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2010 Fiscal Year Final Research Report

Development of PET Imaging through Rapid Azaelectrocyclization and Oligosaccharide-Engineered Functional Macromolecules

Research Project

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Project/Area Number 19681024
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Living organism molecular science
Research InstitutionOsaka University

Principal Investigator

TANAKA Katsunori  Osaka University, 大学院・理学研究科, 助教 (00403098)

Project Period (FY) 2007 – 2010
Keywordsアザ電子環状反応 / PET / 標識化 / イメージング / 糖鎖
Research Abstract

Efficient labeling of peptides, proteins, and antibodies were developed based on the rapid azaelectrocyclization, and the method was applied to the PET and the noninvasive fluorescence imaging. General solid-supported synthesis of N-glycans was established and their dendrimer-type clusters, mimicking the "glycan multivalency effects" in vivo, were efficiently prepared by his own "self-activating" Huisgen 1,3-dipolar cycloaddition. Modification of the proteins and/or the living cell surfaces by N-glycans were also established by rapid azaelectrocyclization. PET and noninvasive fluorescence imaging successfully visualized the trafficking of N-glycoclusters and N-glycan-engineered living cells to the specific organs and/or tumors implanted in living animals.

  • Research Products

    (60 results)

All 2011 2010 2009 2008 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (35 results) Book (5 results) Remarks (11 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Positron Emission Tomography (PET) and Fluorescence Imaging of Dendrimer-type N-Glycan Clusters : Remarkable Structural Dependency of Oligosaccharides on In Vivo Dynamics2010

    • Author(s)
      K.Tanaka, E.R.O.Siwu, K.Minami, K.Hasegawa, S.Nozaki, Y.Kanayama, K.Koyama, C.W.Chen, J.C.Paulson, Y.Watanabe, K.Fukase
    • Journal Title

      Angew.Chem.Int.Ed. 49

      Pages: 8195-8200

    • Peer Reviewed
  • [Journal Article] A Combined 6π-Azaelectrocyclization/Staudinger Approach to Protein&Cell Engineering : Non-Invasive Tumor Targeting by N-Glycan-Engineered Lymphocytes2010

    • Author(s)
      K.Tanaka, K.Minami, T.Tahara, E.R.O.Siwu, K.Koyama, S.Nozaki, H.Onoe, Y.Watanabe, K.Fukase
    • Journal Title

      J.Carbohydr.Chem. 29

      Pages: 118-132

    • Peer Reviewed
  • [Journal Article] Electrocyclization-Based Labeling Allows Efficient In Vivo Imaging of Cellular Trafficking2010

    • Author(s)
      K.Tanaka, K.Minami, T.Tahara, Y.Fujii, E.R.O.Siwu, S.Nozaki, H.Onoe, S.Yokoi, K.Koyama, Y.Watanabe, K.Fukase
    • Journal Title

      ChemMedChem 5

      Pages: 841-845

    • Peer Reviewed
  • [Journal Article] Renaissance of Traditional Organic Reactions under Microfluidic Conditions : A New Paradigm for Natural Products Synthesis2009

    • Author(s)
      K.Tanaka, K.Fukase
    • Journal Title

      Org.Process Res.Dev. 13

      Pages: 983-990

    • Peer Reviewed
  • [Journal Article] Library-directed Synthesis of N-Glycans : Synthesis of Sialic Acid-containing Complex-type N-Glycan on Solid-supports2009

    • Author(s)
      K.Tanaka, Y.Fujii, H.Tokimoto, Y.Mori, S.Tanaka, G.-m.Bao, E.R.O.Siwu, A.Nakayabu, K.Fukase
    • Journal Title

      Chem.Asian J. 4

      Pages: 574-580

    • Peer Reviewed
  • [Journal Article] PET (Positron Emission Tomography) Imaging of Biomolecules Using Metal/DOTA Complexes : A New Collaborative Challenge by Chemists, Biologists, and Physicians for Future Diagnostics and Exploration of In vivo Dynamics2008

