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Polycyclic naphthalenediimide-based nanoparticles for NIR-II fluorescence imaging guided phototherapy

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Abstract

Optical imaging and phototherapy in the second near-infrared window (NIR-II, 900–1700 nm) can reduce tissue auto-fluorescence and photon scattering, which facilitates higher spatial resolution and deeper tissue penetration depth for solid tumor theranostics. Herein, a polycyclic naphthalenediimide (NDI) based chromophore 13-amino-4,5-dibromo-2,7- di(dodecan-6-yl)-1H-isoquinolino[4,5,6-fgh]naphtho[1,8-bc][1,9]phenanthroline-1,3,6,8(2H,7H,9H)-tetraone (NDI-NA) was designed and synthesized. With large polycyclic π-systems, NDI-NA molecule possesses broad near-infrared (NIR) absorption (maximum at 777 nm) and emission (maximum at 921 nm). By nanoprecipitation, NDI-NA nanoparticles (NPs) were formed in aqueous solution with J-aggregative state, which showed huge red-shift in both absorption spectrum (maximum at 904 nm) and emission spectrum (maximum at 1,020 nm), endowing NDI-NA NPs efficient NIR-II fluorescence imaging capability. Besides, the NPs present effective tumor-targeting capability in vivo based on the enhanced permeation and retention (EPR) effect. More importantly, NDI-NA NPs simultaneously have high photothermal conversion efficiency (30.8%) and efficient reactive oxygen species generation ability, making them remarkably phototoxic to cancer cells. The polycyclic chromophore based multifunctional NDI-NA NPs as NIR-II phototheranostic agents possess bright future for clinical NIR-II imaging-guided cancer phototherapy.

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Acknowledgements

The work was supported by Jiangsu Provincial Key Research and Development Plan (BE2017741), Natural Science Foundation of Jiangsu Province (BK20180136, BK20160051), Jiangsu Provincial Medical Youth Talent (QNRC 2016121), and Nanjing Foundation for Development of Science and Technology (2017sc512031, 201605042).

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  1. These authors contributed equally to this work.

Authors and Affiliations

  1. Central Laboratory of Stomatology, Nanjing Stomatological Hospital, Medical School of Nanjing University, Nanjing, 210008, China

    Chuanchao Tang, Chuanhui Song, Zheng Wei, Jianchuan Ran, Yu Cai & Wei Han

  2. Department of Oral and Maxillofacial Surgery, Nanjing Stomatological Hospital, Medical School of Nanjing University, Nanjing, 210008, China

    Chuanchao Tang, Chuanhui Song, Jianchuan Ran & Wei Han

  3. School of Chemistry and Materials Science, Nanjing University of Information Science & Technology, Nanjing, 210044, China

    Chen Liang & Xiaochen Dong

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  1. Chuanchao Tang
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  2. Chuanhui Song
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  4. Chen Liang
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Correspondence to Yu Cai, Xiaochen Dong or Wei Han.

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Tang, C., Song, C., Wei, Z. et al. Polycyclic naphthalenediimide-based nanoparticles for NIR-II fluorescence imaging guided phototherapy. Sci. China Chem. 63, 946–956 (2020). https://doi.org/10.1007/s11426-020-9723-9

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  • DOI: https://doi.org/10.1007/s11426-020-9723-9

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