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Synthesis of ^<18>F-labeled GABA, amino acids, and lactic acids by using oxazoline precursors

Research Project

Project/Area Number 19790028
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionThe Institute of Physical and Chemical Research

Principal Investigator

DOI Hisashi  The Institute of Physical and Chemical Research, 分子イメージング標識化学研究チーム, チームリーダー (00421818)

Project Period (FY) 2007 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥600,000)
Fiscal Year 2010: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2009: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2008: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2007: ¥1,200,000 (Direct Cost: ¥1,200,000)
Keywords合成化学 / 生体分子 / 生理活性 / 脳神経 / 放射線 / PET / ^<18>F放射核 / 標識化学 / 生物活性有機化合物 / GABA / アミノ酸 / 乳酸 / ^18F放射核
Research Abstract

In order to realize synthesis of ^<18>F-labeled GABA, amino acid, and lactic acid, we have investigated ^<18>F-labeling reaction using oxazoline precursors under PET radiolabeling conditions. However, we encountered difficulties to conduct the ^<18>F-labeling under anhydrous conditions by remote-controlling radiolabeling system, and unfortunately, oxazoline precursors underwent radiolysis under the conditions, giving many side products due to decomposition. In the circumstances, we have tried to develop Pd^0-mediated rapid C-[^<18>F]fluoromethylation in parallel and have explored other 18F-labeling methods for the target compounds.

Report

(6 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report   Self-evaluation Report ( PDF )
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (37 results)

All 2011 2010 2009 2008 2007 Other

All Journal Article (8 results) (of which Peer Reviewed: 7 results) Presentation (14 results) Book (4 results) Remarks (2 results) Patent(Industrial Property Rights) (9 results)

  • [Journal Article] General Method for ^<11>C-Labeling of 2-Arylpropionic Acids and Their Esters : Construction of a PET Tracer Library for a Study of Biological Events Involved in COXs Expression2010

    • Author(s)
      Misato Takashima-Hirano
    • Journal Title

      Chemistry-A European Journal (印刷中)

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium(0)-Mediated Rapid Methylation and Fluoromethylation on Carbon Frameworks by Reacting Methyl and Fluoromethyl Iodide with Aryl and Alkenyl Boronic Acid Esters Useful for the Synthesis of [^<11>C]CH_3-C-and [^<18>F]FCH_2-C-Containing PET Tracers2009

    • Author(s)
      Hisashi Doi, Ikuya Ban, Akihito Nonoyama, Kengo Sumi, Chunxiang Kuang, Takamitsu Hosoya, Hideo Tsukada, Masaaki Suzuki
    • Journal Title

      Chem.Eur.J. 15

      Pages: 4165-4171

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium(0)-Mediated Rapid Methylation and Fluoromethylation on Carbon Frameworks by Reacting Methyl and Fluoromethyl Iodide with Aryl and Alkenyl Boronic Acid Esters Useful for the Synthesis of [11C]CH3-C- and [18F]FCH2-C-Containing PET Tracers2009

    • Author(s)
      Hisashi Doi, Ikuya Ban, Akihito Nonoyama, Kengo Sumi, Chunxiang Kuang, Takamitsu Hosoya, Hideo Tsukada, Masaaki Suzuki
    • Journal Title

      Chem. Eur. J. 15

      Pages: 4165-4171

    • Related Report
      2009 Self-evaluation Report
    • Peer Reviewed
  • [Journal Article] Palladium(O)-Mediated Rapid Methylation and Fluoromethylation on Carbon Frameworks by Reacting Methyl and Fluoromethyl Iodide with Aryl and Alkenyl Boronic Acid Esters Useful for the Synthesis of C-^<11>CH_3- and C-^<18>FCH_2-Containing PET Tracers2009

