1α,20S-Dihydroxyvitamin D3 Interacts with Vitamin D Receptor: Crystal Structure and Route of Chemical Synthesis
Identifieur interne : 001350 ( Main/Curation ); précédent : 001349; suivant : 0013511α,20S-Dihydroxyvitamin D3 Interacts with Vitamin D Receptor: Crystal Structure and Route of Chemical Synthesis
Auteurs : Zongtao Lin [États-Unis] ; Hao Chen [États-Unis] ; Anna Y. Belorusova [France, Suède] ; John C. Bollinger [États-Unis] ; Edith K. Y. Tang ; Zorica Janjetovic [États-Unis] ; Tae-Kang Kim [États-Unis] ; Zhongzhi Wu [États-Unis] ; Duane D. Miller [États-Unis] ; Andrzej T. Slominski [États-Unis] ; Arnold E. Postlethwaite [États-Unis] ; Robert C. Tuckey ; Natacha Rochel [France] ; Wei Li [États-Unis]Source :
- Scientific Reports [ 2045-2322 ] ; 2017.
Abstract
1α,20
Url:
DOI: 10.1038/s41598-017-10917-7
PubMed: 28860545
PubMed Central: 5579064
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Le document en format XML
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-Dihydroxyvitamin D<sub>3</sub>
Interacts with Vitamin D Receptor: Crystal Structure and Route of Chemical Synthesis</title>
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-Dihydroxyvitamin D<sub>3</sub>
Interacts with Vitamin D Receptor: Crystal Structure and Route of Chemical Synthesis</title>
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<author><name sortKey="Miller, Duane D" sort="Miller, Duane D" uniqKey="Miller D" first="Duane D." last="Miller">Duane D. Miller</name>
<affiliation wicri:level="2"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 0386 9246</institution-id>
<institution-id institution-id-type="GRID">grid.267301.1</institution-id>
<institution>Department of Pharmaceutical Sciences,</institution>
<institution>University of Tennessee Health Science Center, 881 Madison Avenue, Room 561,</institution>
</institution-wrap>
Memphis, TN 38163 United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<placeName><region type="state">Tennessee</region>
</placeName>
<wicri:cityArea>Memphis</wicri:cityArea>
</affiliation>
</author>
<author><name sortKey="Slominski, Andrzej T" sort="Slominski, Andrzej T" uniqKey="Slominski A" first="Andrzej T." last="Slominski">Andrzej T. Slominski</name>
<affiliation wicri:level="2"><nlm:aff id="Aff5"><institution-wrap><institution-id institution-id-type="ISNI">0000000106344187</institution-id>
<institution-id institution-id-type="GRID">grid.265892.2</institution-id>
<institution>Department of Dermatology,</institution>
<institution>University of Alabama at Birmingham,</institution>
</institution-wrap>
Birmingham, AL 35294 United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<placeName><region type="state">Alabama</region>
</placeName>
<wicri:cityArea>Birmingham</wicri:cityArea>
</affiliation>
<affiliation wicri:level="2"><nlm:aff id="Aff6"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 0419 1326</institution-id>
<institution-id institution-id-type="GRID">grid.280808.a</institution-id>
<institution>VA Medical Center,</institution>
</institution-wrap>
Birmingham, AL 35294 United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<placeName><region type="state">Alabama</region>
</placeName>
<wicri:cityArea>Birmingham</wicri:cityArea>
</affiliation>
</author>
<author><name sortKey="Postlethwaite, Arnold E" sort="Postlethwaite, Arnold E" uniqKey="Postlethwaite A" first="Arnold E." last="Postlethwaite">Arnold E. Postlethwaite</name>
<affiliation wicri:level="2"><nlm:aff id="Aff7"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 0386 9246</institution-id>
<institution-id institution-id-type="GRID">grid.267301.1</institution-id>
<institution>Department of Medicine,</institution>
<institution>University of Tennessee Health Science Center,</institution>
</institution-wrap>
Memphis, TN 38163 United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<placeName><region type="state">Tennessee</region>
