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Published on: August 1, 2019
Construction of Triphenylamine-Based Aggregation-Induced Emission Luminogens for Lysosomes Imaging and Its
Zhanguo Sun1, Bin Liu2, Huijun Liu1
1School of Chemistry and Chemical Engineering, Shanxi Datong University, Datong 037009, China.
Abstract:
Lysosomes are important acidic subcellular organelles whose dysfunction can lead to some related diseases. The development of new lysosome-imaging-guided AIEgens for the photodynamic therapy of cancer cells is important. In this work, two novel organic compounds with AIE characteristics, namely, TPAB-CF3 and TPAB-diCF3, were designed and synthesized by introducing the weakly basic morpholinyl moiety with lysosome-targeting ability into a triphenylamine-based luminogen. The distorted spatial feature of TPA and the D1-D2-π-A structure of these AIEgens prevented the aggregation-caused quenching of traditional fluorescent molecules and efficiently promoted the separation of the HOMO and LUMO. The outcomes were AIE features and a narrow single-triplet energy gap. Furthermore, TPAB-CF3 and TPAB-diCF3 showed bright yellow fluorescence emission peaks at 577 and 601 nm; large Stokes shifts of 234 and 256 nm, respectively; and excellent lysosome-targeted imaging of HeLa cells (Pearson's coefficient = 0.90). In addition to the good 1O2-generation ability under light irradiation, these AIEgens achieved the high-efficiency bright lysosome imaging-guided photodynamic killing of cancer cells under white-light irradiation.
Insights
Researchers developed novel AIEgens (aggregation-induced emission molecules) for precise lysosome imaging and photodynamic cancer therapy. These compounds effectively target lysosomes, enabling bright imaging and efficient cancer cell killing under white light.
Area of Science:
- Organic Chemistry
- Biomedical Engineering
- Cell Biology
Background:
- Lysosomes are vital acidic organelles; their dysfunction is linked to various diseases.
- Developing advanced lysosome-imaging agents for photodynamic therapy (PDT) is crucial for cancer treatment.
- Aggregation-induced emission (AIE) luminogens offer unique optical properties for bioimaging.
Purpose of the Study:
- To design and synthesize novel AIEgens for lysosome-targeted imaging and PDT.
- To investigate the photophysical properties and cellular imaging capabilities of the synthesized compounds.
- To evaluate the efficacy of AIEgens in guiding photodynamic cancer cell killing.
Main Methods:
- Synthesis of two triphenylamine-based AIEgens, TPAB-CF3 and TPAB-diCF3, incorporating a lysosome-targeting morpholinyl moiety.
- Characterization of AIE properties, including fluorescence emission, Stokes shift, and HOMO/LUMO separation.
- Live-cell imaging of HeLa cells to assess lysosome targeting and evaluate 1O2 generation for PDT.
Main Results:
- TPAB-CF3 and TPAB-diCF3 exhibited strong AIE characteristics with yellow fluorescence emission.
- The compounds demonstrated large Stokes shifts and efficient lysosome-specific imaging in HeLa cells (Pearson's coefficient = 0.90).
- Effective generation of singlet oxygen (1O2) under light irradiation was confirmed, enabling photodynamic cancer cell killing.
Conclusions:
- The novel AIEgens show excellent lysosome-targeting ability and bright fluorescence for bioimaging.
- These AIEgens are effective tools for lysosome imaging-guided photodynamic therapy of cancer cells.
- The study highlights the potential of tailored AIEgens in advanced cancer treatment strategies.