    • Author(s)
      Hisashi Doi
    • Journal Title

      Chemistry-A European Journal 15

      Pages: 4165-4171

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd(0)-Mediated Rapid Coupling between Methyl Iodide and Hetero-Arylstannanes : an Efficient and General Method for the Incorporation of a Positron-Emitting ^<11>C Radionuclide into Heteroaromatic Frameworks2009

    • Author(s)
      Masaaki Suzuki
    • Journal Title

      Chemistry-A European Journal 15

      Pages: 12489-12495

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ^<11>C-PK11195 PET for the In Vivo Evaluation of Neuroinflammation in the Rat Brain After Cortical Spreading Depression2009

    • Author(s)
      Yilong Cui
    • Journal Title

      The Journal of Nuclear Medicine 50

      Pages: 1904-1911

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium(O)-Mediated Rapid Methylation and Fluoromethylation on Carbon Frameworks by Reacting Methyl and Fluoromethyl Iodide with Aryl andAlkenyl Boronic Acid Esters Useful for the Synthesis of C-^<11>CH_3- and C-^<18>FCH_2-Containing PET Tracers2009

    • Author(s)
      土居久志
    • Journal Title

      Chemistry - A European Journal (印刷中)

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] PET法による分子イメージング研究の新展開-創薬プロセス・疾患診断の革新を目指して2007

    • Author(s)
      鈴木正昭
    • Journal Title

      化学工業 58

      Pages: 351-359

    • Related Report
      2007 Annual Research Report
  • [Presentation] Pd^0-mediated rapid C-[^<18>F]fluoromethylation : Coupling reaction of an organoboron compound with a [^<18>F]fluoromethyl halide2010

    • Author(s)
      H.Doi, M.Goto, M.Suzuki
    • Organizer
      2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2010-12-15
    • Related Report
      2010 Final Research Report
  • [Presentation] [^<18>F]FCH_2基含有PETトレーサーの新規合成法の開発2010

    • Author(s)
      後藤美樹
    • Organizer
      日本ケミカルバイオロジー学会 第5回年会
    • Place of Presentation
      慶応義塾大学(横浜)
    • Year and Date
      2010-05-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] 理研におけるPET標識化学の展開:^<11>Cおよび^<18>F-標識法の現状と将来展望2010

    • Author(s)
      土居久志
    • Organizer
      分子イメージング研究シンポジウム2010
    • Place of Presentation
      日経ホール(東京)
    • Year and Date
      2010-01-22
    • Related Report
      2009 Annual Research Report
  • [Presentation] Pd^0-mediated rapid C-[^<18>F]fluoromethylation by the reaction of a [^<18>F]fluoromethyl halide and an organoboron compound2010

    • Author(s)
      H.Doi, M.Goto, M.Suzuki
    • Organizer
      15th European Symposium On Radiopharmacy And Radiopharmaceuticals, Abstract, Q.J.Nucl.Med.Mol.Imaging, 54, Suppl.1 to No.2, pp 18.19.
    • Place of Presentation
      Edinburgh, Scotland (UK)
    • Related Report
      2010 Final Research Report
  • [Presentation] [^<18>F]FCH_2基含有PETトレーサーの新規合成法の開発;New Methodology of the Synthesis of [^<18>F]FCH_2-Incorporated PET Tracers2010

    • Author(s)
      後藤美樹、土居久志、鈴木正昭
    • Organizer
      日本ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      慶応義塾大学、横浜
    • Related Report
      2010 Final Research Report
  • [Presentation] 理研におけるPET標識化学の展開:^<11>Cおよび^<18>F-標識法の現状と将来展望2010

    • Author(s)
      土居久志
    • Organizer
      分子イメージング研究シンポジウム2010-未来を拓く創薬・疾患診断研究-,Molecular Imaging 2010, The Future with Drug Discovery and PET Diagnosis
    • Place of Presentation
      日経ビル3階日経ホール、東京
    • Related Report
      2010 Final Research Report
  • [Presentation] 「理研におけるPET標識化学の展開:11Cおよび18F-標識法の現状と将来展望」、分子イメージング研究シンポジウム2010-未来を拓く創薬・疾患診断研究-2010

