Structural evaluation of new 14-epimerized tachysterol analogs as hVDR agonists

• Project/Area Number: 23590015
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• 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: ¥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.

Research Products

• [Journal Article] Design and synthesis of 2α-(tetrazolylethyl)-1α,25-dihydroxyvitamin D3 as a high affinity ligand for vitamin D receptor (2014)
  • 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
  • Journal Title: J. Steroid Biochem. Mol. Biol. Volume: in press Pages: 201-203
  • DOI: 10.1016/j.jsbmb.2013.09.001
  • Peer Reviewed
• [Journal Article] Synthesis and Biological Activity of 1α,2α,25-Trihydroxyvitamin D₃: Active Metabolite of 2α-(3-Hydroxypropoxy)-1α,25-dihydroxyvitamin D₃ by Human CYP3A4 (2014)
  • Author(s): Masashi Takano, Saori Ohya, Kaori Yasuda, Miyu Nishikawa, Akiko Takeuchi, Daisuke Sawada, Toshiyuki Sakaki, and Atsushi Kittaka
  • Journal Title: Chemical and Pharmaceutical Bulletin Volume: 62 Issue: 2 Pages: 182-184
  • DOI: 10.1248/cpb.c13-00646
  • NAID: 130003390755
  • ISSN: 0009-2363, 1347-5223
  • Peer Reviewed
• [Journal Article] Synthesis of 2α-Heteroarylalkyl Active Vitamin D3 with Therapeutic Effect on Enhancing Bone Mineral Density in vivo (2013)
  • 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
  • Journal Title: ACS Med. Chem. Lett. Volume: 4 Issue: 7 Pages: 671-674
  • DOI: 10.1021/ml400098w
  • Peer Reviewed
• [Journal Article] Synthesis of 14-epi-2α-hydroxypropoxy-1α,25-dihydroxy-19- nortachysterol and its hVDR binding (2013)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Kenichiro Takagi, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: J. Steroid Biochem. Mol. Biol Volume: 136 Pages: 27-29
  • Peer Reviewed
• [Journal Article] 14-エピ-タキステロール類の合成とVDR結合様式の解明 (2013)
  • Author(s): 澤田大介、堀江恭平、落合鋭士、竹内明子、角田真二、上村みどり、橘高敦史
  • Journal Title: ビタミン Volume: 87 (4) Pages: 220-220
• [Journal Article] 2α-アゾールエチル基を有する1α,25-ジヒドロキシビタミンD_3の合成と生物活性評価 (2013)
  • Author(s): 橘高敦史、松尾実紀、長谷川麻美、高野真史、澤田大介、齋藤博、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、竹之内一弥
  • Journal Title: ビタミン Volume: 87 (11) Pages: 652-652
• [Journal Article] 2α-アゾールエチル基を有する1α,25-ジヒドロキシビタミンD3の合成と生物活性評価 (2013)
  • Author(s): 橘高敦史、松尾実紀、長谷川麻美、高野真史、澤田大介、齋藤 博、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、竹之内一弥
  • Journal Title: ビタミン Volume: 87 Pages: 652-652
• [Journal Article] Synthesis of 14-epi-2α-hydroxypropoxy-1α,25-dihydroxy-19-nortachysterol and its hVDR binding (2013)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Kenichiro Takagi, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: J. Steroid Biochem. Mol. Biol. Volume: 121
  • Peer Reviewed