    • Author(s)
      K.Tanaka, K.Fukase
    • Journal Title

      Org.Biomol.Chem. 6

      Pages: 815-828

    • Peer Reviewed
  • [Journal Article] A Submicrogram-scale Protocol for Biomolecule-based PET Imaging via Rapid 6π-Azaelectrocyclization : First Visualization of Sialic Acid-dependent Circulatory Residence of Glycoproteins2008

    • Author(s)
      K.Tanaka, T.Masuyama, K.Hasegawa, T.Tahara, H.Mizuma, Y.Wada, Y.Watanabe, K.Fukase
    • Journal Title

      Angew.Chem.Int.Ed. 47

      Pages: 102-105

    • Peer Reviewed
  • [Presentation] 効率的結合形成反応から始まるシンセティックバイオロジーの新戦略2011

    • Author(s)
      田中克典
    • Organizer
      「生体分子の化学」シンポジウム,Host:伊藤幸成主任
    • Place of Presentation
      独立行政法人理化学研究所
    • Year and Date
      2011-01-21
  • [Presentation] A New Strategy in Synthetic Biology: From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry, Georgia State university,Host : Professor Binghe Wang
    • Place of Presentation
      Atlanta
    • Year and Date
      2010-11-18
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Departments of Chemistry and Medicinal Chemistry, University of Michigan,Host : Anna Mapp
    • Place of Presentation
      Michigan
    • Year and Date
      2010-11-16
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry, The University of Toledo,Host : Kana Yamamoto
    • Place of Presentation
      Ohio
    • Year and Date
      2010-11-15
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Wayne State university,Host : Professor Zhongwu Guo
    • Place of Presentation
      Detroit
    • Year and Date
      2010-11-12
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at North Carolina State university,Host : Christian Melander
    • Place of Presentation
      North Carolina
    • Year and Date
      2010-11-10
  • [Presentation] New strategy from synthetic chemistry & molecular imaging, Asian Communications of Glycobiology and Glycotechnology2010

    • Author(s)
      田中克典
    • Organizer
      2nd Annual Conference for Asian Communicationsof Glycobiology and Glycotechnology
    • Place of Presentation
      台湾
    • Year and Date
      2010-10-29
  • [Presentation] 実用的合成を指向したマイクロフロー反応の適応範囲と可能性:生理活性天然物の合成を例として2010

    • Author(s)
      田中克典
    • Organizer
      塩野義製薬株式会社セミナー
    • Place of Presentation
      大阪
    • Year and Date
      2010-10-12
  • [Presentation] 非侵襲的イメージングを用いたタンパク質、細胞、およびデンドリマー上のN-結合型糖鎖の機能解析-N-結合型糖鎖による非侵襲的イメージングとターゲティング-2010

    • Author(s)
      田中克典
    • Organizer
      第59回高分子討論会
    • Place of Presentation
      北海道大学
    • Year and Date
      2010-09-15
  • [Presentation] 革新的結合形成反応の糖鎖科学への応用:マイクロフロー/固相合成システムによるN-結合型糖鎖の合成と非侵襲的イメージング2010

    • Author(s)
      田中克典
    • Organizer
      財団法人野口研究所セミナー,Host:水野真盛研究員
    • Place of Presentation
      東京
    • Year and Date
      2010-05-28
  • [Presentation] STELLA+標識キットの開発と生体内イメージング2010

    • Author(s)
      田中克典
    • Organizer
      (株)キシダ化学セミナー
    • Place of Presentation
      兵庫
    • Year and Date
      2010-05-12
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Center for Chemical Methodology and Library Department,Host : Professor John A.Porco Jr.
    • Place of Presentation
      Boston University
    • Year and Date
      2010-03-03
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Radiology, Memorial Sloan-Kettering Cancer Center,Host : Dr Jason S.Lewis
    • Place of Presentation
      New York
    • Year and Date
      2010-03-01
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2010

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry and Chemical Biology,Host : Professor Gregory Verdine
    • Place of Presentation
      Harvard University
    • Year and Date
      2010-02-26
  • [Presentation] タンパク質および細胞上での革新的化学反応を基盤とする糖鎖関連物質の非侵襲的イメージング2009