    • Author(s)
      土居久志
    • Organizer
      Molecular Imaging 2010, The Future with Drug Discovery and PET Diagnosis
    • Place of Presentation
      日経ビル3階日経ホール、東京
    • Related Report
      2009 Self-evaluation Report
  • [Presentation] PETを活用した分子イメージング創薬化学の展開2009

    • Author(s)
      土居久志
    • Organizer
      第7回糖鎖科学コンソーシアムシンポジウム~糖鎖研究と他領域との統合
    • Place of Presentation
      千里ライフサイエンスセンター(大阪)
    • Year and Date
      2009-12-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] PETプローブの一般的合成法の開発とPETケミカルバイオロジーへの展開2009

    • Author(s)
      土居久志
    • Organizer
      日本ケミカルバイオロジー学会 第4回年会
    • Place of Presentation
      神戸市産業振興センター(神戸)
    • Year and Date
      2009-05-19
    • Related Report
      2009 Annual Research Report
  • [Presentation] PETを活用した分子イメージング創薬化学の展開;Molecular imaging medicinal chemistry by PET in RIKEN CMIS2009

    • Author(s)
      土居久志
    • Organizer
      第7回糖鎖科学コンソーシアムシンポジウム~糖鎖研究と他領域との統合
    • Place of Presentation
      千里ライフサイエンスセンター、大阪
    • Related Report
      2010 Final Research Report 2009 Self-evaluation Report
  • [Presentation] PETプローブの一般的合成法の開発とPETケミカルバイオロジーへの展開;Development of General Synthetic Methodologies of PET Probes and Its Applications to PET Chemical Biology2009

    • Author(s)
      土居久志、橋爪良信、畑中恵子、高島好聖、後藤美樹、長田浩子、斯琴、倉橋正浩、鈴木正昭
    • Organizer
      日本ケミカルバイオロジー学会第4回年会
    • Place of Presentation
      神戸市産業振興センター、神戸
    • Related Report
      2010 Final Research Report 2009 Self-evaluation Report
  • [Presentation] 新規^<11>C-標識反応の開発とPETプローブ化への応用2008

    • Author(s)
      土居久志
    • Organizer
      分子イメージング研究シンポジウム2008
    • Place of Presentation
      神戸国際会議場
    • Year and Date
      2008-11-14
    • Related Report
      2008 Annual Research Report
  • [Presentation] Pd(0)-Mediated Rapid C-Methylations for the Synthesis of 11C-Incorporated PET Tracers2008

    • Author(s)
      土居久志
    • Organizer
      1st International Conference on Drug Design & Discovery
    • Place of Presentation
      ドバイ世界貿易センター,UAE
    • Year and Date
      2008-02-05
    • Related Report
      2007 Annual Research Report
  • [Presentation] PETトレーサーの新合成法の開発と応用2007

    • Author(s)
      土居久志
    • Organizer
      第47回日本核医学会学術総会
    • Place of Presentation
      仙台国際センター
    • Year and Date
      2007-11-04
    • Related Report
      2007 Annual Research Report
  • [Book] 科学と工業(大阪工研協会会誌),85(4)(短寿命PET分子プローブの合成のための高速化学反応の開発)2011

    • Author(s)
      土居久志
    • Related Report
      2010 Final Research Report
  • [Book] 遺伝子医学MOOK18号 創薬研究への分子イメージング応用,"第1章3.PET分子プローブの合成法"2010

    • Author(s)
      土居久志
    • Publisher
      メディカルドゥ
    • Related Report
      2010 Final Research Report
  • [Book] 臨床医とコメディカルのための最新クリニカルPET,"第15章2.PET分子プローブの開発研究とその進歩"2010

    • Author(s)
      土居久志
    • Publisher
      先端医療技術研究所
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Book] 創薬研究への分子イメージング応用,"第1章3.PET分子プローブの合成法"2010

