Extended Pyrazinacenes as a New Class of Near-Infrared Emissive Materials for Potential Bioimaging Applications

2023 Fiscal Year Final Research Report

• Project/Area Number: 21K05044
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Shibaura Institute of Technology
• Principal Investigator: RICHARDS GARY 芝浦工業大学, 工学部, 准教授 (00708620)
• Co-Investigator(Kenkyū-buntansha): 堀 顕子 芝浦工業大学, 工学部, 教授 (90433713)
• Project Period (FY): 2021-04-01 – 2024-03-31
• Keywords: Pyrazinacenes / Near Infrared / Fluorescence / Cellular Imaging / Bioimaging / Acenes

Outline of Final Research Achievements

An extended pyrazinacenes consisting of 7 rectilinearly fused pyrazine units appended with hydrophilic triethylene glycol groups was synthesised. The synthesis of the compound and its purification was optimized. The compound was used in cellular imaging studies in the near-infrared region. Interestingly, this new fluorescent dye can distinguish DNA and RNA cellular structures by simply changing excitation and observation wavelengths.
Redox-active pyrazinacenes consisting of four or five fused pyrazine rings appended with electron-donating triphenylamine groups were synthesized. These compounds exhibit redox-coupled fluorescence switching between visible and near infrared or shortwave infrared regions. We are now developing related compounds as new types of probes for biological and cellular redox states.

Free Research Field

Organic chemistry

Academic Significance and Societal Importance of the Research Achievements

細胞イメージングは、生物学、医学、薬学研究において非常に重要な分野である。近赤外領域に活性を持つ蛍光分子を用いることで、細胞を傷つけることなく、長期間にわたって細胞のプロセスを研究することが可能になる。近赤外領域に活性を持つ蛍光色素の多くは、蛍光量子収率の低さや光退色という問題を抱えている。本研究では、これらの問題を克服する新しいタイプの近赤外蛍光分子の開発を目指す。