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Creation of Novel Thiochromone-Caged Compounds and their Application to Developing New Cell Sorters

Research Project

Project/Area Number 15K12748
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)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords生体分子 / ケージド化合物 / チオクロモン誘導体 / アンチセンスオリゴ核酸 / シクロデキストリン / コレステロール / 水溶性 / アンケージング / チオクロモン / 生理活性分子 / 長波長紫外光照射 / 核酸 / アンチセンス分子 / ルシフェリン-ルシフェラーゼ反応
Outline of Final Research Achievements

We aimed to synthesize and functionalize novel caged compounds, to which the thiochromone-type photolabile protecting group (TCM) is introduced. This TCM can protect various alcohols, amines, and phosphoric acids, and can be converted to a highly fluorescent compound after the uncaging process. We synthesized thymidine, resveratrol, and beta-cyclodextrin caged compounds with our TCM. Photoirradiation, namely uncaging, of these TCM-caged thymidine, resveratrol, and beta-cyclodextrin led to the recovery of their original compounds, respectively. Recovered compounds showed their own biological activity. Totally, we could demonstrate that the TCM protecting group is effective for the creation of various types of caged compounds.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (26 results)

All 2018 2017 2016 2015 Other

All Journal Article (4 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 4 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) (of which Int'l Joint Research: 8 results,  Invited: 1 results) Remarks (2 results)

  • [Journal Article] Quantitative Photodeprotection Assessment of Caged Resveratrol by Fluorescence Measurement2017

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

      ACS Omega

      Volume: 2 Issue: 5 Pages: 2300-2307

    • DOI

      10.1021/acsomega.7b00250

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols2017

    • Author(s)
      Chi Ma, Youlai Zhang, Huan Zhang, Junru Li, Yasuhiro Nishiyama, Hiroki Tanimoto, Tsumoru Morimoto, and Kiyomi Kakiuchi
    • Journal Title

      Synlett

      Volume: 28 Issue: 05 Pages: 560-564

    • DOI

      10.1055/s-0036-1588915

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Study of the Paterno-Buchi Type Photolabile Protecting Group and Application to Various Acids2016

    • Author(s)
      Youlai Zhang, Huan Zhang, Chi Ma, Junru Li, Yasuhiro Nishiyama, Hiroki Tanimoto, Tsumoru Morimoto, and Kiyomi Kakiuchi
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 47 Pages: 5179-5184

    • DOI

      10.1016/j.tetlet.2016.09.065

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [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 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis of Caged Methyl-β-Cyclodextrin and its Application to Simulated Biological Membrane2018

    • Author(s)
      Shohei Maehara, Katsuhiro Takahashi, Tsumoru Morimoto, Kazuma Yasuhara, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Organizer
      International Symposium on Caged Compounds
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Quantitative Photodeprotection Assessment of Caged Resveratrol by Fluorescence Measurement2018

    • Author(s)
      Shin Hikage, Yasuhiro Nishiyama, Tsumoru Morimoto, Kiyomi Kakiuchi
    • Organizer
      International Symposium on Caged Compounds
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ケージドメチル-β-シクロデキストリンの合成と擬似生体膜への応用2018

    • Author(s)
      前原渉平、高橋克洋、森本積、安原主馬、西山靖浩、垣内喜代三
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 蛍光測定による新規ケージド化合物からの生理活性機能復元能評価2017

    • Author(s)
      西山靖浩、日影薪、高橋克洋、前原渉平、垣内喜代三
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應大学日吉キャンパス(神奈川県・横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] ケージドシクロデキストリンを用いたコレステロール包摂能の光制御2017

    • Author(s)
      前原渉平、高橋克洋、西山靖浩、垣内喜代三
    • Organizer
      第38回光化学若手の会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ケージドシクロデキストリンの合成と擬似生体膜への応用2017

    • Author(s)
      前原渉平、高橋克洋、西山靖浩、北又学、末次志郎、垣内喜代三
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Monitoring of the Bioactivity Recovery with Fluorescence Emission Generated by Photoirradiation to Caged Compounds2016

    • Author(s)
      Yasuhiro Nishiyama, Shin Hikage, Katsuhiro Takahashi, Kiyomi Kakiuchi
    • Organizer
      9th Asian and Oceanian Photochemistry Conference (APC2016)
    • Place of Presentation
      Nanyang Technological University (Singapore)
    • Year and Date
      2016-12-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of The Second Generation of Thiochromone-type Photolabile Protecting Groups2016

    • Author(s)
      Shin Hikage, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Organizer
      The 10th International Symposium on Integrated Synthesis (ISONIS-10)
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県・淡路市)
    • Year and Date
      2016-11-18
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] ケージドシクロデキストリンを用いたコレステロール包接能の光制御2016

    • Author(s)
      高橋克洋、日影薪、西山靖浩、垣内喜代三
    • Organizer
      第60回香料・テルペンおよび精油化学に関する討論会
    • Place of Presentation
      東京農業大学オホーツクキャンパス(北海道・網走市)
    • Year and Date
      2016-10-29
    • Related Report
      2016 Research-status Report
  • [Presentation] Monitoring of the bioactivity with fluorescence emission generated by photoirradiation of caged compounds2016

    • Author(s)
      Shin Hikage, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場キャンパス(東京都・目黒区)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
  • [Presentation] 蛍光測定を利用した生理活性発現の定量評価2016

    • Author(s)
      日影薪、佐々木康雄、西山靖浩、垣内喜代三
    • Organizer
      第37回光化学若手の会
    • Place of Presentation
      アイアイランド(大阪府・四条畷市)
    • Year and Date
      2016-06-17
    • Related Report
      2016 Research-status Report
  • [Presentation] Control of an Enzyme Reaction Using Caged Resveratorol Having Thiochromone-Type Photolabile Protecting Group2016

    • Author(s)
      Shin Hikage, Yasuo Sasaki, Yasuhiro Nishiyama, Kiyomi Kakiuchi
    • Organizer
      26th IUPAC International Symposium on Photochemistry
    • Place of Presentation
      大阪中央公会堂(大阪府・大阪市)
    • Year and Date
      2016-04-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [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 Research-status 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 Research-status Report
    • Int'l Joint Research
  • [Presentation] ynthesis 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 Research-status 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 Research-status 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 Research-status 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 Research-status 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 Research-status 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 Research-status Report
  • [Remarks] 奈良先端科学技術大学院大学 先端科学技術研究科 反応制御科学研究室

    • URL

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

    • Related Report
      2017 Annual Research 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
      2016 Research-status Report 2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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