Development of live cell full-color mapping measurement by using RGB fluorophore in a single molecule

• Project/Area Number: 17K08211
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Aichi Gakuin University (2019); Okayama University (2017-2018)
• Principal Investigator: Kamino Shinichiro 愛知学院大学, 薬学部, 教授 (20537237)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Project Status: Completed (Fiscal Year 2019)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: キサンテン系色素 / ローダミン / アクチベータブル分子 / シアニン系色素 / 近赤外光 / アミノベンゾピラノキサンテン系色素 / pH / フォトクロミズム / アシドクロミズム / ローダミン系色素 / 蛍光イメージング

Outline of Final Research Achievements

We have been working on the development of activatable molecules based on aminobenzopyranoxanthene (ABPX) containing fused-rhodamines dyes. Through this project, we have succeeded in obtaining the three new results as shown below.
[1] Development of activatable molecules, the structure and color of which change in two steps in response to pH. [2] Development of activatable molecule which shows the stepwise structural and fluorescence color conversion based on light and acid stimulations.[3] Development of a new class of ring-fused cyanine dye, the fluorescence wavelength of which is switched from visible region to near infrared region

Academic Significance and Societal Importance of the Research Achievements

外部刺激に応答して，分子構造と色が2段階に変化するABPXの特徴は，刺激の強さや観測対象となる物質の濃度に応じて，波長が変化するアクチベータブル分子となり，ライフサイエンス，環境や衛生化学などの分野に資する分析・計測技術となる。今後，発色団の誘導化を継続し，顕微鏡を必要としない新たなバイオイメージング法の開発に繋げたい。また近赤外領域の光を発光する有機分子は，セキュリティ・インク，フォトリソグラフィや生体イメージングなど，幅広い分野で利用されている。本研究で見いだした縮合型シアニン系色素は，これら近赤外光技術を進展させ，機能性物質科学の発展に寄与できる成果となる。

Research Products

• [Journal Article] Development and characterization of a 68Ga-labeled A20FMDV2 peptide probe for the PET imaging of αvβ6 integrin-positive pancreatic ductal adenocarcinoma (2020)
  • Author(s): Ui Takashi、Ueda Masashi、Higaki Yusuke、Kamino Shinichiro、Sano Kohei、Kimura Hiroyuki、Saji Hideo、Enomoto Shuichi
  • Journal Title: Bioorganic & Medicinal Chemistry Volume: 28 Issue: 1 Pages: 115189-115189
  • DOI: 10.1016/j.bmc.2019.115189
  • NAID: 120007170524
  • Peer Reviewed
• [Journal Article] Stepwise structural and fluorescent colour conversion in rhodamine analogues based on light and acid stimulations (2020)
  • Author(s): Tanioka Masaru、Kamino Shinichiro、Koga Natsumi、Sawada Daisuke
  • Journal Title: Journal of Materials Chemistry C Volume: 8 Issue: 2 Pages: 543-549
  • DOI: 10.1039/c9tc05054j
  • Peer Reviewed
• [Journal Article] Development of External Stimuli-responsive Organic π Molecules and the Creation of Novel Photo-functions (2019)
  • Author(s): Kamino Shinichiro
  • Journal Title: YAKUGAKU ZASSHI Volume: 139 Issue: 7 Pages: 975-986
  • DOI: 10.1248/yakushi.19-00005
  • NAID: 130007670798
  • ISSN: 0031-6903, 1347-5231
  • Year and Date: 2019-07-01
  • Peer Reviewed
• [Journal Article] Syntheses and Acid-Stimulus Responsiveness of Aminobenzopyranoxanthene Spiroethers (2019)
  • Author(s): Kamino Shinichiro、Sawada Daisuke、Hosoda Ryosuke、Ueda Masashi
  • Journal Title: HETEROCYCLES Volume: 99 Issue: 2 Pages: 820-820
  • DOI: 10.3987/com-18-s(f)66
  • Peer Reviewed
• [Journal Article] SYNTHESES AND ACID-STIMULUS RESPONSIVENESS OF AMINOBENZOPYRANOXANTHENE SPIROETHERS (2019)
  • Author(s): Ryosuke Hosoda, Shinichiro Kamino, Masashi Ueda, Daisuke Sawada
  • Journal Title: Heterocycles Volume: 99
• [Journal Article] Development of Chromic Molecule that Can Change Color and Absorption/Fluorescence Wavelengths Largely in Response to External Stimuli (2018)
  • Author(s): Shinichiro Kamino, Masaru Tanioka, Daisuke Sawada
  • Journal Title: Journal of Synthetic Organic Chemistry, Japan Volume: 76 Issue: 10 Pages: 1066-1075
  • DOI: 10.5059/yukigoseikyokaishi.76.1066
  • NAID: 130007496520
  • ISSN: 0037-9980, 1883-6526
  • Year and Date: 2018-10-01
  • Peer Reviewed
• [Journal Article] Synthesis of Aminobenzopyranoxanthenes with Nitrogen-Containing Fused Rings (2017)
  • Author(s): Natsumi Fukino, Shinichiro Kamino, Minami Takahashi, Daisuke Sawada
  • Journal Title: The Journal of Organic Chemistry Volume: 82 Issue: 24 Pages: 13626-13631
  • DOI: 10.1021/acs.joc.7b02290
  • Peer Reviewed
• [Presentation] マルチカラー応答性を示す Rhodamine 系 pH センサーの開発 (2019)
  • Author(s): 古賀奈津美，神野 伸一郎，澤田大介
  • Organizer: 日本薬学会第137年会(千葉)
• [Presentation] Hに応答して構造と色が2段階に変化する アクチベータブルプローブの開発 (2019)
  • Author(s): 神野伸一郎，古賀奈津美，澤田大介
  • Organizer: 有機合成化学セミナー(岐阜)
• [Presentation] 外部刺激で光機能と構造を段階的に操作する分子技術の開発 (2019)
  • Author(s): 神野伸一郎
  • Organizer: 有機合成若手講演会 先魁プロジェクト 2018 セミナー 有機元素化学が切り拓く創薬研究(金沢)
  • Invited
• [Presentation] キノジメタン系安定ラジカルカチオンの 合成と性質 (2019)
  • Author(s): 谷岡卓，原田芽生，村中厚哉，岡本悠汰，宮本和範，神野伸一郎，内山真伸
  • Organizer: 反応と合成の進歩シンポジウム(岡山)
• [Patent(Industrial Property Rights)] 新規近赤外発光化合物及びその製造方法 (2018)
  • Inventor(s): 神野伸一郎、澤田大介、榎本秀一、渡辺恭良
  • Industrial Property Rights Holder: 神野伸一郎、澤田大介、榎本秀一、渡辺恭良
  • Industrial Property Rights Type: 特許
  • Filing Date: 2018