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Silicon phthalocyanine modified by uridine derivatives and preparation method and application of silicon phthalocyanine

A technology of uridine derivatives and silicon phthalocyanine, which is applied in the field of silicon phthalocyanine modified by uridine derivatives and its preparation, which can solve the problems of lack of selectivity for tumor tissue and cancer cells, clinical application limitations, and high skin phototoxicity. , to achieve the effects of fast preparation, easy separation and purification, and high bioselectivity

Active Publication Date: 2012-12-19
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Hematoporphyrin derivatives have shown certain curative effects, but also exposed serious disadvantages: the maximum absorption wavelength (380-420nm) is not in the red light region (650-800nm) with better transmittance to human tissue, and the skin has high phototoxicity. It is a mixture and its composition is unstable, so its clinical application is limited, so the development of a new generation of photodynamic drugs (photosensitizers) is an international research hotspot
In addition, the current photosensitizers (including phthalocyanine photosensitizers) in clinical trials still lack selectivity to tumor tissues and cancer cells, which is also a problem that needs to be overcome at present

Method used

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preparation example Construction

[0030] The preparation method of the silicon phthalocyanine modified by uridine derivatives of the present invention is: (1) under ice-water bath~room temperature, uridine (or 5-methyluridine) and p-toluenesulfonic acid are placed in acetone and stirred for 2~ For 20 hours, the molar ratio of the two was 1:8~12, and purified by solvent method, extraction method and chromatography to obtain 2', 3'-O-isopropyl-uridine (or 2', 3'- O-isopropyl-5-methyluridine). (2) With dichlorosilicon phthalocyanine and 2', 3'-O-isopropyl-uridine (or 2', 3'-O-isopropyl-5-methyluridine) as reactants, two The feeding molar ratio of the former is 1:4~10; with toluene, xylene or dioxane as solvent, the solvent consumption is 1mmol dichlorosilicon phthalocyanine needs 40~400ml, in the presence of sodium hydride and under the protection of nitrogen, React at 100~130°C for 18~48 hours to obtain the crude product; remove excess raw materials and impurities by solvent method, extraction method, and / or ch...

Embodiment 1

[0038] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-uridineoxy]silicone phthalocyanine

[0039] (1) Synthesis of 2’, 3’-O-isopropyl-uridine

[0040] Dissolve 245 mg (1 mmol) of uridine in 10-30 ml (preferably 20 ml) of acetone, and 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid in 10-30 ml (preferably 20 ml) of acetone. Slowly add p-toluenesulfonic acid acetone solution to uridine acetone solution dropwise under ice-water bath, and stir at room temperature for 2-10 h (preferably 6 h). The reaction mixture was added to 4% sodium bicarbonate ice solution, extracted several times with dichloromethane (or trichloromethane), the organic layer was collected, dried over magnesium sulfate, filtered, concentrated, and dried to obtain a yellow powder product. Yield 85%.

[0041] The characterization data of the product are as follows: MS (EI-60) m / z: 283.4 [M-H] - .

[0042] IR (KBr, cm -1 ): 1467, 2935 (CH 3 ); 1703 (C=O); 1671 (C=C); 1467, 2935 (CH 2 ); 3245 (NH,OH); 1121...

Embodiment 2

[0052] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-5-methyluridineoxy]silicone phthalocyanine

[0053] (1) Synthesis of 2',3'-O-isopropyl-5-methyluridine

[0054] Dissolve 258 mg (1 mmol) of 5-methyluridine in 10-30 ml (preferably 20 ml) of acetone, and dissolve 8-12 mmol (preferably 10 mmol) of p-toluenesulfonic acid in 10-30 ml (preferably 20 ml) of acetone. Add p-toluenesulfonic acid acetone solution slowly dropwise to 5-methyluridine acetone solution under ice-water bath, stir at room temperature for 12~20 h (preferably 16 h), and obtain light yellow gum. The reaction mixture was added to 4% sodium bicarbonate ice solution while stirring, and the pH was adjusted to 8. Extracted several times with dichloromethane, collected the organic layer, dried over magnesium sulfate, filtered, concentrated and dried to obtain the crude product. The crude product was purified through a silica gel column, using ethyl acetate as the eluent, and the eluted fractions were collected, concentr...

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Abstract

The invention discloses silicon phthalocyanine modified by uridine derivatives and a preparation method and application of the silicon phthalocyanine, and belongs to the field of preparation of photodynamic drugs or photosensitizer. The silicon phthalocyanine modified by the uridine derivatives can be used as a photosensitizer for photodynamic therapy, photodynamic diagnosis or photodynamic disinfection, has the advantages of high selectivity, high photodynamic activity and the like, and is explicit in composition and easy to prepare and industrialize.

Description

technical field [0001] The invention belongs to the field of preparation of photodynamic drugs or photosensitizers, and in particular relates to a silicon phthalocyanine modified by uridine derivatives and a preparation method and application thereof. Background technique [0002] Phthalocyanine complexes are an important class of functional materials, which can be developed into functional materials for different purposes through different structural modifications. By introducing suitable substituents and central ions on the phthalocyanine ring, it is possible to develop oxidation catalysts, desulfurization catalysts, nonlinear optical materials, photosensitive drugs, liquid crystal materials, optical recording materials or photoconductive materials, but how to regulate substituents and central ions To obtain the target functional compound, it requires creative work. [0003] The application prospect of phthalocyanine complexes as photosensitizers in photodynamic therapy ...

Claims

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Application Information

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IPC IPC(8): C07H23/00C07H1/00A61K41/00A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/00A61P31/12A61L2/16A61L2/08C02F1/50A61L101/44
Inventor 黄剑东沈小敏郑碧远
Owner FUZHOU UNIV
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