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Development of fluorescent quinazolines as ion probes

Research Project

Project/Area Number 15K07868
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionSophia University

Principal Investigator

Suzuki Yumiko  上智大学, 理工学部, 准教授 (20295546)

Research Collaborator MOTOYAMA Miho  上智大学, 大学院・理工学研究科
OTAKE Ryo  上智大学, 大学院・理工学研究科
FUJIMAKI Yuki  上智大学, 大学院・理工学研究科
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords蛍光団 / 分子プローブ / キナゾリン / 蛍光プローブ / フォトルミネッセンス / 金属イオンセンサー
Outline of Final Research Achievements

Novel fluorescent quinazolines were designed and synthesized, including derivatives with high quantam yield, red-emission, and large Stokes shift. The HOMO-LUMO energy gaps calculated from the results of UV spectra and CV experiments were consistent with DFT calculation.
Synthesized quinaolines with a metal-recognition moiety responded to a certain type of metal ions. An anti-cancer fluorescent quinazoline was used as a fluorescent probe in cultured cancer cells to visualize its intracellular distribution by fluorescence microscopy. It can be used as a tool for further study to elucidation of its action mechanism.

Report

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

    (51 results)

All 2018 2017 2016 2015 Other

All Int'l Joint Research (4 results) Journal Article (8 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 8 results,  Open Access: 2 results) Presentation (39 results) (of which Int'l Joint Research: 8 results,  Invited: 5 results)

  • [Int'l Joint Research] CNRS/Normandie Université/ENSICAEN & UNICAEN(フランス)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] ENSICAEN & UNICAEN(フランス)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] ENSICAEN & UNICAEN(フランス)

    • Related Report
      2015 Research-status Report
  • [Int'l Joint Research]

    • Related Report
      2015 Research-status Report
  • [Journal Article] Selective Synthesis of 1,4,5-Trisubstituted Imidazoles from alpha-Imino Ketones Prepared by N-Heterocyclic Carbene-Catalyzed Aroylation2018

    • Author(s)
      Ryo Takashima, Maki Shinozaki, Kaoru Tsunekawa, Yumiko Suzuki
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 18 Pages: 2261-2267

    • DOI

      10.1016/j.tet.2018.03.048

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Michael Addition Mediated by Chiral Ionic Liquids2018

    • Author(s)
      Yumiko Suzuki
    • Journal Title

      Mini-Reviews in Organic Chemistry

      Volume: 印刷中 Issue: 3 Pages: 236-245

    • DOI

      10.2174/1570193x15666171211165344

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Nucleophilic Aroylation on Fluoroquinazolines Catalyzed by N-Heterocyclic Carbenes2018

    • Author(s)
      Masashi Tachikawa, Mizuki Nakagawa, Yumiko Suzuki
    • Journal Title

      Heterocycles

      Volume: 96 Issue: 4 Pages: 716-716

    • DOI

      10.3987/com-18-13880

    • NAID

      40021543253

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Alkanoylation of quinazoline by nucleophilic aromatic substitution: Combined experimental and computational study2018

    • Author(s)
      Suzuki Yumiko、Iwata Naoto、Dobashi Kohei、Takashima Ryo、Arulmozhiraja Sundaram、Ishitsubo Erika、Matsuo Naoya、Tokiwa Hiroaki
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 3 Pages: 392-400

    • DOI

      10.1016/j.tet.2017.11.071

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The electromagnetic wave energy effect(s) in microwave-assisted organic syntheses (MAOS)2018

    • Author(s)
      Satoshi Hirikoshi, Tomoki Watanabe, Atsushi Narita, Yumiko Suzuki, Nick Serpone
    • Journal Title

      Scientific Reports

      Volume: 8 Issue: 1 Pages: 5151-5151

    • DOI

      10.1038/s41598-018-23465-5

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Fluorescent anticancer quinazolines as molecular probes for β-tubulin colchicine site competition assay and visualization of microtubules as intracellular targeting sites2017

    • Author(s)
      Yumiko Suzuki, Jun-ichi Sawada, Paulina Hibner, Hirosuke Ishii, Kenji Matsuno, Masayuki Sato, Bernhard Witulski, Akira Asai
    • Journal Title

