Structural evaluation of new 14-epimerized tachysterol analogs as hVDR agonists
Project/Area Number |
23590015
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Multi-year Fund |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | Okayama University (2013) Teikyo University (2011-2012) |
Principal Investigator |
SAWADA Daisuke 岡山大学, 医歯(薬)学総合研究科, 教授 (00338691)
|
Project Period (FY) |
2011 – 2013
|
Project Status |
Completed (Fiscal Year 2013)
|
Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
|
Keywords | タキステロール / ビタミンD / 有機合成化学 / X線結晶構造解析 / 国際情報交換(フランス、台湾) / 国際情報交流(フランス、台湾) / ビタミンD |
Research Abstract |
I found that 14-epi-19-nortachysterol derivatives was able to be isolated by 14 epimerization. And I succeeded in their chemical synthesis and revealed their marked stability in comparison with natural tachysterol and they showed their potent VDR binding affinity. Also, X-ray co-crystallographic analyses were performed using their complex with the ligand binding domain of the human VDR, and surprisingly, they exhibited an unprecedented binding configurations, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of vitamin D3.
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Report
(4 results)
Research Products
(83 results)
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[Journal Article] Design and synthesis of 2α-(tetrazolylethyl)-1α,25-dihydroxyvitamin D3 as a high affinity ligand for vitamin D receptor2014
Author(s)
Miki Matsuo, Asami Hasegawa, Masashi Takano, Hiroshi Saito, Shinji Kakuda, Kenichiro Takagi, Eiji Ochiai, Kyohei Horie, Midori Takimoto-Kamimura, Kazuya Takenouchi, Daisuke Sawada, and Atsushi Kittaka
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Journal Title
J. Steroid Biochem. Mol. Biol.
Volume: in press
Pages: 201-203
DOI
Related Report
Peer Reviewed
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[Journal Article] Synthesis and Biological Activity of 1α,2α,25-Trihydroxyvitamin D<sub>3</sub>: Active Metabolite of 2α-(3-Hydroxypropoxy)-1α,25-dihydroxyvitamin D<sub>3</sub> by Human CYP3A42014
Author(s)
Masashi Takano, Saori Ohya, Kaori Yasuda, Miyu Nishikawa, Akiko Takeuchi, Daisuke Sawada, Toshiyuki Sakaki, and Atsushi Kittaka
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Journal Title
Chemical and Pharmaceutical Bulletin
Volume: 62
Issue: 2
Pages: 182-184
DOI
NAID
ISSN
0009-2363, 1347-5223
Related Report
Peer Reviewed
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[Journal Article] Synthesis of 2α-Heteroarylalkyl Active Vitamin D3 with Therapeutic Effect on Enhancing Bone Mineral Density in vivo2013
Author(s)
Miki Matsuo, Asami Hasegawa, Masashi Takano, Hiroshi Saito, Shinji Kakuda, Takayuki Chida, Ken-ichiro Takagi, Eiji Ochiai, Kyohei Horie, Yoshifumi Harada, Midori Takimoto-Kamimura, Kazuya Takenouchi, Daisuke Sawada, and Atsushi Kittaka
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Journal Title
ACS Med. Chem. Lett.
Volume: 4
Issue: 7
Pages: 671-674
DOI
Related Report
Peer Reviewed
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[Journal Article] Synthesis and Biological Activities of 1α,4α,25- and 1α,4β,25-Trihydroxyvitamin D<sub>3</sub> and Their Metabolism by Human CYP24A1 and UDP-Glucuronosyltransferase2012
Author(s)
Daisuke Sawada, Yuya Tsukuda, Kaori Yasuda, Toshiyuki Sakaki, Hiroshi Saito, Ken-ichiro Takagi, Kazuya Takenouchi, Tai C. Chen, G. Satyanarayana Reddy, and Atsushi Kittaka
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Journal Title
Chemical and Pharmaceutical Bulletin
Volume: 60
Issue: 10
Pages: 1343-1346
DOI
NAID
ISSN
0009-2363, 1347-5223
Related Report
Peer Reviewed
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[Journal Article] C15-functionalized 16-Ene-1α,25-dihydroxyvitamin D_3 is a New Vitamin D Analog with Unique Biological Properties2012
Author(s)
Go Kumagai, Masashi Takano, Kanako Shindo, Daisuke Sawada, Nozomi Saito, Hiroshi Saito, Shinji Kakuda, Ken-ichiro Takagi, Midori Takimoto-Kamimura, Kazuya Takenouchi, Tai C. Chen, Atsushi Kittaka
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Journal Title
Anticancer Res
Volume: 32
Pages: 311-318
Related Report
Peer Reviewed
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[Journal Article] C15-Functionalized 16-Ene-1α,25-dihydroxyvitamin D3 is a New Vitamin D Analog with Unique Biological Properties2012
Author(s)
G. Kumagai, M. Takano, K. Shindo, D. Sawada, N. Saito, H. Saito, S. Kakuda, K. Takagi, M. Takimoto-Kamimura, K. Takenouchi, T. C. Chen and A. Kittaka
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Journal Title
Anticancer Res.
