☆ 4.6 Article

Photostable BODIPY-based molecule with simultaneous type I and type II photosensitization for selective photodynamic cancer therapy

JOURNAL OF MATERIALS CHEMISTRY B (2014)

期刊

JOURNAL OF MATERIALS CHEMISTRY B

卷 2, 期 11, 页码 1576-1583

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ROYAL SOC CHEMISTRY

DOI: 10.1039/c3tb21547d

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Materials Science, Biomaterials

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National Science Council of Taiwan [NSC 101-2113-M-005-016-MY3]

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We introduce a new class of photostable, efficient photosensitizers based on boron-dipyrromethene (BODIPY) derivatives that can generate singlet oxygen and superoxide simultaneously under irradiation. First, we report the synthesis and design of how to control the generation of a specifically substituted position of BODIPY. Second, after biologically evaluating the uptake, localization and phototoxicity in cell lines, we conclude that 2,6-di-anisole substituted BODIPY is a potentially selective photodynamic therapy candidate because its photodamage is more efficient in cancer cells than in normal cells without significant dark toxicity.

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An AIE Photosensitizer with Simultaneous Type I and Type II ROS Generation: Efficient Bacterial Elimination and Hypoxic Tumor Ablation

Yuwei Wang, Jinghan Liao, Yanting Lyu, Qianqian Guo, Zhirong Zhu, Xupeng Wu, Jiahong Yu, Qi Wang, Wei-Hong Zhu

Summary: Aggregation induced emission (AIE) photosensitizers have gained significant attention in photodynamic therapy (PDT) due to their excellent performance. However, the therapeutic effect of AIE photosensitizers is often influenced by the biological microenvironment as it is challenging to generate both type I and type II reactive oxygen species (ROS) simultaneously. In this study, a novel electron-rich anion-pi(+) AIEgen Pys-QM-TT is introduced, which can efficiently produce type I and type II ROS and enable near-infrared fluorescence imaging concurrently. The rational design of the AIE photosensitizer incorporates a strong electron-donating triphenylamine unit, a pi-bridge thiophene, and an electron-withdrawing pyridinium salt unit to enhance D-pi-A behavior, thus improving intramolecular charge transfer and extending the wavelength. Moreover, the strong D-pi-A effect is believed to minimize increment ES-T and promote intersystem crossing processes, significantly enhancing ROS generation. Furthermore, the negatively charged anion in the pyridinium salt group provides an electron-rich environment, enabling efficient electron transfer for type I ROS generation. Consequently, Pys-QM-TT demonstrates the simultaneous production of type I and type II ROS with minimal dependence on the environmental conditions, effectively inhibiting bacterial infections, and ablating tumor tissue through the promotion of tumor cell apoptosis, inhibition of tumor cell proliferation, and anti-angiogenesis.

ADVANCED FUNCTIONAL MATERIALS (2023)