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

Z. Lin, S.R. Marepally, D. Ma, T.K. Kim, A.S. Oak, L.K. Myers, Robert Tuckey, A.T. Slominski, D.D. Miller, W. Li

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

© 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.
Original languageEnglish
Pages (from-to)5102-5108
JournalJournal of Medicinal Chemistry
Volume59
Issue number10
DOIs
Publication statusPublished - 2016

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Cholecalciferol
25-Hydroxyvitamin D3 1-alpha-Hydroxylase
Calcitriol Receptors
Esters
Anti-Inflammatory Agents
dihydroxy-vitamin D3

Cite this

Lin, Z. ; Marepally, S.R. ; Ma, D. ; Kim, T.K. ; Oak, A.S. ; Myers, L.K. ; Tuckey, Robert ; Slominski, A.T. ; Miller, D.D. ; Li, W. / Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer. In: Journal of Medicinal Chemistry. 2016 ; Vol. 59, No. 10. pp. 5102-5108.
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author = "Z. Lin and S.R. Marepally and D. Ma and T.K. Kim and A.S. Oak and L.K. Myers and Robert Tuckey and A.T. Slominski and D.D. Miller and W. Li",
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Lin, Z, Marepally, SR, Ma, D, Kim, TK, Oak, AS, Myers, LK, Tuckey, R, Slominski, AT, Miller, DD & Li, W 2016, 'Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer' Journal of Medicinal Chemistry, vol. 59, no. 10, pp. 5102-5108. https://doi.org/10.1021/acs.jmedchem.6b00182

Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer. / Lin, Z.; Marepally, S.R.; Ma, D.; Kim, T.K.; Oak, A.S.; Myers, L.K.; Tuckey, Robert; Slominski, A.T.; Miller, D.D.; Li, W.

In: Journal of Medicinal Chemistry, Vol. 59, No. 10, 2016, p. 5102-5108.

Research output: Contribution to journalArticle

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

Y1 - 2016

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.

U2 - 10.1021/acs.jmedchem.6b00182

DO - 10.1021/acs.jmedchem.6b00182

M3 - Article

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 10

ER -