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Tyrosine phthalocyanines derivates, preparation thereof and applications in preparation of photodynamic drugs

A technology of tyrosine phthalocyanines and derivatives, which is applied in the field of photosensitizers, can solve the problems of limiting the expansion of phthalocyanine derivatives, failing to solve the purpose of accumulation, and limiting applications, and achieves excellent photosensitivity and good targeting. Function, effect of good physiological compatibility

Inactive Publication Date: 2008-10-22
NANJING NORMAL UNIVERSITY
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Problems solved by technology

[0004] However, clinical experiments and related research results show that phthalocyanine photosensitizers that can be used for PDT still have some defects, the most important of which is that phthalocyanine photosensitizers mainly exist in the form of various types of aggregates in water, not only significantly Reduce the photosensitization efficiency of photosensitizers, and easily cause capillary embolism
This defect severely limits the further expansion of phthalocyanine derivatives in the field of clinical application of photodynamic therapy
At present, workers engaged in the research of phthalocyanine derivatives synthesize a series of new phthalocyanine derivatives, such as those with different water-soluble groups (carboxyl, sulfonic acid, phosphate, amine, glucose, etc.) around them. Phthalocyanine derivatives, axially coordinated water-soluble phthalocyanine derivatives, dendritic phthalocyanine compounds, and amphiphilic phthalocyanine derivatives, but so far, under the premise of considering the photosensitizer’s photosensitizing activity, the above-mentioned All kinds of derivatives can not achieve the purpose of solving its accumulation in aqueous solution
In addition, researchers have also tried to use techniques such as surfactant micelles or liposome encapsulation. Although these techniques can better solve the problem of the accumulation of phthalocyanine photosensitizer molecules, due to the stability and biocompatibility of the system, etc. problems, which greatly limit the application of these techniques in actual treatment

Method used

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  • Tyrosine phthalocyanines derivates, preparation thereof and applications in preparation of photodynamic drugs
  • Tyrosine phthalocyanines derivates, preparation thereof and applications in preparation of photodynamic drugs
  • Tyrosine phthalocyanines derivates, preparation thereof and applications in preparation of photodynamic drugs

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Experimental program
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Embodiment 1

[0037] Embodiment 1, the specific steps of tyrosine zinc phthalocyanine synthesis are as follows:

[0038](1) Under the protection of nitrogen, add 8.67mmoL 4-nitrophthalonitrile, 5.79mmoL-Boc-tyrosine ethyl ester, 11.55mmoL potassium carbonate and 20mL N,N-dimethylformamide in sequence, and wait until all After dissolving, it was reacted at 40°C for 8 hours, then washed with dichloromethane and saturated brine respectively, dried over anhydrous sodium sulfate, and finally separated by column chromatography (ethyl acetate:petroleum ether=1:5), and the solution was spin-dried to obtain white The crystalline solid (II) was 2.4626 g, and the yield was 97.7%.

[0039] Compound Identification:

[0040] NMR (δ 1 H, CDCl 3 ):7.72(d,1H);7.26(dd,2H);7.24(dd,2H);7.0(d,2H);3.0(dd,2H);4.5(dd,1H);5.1(d,1H ); 4.2 (dd, 2H); 1.42 (s, 9H); 1.27 (t, 3H).

[0041] Infrared absorption (KBr, cm -1 ): 2231 (CN); 1206 (=CH-O-CH=); 3346 (O=C-NH); 1726 (O=C-O).

[0042] Mass spectrometry: m / z 4...

Embodiment 2

[0060] Embodiment 2 is substantially the same as the steps (1), (2), and (3) of Example 1, but without the step (4) of Example 1, the final product is ethyl tyrosine zinc phthalocyanine.

Embodiment 3

[0061] Example 3 is substantially the same as Example 1, but the pH value of the solution is not adjusted in the step (4) of Example 1, and the final product is sodium tyrosine zinc phthalocyanine. (Since the solution is an alkaline solution at this time, it is impossible for tyrosine to exist, it can only exist in the form of sodium tyrosine)

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Abstract

The invention relates to a tyrosine phthalocyanine derivative which has a structural general formula as the right, in the formula, M is equal to Zn or Al, R is equal to H, Na or CH2CH3. The preparation method for the tyrosine phthalocyanine derivative is: (1) an intermediate II is obtained through the reaction of tyrosine and 4-nitrophthalic nitrile with protected amino group; (2) an intermediate III can be obtained by detracting Boc in the solution of dichloromethane and trifluoroacetic acid; (3) the tyrosine phthalocyanine derivative I can be obtained by cyclizing of the dinitriles intermediate that comprises the tyrosine; wherein, the Boc is di-tert-butyl dicarbonate, a DMF is N, N-dimethylformamide, and a DBU is 1,8-diazacyclo(5,4,0)hendecene-7. The invention also comprises the application of the tyrosine phthalocyanine photosensitizers in preparing photodynamic medicines.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, and relates to a class of tyrosine-substituted phthalocyanine derivatives. The invention also relates to a preparation method of the tyrosine phthalocyanine derivatives and their application in the preparation of photodynamic drugs. in the application. Background technique [0002] Photodynamic therapy (PDT) is a new clinical treatment technology under research and development. Photodynamic therapy began to be used in the clinical diagnosis and treatment of malignant tumors in the late 1970s. In the 1990s, it began to develop in the direction of some common diseases that were difficult to cure by conventional therapy, such as the treatment of port wine stains, microvascular diseases, and macular degeneration. And atherosclerosis, etc., and made outstanding progress. It has also made remarkable achievements in clinical cancer treatment. In 1993, the Canadian h...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07F5/06C07F3/06A61K31/409A61K31/555A61P43/00A61P35/00
Inventor 魏少华林云季春姜巍巍戴冬平周家宏
Owner NANJING NORMAL UNIVERSITY
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