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Synthesis of new substrates for near-infrared bioluminescence imaging

Research Project

Project/Area Number 23710266
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical biology
Research InstitutionTokyo Medical and Dental University

Principal Investigator

YOSHIDA Suguru  東京医科歯科大学, 生体材料工学研究所, 助教 (10583750)

Co-Investigator(Renkei-kenkyūsha) INOUYE Satoshi  JNC株式会社, 横浜研究所, 主席研究員 (40426622)
Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2012: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsケミカルバイオロジー / 有機化学 / 分子プローブ / 生物発光
Research Abstract

In vivo molecular imaging that enables non-invasive observation of molecule of interest in organisms is a valuable technique to promote life science and drug discovery. In particular, the methods using near-IR luminescence have been aggressively developed in recent years. In order to develop a near-IR bioluminescence system based on coelenterazine (CTZ)-utilizing luciferase, we have established a concise synthetic method of v-CTZ, an analog that is known to show red-shifted light emission applicable to in vivo molecular imaging. The ten-step synthetic route of v-CTZ includes three consecutive regioselective cross-coupling reactions and ring closing metathesis as key reactions, which is suitable for preparing various analogs. We also synthesized C2-CF3-analog of v-CTZ, cf3-v-CTZ, and showed that it also serves as a good substrate for Renilla luciferases with increased stability.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (23 results)

All 2013 2012 2011 Other

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (14 results) Remarks (1 results) Patent(Industrial Property Rights) (3 results) (of which Overseas: 3 results)

  • [Journal Article] Expression, purification and luminescence properties of coelenterazine-utilizing luciferases from Renilla, Oplophorus and Gaussia: Comparison of substrate specificity for C2-modified coelenterazines2013

    • Author(s)
      Satoshi Inouye, Yuiko Sahara-Miura, Jun-ichi Sato, Rie Iimori, Suguru Yoshida, Takamitsu Hosoya
    • Journal Title

      Protein Expression and Purification

      Volume: 88 Issue: 1 Pages: 150-156

    • DOI

      10.1016/j.pep.2012.12.006

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] 生物発光系によるin vivoイメージングを指向した発光基質の開発2013

    • Author(s)
      細谷孝充、隅田有人、吉田優、鈴木崇弘
    • Journal Title

      井上敏日本分子イメージング学会機関誌

      Volume: 6 Pages: 3-6

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of diverse aromatic oxophosphorus compounds by the Michaelis-Arbuzov-type reaction of arynes2013

    • Author(s)
      Suguru Yoshida
    • Journal Title

      Takamitsu HosoyaChemistry Letters

      Volume: 42(in press) Issue: 6 Pages: 583-585

    • DOI

      10.1246/cl.130116

    • NAID

      10031176015

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of diverse aromatic oxophosphorus compounds by the Michaelis-Arbuzov-type reaction of arynes2013

    • Author(s)
      Suguru Yoshida, Takamitsu Hosoya
    • Journal Title

      Chemistry Letters

      Volume: 42

    • NAID

      10031176015

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 生物発光系によるin vivoイメージングを指向した発光基質の開発2013

    • Author(s)
      細谷孝充、隅田有人、吉田優、鈴木崇弘、井上敏
    • Journal Title

      日本分子イメージング学会機関誌

      Volume: 6 Pages: 3-6

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis of aromatic oxophosphorus compounds by the Michaelis-Arbuzov-type reaction of aryne2012

    • Author(s)
      吉田優、細谷孝充
    • Organizer
      The Twelfth International Kyoto Conference onNew Aspect of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都
    • Year and Date
      2012-11-14
    • Related Report
      2012 Final Research Report
  • [Presentation] アラインのMichaelis-Arbuzov型反応を利用した芳香族ホスホン酸類の新規合成法の開発2012

    • Author(s)
      吉田優、細谷孝充
    • 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(東京)
    • Year and Date
      2012-10-14
    • Related Report
      2012 Final Research Report
  • [Presentation] 高反応性化学種を利用する反応開発と生命科学研究への展開2012

    • Author(s)
      吉田優
    • Organizer
      第47回天然物談話会
    • Place of Presentation
      阿蘇プラザホテル
    • Year and Date
      2012-07-05
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] Concise synthesis of v-coelenterazine toward near-infrared bioluminescence imaging2011

    • Author(s)
      吉田優 、隅田有人、飯森理絵、三浦由依子、佐藤淳一、井上敏、細谷孝充
    • Organizer
      10th International Symposium on Organic Reactions (ISOR10)
    • Place of Presentation
      慶應大学矢上キャンパス(横浜)
    • Year and Date
      2011-11-23
    • Related Report
      2012 Final Research Report
  • [Presentation] 新しい近赤外生物発光基質の創製を目指したv-Coelenterazine合成法の開発2011

