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Development of the Second Generation of Caged Compounds toward to New Cell Sorters

Research Project

Project/Area Number 25560404
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Biomolecular chemistry
Research InstitutionNara Institute of Science and Technology

Principal Investigator

Kakiuchi Kiyomi  奈良先端科学技術大学院大学, 物質創成科学研究科, 教授 (60152592)

Co-Investigator(Renkei-kenkyūsha) HOSOKAWA YOUICHIRO  奈良先端科学技術大学院大学, 物質創成科学研究科, 准教授 (20448088)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsケージド化合物 / ホタルルシフェリン / ルシフェリン-ルシフェラーゼ反応 / チオクロモン / 蛍光 / 核酸 / アンチセンス分子 / アンケージング / 生理活性分子 / 長波長紫外光照射 / ルシフェリン-ルシフェラーゼ反応 / オリゴ核酸 / ルシフェラーゼ反応
Outline of Final Research Achievements


In this research, we tried to apply our novel photolabile protecting group to caged compounds. A firefly luciferin was selected as a target bioactive compound, and we examined the Photodeprotection reaction of the synthesized caged firefly luciferin in water. After photoirradiation, the original firefly luciferin was released from caged compounds with increasing the irradiation time. In in vivo experiment, however, the enzyme in the cell dissociates the chemical bond (ester bond) between a firefly luciferin and a photolabile protecting group. Next, we selected thymidine as a new target compound, and synthesized caged thymidine with ether bond to suppress the bond dissociation by the enzyme. After photoirradiation to the synthesized caged thymidine, we confirmed the regeneration of thymidine. In addition, we applied caged thymidine to the caged antisense oligomer. This caged antisense oligomer enabled to recover the original function as antisense oligomer after photoirradiation.

Report

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

    (25 results)

All 2016 2015 2014 2013 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (21 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Remarks (2 results)

  • [Journal Article] Synthesis of novel caged antisense oligonucleotides with fluorescence property2016

    • Author(s)
      Shin Hikage, Yasuo Sasaki, Terunobu Hisai, Hiroki Tanimoto, Tsumoru Morimoto, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 未定 Pages: 175-183

    • DOI

      10.1016/j.jphotochem.2016.01.007

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and evaluation of new caged compound with thiochromone derivative2014

    • Author(s)
      Yasuo Sasaki, Ryo Sugiura, Yasuhiro Nishiyama, Hiroki Tanimoto, Tsumoru Morimoto, Kiyomi Kakiuchi
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 43 Pages: 7973-7976

    • DOI

      10.1016/j.tet.2014.08.047

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] チオクロモン型光解離性保護基を有する新規ケージドレスベラトロールの蛍光測定による脱保護評価2016

    • Author(s)
      日影 薪、佐々木 康雄、西山 靖浩、垣内 喜代三
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis of Novel Caged Resveratrol with Thiochromone-type Photolabile Protecting Group2015

    • Author(s)
      Shin Hikage, Yasuo Sasaki, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Organizer
      GIST/NAIST/NCTU Joint Symposium 2015
    • Place of Presentation
      Hsinchu(Taiwan)
    • Year and Date
      2015-11-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Evaluation of Novel Caged Nucleic Acids possessing Fluorescence Property2015

    • Author(s)
      Yasuhiro Nishiyama, Yasuo Sasaki, Shin Hikage, Kiyomi Kakiuchi
    • Organizer
      International Symposium Photonic and Electronic Molecular Machines
    • Place of Presentation
      Toulouse(France)
    • Year and Date
      2015-10-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Photodeprotection of the Caged Resveratrol with Thiochromone-type Photolabile Protecting Group2015

    • Author(s)
      Shin Hikage, Yasuo Sasaki, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Organizer
      2015年光化学討論会
    • Place of Presentation
      大阪市立大学杉本キャンパス(大阪府・大阪市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] 蛍光発光特性を有する光解離性保護基を導入したケージド核酸の合成2015

    • Author(s)
      日影 薪、佐々木 康雄、西山 靖浩、垣内 喜代三
    • Organizer
      第35回有機合成若手セミナー
    • Place of Presentation
      京都府立大学下鴨キャンパス(京都府・京都市)
    • Year and Date
      2015-08-01
    • Related Report
      2015 Annual Research Report
  • [Presentation] 光脱保護時に蛍光発光する新規ケージド化合物の合成と評価2015

    • Author(s)
      西山 靖浩、佐々木 康雄、日影 薪、垣内 喜代三
    • Organizer
      生体機能関連化学部会若手の会 第27回サマースクール
    • Place of Presentation
      神戸セミナーハウス(兵庫県・神戸市)
    • Year and Date
      2015-07-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Evaluation of Novel Caged Antisense Oligonucleotides possessing Fluorescence Property2015

    • Author(s)
      Yasuhiro Nishiyama, Yasuo Sasaki, Shin Hikage,and Kiyomi Kakiuchi
    • Organizer
      The 11th Korea-Japan Symposium on Frontier Photoscience(KJFP-2015)
    • Place of Presentation
      Jeju(Korea)
    • Year and Date
      2015-06-26
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] チオクロモン型光解離性保護基の核酸への展開2015

