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Design and Synthesis of Near-infrared Fluorescent Probes for Bioimaging

Research Project

Project/Area Number 25410137
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Analytical chemistry
Research InstitutionHirosaki University

Principal Investigator

KAWAKAMI JUN  弘前大学, 理工学研究科, 准教授 (60261426)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords近赤外蛍光 / 蛍光プローブ / 2-アミノトリプタンスリン / 蛍光共鳴エネルギー移動 / 金属イオン / 2-ヒドロキシトリプタンスリン / 励起状態分子内プロトン移動 / 近赤外蛍光色素
Outline of Final Research Achievements

The near-infrared (NIR) region (650-900 nm) is referred to as the “optical window” of cells and tissues because of the lack of efficient endogenous absorbers in this spectral range and the subsequent high penetration depth (of the order of a few millimeters) in most tissues. Organic fluorescent dyes that emit NIR fluorescence are preferable for applications in biological systems because they can reduce auto-fluorescence and photodamage to living cells. Therefore, we synthesized some new NIR fluorescent dyes for fluorescent imaging probes. For example, the absorption maxima of 2-Hydroxytryptanthrin under a pH range from 1.3 to 7.2 and from 8.5 to 10.6 were ca. 410 nm and ca. 495 nm, respectively. Moreover, the fluorescence maxima were ca. 660 nm regardless of the pH range. Its sodium salt (sodium tryptanthrin-2-olate) was water soluble and the fluorescence maxima were ca. 660 nm in both aprotic and protic solvents.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (21 results)

All 2016 2015 2014 2013 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 2 results,  Acknowledgement Compliant: 4 results) Presentation (15 results) Remarks (2 results)

  • [Journal Article] Photophysical Properties of the 2-Hydroxytryptanthrin and Its Sodium Salt as Near-infrared Dyes for Fluorescent Imaging2016

    • Author(s)
      Jun Kawakami, Masahiro Takahashi, Shunji Ito, Haruo Kitahara
    • Journal Title

      Analytical Sciences

      Volume: 32 Issue: 2 Pages: 251-253

    • DOI

      10.2116/analsci.32.251

    • NAID

      130005125637

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Naphthalene Ring-Fused 2-Aminotryptanthrin as a Fluorescent Chemosensor for Al<sup>3+</sup>2016

    • Author(s)
      Jun Kawakami, Akihiro Tsuiki, Shunji Ito, Haruo Kitahara
    • Journal Title

      Transactions of the Materials Research Society of Japan

      Volume: 41 Issue: 1 Pages: 131-133

    • DOI

      10.14723/tmrsj.41.131

    • NAID

      130005126129

    • ISSN
      1382-3469, 2188-1650
    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Spectral Characteristics of Highly Fluorescent 2-(N,N-dimethylamino)tryptanthrin2016

    • Author(s)
      Jun Kawakami, Takuma Kadowaki, Mari Ikeda, Yoichi Habata, Shunji Ito, Haruo Kitahara
    • Journal Title

      Transactions of the Materials Research Society of Japan

      Volume: 41

    • NAID

      130005155999

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] 2-Aminotryptanthrin Derivative with Pyrene as a FRET-based Fluorescent Chemosensor for Metal Ions2014

    • Author(s)
      Jun KAWAKAMI, Arisa SOMA, Kenta KIKUCHI, Yoh KIKUCHI, Shunji ITO, Haruo KITAHARA
    • Journal Title

      Analytical Sciences

      Volume: 30 Issue: 10 Pages: 949-954

    • DOI

      10.2116/analsci.30.949

    • NAID

      130004694053

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] 2-アミノトリプタンスリン誘導体の合成と分光学的性質2015

    • Author(s)
      門脇拓真・川上 淳・伊東俊司
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] 2-ヒドロキシ及び 2-(4-アミノ)フェニルトリプタンスリン誘導体の合成と分光学的性質2015