• [Journal Article] Potent 19-Norvitamin D Analogs for Prostate and Liver Cancer Therapy (2012)
  • Author(s): Atsushi Kittaka, Akihiro Yoshida, Kun-Chun Chiang, Masashi Takano, Daisuke Sawada, Toshiyuki Sakaki, and Tai C. Chen
  • Journal Title: Future Med. Chem Volume: 4 (16) Issue: 16 Pages: 2049-2065
  • DOI: 10.4155/fmc.12.130
  • Peer Reviewed
• [Journal Article] Synthesis and Biological Activities of 1α,4α,25- and 1α,4β,25-Trihydroxyvitamin D₃ and Their Metabolism by Human CYP24A1 and UDP-Glucuronosyltransferase (2012)
  • 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
  • Journal Title: Chemical and Pharmaceutical Bulletin Volume: 60 Issue: 10 Pages: 1343-1346
  • DOI: 10.1248/cpb.c12-00526
  • NAID: 130001852369
  • ISSN: 0009-2363, 1347-5223
  • Peer Reviewed
• [Journal Article] The Difference between 14-Epi-previtamin D_3 and 14-Epi-19-norprevitmain D_3: Their Synthesis and Binding Affinity for Human VDR (2012)
  • Author(s): Daisuke Sawada, Tomoyuki Katayama, Yuya Tsukuda, Nozomi Saito, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: Anticancer Res Volume: 32 Pages: 319-326
  • Peer Reviewed
• [Journal Article] C15-functionalized 16-Ene-1α,25-dihydroxyvitamin D_3 is a New Vitamin D Analog with Unique Biological Properties (2012)
  • 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
  • Journal Title: Anticancer Res Volume: 32 Pages: 311-318
  • Peer Reviewed
• [Journal Article] 2alpha-(3-ヒドロキシプロピル)-1alpha,25-ジヒドロキシ-19-ノルビタミンD_3(MART-10)とその類縁体の合成と制がん活性等 (2012)
  • Author(s): 高野真史、澤田大介、橘高敦史、高木健一郎、千田貴之、原田善文、齋藤博、山本恵子、榊利之、Kun-Chun Chiang、Shasha Zheng、John N. Flanagan、Tai C. Chen
  • Journal Title: ビタミン Volume: 86 (12) Pages: 694-696
• [Journal Article] ヒト由来CYP24A1抵抗性ビタミンD誘導体合成とATRA耐性APL細胞分化誘導 (2012)
  • Author(s): 高野真史、松本直樹、林恵子、生城真一、榊利之、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、澤田大介、野尻久雄、橘高敦史
  • Journal Title: ビタミン Volume: 86 (4) Pages: 243-243
• [Journal Article] 14-エピ-19-ノルタキステロールの合成とVDRリガンド骨格としての可能性 (2012)
  • Author(s): 澤田大介、佃勇也、橘高敦史、齋藤博、角田真二、上村みどり、竹之内一弥
  • Journal Title: ビタミン Volume: 86 (3) Pages: 181-182
• [Journal Article] The Difference between 14-Epi-previtamin D3 and 14-Epi-19-norprevitamin D3: Their Synthesis and Binding Affinity for Human VDR (2012)
  • Author(s): Daisuke Sawada, Tomoyuki Katayama, Yuya Tsukuda, Nozomi Saito, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: Anticancer Res. Volume: 32 Pages: 319-326
  • Peer Reviewed
• [Journal Article] C15-Functionalized 16-Ene-1α,25-dihydroxyvitamin D3 is a New Vitamin D Analog with Unique Biological Properties (2012)
  • 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
  • Journal Title: Anticancer Res. Volume: 32 Pages: 311-318
  • Peer Reviewed
• [Journal Article] 14-エピ-19-ノルタキステロールの合成とVDRリガンド骨格としての可能性 (2012)