    • Author(s)
      日影 薪、佐々木 康雄、西山 靖浩、垣内 喜代三
    • Organizer
      第36回光化学若手の会
    • Place of Presentation
      静岡大学浜松キャンパス(静岡県・浜松市)
    • Year and Date
      2015-06-06
    • Related Report
      2015 Annual Research Report
  • [Presentation] Synthesis and Evaluation of Novel Caged Antisenseoligonucleotide possessing fluoresence property2015

    • Author(s)
      Yasuhiro Nishiyama, Yasuo Sasaki, Terunobu Hisai, Shin Hikage, Kiyomi Kakiuchi
    • Organizer
      日本化学会 第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス (千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] フェムト秒レーザーを用いた植物単細胞への巨大分子の導入2015

    • Author(s)
      片桐 大輔, 坂口 さやか, 米田 新, 出村 拓, 細川 陽一郎
    • Organizer
      第62回応用物理学会春季学術講演会
    • Place of Presentation
      東海大学湘南キャンパス (神奈川県平塚市)
    • Year and Date
      2015-03-11 – 2015-03-14
    • Related Report
      2014 Research-status Report
  • [Presentation] Evaluation of trade-off between femtosecond laser manipulation and viability of plant cell2015

    • Author(s)
      Daisuke Katagiri, Sayaka Sakaguchi, Arata Yoneda, Taku Demura, Yoichiroh Hosokawa
    • Organizer
      PSROC 2015 Annual Meeting
    • Place of Presentation
      National Tsing Hua University (Hsinchu, Taiwan)
    • Year and Date
      2015-01-28 – 2015-01-30
    • Related Report
      2014 Research-status Report
  • [Presentation] 遺伝情報を高次に制御するケージド化合物の創成2015

    • Author(s)
      西山靖浩
    • Organizer
      高次複合光応答分子システムの開拓と学理の構築第2回公開シンポジウム
    • Place of Presentation
      千里ライフサイエンスセンター (大阪府豊中市)
    • Year and Date
      2015-01-23 – 2015-01-24
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of Novel Caged Thymidine for Caged Oligonucleotide2014

    • Author(s)
      Yasuhiro Nishiyama, Yasuo Sasaki, Terunobu Hisai, Shin Hikage, Kiyomi Kakiuchi
    • Organizer
      The 8th Asian Photochemistry Coference (APC-2014)
    • Place of Presentation
      The Leela Hotel (Kovalam, India)
    • Year and Date
      2014-11-10 – 2014-11-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 蛍光特性を有する新規ケージドDNAの合成と評価2014

    • Author(s)
      佐々木康雄, 久井輝亘, 日影 薪, 西山靖浩, 垣内喜代三
    • Organizer
      2014年 光化学討論会
    • Place of Presentation
      北海道大学 札幌キャンパス (北海道札幌市)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 蛍光性光解離性保護基を用いたケージド化合物の開発2014

    • Author(s)
      西山靖浩
    • Organizer
      第4回グリーンフォト二クスセミナー-異分野融合による生体内の力場・反応場の理解-
    • Place of Presentation
      奈良先端科学技術大学院大学 (奈良県生駒市)
    • Year and Date
      2014-09-02
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 新規ケージド核酸の合成とその脱保護の評価2014

    • Author(s)
      日影 薪, 佐々木康雄, 久井輝亘, 西山靖浩, 垣内喜代三
    • Organizer
      第35回光化学若手の会
    • Place of Presentation
      休暇村志賀島 (福岡県福岡市)
    • Year and Date
      2014-06-13 – 2014-06-15
    • Related Report
      2014 Research-status Report
  • [Presentation] 蛍光発光特性を有する新規ケージド化合物の創成2014

    • Author(s)
      久井 輝亘
    • 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(名古屋市千種区)
    • Related Report
      2013 Research-status Report
  • [Presentation] 新規光解離性保護基を活用したケージド化合物の創成2013

    • Author(s)
      久井 輝亘
    • Organizer
      第34回 光化学若手の会
    • Place of Presentation
      神戸セミナーハウス(神戸市北区)
    • Related Report
      2013 Research-status Report
  • [Presentation] チオクロモン誘導体を用いた新規ケージド化合物の合成と機能評価2013

    • Author(s)
      西山 靖浩
    • Organizer
      2013年 光化学討論会
    • Place of Presentation
      愛媛大学城北地区(松山市道後樋又)
    • Related Report
      2013 Research-status Report
  • [Presentation] Creation of Novel Caged Compound Possessing Fluorescene Property2013

    • Author(s)
      久井 輝亘
    • Organizer
      GIST-NAIST-NCTU international joint symposium 2013
    • Place of Presentation
      奈良先端大(生駒市高山町)
    • Related Report
      2013 Research-status Report
  • [Presentation] Synthesis and Evaluation of New Novel Caged Compound2013

    • Author(s)
      西山 靖浩
    • Organizer
      2013 Korea-Japan Symposium on Frontier Photoscience
    • Place of Presentation
      Seoul National University (Seoul, Korea)
    • Related Report
      2013 Research-status Report
  • [Remarks] 奈良先端科学技術大学院大学 物質創成科学研究科 反応制御科学研究室

    • URL

      http://mswebs.naist.jp/LABs/kakiuchi/index-j.html

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
  • [Remarks] 奈良先端科学技術大学院大学 物質創成科学研究科 反応制御科学研究室

    • URL

      http://mswebs.naist.jp/LABs/kakiuchi/index-j.html

    • Related Report
      2013 Research-status Report

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

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