    • Author(s)
      髙橋正寛・川上 淳・伊東俊司
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] 2-アミノ-9-フェニルエチニルトリプタンスリン誘導体の合成と分光学的性質2015

    • Author(s)
      橋本 凌・川上 淳・伊東俊司
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Photophysical Properties of 2-Aminotryptanthrin Derivatives2015

    • Author(s)
      門脇拓真,川上 淳,伊東俊司
    • Organizer
      平成27年度化学系学協会東北大会
    • Place of Presentation
      弘前大学(弘前)
    • Year and Date
      2015-09-12
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Photophysical Properties of 2-Hydroxytryptanthrin Derivatives and 2-(4-Amino)phenyltryptanthrin Derivatives2015

    • Author(s)
      髙橋正寛,川上 淳,伊東俊司
    • Organizer
      平成27年度化学系学協会東北大会
    • Place of Presentation
      弘前大学(弘前)
    • Year and Date
      2015-09-12
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Photophysical Properties of 2-Amino-9-phenylethynyltryptanthrin Derivatives2015

    • Author(s)
      橋本 凌,川上 淳,伊東俊司
    • Organizer
      平成27年度化学系学協会東北大会
    • Place of Presentation
      弘前大学(弘前)
    • Year and Date
      2015-09-12
    • Related Report
      2015 Annual Research Report
  • [Presentation] 2-アミノおよび2-ヒドロキシトリプタンスリン誘導体の吸収・発光特性2015

    • Author(s)
      川上 淳,高橋正寛,門脇拓真,築城彰洋,木村光輝,橋本 凌,伊東俊司
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(船橋)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 7-置換クマリン-2-アミノトリプタンスリン誘導体による金属イオン用FRET型蛍光性化学センサー2014

    • Author(s)
      邊見世統,川上 淳,伊東俊司
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 環拡張型BODIPY-2-アミノトリプタンスリン誘導体の吸収発光特性2014

    • Author(s)
      木村光輝,川上 淳,伊東俊司
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 環拡張型2-アミノトリプタンスリン誘導体の吸収発光特性2014

    • Author(s)
      築城彰洋,川上 淳,伊東俊司
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 2-アミノトリプタンスリン誘導体の合成と蛍光性化学センサーへの応用2014

    • Author(s)
      川上 淳, 築城彰洋, 原田裕貴, 邊見世統, 木村光輝, 伊東俊司
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] Fluorescence properties of 2-Aminotryptanthrin Derivatives with Pyrene2013

    • Author(s)
      Y.Harada, J. Kawakami, S. Ito
    • Organizer
      The International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      Kawauchi-kita Campus, Tohoku University, Sendai, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] 2-Aminotryptanthrin Derivatives with 7-Substituted Coumarin as FRET-based Fluorescent Chemosensors for Metal Ions2013

    • Author(s)
      T. Henmi, N. Narita, J. Kawakami, S. Ito
    • Organizer
      The International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      Kawauchi-kita Campus, Tohoku University, Sendai, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis and Photophysical Properties of Aromatic-ring-fused 2-Aminotryptanthrin Derivatives2013

    • Author(s)
      A. Tsuiki, J. Kawakami, S. Ito
    • Organizer
      The International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      Kawauchi-kita Campus, Tohoku University, Sendai, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis of 2-Aminotryptanthrin Derivatives with Benzo-fused BODIPY2013

    • Author(s)
      K. Kimura, J. Kawakami, S. Ito
    • Organizer
      The International Symposium for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      Kawauchi-kita Campus, Tohoku University, Sendai, Japan
    • Related Report
      2013 Research-status Report
  • [Remarks] 川上研究室(弘前大学大学院理工学研究科)

    • URL

      http://www.st.hirosaki-u.ac.jp/~jun/jklab/jklab001.html

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
  • [Remarks] 川上研究室(弘前大学大学院理工学研究科)

    • URL

      http://www.st.hirosaki-u.ac.jp/~jun/jklab/jklab001.html

    • Related Report
      2013 Research-status Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

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