Lysosome targeted photosensitizer, synthesis method and application in biological imaging

A technology of lysosome and photosensitizer, applied in the field of medicinal chemistry, can solve the problems of easy aggregation of photosensitizing molecules, affecting the efficiency of photosensitization, etc., and achieve the effect of good lysosome targeting performance.

Active Publication Date: 2020-12-04
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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  • Lysosome targeted photosensitizer, synthesis method and application in biological imaging
  • Lysosome targeted photosensitizer, synthesis method and application in biological imaging
  • Lysosome targeted photosensitizer, synthesis method and 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 as well as a synthesis method and application thereof in biological imaging. The lysosome targeted photosensitizer and (MP-TPEDCH) are formed by connecting MP as a lysosome targeted group and TPEDCH as a photosensitive molecule through a synthetic reaction. The lysosome targeted photosensitizer can spontaneously stabilize fluorescence inan aqueous medium through an aggregation-induced effect, stimulates the fluorescence to transfer electrons to surrounding oxygen molecules under laser irradiation so as to generate active oxygen, generates strong cytotoxicity to kill tumor cells, and realizes photodynamic therapy. The invention also relates to a method for synthesizing the lysosome targeted photosensitizer and application of thelysosome targeted photosensitizer 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 Applications(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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