    • Author(s)
      土居久志
    • Publisher
      メディカルドゥ
    • Related Report
      2010 Annual Research Report
  • [Remarks] ホームページ等 理化学研究所分子イメージング科学研究センター

    • URL

      http://www.cmis.riken.jp/

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.cmis.riken.jp/

    • Related Report
      2009 Self-evaluation Report
  • [Patent(Industrial Property Rights)] 高速フルオロメチル化法及びそれを利用したPETトレーサーの製造方法2010

    • Inventor(s)
      鈴木正昭、土居久志、、後藤美樹
    • Industrial Property Rights Holder
      (独)理化学研究所
    • Filing Date
      2010-12-03
    • Related Report
      2010 Final Research Report
  • [Patent(Industrial Property Rights)] 高速フルオロメチル化法及びそれを利用したpetトレーサーの製造方法2009

    • Inventor(s)
      鈴木正昭、土居久志、後藤美樹
    • Industrial Property Rights Holder
      (独)理化学研究所
    • Filing Date
      2009-12-04
    • Related Report
      2009 Self-evaluation Report
  • [Patent(Industrial Property Rights)] ^<18>F標識アジド化合物、^<18>F標識化用試薬及びそれを用いたアルキン化合物の^<18>F標識方法2009

    • Inventor(s)
      渡辺恭良、鈴木正昭、土居久志、窪山剛之、小比賀聡、今西武
    • Industrial Property Rights Holder
      独立行政法人理化学研究所、国立大阪大学
    • Industrial Property Number
      2009-118505
    • Filing Date
      2009-05-15
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] PET用標識化合物2009

    • Inventor(s)
      渡辺恭良、尾上浩隆、高橋佳代、鈴木正昭、土居久志、細谷孝充
    • Industrial Property Rights Holder
      独立行政法人理化学研究所
    • Industrial Property Number
      2009-159129
    • Filing Date
      2009-07-03
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] アイソトープ標識2-アリールプロピオン酸類及びその製造方法、並びに陽電子放射断層画像撮像用分子プローブ及びそれを用いたシクロオキシゲナーゼのイメージング方法2009

    • Inventor(s)
      高島好聖、宿里充穂、後藤美樹、土居久志、尾上浩隆、鈴木正昭、渡辺恭良
    • Industrial Property Rights Holder
      独立行政法人理化学研究所
    • Industrial Property Number
      2009-181122
    • Filing Date
      2009-08-03
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] アイソトープ標識化合物及びアイソトープ標識化合物前駆体2009

    • Inventor(s)
      桑田一夫、木村力、武藤淳二、古山浩子、鈴木正昭、渡辺恭良、土居久志、佐古健生
    • Industrial Property Rights Holder
      独立行政法人理化学研究所、国立岐阜大学
    • Industrial Property Number
      2009-218247
    • Filing Date
      2009-09-21
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 高速フルオロメチル化法及びそれを利用したPETトレーサーの製造方法2009

    • Inventor(s)
      鈴木正昭、土居久志、後藤美樹
    • Industrial Property Rights Holder
      独立行政法人理化学研究所
    • Industrial Property Number
      2009-277028
    • Filing Date
      2009-12-04
    • Related Report
      2009 Annual Research Report
  • [Patent(Industrial Property Rights)] 特許2008

    • Inventor(s)
      鈴木正昭
    • Industrial Property Rights Holder
      理化学研究所岐阜大学
    • Industrial Property Number
      2008-335250
    • Filing Date
      2008-12-26
    • Related Report
      2008 Annual Research Report
  • [Patent(Industrial Property Rights)] 特許2007

    • Inventor(s)
      鈴木正昭
    • Industrial Property Rights Holder
      理化学研究所
    • Industrial Property Number
      2007-284030
    • Filing Date
      2007-10-31
    • Related Report
      2007 Annual Research Report

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Published: 2007-04-01   Modified: 2016-04-21  

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