  • Author(s): 澤田大介、佃 勇也、橘高敦史、齋藤 博、角田真二、上村みどり、竹之内一弥
  • Journal Title: ビタミン Volume: 86 Pages: 181-182
• [Journal Article] ヒト由来CYP24A1抵抗性ビタミンD誘導体合成とATRA耐性APL細胞分化誘導 (2012)
  • Author(s): 高野真史、松本直樹、林 恵子、生城真一、榊 利之、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、澤田大介、野尻久雄、橘高敦史
  • Journal Title: ビタミン Volume: 86 Pages: 243-243
• [Journal Article] A Multivalent Probe for AI-2 Quorum-Sensing Receptors (2011)
  • Author(s): Amanda L. Garner, Junguk Park, Joseph S. Zakhari, Colin A. Lowery, Anjali Kumari Struss, Daisuke Sawada, Gunnar F. Kaufmann, and Kim D. Janda
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 15934-15937
  • Peer Reviewed
• [Journal Article] New C15-Substituted Active Vitamin D_3 (2011)
  • 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
  • Journal Title: Org. Lett Volume: 13 Pages: 2852-2855
  • Peer Reviewed
• [Journal Article] Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor (2011)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 7215-7221
  • Peer Reviewed
• [Journal Article] Evaluation and characterization of 14-epi-19-nortachysterol analogs from 14-epi-19-norprevitamin D_3 (2011)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Ken-ichiro Takagi, Shinji Kakuda, Midori Takimoto-Kamimura, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: Anticancer Res Volume: 31 Pages: 1501-1501
• [Journal Article] Synthesis of C15-Modified 16-ene-active vitamin D_3 analogs for the receptor-ligand interaction studies (2011)
  • 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
  • Journal Title: Anticancer Res Volume: 31 Pages: 1500-1501
• [Journal Article] 2□位にアゾール環側鎖を有する活性型ビタミンD_3の合成と生物活性評価 (2011)
  • Author(s): 高野真史、松尾実紀、長谷川麻美、中村優子、齋藤博、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、竹之内一弥、澤田大介、橘高敦史
  • Journal Title: ビタミン Volume: 85 (4) Pages: 236-236
• [Journal Article] 変異VDR(Arg274Leu)に対するセコステロイドリガンドの設計と合成 (2011)
  • Author(s): 本澤忍、高橋尚志、山本康弘、荒井緑、高野真史、澤田大介、山下純、杉浦隆之、橘高敦史、角田真二、齋藤博、高木健一郎、上村みどり、石塚誠一、竹之内一弥、榊利之、加藤茂明、栗原正明
  • Journal Title: ビタミン Volume: 85 Pages: 166-167
• [Journal Article] Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor (2011)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, and Atsushi Kittaka
  • Journal Title: J. Am. Chem. Soc. Volume: 133 Pages: 7215-7221
  • Peer Reviewed
• [Journal Article] New C15-Substituted Active Vitamin D3 (2011)
  • 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)
  • Journal Title: Org. Lett. Volume: 13 Pages: 2852-2855
  • Peer Reviewed
• [Journal Article] A Multivalent Probe for AI-2 Quorum-Sensing Receptors (2011)
  • Author(s): Amanda L. Garner, Junguk Park, Joseph S. Zakhari, Colin A. Lowery, Anjali Kumari Struss, Daisuke Sawada, Gunnar F. Kaufmann, and Kim D. Janda