Volume: 32
Pages: 311-318
Related Report
Peer Reviewed
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[Journal Article] New C15-Substituted Active Vitamin D_32011
Author(s)
Kanako Shindo, Go Kumagai, Masashi Takano, Daisuke Sawada, Nozomi Saito, Hiroshi Saito, Shinji Kakuda, Ken-ichiro Takagi, Eiji Ochiai, Kyouhei Horie, Midori Takimoto-Kamimura, Seiichi Ishizuka, Kazuya Takenouchi, Atsushi Kittaka
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Journal Title
Org. Lett
Volume: 13
Pages: 2852-2855
Related Report
Peer Reviewed
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[Journal Article] Synthesis of C15-Modified 16-ene-active vitamin D_3 analogs for the receptor-ligand interaction studies2011
Author(s)
Atsushi Kittaka, Go Kumagai, Masashi Takano, Daisuke Sawada, Hiroshi Saito, Shinji Kakuda, Ken-ichiro Takagi, Eiji Ochiai, Kyohei Horie, Kazuya Takenouchi, Midori Takimoto-Kamimura, and Tai C. Chen
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Journal Title
Anticancer Res
Volume: 31
Pages: 1500-1501
Related Report
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[Journal Article] New C15-Substituted Active Vitamin D32011
Author(s)
Kanako Shindo,Go Kumagai,Masashi Takano,Daisuke Sawada,Nozomi Saito,Hiroshi Saito,Shinji Kakuda,Midori Takimoto-Kamimura,Seiichi Ishizuka,Kazuya Takenouchi,Atsushi Kittaka (他3名)
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Journal Title
Org. Lett.
Volume: 13
Pages: 2852-2855
Related Report
Peer Reviewed
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[Presentation] DESIGN AND SYNTHESIS OF 2α-HETEROARALKYL-1α,25-DIHYDROXYVITAMIN D3 ANALOGS AS STRONG LIGANDS FOR VITAMIN D RECEPTOR2013
Author(s)
M. Matsuo, A. Hasegawa, M. Takano, Y. Nakamura, H. Saitou, S. Kakuda, K. Takagi, E. Ochiai, K. Horie, M. T. Kamimura, K. Takenouchi, D. Sawada, and A. Kittaka
Organizer
16th Vitamin D Workshop(San Francisco, USA)
Place of Presentation
San Francisco, USA
Related Report
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[Presentation] C5-C6 Coupling of MART-10 Synthesis and Its Clinical Implication in Cancer Treatment and Prevention2013
Author(s)
Masashi Takano, Kun-Chun Chiang, Horng-Heng Juang, Kaori Yasuda, Toshiyuki Sakaki, Toshimasa Itoh, Keiko Yamamoto, Daisuke Sawada, John N. Flanagan, Gunnar Norstedt, Tai C. Chen, and Atsushi Kittaka
Organizer
第10回カルボアニオン化学国際会議(ISCC-10、同志社大学)
Place of Presentation
京都
Related Report
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[Presentation] Synthesis Of New C15-Substituted 16-Ene-1α,25-dihydroxyvitamin D3 Analogs and The Receptor-ligand Interaction Studies2012
Author(s)
A. Kittaka, G. Kumagai, K. Shindo, M. Takano, N. Saito, D. Sawada, H. Saito, S. Kakuda, K. Takagi, E. Ochiai, K. Horie, K. Takenouchi, T.C. Chen, M. Takimoto-Kamimura
Organizer
13th Tetrahedron Symposium
Place of Presentation
台北
Related Report
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[Presentation] Synthesis of 1α,2α,25-Trihydroxyvitamin D3: Major Metabolite of 2α-(3-Hydroxypropoxy)-1α,25-dihydroxyvitamin D3 by CYP3A42012
Author(s)
Masashi Takano, Saori Ohya, Kaori Yasuda, Manabu Uchida, Junya Uryu, Tatsuya Kanai, Ami Shiotani, Hitomi Takeuchi, Yasuyo Yamamoto, Daisuke Sawada, Toshiyuki Sakaki, and Atsushi Kittaka
Organizer
チトクロームP450発見50周年記念シンポジウム
Place of Presentation
九州大学医学部コラボレーション
Related Report
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[Presentation] 活性型ビタミンD3誘導体の2α側鎖上の二級水酸基の効果と生物活性評価2012
Author(s)
高野真史, 林 恵子, 生城真一, 榊 利之, 松本直樹, 野尻久雄,角田真二, 高木健一郎, 落合鋭士, 堀江恭平, 上村みどり, 杉浦隆之, 澤田大介, 橘高敦史
Organizer
日本薬学会 第132年会
Place of Presentation
札幌
Related Report
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