</placeName>
<wicri:cityArea>Memphis</wicri:cityArea>
</affiliation>
<affiliation wicri:level="2"><nlm:aff id="Aff8"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 0420 4721</institution-id>
<institution-id institution-id-type="GRID">grid.413847.d</institution-id>
<institution>VA Medical Center,</institution>
</institution-wrap>
Memphis, TN 38104 United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<placeName><region type="state">Tennessee</region>
</placeName>
<wicri:cityArea>Memphis</wicri:cityArea>
</affiliation>
</author>
<author><name sortKey="Tuckey, Robert C" sort="Tuckey, Robert C" uniqKey="Tuckey R" first="Robert C." last="Tuckey">Robert C. Tuckey</name>
<affiliation><nlm:aff id="Aff4"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 1936 7910</institution-id>
<institution-id institution-id-type="GRID">grid.1012.2</institution-id>
<institution>School of Chemistry and Biochemistry, University of Western Australia,</institution>
</institution-wrap>
Crawley, WA 6009 Australia</nlm:aff>
<wicri:noCountry code="subfield">WA 6009 Australia</wicri:noCountry>
</affiliation>
</author>
<author><name sortKey="Rochel, Natacha" sort="Rochel, Natacha" uniqKey="Rochel N" first="Natacha" last="Rochel">Natacha Rochel</name>
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<institution-id institution-id-type="GRID">grid.420255.4</institution-id>
<institution>Department of Integrative Structure Biology,</institution>
<institution>IGBMC - CNRS UMR7104 – Inserm U964, 1, rue Laurent Fries,</institution>
</institution-wrap>
Illkirch, 67400 France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Illkirch</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Li, Wei" sort="Li, Wei" uniqKey="Li W" first="Wei" last="Li">Wei Li</name>
<affiliation wicri:level="2"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0004 0386 9246</institution-id>
<institution-id institution-id-type="GRID">grid.267301.1</institution-id>
<institution>Department of Pharmaceutical Sciences,</institution>
<institution>University of Tennessee Health Science Center, 881 Madison Avenue, Room 561,</institution>
</institution-wrap>
Memphis, TN 38163 United States</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<placeName><region type="state">Tennessee</region>
</placeName>
<wicri:cityArea>Memphis</wicri:cityArea>
</affiliation>
</author>
</analytic>
<series><title level="j">Scientific Reports</title>
<idno type="eISSN">2045-2322</idno>
<imprint><date when="2017">2017</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p id="Par1">1α,20<italic>S</italic>
-Dihydroxyvitamin D3 [1,20<italic>S</italic>
(OH)<sub>2</sub>
D<sub>3</sub>
], 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. 1,20<italic>S</italic>
(OH)<sub>2</sub>
D<sub>3</sub>
interacts with the vitamin D receptor (VDR), with similar potency to its native ligand, 1α,25-dihydroxyvitamin D<sub>3</sub>
[1,25(OH)<sub>2</sub>
D<sub>3</sub>
] as illustrated by its ability to stimulate translocation of the VDR to the nucleus, stimulate VDRE-reporter activity, regulate VDR downstream genes (<italic>VDR</italic>
, <italic>CYP24A1</italic>
, <italic>TRPV6</italic>
and <italic>CYP27B1</italic>
), and inhibit the production of inflammatory markers (IFNγ and IL1β). However, their co-crystal structures revealed differential molecular interactions of the 20<italic>S</italic>
-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 1,20<italic>S</italic>
(OH)<sub>2</sub>
D<sub>3</sub>
using the intermediate 1α,3β-diacetoxypregn-5-en-20-one (3), and provides a molecular and biological basis for the development of 1,20<italic>S</italic>
(OH)<sub>2</sub>
D<sub>3</sub>
and its analogs as potential therapeutic agents.</p>
</div>
</front>
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</listBibl>
</div1>
</back>
</TEI>
</record>
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