  • Journal Title: J. Am. Chem. Soc. Volume: 133 Pages: 15934-15937
  • Peer Reviewed
• [Journal Article] 変異VDR（Arg274Leu）に対するセコステロイドリガンドの設計と合成 (2011)
  • Author(s): 本澤 忍、高橋尚志、山本康弘、荒井 緑、高野真史、澤田大介、山下 純、杉浦隆之、橘高敦史、角田真二、齋藤 博、高木健一郎、上村みどり、石塚誠一、竹之内一弥、榊 利之、加藤茂明、栗原正明
  • Journal Title: ビタミン Volume: 85 Pages: 166-167
• [Presentation] 14-エピ-8,9-ジヒドロ-1α,25-ジヒドロキシ-19-ノルタキステロールの合成 (2014)
  • Author(s): 澤田大介、他3名
  • Organizer: 日本薬学会第134年会
  • Place of Presentation: 熊本
• [Presentation] 14-エピ-8,9-ジヒドロ-1α,25-ジヒドロキシ-19-ノルタキステロールの合成 (2014)
  • Author(s): 澤田大介、松本洋太郎、竹内明子、橘高敦史
  • Organizer: 日本薬学会 第134年会（熊本）
  • Place of Presentation: 熊本
• [Presentation] 2-[3-(テトラゾール-2-イル)プロピル]-1α,25(OH)2-19-ノルビタミンD3の合成 (2014)
  • Author(s): 高野真史，樋口恵理香，東 和成，平野圭祐，竹内明子，澤田大介，橘高敦史
  • Organizer: 日本薬学会 第134年会（熊本）
  • Place of Presentation: 熊本
• [Presentation] 7,8-cis-1α,25(OH)_2-19-norvitamin D_3の合成と活性評価 (2013)
  • Author(s): 澤田大介、他6名
  • Organizer: 第57回日本薬学会関東支部大会
  • Place of Presentation: 帝京大学
  • Year and Date: 2013-10-26
• [Presentation] DESIGN AND SYNTHESIS OF 2α-HETEROARALKYL-1α,25-DIHYDROXY VITAMIN D_3 ANALOGS AS STRONG LIGANDS FOR VITAMIN D RECEPTOR (2013)
  • Author(s): Matsuo M.他12名内、Sawada D.含む
  • Organizer: 16th Vitamin D Workshop
  • Place of Presentation: San Francisco, USA
• [Presentation] Synthesis of 14-Epi-19-Nortachysterol and Elucidation of Its Binding Affinity and Configuration for the Human Vitamin D Receptor (2013)
  • Author(s): Sawada D.他11名
  • Organizer: 14th Tetrahedron Symposium
  • Place of Presentation: Vienna, Austria
• [Presentation] C5-C6 Coupling of MART-10 Synthesis and Its Clinical Implication in Cancer Treatment and Prevention (2013)
  • Author(s): Takano M.他11名内、Sawada D.含む
  • Organizer: 第10回カルボアニオン化学国際会議
  • Place of Presentation: ISCC-10、同志社大学
• [Presentation] 14-epi-tachysterol類の合成、生物活性評価、及び受容体結合様式の解明 (2013)
  • Author(s): 澤田大介、他6名
  • Organizer: 第31回メディシナルケミストリーシンポジウム
  • Place of Presentation: 広島アステールプラザ
• [Presentation] 7,8-cis-vitamin D_3類の合成、活性評価、及びVDR結合様式の解明 (2013)
  • Author(s): 澤田大介、他6名
  • Organizer: 第39回反応と合成の進歩シンポジウム
  • Place of Presentation: 九州大学
• [Presentation] 14-epi-tachysterol類の合成とVDR結合様式の解明 (2013)
  • Author(s): 澤田大介、他6名
  • Organizer: 日本ビタミン学会第65回大会
  • Place of Presentation: 東京
• [Presentation] 7,8-cis-14-epi-19-Norvitamin D_3誘導体の合成と活性評価 (2013)
  • Author(s): 澤田大介、他4名
  • Organizer: 日本薬学会第133年会
  • Place of Presentation: 横浜
• [Presentation] 14-epi-tachysterol類の合成とVDR結合様式の解明 (2013)
  • Author(s): 澤田大介、堀江恭平、落合鋭士、竹内明子、角田真二、上村みどり、橘高敦史
  • Organizer: 日本ビタミン学会第65回大会(東京）
  • Place of Presentation: 東京
• [Presentation] DESIGN AND SYNTHESIS OF 2α-HETEROARALKYL-1α,25-DIHYDROXYVITAMIN D3 ANALOGS AS STRONG LIGANDS FOR VITAMIN D RECEPTOR (2013)
  • 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
