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Synthetic study of catechin probes for development of highly sensitive quantitative analysis

Research Project

Project/Area Number 24790017
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionUniversity of Shizuoka

Principal Investigator

ASAKAWA Tomohiro  静岡県立大学, 薬学部, 助教 (80571257)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
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)
Keywordsカテキン / フラボノイド / 食品中有効成分 / 薬食融合 / ケミカルバイオロジー / テアフラビン / EGCg / メチル化カテキン / カテキン抗体 / ケミカルプローブ / プローブ化 / theaflavin / benzotroporon / ELIZA
Outline of Final Research Achievements

The generation of antibodies specific to EGCg and rare derivatives would be useful for immunological detection of subcellular and tissue localization. Furthermore, enzyme-linked immunosorbent assays (ELISA) with color or fluorescence endpoints would be useful for quantitating trace amounts of EGCg derivatives. An efficient synthesis of 6-(5-aminopentyl)-5,7-deoxyepigallalo-EGCG (APDOEGCg) as probe precursor was accomplished by the Suzuki-Miyaura coupling, Mitsunobu reaction with our Ns (nitrobenzensulfonyl) amide, and the construction of the dihydrobenzopyran ring. The reactive amine group of APDOEGCg was readily connect to career protein without the need for phenol protection. This hapten enabled the generation of EGCg antibodies. On the other hand, the synthesis of TF analogue which possess a reactive aminoalkyl side chain was accomplished by using biomimetic dimerization with Ns protective method. It would be readily converted into hapten probe.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (14 results)

All 2015 2014 2013 2012

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Open Access: 1 results) Presentation (9 results) Book (2 results)

  • [Journal Article] Use of positron emission tomography for real-time imaging of biodistribution of green tea catechin2014

    • Author(s)
      Kosuke Shimizu, Tomohiro Asakawa, Norihiro Harada, Dai Fukumoto, Hideo Tsukada, Tomohiro Asai, Shizuo Yamada, Toshiyuki Kan, and Naoto Oku
    • Journal Title

      PLOS ONE

      Volume: 9 Issue: 2 Pages: e85520-e85520

    • DOI

      10.1371/journal.pone.0085520

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chemical synthesis of tea polyphenols and related compounds2013

    • Author(s)
      Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
    • Journal Title

      Current Pharmaceutical Design

      Volume: 19 Issue: 34 Pages: 6207-6217

    • DOI

      10.2174/1381612811319340012

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Theaflavins via Biomimetic Oxidative Coupling Reaction2013

    • Author(s)
      Yusuke Kawabe, Yoshiyuki Aihara, Yoshitsugu Hirose, Asuka Sakurada, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
    • Journal Title

      Synllet

      Volume: - Pages: 479-482

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] カテキンプローブの効率的合成と分子イメージングによる動態解析2015

    • Author(s)
      浅川 倫宏,菅 敏幸,清水 広介,奥 直人, 伊藤 邦彦,原田 典弘,塚田 秀夫
    • Organizer
      第30回茶学術研究会
    • Place of Presentation
      静岡
    • Year and Date
      2015-03-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Efficient Synthesis of Catechin Probe and its Molecular Dynamics2014

    • Author(s)
      Toshiyuki Kan, Tomohiro Asakawa, Kosuke Shimizu, Norihiro Harada, Hideo Tsukada, Makoto Inai, Masahiro Egi, Yoshitaka Hamashima, Naoto Oku
    • Organizer
      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
    • Place of Presentation
      Nagoya
    • Year and Date
      2014-09-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthetic Studies of Tea Polyphenols and its Probes.2014

    • Author(s)
      Yusuke Kawabe, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
    • Organizer
      The XXVIIth International Conference on Polyphenols & The 8th Tannin Conference
    • Place of Presentation
      Nagoya
    • Year and Date
      2014-09-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] フラボンおよびフラバノンの合成研究2013

    • Author(s)
      塚口雄太,飛坐愛輝,小川貴大,赤石樹泰,阿部和穂,稲井 誠,浅川倫宏,濱島義隆,菅 敏幸
    • Organizer
      第30回有機合成化学セミナー
    • Place of Presentation
      岡山
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic studies of tea polyphenols and its probes2013

    • Author(s)
      Yusuke Kawabe, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
    • Organizer
      第18回静岡健康・長寿学術フォーラム
    • Place of Presentation
      静岡
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthetic studies of tea polyphenols and its probes2013

    • Author(s)
      Yusuke Kawabe, Atsushi Yoshida, Makoto Inai, Tomohiro Asakawa, Yoshitaka Hamashima, Toshiyuki Kan
    • Organizer
      The 5th International Conference on O-CHA (Tea) Culture and Science
    • Place of Presentation
      静岡
    • Related Report
      2013 Research-status Report
  • [Presentation] フラボンおよびフラバノンの合成研究2013

    • Author(s)
      塚口雄太,飛坐愛輝,小川貴大,赤石樹泰,阿部和穂,稲井 誠,浅川倫宏,濱島義隆,菅 敏幸
    • Organizer
      日本病院薬剤師会東海ブロック・日本薬学会東海支部合同学術大会
    • Place of Presentation
      三重
    • Related Report
      2013 Research-status Report
  • [Presentation] テアフラビン類の合成研究2012

    • Author(s)
      河辺佑介,吉田篤史,稲井誠,浅川倫宏,濱島義隆,菅 敏幸
    • Organizer
      新規素材探索研究会 第11回セミナー
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] テアフラビン類の合成研究2012

    • Author(s)
      河辺佑介,吉田篤史,稲井誠,浅川倫宏,濱島義隆,菅 敏幸
    • Organizer
      第9回日本カテキン学会
    • Place of Presentation
      静岡
    • Related Report
      2012 Research-status Report
  • [Book] 月刊化学2014

    • Author(s)
      菅 敏幸、浅川倫宏、奥 直人、清水広介、山田静雄、原田典弘、塚田秀夫
    • Total Pages
      5
    • Publisher
      化学同人
    • Related Report
      2013 Research-status Report
  • [Book] 新版 茶の機能2013

    • Author(s)
      菅 敏幸,浅川倫宏,奥 直人,塚田秀夫
    • Total Pages
      5
    • Publisher
      農山漁村文化協会
    • Related Report
      2013 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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