      Dyes and Pigments

      Volume: 145 Pages: 233-238

    • DOI

      10.1016/j.dyepig.2017.05.050

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Microwave-assisted organic syntheses: microwave effect on intramolecular reactios - the Claisen rearrangement of allylphenyl ether and 1-allyloxy-4-methoxybenzene2015

    • Author(s)
      Satoshi Horikoshi, Tomoki Watanabe, Monoko Kamata, Yumiko Suzuki, Nick Serpone
    • Journal Title

      RSC Advances

      Volume: 5 Issue: 110 Pages: 90272-90280

    • DOI

      10.1039/c5ra18039b

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis and Structure-Activity Relationship Study of 1 Phenyl-1-(quinazolin-4-yl)ethanols as Anticancer Agents2015

    • Author(s)
      Kenta Kuroiwa, Hirosuke Ishii, Kenji Matsuno, Akira Asai, Yumiko Suzuki
    • Journal Title

      ACS Med. Chem. Lett.

      Volume: 6 Issue: 3 Pages: 287-291

    • DOI

      10.1021/ml5004684

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Presentation] 2-ジメチルアミノ-4-フェニルキナゾリン誘導体の蛍光特性2018

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Termicalcicolanone B の全合成2018

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 蛍光団を内蔵する抗がん活性キナゾリンの分子プローブとしての利用2017

    • Author(s)
      鈴木由美子
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC触媒を用いた芳香族求核置換反応による4-アロイルクマリンの合成2017

    • Author(s)
      鈴木由美子
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC 触媒反応を経由した三置換イミダゾールの合成とその誘導化の検討2017

    • Author(s)
      鈴木由美子
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC触媒を用いたTermicalcicolanone Bの全合成2017

    • Author(s)
      鈴木由美子
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] 抗がん活性キナゾリンPVHD121のエナンチオ選択的合成研究2017

    • Author(s)
      鈴木由美子
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] 抗がん性キナゾリン誘導体の構造活性相関研究 および蛍光性誘導体の発見と利用2017

    • Author(s)
      鈴木由美子
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC触媒を用いた芳香族求核置換反応によるアロイルキナゾリン類の合成2017

    • Author(s)
      鈴木由美子
    • Organizer
      第112回 有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC触媒反応を鍵反応として利用した三置換イミダゾールの位置選択的合成法の開発2017

    • Author(s)
      鈴木由美子
    • Organizer
      第112回 有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] NHC触媒反応を経由した1,4,5位3置換イミダゾール合成法の開発2017

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県・横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis and fluorescence properties of 4- and 6-substitued 2-aminoquinazolines2017

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県・横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] NHC触媒反応を利用したクマリン環4位への直接的アロイル化反応2017

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県・横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] Asymmetric synthesis of anticancer quinazoline PVHD121 by enantioselective methylation of ketone2017

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(神奈川県・横浜市)
    • Related Report
      2016 Research-status Report
  • [Presentation] NHC触媒を用いた新規アロイルキナゾリン類の合成2017

    • Author(s)
      鈴木由美子
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学(宮城県・仙台市)
    • Related Report
      2016 Research-status Report
  • [Presentation] NHC触媒反応を経由したキサントン天然物termicalcicolanone A の合成研究2016

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京都
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] NHC触媒反応を経由した3置換キノキサリンの位置選択的合成法の開発研究2016

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京都
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 蛍光性キナゾリンにおける2,6位置換基の効果2016

    • Author(s)
      鈴木由美子
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京都
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Challenges to Organocatalytic Asymmetric Synthesis of Chiral Alcohols2016

    • Author(s)
      鈴木由美子
    • Organizer
      5th UK-Japanese Symposium on Asymmetric Catalysis
    • Place of Presentation
      マンチェスター大学、マンチェスター、イギリス
    • Year and Date
      2016-03-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Bioactive Heterocycles via Organocatalysis - What can a NHC do for you?2016

    • Author(s)
      鈴木由美子
    • Organizer
      Journeess Scientifiques Labex SynOrg
    • Place of Presentation
      ルーアン大学(ルーアン、フランス)
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] NHC触媒反応を経由したイミダゾールの位置選択的合成法の開発2016

