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Preparation method and application of water-soluble aminopolycarboxylic acid modified phthalocyanine compound

An aminopolycarboxylic acid and aminopolycarboxylic acid anhydride technology, applied in the field of preparation and modification of water-soluble aminopolycarboxylic acid phthalocyanine compounds, can solve the problems of poor water solubility of optical imaging probes, low fluorescence quantum yield, complex synthesis process and the like , to achieve high fluorescence quantum yield and optical stability, broad application prospects, and simple preparation methods.

Active Publication Date: 2014-01-29
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the shortcomings of existing photosensitizers such as poor water solubility, weak curative effect, large side effects, complex synthesis process, poor water solubility of optical imaging probes, low fluorescence quantum yield in the near-infrared region, poor optical stability, etc., and provide a A kind of water-soluble amino polycarboxylic acid modified phthalocyanine compound

Method used

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  • Preparation method and application of water-soluble aminopolycarboxylic acid modified phthalocyanine compound
  • Preparation method and application of water-soluble aminopolycarboxylic acid modified phthalocyanine compound
  • Preparation method and application of water-soluble aminopolycarboxylic acid modified phthalocyanine compound

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Embodiment 1

[0058] 0.5g phthalocyanine active intermediate (I, M 1 =Zn, Y=NH 2 ) and 0.35g of diethylenetriaminepentaacetic acid bicyclic anhydride were dissolved in 120mL of N,N-dimethylformamide, then 100μL of triethylamine was added, stirred at room temperature for 26h, after the reaction was completed, 230mL of anhydrous ether was added, and left to stand After the precipitation was complete, 0.52 g of an aminopolycarboxylic acid-modified phthalocyanine compound soluble in aqueous sodium bicarbonate solution was obtained by purification and separation, with a yield of 63.63%. For the characterization spectrum, see Figure 1-6 , the structural formula is as follows:

[0059]

[0060] The corresponding water-soluble amino polycarboxylic acid modified phthalocyanine compound can be prepared by replacing the above-mentioned diethylenetriaminepentaacetic acid bicyclic anhydride with amine triacetic acid bicyclic anhydride or ethylenediaminetetraacetic acid bicyclic anhydride or triethy...

Embodiment 2

[0062] 0.3g phthalocyanine active intermediate (I, M 1 =H, Y=NH 2 ) and 0.1g of diethylenetriaminepentaacetic acid bicyclic anhydride were dissolved in 40mL of dimethyl sulfoxide, then 10mg of 4-dimethylaminopyridine was added, stirred at room temperature for 3h, after the reaction was completed, 160mL of acetone was added, and left to stand until the precipitation was complete , purified and separated to obtain 0.31 g of amino polycarboxylic acid modified phthalocyanine compound soluble in aqueous sodium bicarbonate solution, yield 62.42%, see Figure 7 , 8, the structural formula is as follows:

[0063]

[0064] The corresponding water-soluble amino polycarboxylic acid modified phthalocyanine compound can be prepared by replacing the above-mentioned diethylenetriaminepentaacetic acid bicyclic anhydride with amine triacetic acid bicyclic anhydride or ethylenediaminetetraacetic acid bicyclic anhydride or triethylenetetraaminehexaacetic acid bicyclic anhydride .

Embodiment 3

[0066] 0.7g phthalocyanine active intermediate (I, M 1 =Fe, Y=OH) and 0.6g of ethylenediaminetetraacetic acid bicyclic anhydride were dissolved in 200mL of N,N-dimethylformamide, then added 12mg of sodium carbonate, stirred at room temperature for 48h, and added 300mL of ethyl acetate , standing still until the precipitation is complete, purified and separated to obtain 0.66 g of amino polycarboxylic acid modified phthalocyanine compound soluble in aqueous sodium bicarbonate solution, the yield is 64.18%, and the characterization spectrum is shown in Figure 9 , 10, the structural formula is as follows:

[0067]

[0068] The corresponding water-soluble aminopolycarboxylic acid-modified phthalocyanine compound can be prepared by replacing the above-mentioned ethylenediaminetetraacetic acid bicyclic anhydride with amine triacetic acid bicyclic anhydride or diethylenetriaminepentaacetic acid bicyclic anhydride or triethylenetetraaminehexaacetic acid bicyclic anhydride .

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Abstract

The invention discloses a water-soluble aminopolycarboxylic acid modified phthalocyanine compound as well as a preparation method and an application thereof. The water-soluble aminopolycarboxylic acid modified phthalocyanine compound is characterized in that the side chain or the center is connected to aminopolycarboxylic acid, the aminopolycarboxylic acid connected to the side chain is as shown in a structure (I) in the description, and the aminopolycarboxylic acid connected to the center is as shown in a structure (II) in the description. The preparation method of the water-soluble aminopolycarboxylic acid modified phthalocyanine compound is simple and easy to operate. After the phthalocyanines compound is modified by the method, the phthalocyanine compound has stable chemical property and can be completely dissolved in a sodium bicarbonate aqueous solution, the degree of self aggregation of phthalocyanine is reduced, and the phthalocyanine compound is absorbed in a 600-900 nm near-infrared zone and can be applied to the fields of near infrared fluorescence imaging or photodynamic tumor treatment.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, and specifically relates to a water-soluble amino polycarboxylic acid modified phthalocyanine compound, a preparation method and application. In particular, it involves the reaction of phthalocyanine active intermediates with amino polycarboxylic acid anhydrides to obtain amino polycarboxylic acid modified phthalocyanine compounds that can be dissolved in aqueous sodium bicarbonate solution, and the amino polycarboxylic acid modified phthalocyanine compounds in photodynamic therapy of tumors and near-infrared fluorescence imaging. Background technique [0002] Malignant tumor is one of the most difficult diseases to cure in the world today, and about 7.6 million people die from it every year in the world. The current clinical treatment methods for tumors include chemotherapy, radiotherapy, surgery, and biological control, but there is no treatment that can eradicate tumors and take ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61K49/00A61P35/00
CPCA61K41/0071A61K49/0036C07D487/22
Inventor 刘天军郭江红洪阁
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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