1α,20S-Dihydroxyvitamin D3 Interacts with Vitamin D Receptor: Crystal Structure and Route of Chemical Synthesis View Full Text


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Article Info

DATE

2017-08-31

AUTHORS

Zongtao Lin, Hao Chen, Anna Y. Belorusova, John C. Bollinger, Edith K. Y. Tang, Zorica Janjetovic, Tae-Kang Kim, Zhongzhi Wu, Duane D. Miller, Andrzej T. Slominski, Arnold E. Postlethwaite, Robert C. Tuckey, Natacha Rochel, Wei Li

ABSTRACT

1α,20S-Dihydroxyvitamin D3 [1,20S(OH)2D3], a natural and bioactive vitamin D3 metabolite, was chemically synthesized for the first time. X-ray crystallography analysis of intermediate 15 confirmed its 1α-OH configuration. 1,20S(OH)2D3 interacts with the vitamin D receptor (VDR), with similar potency to its native ligand, 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3] as illustrated by its ability to stimulate translocation of the VDR to the nucleus, stimulate VDRE-reporter activity, regulate VDR downstream genes (VDR, CYP24A1, TRPV6 and CYP27B1), and inhibit the production of inflammatory markers (IFNγ and IL1β). However, their co-crystal structures revealed differential molecular interactions of the 20S-OH moiety and the 25-OH moiety to the VDR, which may explain some differences in their biological activities. Furthermore, this study provides a synthetic route for the synthesis of 1,20S(OH)2D3 using the intermediate 1α,3β-diacetoxypregn-5-en-20-one (3), and provides a molecular and biological basis for the development of 1,20S(OH)2D3 and its analogs as potential therapeutic agents. More... »

PAGES

10193

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URI

http://scigraph.springernature.com/pub.10.1038/s41598-017-10917-7

DOI

http://dx.doi.org/10.1038/s41598-017-10917-7

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PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/28860545


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