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Radical induced quartet photosensitizers with high 1O2 production for in vivo cancer photodynamic therapy

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Abstract

Singlet oxygen (1O2) is a strong oxidant which plays important roles in photodynamic therapy (PDT). The exploitation of photosensitizers with high 1O2 production is crucial to improve PDT efficiency. In this study, a radical labeled quartet photosensitizer Cy-DENT is reported with high singlet oxygen quantum yield (ΦΔ=32.3%) due to a radical enhanced inter-system crossing (ISC) process. After the introduction of 2,2,6,6-tetramethylpiperidinyloxy (TEMPO) radical, quartet state 4[R,T] of Cy-DENT could be formed to give an over 20-fold enhancement of singlet oxygen quantum yield compared to Cy-DEN (without TEMPO radical) under irradiation of near infrared (NIR) light. In addition, the 1O2 production is well controlled by varying the electron-donating ability of the terminal substituent group. Cy-DENT possesses good cell permeability and is localized in mitochondria. Under the irradiation of 700 nm light, Cy-DENT can produce high levels of ROS to destroy the mitochondria membrane potential and induce cell apoptosis. Through the encapsulation of PEG-SS-PCL micelle, Cy-DENT can be effectively delivered to tumors and suppresses the tumor growth after PDT treatment.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21421005, 21576037, U1608222).

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, China

    Feng Xu, Haoying Ge, Ning Xu, Qichao Yao, Saran Long, Wen Sun, Jiangli Fan & Xiaojun Peng

  2. School of Physics and Electronic Information, Anhui Normal University, Wuhu, 241000, China

    Cheng Yang & Xinsheng Xu

  3. Anhui Province Key Laboratory of Optoelectric Materials Science and Technology, Anhui Normal University, Wuhu, 241000, China

    Xinsheng Xu

  4. Ningbo Institute of Dalian University of Technology, Ningbo, 315016, China

    Xiaojun Peng

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  1. Feng Xu
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  2. Haoying Ge
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  3. Ning Xu
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  4. Cheng Yang
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  5. Qichao Yao
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  7. Wen Sun
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  8. Jiangli Fan
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  9. Xinsheng Xu
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  10. Xiaojun Peng
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Correspondence to Xiaojun Peng.

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Xu, F., Ge, H., Xu, N. et al. Radical induced quartet photosensitizers with high 1O2 production for in vivo cancer photodynamic therapy. Sci. China Chem. 64, 488–498 (2021). https://doi.org/10.1007/s11426-020-9922-3

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  • DOI: https://doi.org/10.1007/s11426-020-9922-3

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