Chemical Biology of Stem cell differentiation

2009 Fiscal Year Final Research Report

• Project/Area Number: 19310138
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: Waseda University
• Principal Investigator: NAKAO Yoichi Waseda University, 理工学術院, 准教授 (60282696)
• Co-Investigator(Kenkyū-buntansha): 宮本 和明 独・国立病院機構, 中国がんセンター臨床研究部 (30332373)
• Project Period (FY): 2007 – 2009
• Keywords: 生理活性物質 / ケミカルバイオロジー

Research Abstract

We were planning to find small molecules useful for the study of the controlling mechanism of stem cell differentiation to vascular systems. We have studied application of marine natural anti-angiogenic compounds, azumamides, to the in vitro vascular re-organizing model using mouse iPS cells, in which we confirmed their potent effects. Therefore, this model, as well as that using mouse ES cells, was shown to be useful for the study of stem cell differentiation systems. Next, we have evaluated anti-angiogenic effects of analogues of geladine, in which we could identified unknown targets for ageladines besides the known MMP.

Research Products

• [Journal Article] Gracilioethers A-C, Anti-malarial Metabolites from the Marine Sponge Agelas gracilis (2009)
  • Author(s): Ueoka, R. ; Nakao, Y. ; Kawatsu, S. ; Yaegashi, J. ; Matsumoto, Y. ; Matsunaga, S. ; Furihata, K. ; van Soest, R.W.M. ; Fusetani, N.
  • Journal Title: J. Org. Chem. 74 Pages: 4204-4207
  • Peer Reviewed
• [Journal Article] Intramolecular Ester Exchange of Potent Cytotoxic Kulokekahilide-2 (2009)
  • Author(s): Umehara, M. ; Takada, Y. ; Nakao, Y. ; Kimura, J.
  • Journal Title: Tetrahedron Lett 50 Pages: 840-843
  • Peer Reviewed
• [Journal Article] A New Antiangiogenic C24 Oxylipin from the Soft Coral Sinularia numerosa (2009)
  • Author(s): Yamashita, T. ; Nakao, Y. ; Matsunaga, S. ; Oikawa, T. ; Imahara, Y. ; Fusetani, N.
  • Journal Title: Bioorg. Med. Chem. 17 Pages: 2181-2184
  • Peer Reviewed
• [Journal Article] a cytotoxic peptide lactone from a marine sponge Theonella (2008)
  • Author(s): Araki, T. ; Matsunaga, S. ; Nakao, Y. ; Furihata, K; West, L; Faulkner, D.J. ; Fusetani, N. Koshikamide B
  • Journal Title: sp. J. Org. 73 Pages: 7889-7894
  • Peer Reviewed
• [Journal Article] Asteropterin, an Inhibitor of Cathepsin B, from the Marine Sponge Asteropus simplex (2008)
  • Author(s): Murayama, S. ; Nakao, Y. ; Matsunaga, S.
  • Journal Title: Tetrahedron Lett. 49 Pages: 4186-4188
  • Peer Reviewed
• [Journal Article] Aplysinoplides A-C, Cytotoxic Manoalide Derivatives from the Marine Sponge Aplysinopsis digitata (2008)
  • Author(s): Ueoka, R. ; Nakao, Y. ; Fujii, S. ; van Soest, R.W.M. ; Matsunaga, S.
  • Journal Title: J. Nat. Prod. 71 Pages: 1089-1091
  • Peer Reviewed
• [Journal Article] Evaluation of Antiangiogenic Activity of Azumamides by the in vitro Vascular Organization Model Using Mouse Induced Pluripotent Stem (iPS) (2008)
  • Author(s): Nakao, Y. ; Narazaki, G. ; Hoshino, T. ; Maeda, S. ; Yoshida, M. ; Maejima, H. ; Yamashita, J.K.
