Cationic phthalocyanine as well as preparation and application thereof

A cationic and cationic technology, applied in the field of photosensitizers, can solve the problems of dissolution and aggregation of phthalocyanine photosensitizers

Inactive Publication Date: 2014-08-27
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, relevant studies and experiments have shown that there are still many defects in the application of phthalocyanine photosensitizers in PDT, mainly including the dissolution and aggregation of phthalocyanine photosensitizers in water.

Method used

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  • Cationic phthalocyanine as well as preparation and application thereof
  • Cationic phthalocyanine as well as preparation and application thereof
  • Cationic phthalocyanine as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0076] Cationic phthalocyanine 1 and preparation method thereof, represented by reaction formula as figure 2 as shown,

[0077] (1) Under the protection of argon, triphenylchloromethane is dissolved in chloroform, and slowly dripped into the chloroform solution of ethylenediamine and potassium carbonate at constant pressure. The molar ratio of triphenylchloromethane to ethylenediamine and potassium carbonate is 1 : 12: 2, about 2h of titration, reaction 4h, obtain intermediate 5;

[0078] (2) The molar ratio of intermediate 5 and 4-hydroxybenzaldehyde is 1:1.5, add methanol at room temperature, reflux for 3 hours, cool to room temperature, add 1 equivalent of sodium borohydride, continue stirring for 5 hours to obtain intermediate 7;

[0079] (3) Under the protection of argon, the molar ratio of intermediate 7 to 4-nitrophthalonitrile is 1:1.5, and N,N-dimethylformamide is used as a solvent, and the reaction is carried out at 60°C for 3 hours to obtain the intermediate 8;

...

Embodiment 2

[0083] Cationic phthalocyanine 2 and preparation method thereof, represented by reaction formula as image 3 as shown,

[0084] (1) The molar ratio of diethylethylenediamine 5' to 4-hydroxybenzaldehyde is 1:1.5, add methanol at room temperature, reflux for 3 hours, cool to room temperature, add 1 equivalent of sodium borohydride, and continue stirring for 5 hours Obtain intermediate 7';

[0085] (2) Under the protection of argon, the molar ratio of intermediate 7' to 4-nitrophthalonitrile is 1:1.5, N,N-dimethylformamide is used as a solvent, and the reaction is carried out at 60°C for 3 hours to obtain the intermediate Body 8';

[0086] (3) Under argon protection, the intermediate 8', the metal salt ZnCl 2 Add 1,8-diazacyclo[5,4,0]undecene-7 into dimethylaminoethanol, react at 140°C for 12h to obtain phthalocyanine 9';

[0087] (4) Under an ice-water bath, phthalocyanine 9' was treated with methanol as a solvent, under the protection of argon, 40 equivalents of methyl iodi...

Embodiment 3

[0089] Cationic phthalocyanine 3, 4 and preparation method thereof, represented by reaction formula as Figure 4 as shown,

[0090] (1) Under argon protection, the molar ratio of p-hydroxyaniline or p-hydroxybenzylamine to 4-nitrophthalonitrile is 1:1.5, DMF is used as a solvent, and the reaction is carried out at 60° C. for 3 hours to obtain intermediate 10 (10');

[0091] (2) Under the protection of argon, the molar ratio of intermediate 10 (10') and paraformaldehyde is 1:6, the solvent is chloroform, and the reaction is refluxed for 4 hours; 4 equivalents of sodium borohydride are added in batches, and 10% is added after 2 hours of reaction The ammonia water is excessive, obtains intermediate 11 (11');

[0092] (3) Under argon protection, the intermediate 11 (11'), the metal salt ZnCl2 and DBU are added to MDEA in a molar ratio of 4:4:8, and reacted at 140°C for 12 hours to obtain phthalocyanines 12 and 12';

[0093] (4) Under the protection of argon, phthalocyanine 12 (...

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Abstract

The invention discloses cationic phthalocyanine. A structural formula is shown in the figure. The cationic phthalocyanine derivative disclosed by the invention has good water solubility and low aggregation degree, has good photosensitive activity and antitumor activity, and is applicable to being used as a photosensitizer for diphtheria/pertussis/tetanus (DPT) treatment. The invention also relates to a preparation method and an application of the cationic phthalocyanine.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, and relates to a cationic phthalocyanine and its preparation method and application. Background technique [0002] Photodynamic therapy (PDT for short) is a new disease treatment method based on the interaction of light, photosensitizer and oxygen, which has developed rapidly in recent years. The diagnosis and treatment process is generally divided into two steps: first, the photosensitizer is injected into the body and enriched in the lesion tissue; then, the local lesion is irradiated with light of a wavelength that matches the photosensitizer, and a series of photodynamic events occur when the photosensitizer is stimulated. reaction thereby killing or injuring diseased tissue. PDT is mainly used in the diagnosis and treatment of malignant tumors, and also has good applications in some non-tumor diseases such as genital warts and psoriasis. Compared with tr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61K41/00A61P35/00
CPCY02P20/55C07D487/22A61K41/0071
Inventor 魏少华王傲卢珊周林周家宏林云
Owner NANJING NORMAL UNIVERSITY
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