• [Presentation] Synthesis of 14-Epi-19-Nortachysterol and Elucidation of Its Binding Affinity and Configuration for the Human Vitamin D Receptor (2013)
  • Author(s): D. Sawada, Y. Tsukuda, K. Horie, E. Ochiai, S. Kakuda, M. Takimoto-Kamimura, A. Kittaka
  • Organizer: 14th Tetrahedron Symposium（Vienna）
  • Place of Presentation: Austria, Vienna
• [Presentation] C5-C6 Coupling of MART-10 Synthesis and Its Clinical Implication in Cancer Treatment and Prevention (2013)
  • 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
• [Presentation] 7,8-cis-vitamin D3類の合成、活性評価、及びVDR結合様式の解明 (2013)
  • Author(s): 澤田大介、斎藤博、堀江恭平、高木健一郎、竹内明子、上村みどり、橘高敦史
  • Organizer: 第39回反応と合成の進歩シンポジウム（九州大学）
  • Place of Presentation: 福岡
• [Presentation] 14-epi-tachysterol類の合成、生物活性評価、及び受容体結合様式の解明 (2013)
  • Author(s): 澤田大介，佃 勇也，堀江恭平，竹内明子，角田真二，上村みどり，橘高敦史
  • Organizer: 第31回メディシナルケミストリーシンポジウム（広島アステールプラザ）
  • Place of Presentation: 広島
• [Presentation] 7,8-cis-14-epi-19-Norvitamin D3誘導体の合成と活性評価 (2013)
  • Author(s): 澤田大介、齋藤 博、角田真二、上村みどり、橘高敦史
  • Organizer: 日本薬学会 第133年会
  • Place of Presentation: 横浜
• [Presentation] 2α-(3-ヒドロキシプロポキシ)活性型ビタミンD3の代謝物の同定 (2013)
  • Author(s): 塩谷亜実，安田佳織，大屋さおり，竹内ひとみ，山本安代，金井竜也，内田 学，瓜生隼也，高野真史，澤田大介，榊 利之，橘高敦史
  • Organizer: 日本薬学会 第133年会
  • Place of Presentation: 横浜
• [Presentation] 2alpha-(3-ヒドロキシプロピル)-1alpha,25-ジヒドロキシ-19-ノルビタミンD_3(MART-10)とその類縁体の合成と制がん活性等 (2012)
  • Author(s): 橘高敦史、他12名内、澤田大介含む
  • Organizer: 第336回脂溶性ビタミン総合研究委員会
  • Place of Presentation: 東京農業大学
  • Year and Date: 2012-09-28
• [Presentation] Synthesis of 1α,2α,25-Trihydroxyvitamin D_3: Major Metabolite of 2α-(3-Hydroxypropoxy)-1α,25-dihydroxyvitami n D_3 by CYP3A4 (2012)
  • Author(s): Takano M.他12名内、Sawada D.含む
  • 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
• [Presentation] Synthesis Of New C15-Substituted 16-Ene-1α,25-dihydroxyvitamin D_3 Analogs and The Receptor-ligand Interaction Studies (2012)
  • Author(s): Kittaka A.他14名内、Sawada D.含む
  • Organizer: 13th Tetrahedron Symposium
  • Place of Presentation: 台北
• [Presentation] 14-epi-19-Nortachysterol as a New Lead Compound in Vitamin D Family and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor (2012)
  • Author(s): Sawada D.他7名
  • Organizer: XXIInd International Symposium on Medicinal Chemistry
  • Place of Presentation: ISMC 2012, Berlin, Germany
• [Presentation] REVISITING THE MINOR VITAMIN D FAMILY : A NEW TACHYSTEROL ANALOG AND ITS UNPRESEDENTED BINDING CONFIGURATION FOR THE HUMAN VITAMIN D RECEPTOR (2012)
  • Author(s): Sawada D.他8名
  • Organizer: 15th Vitamin D Workshop
  • Place of Presentation: Houston Intercontinental Hotel, USA
• [Presentation] 2α-アルコキシ置換活性型ビタミンD_3誘導体の代謝と合成研究 (2012)
  • Author(s): 高野真史、他6名内、澤田大介含む
