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Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance

Author

Listed:
  • Aiyan Ji

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences)

  • Hongyue Lou

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences)

  • Chunrong Qu

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences)

  • Wanglong Lu

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences)

  • Yifan Hao

    (Shanghai Institute of Technical Physics of the Chinese Academy of Sciences)

  • Jiafeng Li

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences)

  • Yuyang Wu

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Tonghang Chang

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Hao Chen

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences
    University of Chinese Academy of Sciences)

  • Zhen Cheng

    (State Key Laboratory of Drug Research, Molecular Imaging Center, Shanghai Institute of Materia Medica, Chinese Academy of Sciences
    University of Chinese Academy of Sciences
    Bohai rim Advanced Research Institute for Drug Discovery)

Abstract

It is highly important and challenging to develop donor-acceptor-donor structured small-molecule second near-infrared window (NIR-II) dyes with excellent properties such as water-solubility and chem/photostability. Here, we discovery an electron acceptor, 6,7-di(thiophen-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TQT) with highest stability in alkaline conditions, compared with conventional NIR-II building block benzobisthiadiazole (BBT) and 6,7-diphenyl-[1,2,5] thiadiazolo[3,4-g]quinoxaline (PTQ). The sulfonated hydrophilic dye, FT-TQT, is further synthesized with 2.13-fold increased quantum yield than its counterpart FT-BBT with BBT as acceptor. FT-TQT complexed with FBS is also prepared and displays a 16-fold increase in fluorescence intensity compared to FT-TQT alone. It demonstrates real-time cerebral and tumor vessel imaging capability with µm-scale resolution. Dynamic monitoring of tumor vascular disruption after drug treatment is achieved by NIR-II fluorescent imaging. Overall, TQT is an efficient electron acceptor for designing innovative NIR-II dyes. The acceptor engineering strategy provides a promising approach to design next generation of NIR-II fluorophores which open new biomedical applications.

Suggested Citation

  • Aiyan Ji & Hongyue Lou & Chunrong Qu & Wanglong Lu & Yifan Hao & Jiafeng Li & Yuyang Wu & Tonghang Chang & Hao Chen & Zhen Cheng, 2022. "Acceptor engineering for NIR-II dyes with high photochemical and biomedical performance," Nature Communications, Nature, vol. 13(1), pages 1-13, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31521-y
    DOI: 10.1038/s41467-022-31521-y
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    References listed on IDEAS

    as
    1. Rui Wang & Lei Zhou & Wenxing Wang & Xiaomin Li & Fan Zhang, 2017. "In vivo gastrointestinal drug-release monitoring through second near-infrared window fluorescent bioimaging with orally delivered microcarriers," Nature Communications, Nature, vol. 8(1), pages 1-12, April.
    2. Alexander L. Antaris & Hao Chen & Shuo Diao & Zhuoran Ma & Zhe Zhang & Shoujun Zhu & Joy Wang & Alexander X. Lozano & Quli Fan & Leila Chew & Mark Zhu & Kai Cheng & Xuechuan Hong & Hongjie Dai & Zhen , 2017. "A high quantum yield molecule-protein complex fluorophore for near-infrared II imaging," Nature Communications, Nature, vol. 8(1), pages 1-11, August.
    3. D. J. Naczynski & M. C. Tan & M. Zevon & B. Wall & J. Kohl & A. Kulesa & S. Chen & C. M. Roth & R. E. Riman & P. V. Moghe, 2013. "Rare-earth-doped biological composites as in vivo shortwave infrared reporters," Nature Communications, Nature, vol. 4(1), pages 1-10, October.
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