Stereoisomeric engineering of aggregation-induced emission photosensitizers towards fungal killing

Wenping Zhu, Ying Li, Shaoxun Guo, Wu-Jie Guo, Tuokai Peng, Hui Li, Bin Liu, Hui-Qing Peng () and Ben Zhong Tang ()
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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
Ben Zhong Tang: The Chinese University of Hong Kong, Shenzhen

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-34358-7

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