2. Academic Validation
  3. Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer

Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer

  • J Med Chem. 2016 May 26;59(10):5102-8. doi: 10.1021/acs.jmedchem.6b00182.
Zongtao Lin 1,  Srinivasa R Marepally 1,  Dejian Ma 1,  Tae-Kang Kim 2,  Allen Sw Oak 2,  Linda K Myers 3,  Robert C Tuckey 4,  Andrzej T Slominski 2 5,  Duane D Miller 1,  Wei Li 1
Affiliations

Affiliations

  • 1 Department of Pharmaceutical Sciences, University of Tennessee Health Science Center , 881 Madison Avenue, Room 561, Memphis, Tennessee 38163, United States.
  • 2 Department of Dermatology, University of Alabama at Birmingham , Birmingham, Alabama 35294, United States.
  • 3 Department of Medicine, University of Tennessee Health Science Center , Memphis, Tennessee 38163, United States.
  • 4 School of Chemistry and Biochemistry, University of Western Australia , Crawley, Western Australia 6009, Australia.
  • 5 VA Medical Center at Birmingham , Birmingham, Alabama 35294, United States.
PMID: 27070779 DOI: 10.1021/acs.jmedchem.6b00182
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.

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