    • Author(s)
      田中克典
    • Organizer
      第7回糖鎖科学コンソーシアムシンポジウム,千里ライフサイエンスセンター
    • Place of Presentation
      大阪
    • Year and Date
      2009-12-07
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry, Host : Professor Daesung Lee
    • Place of Presentation
      The University of Illinois at Chicago
    • Year and Date
      2009-09-01
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry, Host : Professor Christopher J.Douglas
    • Place of Presentation
      University of Minnesota
    • Year and Date
      2009-08-27
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry and Molecular Biology, Host : Professor Gregory R.Cook
    • Place of Presentation
      NDSU North Dakota State University
    • Year and Date
      2009-08-25
  • [Presentation] マイクロフロー反応を鍵とする生理活性天然物の実用的合成戦略2009

    • Author(s)
      田中克典
    • Organizer
      有機合成化学春季講習会,日本薬学会長井記念ホール
    • Place of Presentation
      東京
    • Year and Date
      2009-06-18
  • [Presentation] 超高速6π-アザ電子環状反応を用いた生体高分子標識化法の開発とPETイメージングへの応用2009

    • Author(s)
      田中克典
    • Organizer
      日本薬学会第129年会有機合成の若い力
    • Place of Presentation
      京都国際会議場
    • Year and Date
      2009-03-26
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry,Host : Professor Babak Borhan
    • Place of Presentation
      Michigan State University
    • Year and Date
      2009-03-13
  • [Presentation] A New Strategy in Synthetic Biology: From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry, Host : Professor Hisashi Yamamoto
    • Place of Presentation
      The University of Chicago
    • Year and Date
      2009-03-13
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry,Host : Professor Akira Kawamura
    • Place of Presentation
      CUNY-Hunter College
    • Year and Date
      2009-03-11
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry,Host : Professor Richard P.Hsung
    • Place of Presentation
      University of Wisconsin at Madison
    • Year and Date
      2009-03-09
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2009

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry,Host : Professor James W.Canary
    • Place of Presentation
      New York University (NYU)
    • Year and Date
      2009-03-06
  • [Presentation] 化合物ではなく"有機反応"を駆使したケミカルバイオロジー2009

    • Author(s)
      田中克典
    • Organizer
      理化学研究所,第8回ケミカルバイオロジー領域研究会Host:谷口直之教授
    • Place of Presentation
      和光
    • Year and Date
      2009-01-28
  • [Presentation] 化合物ではなく"有機反応"を駆使したケミカルバイオロジーの新戦略2008

    • Author(s)
      田中克典
    • Organizer
      平成20年度「戦略的大学連携支援事業」先端科学セミナー京都ケミカルバイオロジーシンポジウム,Host:椿一典教授平成20年度「戦略的大学連携支援事業」先端科学セミナー京都ケミカルバイオロジーシンポジウム,Host:椿一典教授
    • Place of Presentation
      京都府立大学,京都
    • Year and Date
      2008-12-15
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2008

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry,Host : Professor Jeffrey Bode
    • Place of Presentation
      University of Pennsylvania
    • Year and Date
      2008-11-18
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2008

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Chemistry,Host : Professor Koji Nakanishi and Professor Nina Berova
    • Place of Presentation
      Columbia University
    • Year and Date
      2008-11-17
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2008

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Molecular&Medical Pharmacology, Host : Professor Hsian-Rong Tseng
    • Place of Presentation
      UCLA
    • Year and Date
      2008-11-10
  • [Presentation] 革新的電子環状反応による生体高分子の標識化とインビボイメージング2008

    • Author(s)
      田中克典
    • Organizer
      (財)サントリー生物有機科学研究所セミナー,Host:楠本正一所長
    • Year and Date
      2008-10-21
  • [Presentation] A New Strategy in Synthetic Biology : From Enzyme Inhibition, Natural Products Synthesis to PET Imaging by 6π-Azaelectrocyclizations2008

    • Author(s)
      田中克典
    • Organizer
      Departmental Seminar at Department of Organic Chemistry and Biochemistry, Laboratory for Stereoselective Catalysis and Biocatalysis, Rudjer Boskovic Institute,Host : Professor Vitomir Sunjic and Professor Marin Roje
    • Place of Presentation
      Croatia
    • Year and Date
      2008-09-16
  • [Presentation] 酵素阻害機構に学ぶアザ電子環状反応の開発と天然物合成および生体内イメージング2008

