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Application of phthalocyanine and albumin composite in preparing sound-sensitive agent

A complex, albumin technology, applied in the fields of chemicals for biological control, applications, animal repellants, etc., can solve the problems of unstable composition and properties, skin phototoxicity, poor sonosensitization efficacy, etc. Achieve good water solubility and high biocompatibility

Active Publication Date: 2013-12-11
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
[0007]Phthalocyanine derivatives are an important class of functional materials. There are many studies on the photodynamic effect of this type of compound, but the research on their sonodynamic effect is less rarely
In 2005, Milowska et al. found (Milowska K., Gabryelak T. Ultrasound Med. Biol., 2005, 31: 1707-1712.) that unsubstituted zinc phthalocyanine and aluminum phthalocyanine have sonodynamic killing effects on cells, but Unsubstituted zinc phthalocyanine and aluminum phthalocyanine have poor solubility, low bioavailability, and poor sonosensitization performance

Method used

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  • Application of phthalocyanine and albumin composite in preparing sound-sensitive agent
  • Application of phthalocyanine and albumin composite in preparing sound-sensitive agent
  • Application of phthalocyanine and albumin composite in preparing sound-sensitive agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-carboxyphenoxy)zinc phthalocyanine:

[0043] (1) Preparation of intermediate 3-(4-carboxyphenoxy)phthalonitrile:

[0044] 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%.

[0045] The structural characterization data of the product are as follows:

[0046] MS (ESI)...

Embodiment 2

[0052] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(3-carboxyphenoxy)zinc phthalocyanine

[0053] (1) Preparation of intermediate 3-(3-carboxyphenoxy)phthalonitrile:

[0054] 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, washed three times with water, and dried under normal pressure at 70°...

Embodiment 3

[0062] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(2-methoxycarbonylphenoxy)zinc phthalocyanine

[0063] (1) Preparation of intermediate 3-(2-methoxycarbonylphenoxy)phthalonitrile

[0064]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 ).

[0065] The structural characterization data of the product are as follows:

[0066] MS (ESI) m / z: 278.1...

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Abstract

The invention discloses application of a phthalocyanine and albumin composite in preparing a sound-sensitive agent. The phthalocyanine and albumin composite has the advantages of high biocompatibility, high sonodynamic anti-cancer activity and the like while being used as a sound-sensitive agent for preparing a sonodynamic therapeutic drug.

Description

technical field [0001] The invention belongs to the field of functional materials and medicines, and in particular relates to the application of a compound of phthalocyanine and albumin in the preparation of a sound sensitizer. Background technique [0002] Sonodynamic Therapy (SDT) is the use of non-thermal ultrasound to activate the sound sensitizer in the target site, trigger a series of reactions, generate reactive oxygen species or other active substances, thereby killing tumor cells or other abnormal cells, and achieve therapeutic effect. Purpose. As an emerging non-invasive and highly selective treatment method, the application prospect of sonodynamic therapy in the treatment of tumors has attracted attention. [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 t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K41/00A61P17/00A61P35/00A61P31/12A61P31/04A61P31/10A61L2/025A61L2/16A61K8/58A61K8/64A62D3/13A01N43/90A01N55/10A01P1/00A61K31/409A61K47/42A62D101/28A61L101/44
Inventor 黄剑东许赫男郑碧远黄秀蓉
Owner FUZHOU UNIV