Development of Sulfonamide‐Functionalized Charge‐Reversal AIE Photosensitizers for Precise Photodynamic Therapy in the Acidic Tumor Microenvironment

Author:

Yang Xueqin12ORCID,Xu Changhuo1ORCID,Zhang Xun3,Li Pei1,Sun Feiyi1,Liu Xinyue1,Wang Xinyuan13,Kwok Ryan T. K.1,Yang Jinglei1ORCID,Lam Jacky W. Y.1,Liang Yongye3ORCID,Tang Ben Zhong145ORCID

Affiliation:

1. Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction Department of Mechanical and Aerospace Engineering and Guangdong‐Hong Kong‐Macau Joint Laboratory of Optoelectronic and Magnetic Functional Materials The Hong Kong University of Science and Technology Clear Water Bay, Kowloon Hong Kong 999077 China

2. Bioscience and Biomedical Engineering Thrust, System Hub The Hong Kong University of Science and Technology (Guangzhou) Guangdong 511400 China

3. Department of Materials Science and Engineering Southern University of Science and Technology Guangdong 518055 China

4. School of Science and Engineering Shenzhen Institute of Aggregate Science and Technology The Chinese University of Hong Kong Guangdong 518172 China

5. Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates South China University of Technology Guangdong 510640 China

Abstract

AbstractTumor‐targeted photodynamic therapy (PDT) is desirable as it can achieve efficient killing of tumor cells with no or less harm to normal cells. Herein, a facile molecular engineering strategy is developed for photosensitizers (PSs) with aggregation induced emission (AIE) characteristics and responsive properties to the acidic tumor microenvironment (TME). By the marriage of pH‐sensitive sulfonamide moieties with AIE PSs, two near‐infrared AIE luminogens called DBP‐SPy and DBP‐SPh are designed and synthesized. Both luminogens can form negatively charged nanoaggregates in the aqueous medium at physiological pH. The DBP‐SPy nanoaggregates undergo surface charge conversion to become positive at pH close to the signature pH of TME, while DBP‐SPh nanoaggregates show no such property. The endowed response to acidic TME enables the enhanced cellular uptake of DBP‐SPy at pH = 6.8. By contrast, its cellular uptake is much sacrificed at pH 7.4. As a result, under white light irradiation, DBP‐SPy nanoaggregates demonstrate a considerable photodynamic therapeutic effect on cancer cells in vitro and excellent tumor growth inhibition in vivo. Hence, this study not only provides an acidic TME‐responsive AIE PS for precise PDT, but also inspires new design strategies for AIE‐based theragnostic systems with targeting characteristics.

Funder

National Natural Science Foundation of China

Innovation and Technology Commission

Natural Science Foundation of Guangdong Province

Publisher

Wiley

Subject

Electrochemistry,Condensed Matter Physics,Biomaterials,Electronic, Optical and Magnetic Materials

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