Type I photosensitizer based on AIE chromophore tricyano-methylene-pyridine for photodynamic therapy

Chao Pan; Weijun Zhao; Xiaolei Zhao; Zhenxing Liu; Xiangyu Li; Yanting Lyu; Xupeng Wu; Zhirong Zhu; Wei-Hong Zhu; Qi Wang

Green Chemical Engineering (Sep 2023)

Type I photosensitizer based on AIE chromophore tricyano-methylene-pyridine for photodynamic therapy

Chao Pan,
Weijun Zhao,
Xiaolei Zhao,
Zhenxing Liu,
Xiangyu Li,
Yanting Lyu,
Xupeng Wu,
Zhirong Zhu,
Wei-Hong Zhu,
Qi Wang

Affiliations

Chao Pan: 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
Weijun Zhao: 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
Xiaolei Zhao: 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
Zhenxing Liu: 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
Xiangyu Li: 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
Yanting Lyu: 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
Xupeng Wu: 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
Zhirong Zhu: 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
Wei-Hong Zhu: 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
Qi Wang: Corresponding author.; 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

Journal volume & issue: Vol. 4, no. 3
pp. 324 – 330

Abstract

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Image guided photodynamic therapy (PDT) combines fluorescence tracing and phototherapy, which can achieve a more accurate and effective treatment effect. However, traditional photosensitizers are limited by the aggregation-caused fluorescence quenching (ACQ) effect and low reactive oxygen species (ROS) generation in a hypoxic environment, resulting in poor imaging and treatment effect. Herein, we report a tricyano-methylene-pyridine (TCM)-based Type I aggregation-induced emission (AIE) photosensitizer (TCM-MBP), the strong electron acceptance (D-A) effect extends the wavelength to near-infrared (NIR) region to reduce the autofluorescence interference, and oxygen atoms provide lone pair electrons to enhance the inter system crossing (ISC) rate, thereby promoting the generation of more triplet states to produce ROS. The AIE photosensitizer TCM-MBP exhibited low oxygen dependence, NIR emission, and higher ROS production compared to commercially available Ce 6 and RB. After encapsulation with DSPE-PEG2000, TCM-MBP nanoparticles (TCM-MBP NPs) could penetrate to visualize cells and efficiently kill cancer cells upon light irradiation. This study provides an oxygen-independent AIE photosensitizer, which has great potential to replace the commercial ACQ photosensitizers.

Published in Green Chemical Engineering

ISSN: 2666-9528 (Online)
Publisher: KeAi Communications Co. Ltd.
Country of publisher: China
LCC subjects: Technology: Chemical technology: Chemical engineering; Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.keaipublishing.com/en/journals/green-chemical-engineering/

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