  • Organizer: 第30回メディシナルケミストリーシンポジウム
  • Place of Presentation: タワーホール船堀
• [Presentation] 14-epi-1α,25-dihydroxytachysterolの合成と生物活性評価 (2012)
  • Author(s): 澤田大介、他5名
  • Organizer: 第38回反応と合成の進歩シンポジウム
  • Place of Presentation: タワーホール船堀
• [Presentation] 2α-ヘテロアラルキル活性型ビタミンD3の合成と生物活性:2α側鎖長の研究 (2012)
  • Author(s): 高野真史、他12名内、澤田大介含む
  • Organizer: 第42回複素環化学討論会
  • Place of Presentation: 京都テルサ
• [Presentation] 1α,4,25-トリヒドロキシビタミンD_3の合成とヒト水酸化酵素による代謝に関する研究 (2012)
  • Author(s): 澤田大介、他7名
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 札幌
• [Presentation] REVISITING THE MINOR VITAMIN D FAMILY: A NEW TACHYSTEROL ANALOG AND ITS UNPRESEDENTED BINDING CONFIGURATION FOR THE HUMAN VITAMIN D RECEPTOR (2012)
  • Author(s): D. Sawada, Y. Tsukuda, H. Saito, K. Takagi, S. Kakuda, M. Takimoto-Kamimura, E. Ochiai, K. Takenouchi, and A. Kittaka
  • Organizer: 15th Vitamin D Workshop
  • Place of Presentation: Houston Intercontinental Hotel, USA
• [Presentation] ヒト由来CYP24A1抵抗性ビタミンD誘導体合成とATRA耐性APL細胞分化誘導 (2012)
  • Author(s): 高野真史、松本直樹、林 恵子、生城真一、榊 利之、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、澤田大介、野尻久雄、橘高敦史
  • Organizer: 日本ビタミン学会第64回大会
  • Place of Presentation: 長良川国際会議場
• [Presentation] 14-epi-19-Nortachysterol as a New Lead Compound in Vitamin D Family and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor (2012)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, and Atsushi Kittaka
  • Organizer: XXIInd International Symposium on Medicinal Chemistry (ISMC 2012)
  • Place of Presentation: Berlin, Germany
• [Presentation] 2α-ヘテロアラルキル活性型ビタミンD3の合成と生物活性：2α側鎖長の研究 (2012)
  • Author(s): 高野真史、中村優子、齋藤 博、松尾実紀、長谷川麻美、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、竹之内一弥、澤田大介、橘高敦史
  • Organizer: 第42回複素環化学討論会
  • Place of Presentation: 京都テルサ
• [Presentation] Synthesis Of New C15-Substituted 16-Ene-1α,25-dihydroxyvitamin D3 Analogs and The Receptor-ligand Interaction Studies (2012)
  • 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
• [Presentation] 2α-アルコキシ置換活性型ビタミンD3誘導体の代謝と合成研究 (2012)
  • Author(s): 高野真史、大屋さおり、安田佳織、内田 学、瓜生隼也、 澤田大介、榊 利之、橘高敦史
  • Organizer: 第30回メディシナルケミストリーシンポジウム
  • Place of Presentation: タワーホール船堀
• [Presentation] Synthesis of 1α,2α,25-Trihydroxyvitamin D3: Major Metabolite of 2α-(3-Hydroxypropoxy)-1α,25-dihydroxyvitamin D3 by CYP3A4 (2012)
  • 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
• [Presentation] 1α,4,25-トリヒドロキシビタミンD3の合成とヒト水酸化酵素による代謝に関する研究 (2012)
  • Author(s): 澤田大介、佃 勇也、安田佳織、齋藤 博、堀江恭平、竹之内一弥、榊 利之、橘高敦史
  • Organizer: 日本薬学会 第132年会
  • Place of Presentation: 札幌
• [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
• [Presentation] 14-エピ-19-ノルタキステロールの合成とVDRリガンド骨格としての可能性 (2011)
  • Author(s): 澤田大介、他6名
  • Organizer: 第332回脂溶性ビタミン総合研究委員会
  • Place of Presentation: 昭和薬科大学
