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A kind of axial terminal hydroxyl substituted silicon phthalocyanine and its self-assembly

A silicon phthalocyanine and hydroxyl-terminated technology, which is applied in the field of axially-terminated hydroxyl-substituted silicon phthalocyanine and its self-assembly, can solve the problem that the application potential of nano-self-assembly has not yet been explored, the clinical application is limited, and the skin phototoxicity is high. problem, to achieve high photodynamic anticancer activity, high practical application effect, and clear structure effect

Active Publication Date: 2016-09-07
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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] Due to the EPR effect, nano anticancer drugs have relative selectivity to tumor tissue, however, the application potential of phthalocyanine nano self-assembly in photodynamic therapy has not been explored

Method used

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  • A kind of axial terminal hydroxyl substituted silicon phthalocyanine and its self-assembly
  • A kind of axial terminal hydroxyl substituted silicon phthalocyanine and its self-assembly
  • A kind of axial terminal hydroxyl substituted silicon phthalocyanine and its self-assembly

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preparation example Construction

[0029] The preparation method of silicon phthalocyanine substituted by axial terminal hydroxyl group of the present invention is: (1) using dichloro silicon phthalocyanine and triethylene glycol, tetraethylene glycol, PEG400 or PEG600 as reactants, and the molar ratio of the two is 1 :1~20, using toluene, xylene or dioxane as a solvent, under the protection of nitrogen, react at 100~130°C for 1~20 hours, and remove excess raw materials and impurities by solvent method and column chromatography, The resulting axial polyethylene glycol-modified silicon phthalocyanine. (2) Using dichlorosilicon phthalocyanine and p-hydroxyphenylpropionic acid as reactants, the molar ratio of the two is 1:1~20, using toluene, xylene or dioxane as solvent, under the protection of nitrogen , reacted at 100~130°C for 1~20 hours, separated and removed excess raw materials and impurities by solvent method and column chromatography, and obtained axial 3-(4-hydroxyphenyl)ethylcarbonyloxy and 4-(2- Carbo...

Embodiment 1

[0038] Synthesis of bis(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)silyl phthalocyanine

[0039] Under nitrogen protection, dichlorosilicon phthalocyanine (100 mg, 0.164 mmol), triethylene glycol (1.640~3.280 mmol, preferably 2.460 mmol) and NaH (0.01~0.02 mmol, preferably 0.016 mmol) were added to toluene 7~ 15 ml (preferably 10 ml), reflux for 12-24 hours (preferably 14 hours). The solvent was removed by vacuum rotary evaporation, and washed with water to obtain a blue crude product. The crude product was purified by a silica gel column, using ethyl acetate: chloroform (5:1) as the eluent, and the second fraction was collected, concentrated and dried to obtain a blue product with a yield of 32.91%. The maximum absorption peak of the product in DMF is located at 673 nm, and the maximum absorption wavelength in 1% castor oil derivative (Cremophor EL, wt%) aqueous solution is located at 676 nm.

[0040] The structure of the product is shown in the following formula, and the characte...

Embodiment 2

[0045] Synthesis of bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)silyl phthalocyanine

[0046] Under nitrogen protection, dichlorosilicon phthalocyanine (100 mg, 0.164 mmol), triethylene glycol monomethyl ether (1.640~3.280 mmol, preferably 2.460 mmol) and NaH (0.01~0.02 mmol, preferably 0.016 mmol) were added to In 7~15 ml of toluene (preferably 10 ml), reflux for 12~24 hours (preferably 12 hours). The solvent was removed by vacuum rotary evaporation, and washed with water to obtain a blue crude product. The crude product was purified by silica gel column, using ethyl acetate solvent as eluent, and the second component was collected, concentrated and dried to obtain a blue product with a yield of 32.91%. The maximum absorption peak of the product in DMF is located at 674 nm, and the maximum absorption wavelength in 1% castor oil derivative (Cremophor EL, wt%) aqueous solution is located at 677 nm.

[0047] The structure of the product is shown in the following formula, and the c...

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Abstract

The invention discloses axial end hydroxyl substituted silicon phthalocyanine, a self-assembling body of silicon phthalocyanine, as well as a preparation method and application of silicon phthalocyanine, and belongs to the field of preparation of photodynamic medicines or photosensitizers. The axial end hydroxyl substituted silicon phthalocyanine disclosed by the invention can be used as a photosensitizer for photodynamic treatment, photodynamic diagnosis or photodynamic sterilization, and is high in photodynamic activity.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and specifically relates to an axial terminal hydroxyl-substituted silicon phthalocyanine and its self-assembly, as well as their preparation method and application. Background technique [0002] Phthalocyanine compounds 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 compounds as photosensiti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10A61K41/00A61K49/00A61P35/00A61P35/02A61P31/04A61P31/12A61P9/10A61P1/02A61P27/02A61P17/00
Inventor 黄剑东杨小清郑碧远李中井
Owner FUZHOU UNIV
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