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Development of cell membrane-permeable photolabile protecting group and its application to multifunctional Bhc-caged compounds

Research Project

Project/Area Number 15K16568
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Basic / Social brain science
Research InstitutionToho University

Principal Investigator

SUZUKI Akinobu  東邦大学, 理学部, 博士研究員 (30532105)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsケージド化合物 / 細胞膜透過性ペプチド / クリックケミストリー / ケミカルバイオロジー
Outline of Final Research Achievements

In this study, I have developed a new method for intracellular delivery of caged compounds which are biological tools to precisely control their bioactivities with light irradiation. I introduced a cell-penetrating peptide into the 8 position of Bhc group, a photolabile protecting group with high photolysis efficiency, and synthesized caged green fluorescent compounds using it. In living cells, the compounds were distributed intracellularly and cells were stained with green fluorescence by photoactivation of the caged compounds. On the other hand, the caged green fluorescent compound before addition of the cell-penetrating peptide was aggregated and attached to the cell surfaces probably because of its hydrophobicity, and cells were not stained by photoirradiation. These results strongly suggested that an addition of cell-penetrating peptide to a photolabile protecting group provides to caged compounds a great increase of water solubility and an ability of cell permeability.

Report

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

    (25 results)

All 2017 2016 2015

All Presentation (25 results) (of which Int'l Joint Research: 10 results)

  • [Presentation] Latent caged cNMPs that can be photoactivated only in the target cells expressing certain enzymes2017

    • Author(s)
      SAKANO, Taichi; SUZUKI, Akinobu; UENO, Taro; FURUTA, Toshiaki
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Annual Research Report
  • [Presentation] Design and synthesis of modified inhibitors for epigenetic research2016

    • Author(s)
      Kotoko Sakamoto, Akinobu Z. Suzuki, Toshiaki Furuta
    • Organizer
      4th Asian Chemical Biology Conference
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, TAIWAN
    • Year and Date
      2016-11-30
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design and synthesis of caged 4-aminopyridine which can be photoactivated in the presence of specific enzymes2016

    • Author(s)
      Yuki Iketani, Akinobu Z. Suzuki, Toshiaki Furuta
    • Organizer
      4th Asian Chemical Biology Conference
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, TAIWAN
    • Year and Date
      2016-11-29
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Latent caged cNMP that can be photoactivated only in the β-Galactosidase-expressing cells2016

    • Author(s)
      Taichi Sakano, Akinobu Z. Suzuki, Toshiaki Furuta
    • Organizer
      4th Asian Chemical Biology Conference
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, TAIWAN
    • Year and Date
      2016-11-29
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design and synthesis of autophagy inhibitors having cell type specificity2016

    • Author(s)
      Shiori Takeda, Akinobu, Z. Suzuki, Toshiaki Furuta
    • Organizer
      4th Asian Chemical Biology Conference
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, TAIWAN
    • Year and Date
      2016-11-29
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of caged gRNAs for photoactivatable CRISPR-Cas92016

    • Author(s)
      Kazunari Kodama, Shin’nosuke Tada, Akinobu Z. Suzuki, Toshiaki Furuta
    • Organizer
      4th Asian Chemical Biology Conference
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, TAIWAN
    • Year and Date
      2016-11-29
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design and synthesis of site-selectively modified caged plasmid DNAs using modular nucleotide caging agents2016

    • Author(s)
      Shin’nosuke Tada, Akinobu Z. Suzuki, Toshiaki Furuta
    • Organizer
      4th Asian Chemical Biology Conference
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, TAIWAN
    • Year and Date
      2016-11-28
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 細胞種選択的にエピジェネティクスを制御する分子の開発2016

    • Author(s)
      坂元琴子,鈴木商信,古田寿昭
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2016-11-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] CRISPR/Cas9の光制御を目指したケージドgRNAの合成2016

    • Author(s)
      児玉一徳,多田慎之介,鈴木商信,古田寿昭
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2016-11-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 細胞種選択的にオートファジーを阻害する分子の開発2016

    • Author(s)
      竹田詩織,鈴木商信,古田寿昭
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2016-11-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 細胞種選択的に光活性化能を獲得するケージドcNMPの開発2016

    • Author(s)
      坂野太一,鈴木商信,古田寿昭
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2016-11-15
    • Related Report
      2016 Annual Research Report
  • [Presentation] 8位修飾Bhc基の開発と多機能型ケージド化合物への応用2016

    • Author(s)
      鈴木商信,古田 寿昭
    • Organizer
      第10回バイオ関連化学シンポジウム
    • Place of Presentation
      もてなしドーム地下広場(石川県金沢市木ノ新保町2番)
    • Year and Date
      2016-09-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] 酵素存在下で光活性化能を獲得するケージド環状リン酸類の開発2016

    • Author(s)
      坂野 太一,鈴木 商信,古田 寿昭
    • Organizer
      第10回バイオ関連化学シンポジウム
    • Place of Presentation
      もてなしドーム地下広場(石川県金沢市木ノ新保町2番)
    • Year and Date
      2016-09-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] 細胞種選択的に光活性能を獲得する新規ケージド化合物の開発2016

    • Author(s)
      池谷柚季,鈴木商信,古田寿昭
    • Organizer
      第10回バイオ関連化学シンポジウム
    • Place of Presentation
      もてなしドーム地下広場(石川県金沢市木ノ新保町2番)
    • Year and Date
      2016-09-07
    • Related Report
      2016 Annual Research Report
  • [Presentation] 細胞種選択的に働くリアノジンレセプターアゴニストの設計と合成2016

    • Author(s)
      船山瑞季,鈴木商信,上野太郎,齊藤実,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] PLE存在下で光感受性を獲得するケージド4-APの設計と合成2016

    • Author(s)
      池谷柚季,鈴木商信,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 酵素存在下で光感受性を獲得するケージド環状リン酸類の設計と合成2016

    • Author(s)
      坂野太一,鈴木商信,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 細胞種選択的にDNAメチル化を制御する分子の開発2016

    • Author(s)
      坂元琴子,鈴木商信,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 光作動性CRISPR/Cas9の実現を目指したケージドgRNAの合成2016

    • Author(s)
      児玉一徳,多田慎之介,鈴木商信,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] 細胞種選択的にオートファジーを阻害する分子の設計と合成2016

    • Author(s)
      竹田詩織,鈴木商信,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] モジュール型ケージング試薬を利用したケージドオリゴヌクレオチドの設計と合成2016

    • Author(s)
      多田慎之介,鈴木商信,古田寿昭
    • 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
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] Design and synthesis of clickable caged compounds2015

    • Author(s)
      A. Z. Suzuki, R. Aikawa, K. Kakehi, T. Furuta
    • Organizer
      2015 International chemical congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii(USA)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Chemo-enzymatic preparation of site-selectively modified caged DNAs2015

    • Author(s)
      S. Tada, W. Hashiba, E. Ikeda, A. Suzuki, T. Furuta
    • Organizer
      2015 International chemical congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii(USA)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Design and synthesis of new caging groups having cell type specificity2015

    • Author(s)
      Y. Iketani, A. Suzuki, T. Furuta
    • Organizer
      2015 International chemical congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii(USA)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Latent caged cAMPs that can be photoactivated in the presence of specific enzymes2015

    • Author(s)
      T. Sakano, A. Suzuki, T. Ueno, M. Saitoe, T. Furuta
    • Organizer
      2015 International chemical congress of Pacific Basin Societies
    • Place of Presentation
      Hawaii(USA)
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research

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Published: 2015-04-16   Modified: 2018-03-22  

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