TY - JOUR
T1 - Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer
AU - Lin, Z.
AU - Marepally, S.R.
AU - Ma, D.
AU - Kim, T.K.
AU - Oak, A.S.
AU - Myers, L.K.
AU - Tuckey, Robert
AU - Slominski, A.T.
AU - Miller, D.D.
AU - Li, W.
PY - 2016/5/26
Y1 - 2016/5/26
N2 - © 2016 American Chemical Society.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.
AB - © 2016 American Chemical Society.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.
UR - http://www.scopus.com/inward/record.url?scp=84971673894&partnerID=8YFLogxK
U2 - 10.1021/acs.jmedchem.6b00182
DO - 10.1021/acs.jmedchem.6b00182
M3 - Article
C2 - 27070779
SN - 0022-2623
VL - 59
SP - 5102
EP - 5108
JO - Journal of Medicinal Chemistry
JF - Journal of Medicinal Chemistry
IS - 10
ER -