Phthalocyanine silicon modified by amino ethyl groups and phenoxy groups as well as preparation method and application thereof

A technology of aminoethylphenoxy and phthalocyanine silicon, which is applied in the direction of medical preparations containing active ingredients, pharmaceutical formulas, active ingredients of silicon compounds, etc., and can solve complex synthetic routes, clinical application limitations, and high skin phototoxicity, etc. problems, to achieve the effects of low preparation cost, easy separation and purification, and clear structure

Active Publication Date: 2012-09-12
FUZHOU UNIV
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  • 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
However, the synthesis route of Pc4 is complicated, the preparation cost is high, and the stability is poor. More importantly, Pc4 is not a drug with independent intellectual property rights in my country.

Method used

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  • Phthalocyanine silicon modified by amino ethyl groups and phenoxy groups as well as preparation method and application thereof
  • Phthalocyanine silicon modified by amino ethyl groups and phenoxy groups as well as preparation method and application thereof
  • Phthalocyanine silicon modified by amino ethyl groups and phenoxy groups as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis and physical and chemical properties of bis[4-(2-aminoethyl)phenoxy]phthalocyanine silicon (IV) (structure shown in the following formula):

[0036]

[0037] Under nitrogen protection, dichlorosilyl phthalocyanine (244.7mg, 0.4mmol), 4-(2-aminoethyl)phenol 1.2~2 mmol (preferably 1.6mmol) and NaH were added to toluene or xylene or dioxane In 20~50ml (preferably toluene, 30ml), reflux for 12~24 hours (preferably 18 hours). Remove the solvent by rotary evaporation in vacuo, dissolve in 100ml of dichloromethane, centrifuge to remove insoluble matter, extract the dichloromethane solution with water (3×100ml), collect the organic layer, then extract with dilute hydrochloric acid (0.1-0.5 mmol), and collect the aqueous layer. The aqueous layer was neutralized with 1M sodium hydroxide, and a blue precipitate was precipitated, centrifuged, washed with water, and dried in vacuum to obtain a blue product with a yield of 45%. The maximum absorption peak of the product...

Embodiment 2

[0040] Synthesis and physicochemical properties of bis[4-(2-aminoethyl)phenoxy]phthalocyanine silicon (IV) hydrochloride (structure shown in the following formula):

[0041]

[0042] Under nitrogen protection, add dichlorosilicon phthalocyanine (305.8mg, 0.5mmol), 4-(2-aminoethyl)phenol 1.5~2.5mmol (preferably 2mmol) and NaH to toluene 30~60ml (preferably 40ml) , Reflux for 12-24 hours (preferably 18 hours). Remove toluene by vacuum rotary evaporation, dissolve in 120ml of dichloromethane, centrifuge to remove insoluble matter, extract the dichloromethane solution with water (3×100ml), collect the organic layer, then extract with dilute hydrochloric acid (0.1-0.5 mmol), and collect the aqueous layer. Add aqueous sodium chloride solution (preferably saturated aqueous sodium chloride solution) to the water layer to precipitate a blue precipitate, centrifuge, wash with water, and dry under vacuum at room temperature to obtain a blue product with a yield of 50%. The maximum ab...

Embodiment 3

[0045] The method for preparing photodynamic drugs (i.e. photosensitizers) using silicon phthalocyanine described in the present invention is: use water, or a mixed solution of water and other substances (the content of other substances is not higher than 10% (wt%)) as a solvent , dissolving silicon phthalocyanine of the present invention, and preparing a uniform blue solution (ie photosensitizer), the concentration of silicon phthalocyanine in the photosensitizer is 0.08mM. The other substances mentioned can be one or a combination of the following: castor oil derivatives (Cremophor EL), dimethyl sulfoxide, ethanol, glycerin, N,N-dimethylformamide, polyethylene glycol 300- 3000, Cyclodextrin, Dextrose, Tween, Macrogol Monostearate. The silicon bis[4-(2-aminoethyl)phenoxy]phthalocyanine of the present invention can also be converted into a salt form with hydrochloric acid or sulfuric acid or other acidic substances, and then dissolved in the above-mentioned solvent. In the pr...

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Abstract

The invention discloses phthalocyanine silicon modified by amino ethyl groups and phenoxy groups as well as a preparation method and application thereof, which belong to the field of the preparation of photodynamic medicines or photosensitizers. The phthalocyanine silicon modified by the amino ethyl groups and the phenoxy groups, which is provided by the invention, can be used as a photosensitizer for photodynamic therapy, photodynamic diagnosis or photodynamic disinfection, has the advantages of definite composition, simple and convenient preparation, high photodynamic activity and the like, is easy to realize industrialization and has obvious economic and social benefits.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to aminoethylphenoxy-modified silicon phthalocyanine and its preparation method and application. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, and the application prospects of phthalocyanine complexes as photosensitizers in photodynamic therapy (Photodynamic Therapy) are attracting attention. [0003] The so-called photodynamic therapy (or photodynamic therapy), in essence, is the application of the photosensitization reaction of photosensitizers (or photosensitizers) in the medical field. The process of action is to first inject the photosensitizer into the body, and after a period of time (this waiting time is to allow the drug to be relatively enriched in the target body), the target body is irradiated with light of a specific wavelength (for the target in the body cavity, op...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K31/695A61K41/00A61P1/02A61P27/02A61P9/10A61P17/02A61P31/04A61P31/12A61P35/00A61P35/02
Inventor 黄剑东郑碧远郑艺文
Owner FUZHOU UNIV
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