  • Journal Title: Cells Bioorg. Med. Chem. Lett. 18 Pages: 2982-2984
  • Peer Reviewed
• [Journal Article] Ciliatamides A-C, Bioactive Lipopeptides from the Deep-sea Sponge Aaptos ciliata (2008)
  • Author(s): Nakao, Y. ; Kawatsu, S. ; Okamoto, C. ; Okamoto, M. ; Matsumoto, Y. ; Matsunaga, S. ; van Soest, R.W.M. ; Fusetani, N.
  • Journal Title: J. Nat. Prod. 71 Pages: 469-472
  • Peer Reviewed
• [Journal Article] Revised absolute stereochemistry of natural kulokekahilide-2 (2008)
  • Author(s): Takada, Y. ; Umehara, M. ; Nakao, Y. ; Kimura, J.
  • Journal Title: Tetrahedron Lett. 49 Pages: 1163-1165
  • Peer Reviewed
• [Journal Article] Cytotoxic C47-Polyacetylene Carboxylic Acids from a Marine Sponge Pertrosia sp. (2007)
  • Author(s): Okamoto, C. ; Nakao, Y. ; Fujita, T. ; Iwashita, T. ; van Soest, R.W.M. ; Fusetani, N. ; Matsunaga, S.
  • Journal Title: J. Nat. Prod. 70 Pages: 1816-1819
  • Peer Reviewed
• [Journal Article] Absolute Structure of Prunustatin A, a Novel GRP78 Molecular Chaperone Down-Regulator (2007)
  • Author(s): Umeda, Y. ; Furihata, K. ; Sakuda, S. ; Nagasawa, H. ; Ishigami, K. ; Watanabe, H. ; Izumikawa, M. ; Takagi, M. ; Doi, D. ; Nakao, Y. ; Shin-ya, K.
  • Journal Title: Org. Lett. 9 Pages: 4239-4242
• [Journal Article] Reinvestigation of the stereochemistry of kulokekahilide-2 (2007)
  • Author(s): Takada, Y. ; Mori, E. ; Umehara, M. ; Nakao, Y. ; Kimura, J.
  • Journal Title: Tetrahedron Lett. 48 Pages: 7653-7656
  • Peer Reviewed
• [Journal Article] Application of a 6π-1-Azatriene Electrocyclization Strategy to Total Synthesis of the Marine Sponge Metabolite Ageladine A and Biological Evaluation of Synthetic Analogues (2007)
  • Author(s): Meketa, M.L. ; Weinreb, S.M. ; Nakao, Y. ; Fusetani, N.
  • Journal Title: J. Org. Chem. 72 Pages: 4892-4899
• [Journal Article] The Structures of Three New Shishididemniols from a Tunicate of the Family Didemnidae (2007)
  • Author(s): Kobayashi, H. ; Miyata, Y. ; Okada, K. ; Fujita, T. ; Iwashita, T. ; Nakao, Y. ; Fusetani, N. ; Matsunaga, S.
  • Journal Title: Tetrahedron 63 Pages: 6748-6754
  • Peer Reviewed
• [Journal Article] Total Synthesis of Azumamide A and Azumamide E, Evaluation as Histone Deacetylase Inhibitors, and Design of a More Potent Analogue (2007)
  • Author(s): Wen, S. ; Carey, K.L. ; Nakao, Y. ; Fusetani, N. ; Packham, G. ; Ganesan A.
  • Journal Title: Org Lett 9 Pages: 1105-1108
  • Peer Reviewed
• [Presentation] 医薬品素材としての海洋天然化合物 (2010)
  • Author(s): 中尾洋一
  • Organizer: 富士山麓産学官金連携フォーラム2010
  • Place of Presentation: 沼津
  • Year and Date: 20100300
• [Presentation] 海洋生物由来の抗リーシュマニア活性化合物に関する研究 (2010)
  • Author(s): 石上進太郎、中尾洋一
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大坂
  • Year and Date: 2010-03-28
• [Presentation] 海綿由来の細胞毒性物質の探索研究 (2010)
  • Author(s): 勝俣良祐、中尾洋一
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大坂
  • Year and Date: 2010-03-27
• [Presentation] 海洋生物由来の細胞毒性化合物に関する研究 (2010)
  • Author(s): 前島寛、渡部裕喜、中尾洋一
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大坂
  • Year and Date: 2010-03-27
