Tricyano-Methylene-Pyridine Based High-Performance Aggregation-Induced Emission Photosensitizer for Imaging and Photodynamic Therapy

Xupeng Wu; Zhirong Zhu; Zhenxing Liu; Xiangyu Li; Tijian Zhou; Xiaolei Zhao; Yuwei Wang; Yiqi Shi; Qianqian Yu; Wei-Hong Zhu; Qi Wang

doi:10.3390/molecules27227981

Tricyano-Methylene-Pyridine Based High-Performance Aggregation-Induced Emission Photosensitizer for Imaging and Photodynamic Therapy

Molecules. 2022 Nov 17;27(22):7981. doi: 10.3390/molecules27227981.

Authors

Xupeng Wu¹, Zhirong Zhu¹, Zhenxing Liu¹, Xiangyu Li¹, Tijian Zhou¹, Xiaolei Zhao², Yuwei Wang¹, Yiqi Shi¹, Qianqian Yu¹, Wei-Hong Zhu¹, Qi Wang¹

Affiliations

¹ Shanghai Key Laboratory of Functional Materials Chemistry, Key Laboratory for Advanced Materials and Institute of Fine Chemicals, Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China.
² Research Center of Resources and Environment, School of Chemical Engineering and Materials, Changzhou Institute of Technology, Changzhou 213032, China.

Abstract

Photosensitizers equipped with high reactive oxygen species (ROS) generation capability and bright emission are essential for accurate tumor imaging and precise photodynamic therapy (PDT). However, traditional aggregation-caused quenching (ACQ) photosensitizers cannot simultaneously produce desirable ROS and bright fluorescence, resulting in poor image-guided therapy effect. Herein, we report an aggregation-induced emission (AIE) photosensitizer TCM-Ph with a strong donor-π-acceptor (D-π-A) structure, which greatly separates the HOMO-LUMO distribution and reduces the ΔE_ST, thereby increasing the number of triplet excitons and producing more ROS. The AIE photosensitizer TCM-Ph has bright near-infrared emission, as well as a higher ROS generation capacity than the commercial photosensitizers Bengal Rose (RB) and Chlorine e6 (Ce6), and can effectively eliminate cancer cells under image guidance. Therefore, the AIE photosensitizer TCM-Ph has great potential to replace the commercial photosensitizers.

Keywords: ROS generation; aggregation-induced emission; bioimaging; photosensitizer.

MeSH terms

Diagnostic Imaging
Photochemotherapy* / methods
Photosensitizing Agents* / chemistry
Pyridines
Reactive Oxygen Species

Substances

Photosensitizing Agents
Reactive Oxygen Species
Pyridines

Abstract

MeSH terms

Substances

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