  • Year and Date: 2011-09-30
• [Presentation] New Skeleton in Vitamin D Family : 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor (2011)
  • Author(s): Sawada D.他7名
  • Organizer: AIMECS-11
  • Place of Presentation: 8th AFMC International Medicinal Chemistry Symposium, Tokyo
• [Presentation] Evaluation and characterization of 14-epi-19-nortachysterol analogs from 14-epi-19-norprevitamin D_3 (2011)
  • Author(s): Sawada D.他7名
  • Organizer: 4th Symposium Vitamin D Analogs in Cancer Prevention and Therapy
  • Place of Presentation: Homburg, Germany
• [Presentation] 14-epi-19-Nortachysterol類の合成と受容体結合様式の解明 (2011)
  • Author(s): 澤田大介、他6名
  • Organizer: 第37回反応と合成の進歩シンポジウム
  • Place of Presentation: 徳島
• [Presentation] Evaluation and characterization of 14-epi-19-nortachysterol analogs from 14-epi-19-norprevitamin D3 (2011)
  • Author(s): D. Sawada, Y. Tsukuda, H. Saito, K. Takagi, S. Kakuda, M. T. Kamimura, K. Takenouchi, A. Kittaka
  • Organizer: 4th Symposium Vitamin D and Analogs in Cancer Prevention and Therapy
  • Place of Presentation: ドイツ Homburg
• [Presentation] New Skeleton in Vitamin D Family: 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor (2011)
  • Author(s): Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, and Atsushi Kittaka
  • Organizer: AIMECS-11 (8th AFMC International Medicinal Chemistry Symposium)
  • Place of Presentation: 東京 京王プラザホテル
• [Presentation] 2α-アゾールエチル基を有する1α,25-ジヒドロキシビタミンD3の合成と生物活性評価
  • Author(s): 橘高敦史、松尾実紀、長谷川麻美、高野真史、澤田大介、齋藤 博、角田真二、高木健一郎、落合鋭士、堀江恭平、上村みどり、竹之内一弥
  • Organizer: 第340回脂溶性ビタミン総合研究委員会（芝浦工大）
  • Place of Presentation: 東京
• [Presentation] 7,8-cis-1α,25(OH)2-19-norvitamin D3の合成と活性評価
  • Author(s): 澤田大介、森 幸樹、安部成郁、近藤美保、塩田真由美、竹内明子、橘高敦史
  • Organizer: 第57回日本薬学会関東支部大会（帝京大学）
  • Place of Presentation: 東京
• [Presentation] 2α置換基上にアゾール環を有する19-ノル型ビタミンD3の合成研究
  • Author(s): 樋口恵理香、高野真史、澤田大介、橘高敦史
  • Organizer: 第57回日本薬学会関東支部大会（帝京大学）
  • Place of Presentation: 東京
• [Presentation] 2alpha-(3-ヒドロキシプロピル)-1alpha,25-ジヒドロキシ-19-ノルビタミンD3（MART-10）とその類縁体の合成と制がん活性等
  • Author(s): 橘高敦史、高野真史、澤田大介、高木健一郎、千田貴之、原田善文、齋藤 博、山本恵子、榊 利之、Kun-Chun Chiang、Shasha Zheng、John N. Flanagan、Tai C. Chen
  • Organizer: 第336回脂溶性ビタミン総合研究委員会
  • Place of Presentation: 東京農業大学
• [Presentation] 1α,2α,25-トリヒドロキシビタミンD3の合成研究
  • Author(s): 大屋さおり、内田 学、瓜生隼也、高野真史、安田佳織、澤田大介、榊 利之、橘高敦史
  • Organizer: 第56回日本薬学会関東支部大会
  • Place of Presentation: 昭和大学
• [Remarks]
  • URL: http://www.pharm.teikyo-u.ac.jp
• [Remarks]
  • URL: http://www.pharm.okayama-u.ac.jp/department/post-116.html
• [Remarks] 帝京大学薬学部薬化学研究室
  • URL: http://www.pharm.teikyo-u.ac.jp
• [Remarks] 岡山大学薬学部精密有機合成化学分野
  • URL: http://www.pharm.okayama-u.ac.jp/department/post-116.html
• [Remarks] 薬化学研究室
  • URL: http://www.pharm.teikyo-u.ac.jp