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Axial nucleoside asymmetrically-modified silicon phthalocyanine and preparation method and application thereof

An asymmetric, silicon phthalocyanine technology, applied in the field of axial nucleoside asymmetrically modified silicon phthalocyanine and its preparation, can solve the problems of lack of tumor tissue and cancer cell selectivity, clinical application limitations, and high skin phototoxicity , to achieve the effect of excellent amphiphilicity, unique asymmetric substitution characteristics, and clear structure

Active Publication Date: 2013-12-11
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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  • Axial nucleoside asymmetrically-modified silicon phthalocyanine and preparation method and application thereof
  • Axial nucleoside asymmetrically-modified silicon phthalocyanine and preparation method and application thereof
  • Axial nucleoside asymmetrically-modified silicon phthalocyanine and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-uridineoxy]silicone phthalocyanine

[0043] (1) Synthesis of 2’, 3’-O-isopropyl-uridine

[0044] 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%.

[0045] The characterization data of the product are as follows: MS (EI-60) m / z: 283.4 [M-H] - .

[0046] IR (KBr, cm -1 ): 1467, 2935 (CH 3 ); 1703 (C=O); 1671 (C=C); 1467, 2935 (CH 2 ); 3245 (NH,OH); 1121...

Embodiment 2

[0056] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-cytidineoxy]silyl phthalocyanine

[0057] (1) Synthesis of 2’, 3’-O-isopropyl-cytidine

[0058] Dissolve 250 mg (1 mmol) of cytidine 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 the acetone solution of p-toluenesulfonate to the acetone solution of cytidine in an ice-water bath, stir at room temperature for 4-10 hours (preferably 6 hours), centrifuge to collect the white precipitate, wash the precipitate with acetone three to four times, and dissolve it with a small amount of DMF , add ethyl acetate to precipitate, membrane filtration, vacuum drying to obtain a white powder product with a yield of 95%.

[0059] The characterization data of the product are as follows: IR (KBr, cm -1 ): 1383 (CH 3 ); 1123 (-O-); 1727 (C=O); 3067, 1204, 1650 (NH 2 ); 1693 (C=C); 3067, 1204 (-OH).

[0060] 1 H NMR (DMSO-d6, 400MHz, pp...

Embodiment 3

[0068] Synthesis of Bis[5'-(2', 3'-O-isopropyl)-adenosyloxy]silyl phthalocyanine

[0069] (1) Synthesis of 2’, 3’-O-isopropyl-adenosine

[0070] Dissolve adenosine (1 mmol) 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. Add p-toluenesulfonic acid acetone solution slowly dropwise to 2-aminoadenosine acetone solution under ice-water bath, stir at room temperature for 24~72 h (preferably 6 h), pour into 4% sodium bicarbonate ice water solution, and precipitate white precipitate, Suction filter and dry. Purified by Soxhlet extraction with chloroform, and dried to obtain a white powder product. Yield 85%.

[0071] (2) Synthesis of bis[5'-(2',3'-O-isopropyl)-adenosyloxy]silicone phthalocyanine

[0072] Under nitrogen protection, dichlorosilicon phthalocyanine (40 mg, 0.065mmol), 2',3'-O-isopropyl-adenosine (0.260~0.650mmol, preferably 0.52mmol) and NaH (0.48~0.60mmol , preferably...

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Abstract

The invention discloses axial nucleoside asymmetrically-modified silicon phthalocyanine and a preparation method and application thereof, belonging to the preparation field of a photodynamic medicine or a photosensitizer. The axial nucleoside asymmetrically-modified silicon phthalocyanine disclosed by the invention can be applied to photodynamic treatment, photodynamic diagnosis or photodynamic disinfection as a photosensitizer, has the structural characteristic of axial asymmetric substitution, and shows good amphipathicity and excellent photodynamic activity.

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 asymmetrically modified by axial nucleosides and a preparation method and application thereof. Background technique [0002] Phthalocyanine compounds 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 compounds as photosensitizers in photodyna...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10A61K41/00A61K31/695A61P35/00A61P35/02A61P31/04A61P1/02A61P27/02A61P9/10A61P17/02A61P17/00A61P31/12A61P31/10
Inventor 黄剑东石杰
Owner FUZHOU UNIV
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