• [Presentation] 天然化合物を利用したケミカルエピゲノミクス研究の可能性について』 (2009)
  • Author(s): 中尾洋一
  • Organizer: 大阪大学蛋白質研究所セミナー「疾患の基盤としてのエピジェネティクス」
  • Place of Presentation: 大坂
  • Year and Date: 20090600
• [Presentation] Search for Chemical-"Epi"genetic Probes from Marine Invertebrates (2009)
  • Author(s): Nakao, Y.
  • Organizer: Waseda-NUS Joint Symposium, Chemical Epigenomics-The fusion of Epigenetics
  • Place of Presentation: シンガポール
  • Year and Date: 20090300
• [Presentation] Marine Natural Products as Tool for Chemical Biology (2009)
  • Author(s): Nakao, Y.
  • Organizer: The Second Waseda-NTU Symposium in Chemistry 2009
  • Place of Presentation: シンガポール
  • Year and Date: 20090300
• [Presentation] Searching Probe molecules for Chemical-Epigenetics from Marine Invertebrates (2008)
  • Author(s): Nakao, Y.
  • Organizer: 大阪大学蛋白質研究所リトリート2008
  • Place of Presentation: 兵庫
  • Year and Date: 20081200
• [Presentation] 幹細胞のケミカルバイオロジー (2008)
  • Author(s): 中尾洋一
  • Organizer: 理研ケミカルゲノミクスセミナー
  • Place of Presentation: 和光市
  • Year and Date: 20080400
• [Presentation] Bioactive small molecules from marine organisms (2007)
  • Author(s): Nakao, Y.
  • Organizer: Symposium A: Aquatic Ecosystems, 4th Asia-Pacific Conference on Chemical Ecology
  • Place of Presentation: つくば
  • Year and Date: 20070900
• [Presentation] 海洋生物からの血管新生阻害剤の探索 (2007)
  • Author(s): 中尾洋一
  • Organizer: 理化学研究所神戸研究所分子イメージング科学研究センターセミナー
  • Place of Presentation: 神戸
  • Year and Date: 20070500
• [Book] Comprehensive Natural Products ; Chemistry II Chemistry and Biology(Lui, H.-W., Eds., Marine Invertebrates: Sponges. (2010)
  • Author(s): Nakao, Y. ; Fusetani, N., Mander, L.
  • Total Pages: 327-362
  • Publisher: Elsevier
• [Remarks]
  • URL: http://www.chem.waseda.ac.jp/nakao/
• [Patent(Industrial Property Rights)] 新規環状デプシペプチドおよびその用途 (2010)
  • Inventor(s): 山下潤、中尾洋一
  • Industrial Property Rights Holder: 国立大学法人京都大学、学校法人
  • Industrial Property Number: 米国仮出願US 61/334,961
  • Filing Date: 2010-05-17
• [Patent(Industrial Property Rights)] 腔腸動物由来抗原虫化合物 (2010)
  • Inventor(s): 中尾洋一、石上進太郎、後藤康之、河津信一郎、井上昇
  • Industrial Property Rights Holder: 学校法人早稲田大学、国立大学法人帯広畜産大学
  • Industrial Property Number: 出願特許申請特願2010-055150
  • Filing Date: 2010-03-11
• [Patent(Industrial Property Rights)] 環状デプシペプチド (2010)
  • Inventor(s): 木村純二、中尾洋一、梅原将洋
  • Industrial Property Rights Holder: 学校法人青山学院
  • Industrial Property Number: 出願特許申請特願2009-21621
  • Filing Date: 2010-02-02
• [Patent(Industrial Property Rights)] 環状デプシペプチド (2009)
  • Inventor(s): 木村純二、中尾洋一、梅原将洋
  • Industrial Property Rights Holder: 学校法人青山学院
  • Industrial Property Number: 出願特許申請特願2009-21622
  • Filing Date: 2009-02-02
• [Patent(Industrial Property Rights)] Evaluation of Antiangiogenic Activity of Azumamides by the in vitro Vascular Organization Model Using Mouse Induced Pluripotent Stem (iPS) Cells (2008)
  • Inventor(s): 山下潤、中尾洋一
  • Industrial Property Rights Holder: 国立大学法人京都大学、学校法人早稲田大学
  • Industrial Property Number: 米国仮出願US 61/124,721
  • Filing Date: 2008-04-18