A lysosome-targeted photosensitizer, its synthesis method and its application in biological imaging

A technology of photosensitizer and lysosome, which is applied in the field of medicinal chemistry, can solve the problems of easy aggregation of photosensitizing molecules and affecting the efficiency of photosensitization.

Active Publication Date: 2021-12-28
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of these photosensitizers contain conjugated structures such as tetrapyrrole rings, naphthalene or benzophenone. Due to their strong π due to the superposition effect, the photosensitizers are easy to aggregate and cause quenched fluorescence (Aggregation Caused Quenching, ACQ), affecting photosensitization efficiency

Method used

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  • A lysosome-targeted photosensitizer, its synthesis method and its application in biological imaging
  • A lysosome-targeted photosensitizer, its synthesis method and its application in biological imaging
  • A lysosome-targeted photosensitizer, its synthesis method and its application in biological imaging

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Embodiment

[0044] In the present embodiment, the synthetic route of above-mentioned photosensitizer is as follows:

[0045]

[0046] Wherein: the bold number at the bottom of the above structural formula represents the serial number of the intermediate, and the serial number is directly used to replace the structural formula for the convenience of description.

[0047] The synthesis method of the MP-TPEDCH of the present embodiment specifically includes the following steps:

[0048] 1. Add 4,4'-dimethoxybenzophenone (1.96 g, 8.1 mmol), 4-bromobenzoylbenzene (2.74 g, 10.5 mmol) and zinc powder ( 3.05g, 47mmol), and added 40mL of dry tetrahydrofuran under the protection of argon. The mixture was cooled to -78°C, and 2.5 mL of titanium tetrachloride was added dropwise with stirring. After the dropwise addition, the system was gradually raised to room temperature, and heated to reflux for 16 hours. After the reaction, cool to room temperature, slowly add 50 mL of saturated aqueous sodiu...

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Abstract

The invention relates to a lysosome-targeted photosensitizer, a synthesis method and an application in biological imaging. The lysosome-targeted photosensitizer (MP-TPEDCH) is formed by linking MP as a lysosome-targeting group and TPEDCH as a photosensitive molecule through a synthetic reaction. The lysosome-targeted photosensitizer can spontaneously and stably fluoresce through the aggregation-induced effect in aqueous media. Under laser irradiation, it is excited to transfer electrons to surrounding oxygen molecules to generate reactive oxygen species, resulting in strong cytotoxicity and killing Tumor cells for photodynamic therapy. The present invention also relates to a method for synthesizing the lysosome-targeted photosensitizer, and its use in biological imaging.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a lysosome-targeted photosensitizer, a synthesis method and its application in biological imaging. [0002] technical background [0003] Lysosome is an acidic subcellular organelle in eukaryotic cells, which contains more than 60 kinds of acid hydrolases, which can promote the degradation of various cellular exogenous and endogenous macromolecular substances (proteins, polysaccharides, nucleic acids, etc.), and participate in To the regulation of endocrine processes in cells, it is called the digester of cells. In recent years, studies have also found that lysosomes also play an important role in cell signal transduction, cell migration, cholesterol homeostasis, activation of apoptosis, and tissue remodeling. When the lysosomal environment is disrupted, it leads to cellular dysfunction and various diseases, such as neurodegenerative diseases, rheumatoid arthritis, Pa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/24C09K11/06A61K49/00A61K41/00A61P35/00G01N21/64
CPCC07D333/24C09K11/06A61K49/0021A61K41/0057A61P35/00G01N21/6456G01N21/6402G01N21/6428C09K2211/1033C09K2211/1007C09K2211/1092G01N2021/6439
Inventor 王金辉赵玉芬胡静波王东伟
Owner NINGBO UNIV
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