    • Author(s)
      吉田優、隅田有人、飯森理絵、三浦由依子、佐藤淳一、井上敏、細谷孝充
    • Organizer
      第100回有機合成シンポジウム
    • Place of Presentation
      早稲田大学大隈講堂(東京)
    • Year and Date
      2011-11-11
    • Related Report
      2012 Final Research Report
  • [Presentation] 近赤外生物発光イメージングを目指したv-セレンテラジンの高効率合成法の開発2011

    • Author(s)
      隅田有人、飯森理絵、吉田優、三浦由依子、佐藤淳一、井上敏、細谷孝充
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪国際センター
    • Year and Date
      2011-09-28
    • Related Report
      2012 Final Research Report
  • [Presentation] 近赤外生物発光イメージングを目指したv-セレンテラジンの高効率合成法の開発2011

    • Author(s)
      細谷孝充、飯森理絵、隅田有人、吉田優、佐原由依子、佐藤淳一、井上敏
    • Organizer
      第6回日本分子イメージング学会総会・学術集会
    • Place of Presentation
      神戸
    • Year and Date
      2011-05-26
    • Related Report
      2012 Final Research Report 2011 Research-status Report
  • [Presentation] 近赤外生物発光イメージングを目指したv-セレンテラジンの高効率合成法の開発2011

    • Author(s)
      飯森理絵、隅田有人、吉田優、佐原由依子、佐藤淳一、井上敏、細谷孝充
    • Organizer
      日本ケミカルバイオロジー学会第6回年会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2011-05-24
    • Related Report
      2012 Final Research Report
  • [Presentation] 近赤外生物発光イメージングを目指したv-セレンテラジンの高効率合成法の開発2011

    • Author(s)
      飯森理絵,隅田有人,吉田 優,佐原由依子,佐藤淳一,井上 敏,細谷孝充
    • Organizer
      日本ケミカルバイオロジー学会第6回年会
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Presentation] 近赤外生物発光イメージングを目指したv-セレンテラジンの高効率合成法の開発2011

    • Author(s)
      隅田有人,飯森理絵,吉田 優,三浦由依子,佐藤淳一,井上 敏,細谷孝充
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Related Report
      2011 Research-status Report
  • [Presentation] 新しい近赤外生物発光基質の創製を目指したv-Coelenterazine合成法の開発2011

    • Author(s)
      吉田 優,隅田有人,飯森理絵,三浦由依子,佐藤淳一,井上 敏,細谷孝充
    • Organizer
      第100回有機合成シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2011 Research-status Report
  • [Presentation] Concise synthesis of v-coelenterazine toward near-infrared bioluminescence imaging2011

    • Author(s)
      吉田 優,隅田有人,飯森理絵,三浦由依子,佐藤淳一,井上 敏,細谷孝充
    • Organizer
      10th International Symposium on Organic Reactions (ISOR10)
    • Place of Presentation
      Yokohama
    • Related Report
      2011 Research-status Report
  • [Presentation] アラインのMichaelis-Arbuzov型反応を利用した芳香族ホスホン酸類の新規合成法の開発

    • Author(s)
      吉田優、細谷孝充
    • 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
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of aromatic oxophosphorus compounds by the Michaelis-Arbuzov-type reaction of aryne

    • Author(s)
      吉田優、細谷孝充
    • Organizer
      The Twelfth International Kyoto Conference on New Aspect of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      リーガロイヤルホテル京都
    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://chembiolab.sakura.ne.jp/Home.html

    • Related Report
      2012 Final Research Report
  • [Patent(Industrial Property Rights)] v-セレンテラジン化合物の製造方法2012

    • Inventor(s)
      井上敏、佐原由依子、吉田優、細谷孝充
    • Industrial Property Rights Holder
      井上敏、佐原由依子、吉田優、細谷孝充
    • Filing Date
      2012-03-06
    • Related Report
      2012 Final Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] v-セレンテラジン化合物の製造方法2012

    • Inventor(s)
      井上敏、佐原由依子、吉田優、細谷孝充
    • Industrial Property Rights Holder
      井上敏、佐原由依子、吉田優、細谷孝充
    • Filing Date
      2012-03-06
    • Related Report
      2012 Final Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] v-セレンテラジン化合物の製造方法2012

    • Inventor(s)
      井上 敏、佐原由依子、吉田 優、細谷孝充
    • Industrial Property Rights Holder
      井上 敏、佐原由依子、吉田 優、細谷孝充
    • Filing Date
      2012
    • Related Report
      2011 Research-status Report
    • Overseas

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Published: 2011-08-05   Modified: 2019-07-29  

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