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Water-soluble naphthalocyanine base compound, preparation method and application of compound as photosensitizer

A water-soluble, naphthocyanine-based technology, used in organic chemistry, pharmaceutical formulations, drug combinations, etc., can solve the problems of rare naphthocyanine photosensitizers, complex synthesis process, limited application, etc., to achieve good cell killing rate, good affinity Water quality, good solubility effect

Inactive Publication Date: 2013-05-01
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complex synthesis process and poor solubility of naphthalocyanine complexes, the application of these compounds is limited.
Therefore, reports on naphthalocyanine photosensitizers are still very rare.
Especially for the research of water-soluble naphthalocyanine photosensitizer, there is no report so far

Method used

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  • Water-soluble naphthalocyanine base compound, preparation method and application of compound as photosensitizer
  • Water-soluble naphthalocyanine base compound, preparation method and application of compound as photosensitizer
  • Water-soluble naphthalocyanine base compound, preparation method and application of compound as photosensitizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Preparation of 6-[(4-methyl carboxylate)phenoxy]-2,3-naphthalene dinitrile (2a)

[0050] Weigh 1g (3.9mmol) of 6-bromo-2,3-naphthalene dinitrile (1a) and 2g (13mmol) of methyl 4-hydroxybenzoate, and 6g of K 2 CO 3 Dissolved in DMF (80mL), stirred at 130°C for 20h. Then the mixture was poured into ice water to obtain a brown precipitate. After filtration, the solid was dissolved in chloroform and washed repeatedly with water three times. The organic layer was collected and the organic solvent was removed under reduced pressure. The crude product was separated by silica gel column chromatography to obtain a yellow solid with a yield of 22%. 1 H NMR (300MHz, CDCl 3 ), δ(ppm): 3.94(S,3H,CH 3 ),7.14(d,2H,Ar-H,J=8.7),7.38(d,1H,Ar-H,J=2.4Hz),7.56(dd,1H,Ar-H,J 1 =2.4Hz,J 2 =9.0Hz),8.0(d,1H,Ar-H,J=9.0Hz),8.12(d,2H,Ar-H,J=8.7Hz),8.18(s,1H,Ar-H),8.33( s,1H,Ar-H). 13 C NMR (300MHz, CDCl 3 )δ (ppm): 52.25, 108.96, 111.14, 114.03, 115.69, 115.84, 119.39, 124.29, 126.87,...

Embodiment 2

[0057] (1) Preparation of 6-bromo-7-[(4-methyl carboxylate)phenoxy]-2,3-naphthalene dinitrile (2b)

[0058] Weigh 1g (3.0mmol) of 6,7-dibromo-2,3-naphthalene dinitrile (2b) and 1.7g (11mmol) of methyl 4-hydroxybenzoate, and 10g of K 2 CO 3 Dissolve in DMF (80mL), and stir the reaction at 85°C for 20h. Then pour the mixture into ice water to obtain a brown precipitate. After filtration, the solid was dissolved in chloroform and washed repeatedly with water three times. The organic layer was collected and the organic solvent was removed under reduced pressure. The crude product was recrystallized in methanol as a white solid with a yield of 75%. 1 H NMR (300MHz, CDCl 3 ,25℃,TMS):δ=3.95(s,3H,CH 3 ),7.13(s,1H,Ar-H),7.16(s,1H,Ar-H),7.30(s,1H,Ar-H),8.13(d,J=2.4Hz,2H,Ar-H) ,8.16(s,1H,Ar-H),8.26(s,1H,Ar-H),8.33ppm(s,1H,Ar-H); 13 C NMR (75MHz, CDCl 3 ,25℃,TMS):δ=52.30,110.14,111.36,114.92,115.41,115.46,119.18,120.29,127.28,130.30,132.26,133.29,133.98,134.40,134.64,155.45,156 m / ...

Embodiment 3

[0064] Embodiment 3: the central ion is M g 2+ Synthesis of Naphthalocyanine Complexes

[0065] As described in Example 1, the difference is that the zinc acetate dihydrate in step (2) is replaced by equimolar magnesium acetate tetrahydrate to obtain the corresponding tetrakis[(4-heptyl carboxylate)phenoxy] Magnesium Naphthalocyanine. Replacing tetrakis[(4-heptyl formate) phenoxy]naphthocyanine magnesium in the step (3) of Example 1 with equimolar tetrakis[(4-heptyl formate)phenoxy]naphthocyanine zinc, resulting product Four [(4-formic acid) phenoxy] naphthalocyanine magnesium. The structure of the resulting product is identical to the naphthalocyanine product described in Example 1 except that the Zn at the naphthalocyanine center is replaced by Mg.

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Abstract

The invention relates to a water-soluble naphthalocyanine base compound, a preparation method and an application of the compound as a photosensitizer. A structural formula of the compound is as Formula (I) as shown in the specification. The compound is a carboxylic acid base modified water-soluble naphthalocyanine metal complex, has a good singlet oxygen occurrence rate, low cell photophobic toxicity, and excellent phototoxicity under irradiation, and can serve as a near-infrared PDT (Photodynamic Therapy) photosensitizer. The invention also provides a preparation method of the compound. The preparation method is simple in technology and wide in application scope.

Description

technical field [0001] The invention relates to a water-soluble naphthalocyanine compound, a preparation method and an application as a photosensitizer. Background technique [0002] Photodynamic therapy (PDT) is a cancer treatment technology developed in recent decades. This technology uses light to excite photosensitizer molecules (photosensitizer, PS) inside cancer cells to generate highly cytotoxic singlet oxygen to kill cancer cells inside the cells, while protecting normal tissues from damage. It has many advantages and characteristics compared with the three traditional tumor treatment methods such as surgery, chemotherapy and radiotherapy. Since entering clinical research in the 1970s, PDT has made remarkable achievements in the treatment of malignant tumors, and has become a very active field in the research of tumor prevention and treatment. Tumor PDT research has been carried out in many countries, and thousands of cancer patients have benefited from this therap...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00
Inventor 刘伟栾立强刘久荣丁兰兰施佳伟
Owner SHANDONG UNIV
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