Amphiphilic Tetraphenylethene-Based Pyridinium Salt for Selective Cell-Membrane Imaging and Room-Light-Induced Special Reactive Oxygen Species Generation

ACS Applied Materials & Interfaces
Weijie ZhangBen Zhong Tang

Abstract

The cell membrane is the protecting frontier of cells, which is crucial for maintaining cell integrity, and has a close relationship with cell growth and death. There is a growing need for cell membrane imaging and monitoring in both living and dying cells. Herein, we report a new amphiphilic tetraphenylethene-based pyridinium salt (TPE-MEM) with aggregation-induced emission features for discriminatory cell membrane imaging. The fluorogenic probe with high yield was synthesized following asymmetric McMurry reaction, Williamson ether synthesis reaction, Suzuki coupling, and aldol condensation between a double-charged pyridinium salt and hexyloxytetraphenylethene benzaldehyde. TPE-MEM shows good water solubility, biocompatibility, and cell membrane specificity. Interestingly, a reactive oxygen species (ROS) is produced by the molecule (TPE-MEM) under room-light irradiation, which could destroy the integrity of the plasma membrane and cause cell necrosis. This enables a visible observation of cell necrosis and the phototherapeutic effect under a mild condition. Preliminary animal investigations also demonstrated the photodynamic therapy (PDT) effectiveness of TPE-MEM in tumor growth inhibition. We conclude that TPE-MEM is potentia...Continue Reading

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Citations

Mar 10, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Long ZhaoXiaohong Li
Jan 13, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Juechen NiBen Zhong Tang
Feb 11, 2020·Journal of Medicinal Chemistry·Jun DaiYuning Hong
Apr 8, 2021·Topics in Current Chemistry·Lei DongQing-Zheng Yang
Apr 29, 2021·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Sayed Mir SayedXiaolin Lu
Aug 22, 2021·Advanced Healthcare Materials·Yuqing WangXing-Jie Liang
Apr 8, 2020·ACS Applied Materials & Interfaces·Yibin ZhangHaiying Liu

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