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Axial galactose/lactose modified silicon phthalocyanine as well as preparation method and application thereof

A technology of galactose and silicon phthalocyanine, applied in the field of axial galactose/lactose modified silicon phthalocyanine and its preparation, can solve the problems of unclear composition, limited clinical application, rare photosensitizer, etc., and achieve the target compound structure Clear, good biocompatibility, high photodynamic effect

Inactive Publication Date: 2020-07-10
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain anti-tumor efficacy, but also exposed serious shortcomings: the maximum absorption wavelength is not in the red light region (650-800nm) with better transmittance to human tissue, skin phototoxicity lasting for several weeks, The composition is not clear, the stability is poor, etc., so the clinical application is limited
In recent years, great progress has been made in the modification of photosensitizers to improve hydrophilicity and reduce aggregation, but photosensitizers that are targeted and completely non-aggregate are still rare

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Under nitrogen protection, 2-[4-(2-aminoethyl)phenoxy]phthalocyanine silicon (40.50 mg, 0.05 mmol), 1,2,3,4-di-O-isopropylidene- α-D-galacturonic acid (53.98 mg, 0.20 mmol), 1-hydroxybenzotriazole (40.00 mg, 0.30 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiene Add amine hydrochloride (57.36 mg, 0.30 mmol) and N-methylmorpholine (15 μL) into 30 mL of DMF, stir and react at 20-30 °C for 12 hours, then remove the solvent DMF with a rotary evaporator, and then use 100- 200-mesh silica gel chromatography column, separated and purified with ethanol as the eluent, collected the main blue component, and then removed the solvent through a rotary evaporator, slowly added the residue to 100 mL of n-hexane, and let it stand for 10 minutes. A blue solid was precipitated, filtered through a microporous membrane (4 μm in pore size), and dried in vacuo to obtain 55 mg of the product with a yield of 85.09%. The maximum absorption peak of the product in DMF is located at 680 nm, and th...

Embodiment 2

[0041] Under nitrogen protection, take 2-[4-(2-aminoethyl)phenoxy]phthalocyanine silicon (40.50 mg, 0.05 mmol), galacturonic acid hydrate (57.31 mg, 0.30 mmol), 1-hydroxy Benzotriazole (40.00 mg, 0.30 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (57.36 mg, 0.30 mmol) and N-methylmorpholine ( 15 μL) into 30mL DMF, stirred and reacted at 20-30°C for 12 hours, then removed the solvent DMF with a rotary evaporator, and then used a 100-200 mesh silica gel column to separate and purify with ethanol as the eluent, and collected the main For the blue component, use a rotary evaporator to remove the solvent, slowly add the residue dropwise to 100 mL of n-hexane, let it stand for 10 minutes, a blue solid precipitates, filter it with a microporous membrane (4 μm in pore size), and dry it in vacuum , to obtain 42.90 mg of product with a yield of 74.83%. The maximum absorption peak of the product in DMF is located at 680 nm, and the maximum absorption wavelength in aq...

Embodiment 3

[0044] Under nitrogen protection, take 2-[4-(2-aminoethyl)phenoxy]silyl phthalocyanine (40.50 mg, 0.05 mmol), lactobionic acid (105.77 mg, 0.30 mmol), 1-hydroxybenzotriazole (40.00 mg, 0.30 mmol), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (57.36 mg, 0.30 mmol) and N-methylmorpholine NMM (15 μL) Add 5 mL of DMF, stir and react at 20~30°C for 16 hours, then use a rotary evaporator to remove the solvent DMF, and then use a 100-200 mesh silica gel column to elute with DMF:ammonia = 100:1 (v / v) The solvent was separated and purified, the main blue component was collected, and the solvent was removed by a rotary evaporator, and the residue was slowly added dropwise to 100 mL of dichloromethane, and allowed to stand for 10 minutes, and a blue solid was precipitated, and a microporous membrane ( The pore size is 4 μm) and dried in vacuum to obtain 43 mg of product with a yield of 77.02%.

[0045] The structural characterization data of the product are as follows: 1 ...

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Abstract

The invention discloses axial galactose / lactose modified silicon phthalocyanine as well as a preparation method and an application thereof, which belong to the field of preparation of photodynamic drugs or photosensitizers. The axial galactose / lactose modified silicon phthalocyanine provided by the invention has the advantages of non-aggregation in a physiological solution, high activity, high biological safety and the like, and can be used as a photosensitizer for photodynamic therapy, photodynamic diagnosis or photodynamic disinfection.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to an axial galactose / lactose modified silicon phthalocyanine and its preparation method and application. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which can be developed into functional materials for different purposes through different structural modifications. By introducing suitable substituents and central ions on the phthalocyanine ring, it is possible to develop battery materials, fluorescent materials, nonlinear optical materials, biological probes, photosensitive drugs, and liquid crystal materials, but how to regulate substituents and central ions to obtain the target Functional compounds, however, require creative work. [0003] The application prospect of phthalocyanine complexes as photosensitizers in photodynamic therapy (Photodynamic Therapy, PDT) is attractin...

Claims

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Application Information

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IPC IPC(8): C07F7/02A61K41/00A61L2/08
CPCA61K41/0071A61L2/08C07F7/025
Inventor 黄剑东李东柯美荣郑碧远
Owner FUZHOU UNIV
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