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Stereoisomeric engineering of aggregation-induced emission photosensitizers towards fungal killing

Author

Listed:
  • Wenping Zhu

    (Beijing University of Chemical Technology)

  • Ying Li

    (Guangzhou Medical University)

  • Shaoxun Guo

    (Beijing University of Chemical Technology)

  • Wu-Jie Guo

    (Beijing University of Chemical Technology)

  • Tuokai Peng

    (Beijing University of Chemical Technology)

  • Hui Li

    (Beijing University of Chemical Technology)

  • Bin Liu

    (Beijing University of Chemical Technology)

  • Hui-Qing Peng

    (Beijing University of Chemical Technology
    South China University of Technology)

  • Ben Zhong Tang

    (The Chinese University of Hong Kong, Shenzhen)

Abstract

Fungal infection poses and increased risk to human health. Photodynamic therapy (PDT) as an alternative antifungal approach garners much interest due to its minimal side effects and negligible antifungal drug resistance. Herein, we develop stereoisomeric photosensitizers ((Z)- and (E)-TPE-EPy) by harnessing different spatial configurations of one molecule. They possess aggregation-induced emission characteristics and ROS, viz. 1O2 and O2−• generation capabilities that enable image-guided PDT. Also, the cationization of the photosensitizers realizes the targeting of fungal mitochondria for antifungal PDT killing. Particularly, stereoisomeric engineering assisted by supramolecular assembly leads to enhanced fluorescence intensity and ROS generation efficiency of the stereoisomers due to the excited state energy flow from nonradiative decay to the fluorescence pathway and intersystem (ISC) process. As a result, the supramolecular assemblies based on (Z)- and (E)-TPE-EPy show dramatically lowered dark toxicity without sacrificing their significant phototoxicity in the photodynamic antifungal experiments. This study is a demonstration of stereoisomeric engineering of aggregation-induced emission photosensitizers based on (Z)- and (E)-configurations.

Suggested Citation

  • Wenping Zhu & Ying Li & Shaoxun Guo & Wu-Jie Guo & Tuokai Peng & Hui Li & Bin Liu & Hui-Qing Peng & Ben Zhong Tang, 2022. "Stereoisomeric engineering of aggregation-induced emission photosensitizers towards fungal killing," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34358-7
    DOI: 10.1038/s41467-022-34358-7
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