    • Author(s)
      田中克典
    • Organizer
      東京農工大学工学部セミナーHost:長澤和夫教授
    • Year and Date
      2008-07-18
  • [Presentation] 高速アザ電子環状反応を用いたケミカルバイオロジー研究2008

    • Author(s)
      田中克典
    • Organizer
      早稲田大学理工学部セミナー,Host:中尾洋一教授
    • Year and Date
      2008-05-08
  • [Presentation] マイクロー反応を用いた新合成戦略2008

    • Author(s)
      田中克典
    • Organizer
      和歌山県工業技術センターセミナー,Host:森一研究員
    • Year and Date
      2008-02-08
  • [Book] In R.Gerardy-Schahn, P.Delannoy, M.von Itzstein(eds)Topics in Current Chemistry volumes, SialoGlyco Chemistry and Biology2011

    • Author(s)
      K.Tanaka, K.Fukase
    • Publisher
      Chemical Approachto A Whole Body Imaging of Sialo-N-linked Glycans(未定,in press)
  • [Book] In P.Toy(ed)Solid-Phase Organic Synthesis Book. Wiley2011

    • Author(s)
      K.Tanaka, K.Fukase
    • Publisher
      Oligosaccharide Synthesis on Solid-supports(未定,in press)
  • [Book] In B.Fraser-Reid, K.Tatsuta, J.Thiem(eds)Glycoscience. Springer, Berlin2011

    • Author(s)
      K. Tanaka, Y.Fujimoto, S.Tanaka, Y.Mori, K.Fukase
    • Publisher
      Combinatorial Methods in Oligosaccharide Synthesis(未定,in press)
  • [Book] In B. Fraser-Reid, K. Tatsuta, J.Thiem(eds)Glycoscience. Springer, Berlin2011

    • Author(s)
      K.Tanaka, K.Fukase
    • Publisher
      Polymer-supported and Tag-assisted Methods in Oligosaccharide Synthesis(未定,in press)
  • [Book] 複合糖質の化学と最新応用技術(糖鎖のインビボバイオイメージング, 正田晋一郎, 稲津敏行監修)2009

    • Author(s)
      田中克典, 深瀬浩一
    • Total Pages
      235-244
    • Publisher
      株式会社シーエムシー出版
  • [Remarks] ホームページ等

  • [Remarks] 科学新聞(2010年6月4日)

  • [Remarks] 読売新聞(2010年5月日)

  • [Remarks] 読売新聞(HP)(2010年5月21日)

  • [Remarks] 神戸新聞(HP)(2010年5月20日)

  • [Remarks] 日経プレスリリース(HP)(2010年5月20日)

  • [Remarks] 朝日新聞(2010年5月18日)

  • [Remarks] 日経プレスリリース(HP)(2010年4月19日)

  • [Remarks] 化学工業日報(2009年6月22日)

  • [Remarks] (株)キシダ化学ホームページ(2008年4月1日)

  • [Remarks] 理化学研究所ホームページ(2008年4月1日)

  • [Patent(Industrial Property Rights)] リジンデンドリマー型糖鎖クラスターの製造法とその応用2009

    • Inventor(s)
      深瀬浩一、田中克典、渡辺恭良、小山幸一
    • Industrial Property Rights Holder
      国立大学法人大阪大学、独立行政法人理化学研究所、キシダ化学株式会社
    • Industrial Property Number
      PCT/JP2009,080637
    • Filing Date
      2009-03-27
  • [Patent(Industrial Property Rights)] 新規ヘキサトリエン-β-カルボニル化合物2008

    • Inventor(s)
      深瀬浩一、田中克典、渡辺恭良、長谷川功紀、田原強
    • Industrial Property Rights Holder
      国立大学法人大阪大学、独立行政法人理化学研究所
    • Industrial Property Number
      PCT/JP2008,051871
    • Filing Date
      2008-02-05

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Published: 2012-02-13   Modified: 2016-04-21  

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