Silicon phthalocyanine axially modified by aminoethyl phenoxyl and polyethylene glycol oligomer

A technology of aminoethylphenoxy and oligoethylene glycol, applied in chemical instruments and methods, botany equipment and methods, active ingredients of silicon compounds, etc., can solve the problem of lack of tumor tissue and cancer cell selectivity, clinical application Limitations, high skin phototoxicity and other issues, to achieve excellent amphiphilicity, improved tissue penetration ability, and clear structure

Active Publication Date: 2013-08-21
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
In addition, the current photosensitizers (including phthalocyanine photosensitizers) in clinical trials still lack selectivity to tumor tissues and cancer cells, which is also a problem that needs to be overcome at present

Method used

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  • Silicon phthalocyanine axially modified by aminoethyl phenoxyl and polyethylene glycol oligomer
  • Silicon phthalocyanine axially modified by aminoethyl phenoxyl and polyethylene glycol oligomer
  • Silicon phthalocyanine axially modified by aminoethyl phenoxyl and polyethylene glycol oligomer

Examples

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Comparison scheme
Effect test

Embodiment 1

[0037] Synthesis and physicochemical properties of bis[4-(2-aminoethyl)phenoxy]phthalocyanine silicon (structure shown in the following formula):

[0038]

[0039] 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 in DMSO is...

Embodiment 2

[0042] Synthesis and physicochemical properties of silicon phthalocyanine modified by axial aminoethylphenoxy and oligoethylene glycol with the structure shown in the following formula:

[0043]

[0044] Add 40~100ml (preferably 60ml) of triethylene glycol monomethanol to 1mmol of bis[4-(2-aminoethyl)phenoxy]silyl phthalocyanine in toluene (or xylene or dioxane) Ether, after adding a catalytic amount of NaH, continue the reaction at 110°C, monitor the reaction by TLC, and after 5 hours, rotate the reaction mixture to a small amount, add a small amount of DMF to dissolve, add a large amount of water to precipitate, and remove the solvent and reaction materials by membrane filtration And by-products, dry. Purify the crude product through a silica gel column, use ethyl acetate as the elution solvent, and after the first band is completely eluted, use DMF as the elution solvent to collect the target eluted components, spin to a small amount of solvent, filter, spin Evaporate a...

Embodiment 3

[0047] Synthesis and physicochemical properties of axial aminoethylphenoxy and oligoethylene glycol modified silicon phthalocyanines with the following structure:

[0048]

[0049] Add 40~100ml (preferably 60ml) of triethylene glycol to 1mmol of bis[4-(2-aminoethyl)phenoxy]silyl phthalocyanine in toluene (or xylene or dioxane) solution, add Continue the reaction at 110°C after a catalytic amount of NaH, and monitor the reaction by TLC. After 5 hours, rotate the reaction mixture to a small amount, add a small amount of DMF to dissolve, add a large amount of water to precipitate, and remove the solvent, reaction raw materials and by-products by membrane filtration ,dry. Purify the crude product through a silica gel column, use ethyl acetate as the elution solvent, use ethyl acetate as the elution solvent to pass through the silica gel column, after the first band is completely eluted, use a mixed solvent of DMF and triethylamine (volume ratio is 10 : 1) For the elution solve...

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Abstract

The invention discloses silicon phthalocyanine axially modified by aminoethyl phenoxyl and polyethylene glycol oligomer as well as a preparation method and application of silicon phthalocyanine, belonging to the field of preparation of photodynamic medicaments or photosensitizers. The silicon phthalocyanine provided by the invention can be used as a photosensitizer for photodynamic treatment, photodynamic diagnosis or photodynamic sterilization, has the structural characteristic of axially asymmetrical substitution and shows favorable amphipathy and extremely 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 a silicon phthalocyanine modified with axial aminoethylphenoxy and oligoethylene glycol, a preparation method and application thereof. 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 photosensitiz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10A61K41/00A61K31/695A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P17/02A61P17/00A61P31/12A01N55/10A01P1/00A01P3/00A61L2/18A61L101/44
Inventor 黄剑东石杰王蕾
Owner FUZHOU UNIV
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