Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Axial ALA-modified silicon phthalocyanine and preparation method and application thereof

A silicon phthalocyanine, axial technology, applied in the field of axial ALA-modified silicon phthalocyanine and its preparation, can solve the problems of high skin phototoxicity, clinical application limitations, unstable composition, etc., and achieve clear structure and tissue penetration Enhanced capacity and large molar absorption coefficient

Active Publication Date: 2015-08-19
FUZHOU UNIV
View PDF4 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
[0010] So far, no relevant reports have been found on the use of ALA to axially modify silicon phthalocyanine. In this paper, the method of combining silicon phthalocyanine and ALA as two photosensitizers is expected to expand the photodynamic therapy window of phthalocyanine and ALA. , improve the photodynamic therapy effect of photosensitizers, and provide reference for the development of excellent anticancer photosensitizers

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Axial ALA-modified silicon phthalocyanine and preparation method and application thereof
  • Axial ALA-modified silicon phthalocyanine and preparation method and application thereof
  • Axial ALA-modified silicon phthalocyanine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0029] The method for preparing axial ALA-modified silicon phthalocyanine of the present invention is characterized in that: (1) bis[2-(2-hydroxyethoxy)ethoxy] silicon phthalocyanine or bis[2-(2-( 2-Hydroxyethoxy)ethoxy)ethoxy]silicon phthalocyanine or bis[4-(2-aminoethyl)phenoxy]silicon phthalocyanine and N-Boc-5-aminolevulinic acid are reacted The molar ratio of the two materials is 1:2~4 (preferably 1:3). (2) Toluene, xylene or dioxane is used as solvent, and the amount of solvent is 1mmol of phthalocyanine silicon. 50~150ml of solvent (preferably 90ml) is required. Under the protection of nitrogen, react at 20~30℃ for 24~48 hours. Solvent cleaning and column chromatography are used to separate and remove excess raw materials and impurities to obtain corresponding silicon phthalocyanine modified with Boc-ALA and oligoethylene glycol or aminoethylphenoxy.

[0030] The silicon phthalocyanine provided by the present invention can be used to prepare photodynamic drugs or photosen...

Embodiment 1

[0037] Synthesis and physicochemical properties of bis[2-(2-hydroxyethoxy)ethoxy] silicon phthalocyanine (structure shown in the following formula):

[0038]

[0039] Under the protection of nitrogen, weigh out 90 mg (147.17 μmol) of dichlorosilicon phthalocyanine, 1 ml of diethylene glycol, and NaH added to toluene or xylene or 20-50 ml of dioxane (preferably toluene, 30 ml), Reflux for 12-24 hours (preferably 18 hours). The solvent was removed by vacuum rotary evaporation. Dissolve with a small amount of DMF and filter. The filter cake is unreacted dichlorosilica phthalocyanine. A large amount of water is added to the filtrate to precipitate out. The filter cake is vacuum-dried with an organic membrane. Then re-dissolve with dichloromethane and centrifuge to obtain the supernatant of the crude product. It was further subjected to silica gel column chromatography, using ethyl acetate as the eluent, and the target components were collected, evaporated to dryness and vacuum drie...

Embodiment 2

[0042] Synthesis and physicochemical properties of an axial ALA modified silicon phthalocyanine (structure shown in the following formula):

[0043]

[0044] Under the protection of nitrogen, bis[2-(2-hydroxyethoxy)ethoxy]silicon phthalocyanine 50mg (66.7μmol), N-Boc-5-aminolevulinic acid 46.3mg (200.1μmol), DMAP 24.4 mg (200.1 μmol), HOBt 27.0 mg (200.1 μmol), EDCI 38.4 mg (200.1 μmol), 100 μl triethylamine, disperse in 6 ml of dichloromethane and stir for 24 to 48 hours (preferably 36 hours). After the reaction is over, add appropriate amount of water for extraction three times, remove water with anhydrous sodium sulfate, evaporate the solvent, and dry in vacuum. Dissolve in a small amount of dichloromethane and pass through a silica gel column. The eluent is dichloromethane: ethyl acetate=1:1. Collect the target components and evaporate to dryness. Re-dissolve it with a small amount of tetrahydrofuran, then collect the target component through an X3 gel column and evaporate i...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Wavelengthaaaaaaaaaa
Wavelength rangeaaaaaaaaaa
Login to View More

Abstract

The invention discloses axial ALA-modified silicon phthalocyanine and a preparation method and an application thereof, and belongs to the field of photodynamic drug or photosensitizer preparation. The silicon phthalocyanine provided by the invention can be used in photodynamic treatment, photodynamic diagnosis or photodynamic disinfection as a photosensitizer. The silicon phthalocyanine has a structure containing a second-generation photosensitizer ALA. Cells can release two photosensitizers, namely ALA and silicon phthalocyanine. Photodynamic therapy window is expanded. The silicon phthalocyanine provided by the invention shows a good synergistic anticancer effect and a high photodynamic activity.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to an axial ALA-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 oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitive drugs, liquid crystal materials, optical recording materials or photoconductive materials, but how to regulate substituents and central ions To obtain the target functional compound, it requires creative work. [0003] The application prospect of phthalocyanine complexes as photosensitizers in photodynamic therapy (Photodynamic Ther...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07F7/02A61K41/00A61P35/00
Inventor 黄剑东庄静静郑碧远柯美荣黄薇
Owner FUZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com