Construction of Triphenylamine-Based Aggregation-Induced Emission Luminogens for Lysosomes Imaging and Its Application in the Photodynamic Therapy of Cancer Cells

TL;DR

This paper introduces new fluorescent compounds that target lysosomes in cancer cells for imaging and photodynamic therapy.

Contribution

The novel compounds TPAB-CF3 and TPAB-diCF3 combine lysosome targeting with aggregation-induced emission for cancer cell therapy.

Findings

TPAB-CF3 and TPAB-diCF3 exhibit bright yellow fluorescence and excellent lysosome-targeted imaging in HeLa cells.

The compounds show strong 1O2-generation ability and efficient photodynamic killing of cancer cells under white-light irradiation.

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.

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