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Application of non-surrounding displaced phthalocyanine zinc in preparing sonosensitizer

A zinc phthalocyanine, non-peripheral technology, applied in the application field of non-peripheral substituted zinc phthalocyanine in the preparation of sonosensitizers, which can solve the problems of sound sensitization ability to be improved, unstable composition and properties, and clinical application limitations , to achieve high stability, simple preparation and easy operation

Active Publication Date: 2012-07-11
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, sonodynamic therapy has not been able to enter clinical application, and the key problem is the lack of sound sensitizers with good properties
At present, the sonosensitizers widely used in experimental research are the first-generation photosensitizers such as hematoporphyrin and gallium porphyrin derivatives. These sensitizers have disadvantages: they have strong absorption in the 400-500nm region (the light in this band is positively absorbed). It is rich in natural light), resulting in greater skin phototoxicity under natural light (need to avoid light for 2-4 weeks), unstable composition and properties (hematoporphyrin derivatives are mixtures), and the sound sensitization ability needs to be improved. Practical applications are limited
However, in these application fields, there is still a lack of efficient sonosensitizers

Method used

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  • Application of non-surrounding displaced phthalocyanine zinc in preparing sonosensitizer
  • Application of non-surrounding displaced phthalocyanine zinc in preparing sonosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Tetrakis-a-(4-carboxyphenoxy)zinc phthalocyanine (also known as 1,8(11),15(18),22(25)-tetrakis(4-carboxyphenoxy)zinc phthalocyanine ( II) Synthesis of:

[0042] (1) Preparation of intermediate 3-(4-carboxyphenoxy)phthalonitrile:

[0043] Under the protection of nitrogen, dissolve 0.69g (5mmol) 4-hydroxybenzoic acid and 0.87g (5mmol) 3-nitrophthalonitrile in 20ml dimethyl sulfoxide (DMSO), stir at room temperature for 10 minutes, then add 1.5g (10.9mmol) anhydrous potassium carbonate, after 10min, add 1.0g potassium carbonate, continue to react for 12-24 hours (preferably 14 hours). Suction filter the reaction mixture, collect the filtrate, add 200ml ice-water mixture to the filtrate, adjust the pH value to 1~3 (preferably 2) with 2 mol / L HCl solution, the product is precipitated, filtered, washed with water until neutral, The filter cake was collected and dried under normal pressure at 70° C. to obtain 1.12 g of product with a yield of 87%.

[0044] The structural c...

Embodiment 2

[0058] Tetrakis-a-(3-carboxyphenoxy)zinc phthalocyanine (also known as 1,8(11),15(18),22(25)-tetrakis(3-carboxyphenoxy)zinc phthalocyanine ( II)) Synthesis

[0059] (1) Preparation of intermediate 3-(3-carboxyphenoxy)phthalonitrile:

[0060] Add 0.69g (5mmol) 3-hydroxybenzoic acid and 0.69-2.08g (4-6mmol) (preferably 0.87g, 5mmol) 3-nitrophthalonitrile into 35ml DMF, blow nitrogen, stir at room temperature, after 10 minutes Add 2.1g (15mmol) of potassium carbonate and react for 24 hours. Suction filter the reaction mixture, collect the filtrate, add 200ml ice-water mixture to the filtrate, adjust the pH value to 1~3 (preferably 2) with 2 mol / L HCl solution, the product is precipitated, filtered, washed with water until neutral, The filter cake was collected and dried under normal pressure at 70°C to obtain a crude product. The crude product was dissolved in a small amount of DMF, and then a large amount of water was added to precipitate a precipitate, which was filtered, wa...

Embodiment 3

[0076] Tetrakis-a-(2-methoxycarbonylphenoxy)zinc(II) phthalocyanine (also known as 1,8(11),15(18),22(25)-tetrakis(2-methoxycarbonylphenoxy base) phthalocyanine zinc (II)) synthesis

[0077] (1) Preparation of intermediate 3-(2-methoxycarbonylphenoxy)phthalonitrile

[0078] Add 0.3ml (2.3mmol) of methyl salicylate and 0.35g (2mmol) of 3-nitrophthalonitrile into 10ml of DMSO, blow nitrogen, stir and heat up to 60°C, add 0.7g (5mmol) of potassium carbonate after 10min , Reaction for 12-24 hours (preferably 18 hours). The reaction mixture was added to 200ml of ice-water mixture, stirred, and allowed to stand still, flocculent precipitates were precipitated, filtered with suction, washed with water until neutral, the filter cake was collected, and dried under normal pressure at 70°C to obtain a white crude product. Pass the crude product through CHCl 3 Purify by recrystallization, obtain 0.398g white product, productive rate 71.5%, Rf=0.58 (CH 2 CCl 2 ).

[0079] The structur...

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PUM

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Abstract

The invention discloses application of non-surrounding displaced phthalocyanine zinc in preparing sonosensitizer, in particular discloses the non-surrounding displaced phthalocyanine zinc used as sonosensitizer in preparing sonodynamic therapy medicines. The non-surrounding displaced phthalocyanine zinc provided by the invention has a better biological compatibility, better biological selectivityand higher stability; and the preparation is simple, the operation is easy, synthetic raw materials are easy to obtain, and industrialization is easy to realize.

Description

technical field [0001] The invention belongs to the field of organic functional materials and medicines, and in particular relates to the application of non-peripheral substituted zinc phthalocyanine in the preparation of sound sensitizers. Background technique [0002] In recent years, Sonodynamic Therapy (SDT) has received high attention as a new non-invasive and highly selective treatment method. The method is to use non-thermal ultrasound to activate the sound sensitizer in the target site, trigger a series of reactions, and generate active oxygen or other active substances, so as to kill tumor cells or other abnormal cells and achieve the purpose of treatment. [0003] Sonodynamic therapy is established and developed on the basis of photodynamic therapy. Photodynamic therapy (PDT) uses light to activate the photosensitizer enriched in the target tissue to generate active oxygen and destroy the target tissue. With the development of photosensitizers and supporting lase...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61K8/58A61P17/00A61P35/00A61P31/12A61P31/04A61P31/10A61L2/025A61L2/16A62D3/13A01N43/90A01P1/00A62D101/28A61L101/44
Inventor 黄剑东陈晗雪许赫男郑碧远
Owner FUZHOU UNIV
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