    • Author(s)
      鈴木由美子
    • 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)
    • Related Report
      2016 Research-status Report
  • [Presentation] Citreamicin δ のEFG環の合成研究2016

    • Author(s)
      鈴木由美子
    • 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)
    • Related Report
      2016 Research-status Report
  • [Presentation] NHC触媒反応を利用した3置換キノキサリンの位置選択的合成法の開発2016

    • Author(s)
      鈴木由美子
    • 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)
    • Related Report
      2016 Research-status Report
  • [Presentation] 2-アルキルアミノキナゾリンの蛍光特性2016

    • Author(s)
      鈴木由美子
    • 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)
    • Related Report
      2016 Research-status Report
  • [Presentation] NHC触媒反応を用いた芳香族求核置換反応によるアロイルキナゾリン類の合成2016

    • Author(s)
      鈴木由美子
    • 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)
    • Related Report
      2016 Research-status Report
  • [Presentation] キサントン骨格を有する抗がん活性天然物termicalcicolanone Aの合成研究2016

    • Author(s)
      鈴木由美子
    • 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)
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis of 5 to 8-aroylquinazolines by NHC-catalysis2015

    • Author(s)
      鈴木由美子
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター、ホノルル、アメリカ
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Regioselective synthesis of substituted quinoxalines via iminoethanones prepared by N-heterocyclic carbene catalysis2015

    • Author(s)
      鈴木由美子
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター、ホノルル、アメリカ
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthetic study of termicarcicolanone B using NHC-catalysis2015

    • Author(s)
      鈴木由美子
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター、ホノルル、アメリカ
    • Year and Date
      2015-12-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthetic study of antibacterial natural product citreamicin δ2015

    • Author(s)
      鈴木由美子
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター、ホノルル、アメリカ
    • Year and Date
      2015-12-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] N-heterocyclic carbenes for nucleophilic acylation2015

    • Author(s)
      鈴木由美子
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター、ホノルル、アメリカ
    • Year and Date
      2015-12-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of a new set of quinazolines: Strong fluorophores for solution and solid state2015

    • Author(s)
      鈴木由美子
    • Organizer
      PACIFICHEM 2015
    • Place of Presentation
      ハワイコンベンションセンター、ホノルル、アメリカ
    • Year and Date
      2015-12-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] N-Heterocyclic Carbenes as Organocatalysts in Synthesis of Bioactive Compounds2015

    • Author(s)
      鈴木由美子
    • Organizer
      ENSICAEN-LCMT seminar
    • Place of Presentation
      エンシカン&カン大学、カン、フランス
    • Year and Date
      2015-11-23
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 抗がん活性天然物termicalcicolanone Aの合成研究2015

    • Author(s)
      鈴木由美子
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀、東京
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] 2-アミノキナゾリン誘導体の合成とその蛍光特性評価2015

    • Author(s)
      鈴木由美子
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀、東京
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] NHC触媒反応を利用した位置選択的3置換キノキサリン合成法の開発2015

    • Author(s)
      鈴木由美子
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀、東京
    • Year and Date
      2015-10-13
    • Related Report
      2015 Research-status Report
  • [Presentation] NHC 触媒反応の反応解析・基質拡大・天然物合成への利用2015

    • Author(s)
      鈴木由美子
    • Organizer
      第8回有機触媒シンポジウム「有機分子触媒による未来型分子変換」第5回公開シンポジウム
    • Place of Presentation
      沖縄県市町村自治会館、沖縄
    • Year and Date
      2015-05-10
    • Related Report
      2015 Research-status Report
  • [Presentation] N-Heterocyclic carbenes as Organocatalysts for the Syntheses of Bioactive Compounds2015

    • Author(s)
      鈴木由美子
    • Organizer
      30th Philippine Chemistry Congress
    • Place of Presentation
      アテネオ・デ・ダバオ大学、ダバオ、フィリピン
    • Year and Date
      2015-04-15
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Organocatalysis in Synthesis of Bioactive Compounds2015

    • Author(s)
      鈴木由美子
    • Organizer
      Science Week 2015 Science Symposium, University of the Philippines Manila
    • Place of Presentation
      フィリピン大学マニラ校、マニラ、フィリピン
    • Year and Date
      2015-04-14
    • Related Report
      2015 Research-status Report
    • Invited

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

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