Photosensitizer for inducing death of immunogenic cells and preparation method and application thereof

A technology of cell death and immunogenicity, applied in the field of medicine, can solve the problem of less photosensitizer, achieve good biocompatibility, and achieve the effect of inducing anti-tumor immune function

Active Publication Date: 2022-01-21
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few photosensitizers based on pyrrole

Method used

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  • Photosensitizer for inducing death of immunogenic cells and preparation method and application thereof
  • Photosensitizer for inducing death of immunogenic cells and preparation method and application thereof
  • Photosensitizer for inducing death of immunogenic cells and preparation method and application thereof

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preparation example Construction

[0043] The present invention also provides a preparation method of the photosensitizer described in the above technical solution, comprising the following steps:

[0044] (1) Ethyl 4-aminobenzoate, 2,5-dimethoxytetrahydrofuran and the first organic solvent are mixed to react to obtain ethyl 4-(1H-pyrrol-1-yl)benzoate; 4-( 1H-pyrrol-1-yl)ethyl benzoate, N-bromosuccinimide and a second organic solvent are mixed to react to obtain 4-(2,5-dibromo-1H-pyrrol-1-yl)benzoic acid Ethyl ester; 4-(2,5-dibromo-1H-pyrrol-1-yl) ethyl benzoate, 4-triphenylamine borate, catalyst and a third organic solvent are mixed to react to obtain the first intermediate product; the The structural formula of the first intermediate product is as shown in formula 1:

[0045] Formula 1;

[0046] (2) Mix the first intermediate product, phosphorus oxychloride and the fourth organic solvent, and react to obtain the second intermediate product; the structural formula of the second intermediate product is as s...

Embodiment 1

[0110] (1) Synthesis of the first intermediate product:

[0111] Ethyl 4-aminobenzoate (1.6519 g, 10.00 mmol) and 2,5-dimethoxytetrahydrofuran (1.3216 g, 10.00 mmol) were dissolved in 25 mL of acetic acid, then refluxed for 12 h. After cooling to room temperature the solvent was removed and the residue was dissolved in dichloromethane. Wash three times with water and extract with dichloromethane. with anhydrous MgSO 4 Drying and suction filtration under reduced pressure gave the crude product, which was purified by gel chromatography using dichloromethane / petroleum ether (1 / 5, V d / V p ) mixture as eluent to give ethyl 4-(1H-pyrrol-1-yl)benzoate.

[0112] Ethyl 4-(1H-pyrrol-1-yl)benzoate (1.0970 g, 5.10 mmol) was added to 25 mL of dichloromethane. N-bromosuccinimide (1.7694g, 10.00mmol) was dissolved in 5mL of dichloromethane, and slowly dropped into the dichloromethane solution of ethyl 4-(1H-pyrrol-1-yl)benzoate under stirring, Reaction at room temperature for 12h. Th...

Embodiment 2

[0125] Synthesis of MAP-I

[0126] (1) Synthesis of the first intermediate product:

[0127] Ethyl 4-aminobenzoate (1.6519 g, 10.00 mmol) and 2,5-dimethoxytetrahydrofuran (1.0573 g, 8.00 mmol) were dissolved in 25 mL of acetic acid, then refluxed for 12 h. After cooling to room temperature the solvent was removed and the residue was dissolved in dichloromethane. Wash three times with water and extract with dichloromethane. with anhydrous MgSO 4 Drying and suction filtration under reduced pressure gave the crude product, which was purified by gel chromatography using dichloromethane / petroleum ether (1 / 5, V d / V p ) mixture as eluent to give ethyl 4-(1H-pyrrol-1-yl)benzoate.

[0128] Ethyl 4-(1H-pyrrol-1-yl)benzoate (1.0970 g, 5.10 mmol) was added to 25 mL of dichloromethane. N-bromosuccinimide (1.4155g, 8.00mmol) was dissolved in 5mL of dichloromethane, and slowly dropped into the dichloromethane solution of ethyl 4-(1H-pyrrol-1-yl)benzoate under stirring, Reaction at ro...

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Abstract

The invention relates to a photosensitizer for inducing death of immunogenic cells and a preparation method and application thereof, and belongs to the technical field of medicines. The photosensitizer is a polyphenyl pyrrole derivative (named as MAP-I) containing a D-pi-A structure, triphenylamine is introduced to the 2, 5-site of pyrrole to serve as a substituent group, indole salt is introduced to the 3-site of pyrrole to serve as a targeting agent of mitochondria, and then heavy atom iodine is introduced to a receptor group of a molecule to obtain the photosensitizer. The photosensitizer has the functions of high active oxygen generation rate, stimulation of cells to generate damage-related molecular patterns, in-vitro induction of dendritic cells and induction of in-vivo immunogenic cell death process of organisms, and can be applied to the field of cancer treatment.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a photosensitizer for inducing immunogenic cell death and its preparation method and application. Background technique [0002] According to the report of the World Health Organization, cancer has gradually become an important cause of global morbidity and death, seriously endangering people's health. With the advancement of science and technology and the development of society, cancer treatment methods are becoming more and more diverse, but most patients still face the problems of tumor metastasis and recurrence. Therefore, any effective and reliable cancer treatment method or method that can improve the efficacy of current existing treatment methods has practical implications for the treatment of cancer patients. [0003] Immunogenic cell death is a specific variant of regulated cell death that is stress-driven and induces adaptive immunity against dead cell antigens. The a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/06C09K11/06A61K41/00A61P35/00
CPCC07D403/06C09K11/06A61K41/0057A61P35/00C09K2211/1014C09K2211/1029Y02A50/30
Inventor 刘派田孟艳李亚宁任飞石建兵董宇平刘义
Owner TIANJIN POLYTECHNIC UNIV
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