically generated counterparts. The absolute configurations at C24 and its influence on the kinetics of 1α-hydroxylation by CYP27B1 were determined. Their corresponding 1α-hydroxyl derivatives were subsequently produced. Biological comparisons of these products showed different properties with respect to vitamin D3 receptor activation, anti-inflammatory activity, and antiproliferative activity, with 1α,20S,24R(OH)2D3 being the most potent compound.
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    Digital Object Identifier (doi)

    Author List

  • Lin Z; Marepally SR; Ma D; Myers LK; Postlethwaite AE; Tuckey RC; Cheng CYS; Kim TK; Yue J; Slominski AT
  • Start Page

  • 7881
  • End Page

  • 7887
  • Volume

  • 58
  • Issue

  • 19