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Axially substituted silicon phthalocyanine, method for synthesizing same and application of axially substituted silicon phthalocyanine to photodynamic therapy

A silicon phthalocyanine, axial technology, applied in the field of photosensitizers, can solve the problems of easy aggregation, affecting the photosensitization of phthalocyanines, reducing singlet oxygen quantum yield and fluorescence lifetime, etc. Aggregation, the effect of a simple synthesis method

Inactive Publication Date: 2016-11-09
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, there are still many bottlenecks in the application of phthalocyanine photosensitizers in PDT. Due to their large conjugated system, there is a strong hydrophobic effect in aqueous solution, which leads to the phenomenon that phthalocyanine complexes are generally easy to aggregate, reducing the The quantum yield and fluorescence lifetime of singlet oxygen are determined, which affects the photosensitization of phthalocyanines

Method used

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  • Axially substituted silicon phthalocyanine, method for synthesizing same and application of axially substituted silicon phthalocyanine to photodynamic therapy
  • Axially substituted silicon phthalocyanine, method for synthesizing same and application of axially substituted silicon phthalocyanine to photodynamic therapy
  • Axially substituted silicon phthalocyanine, method for synthesizing same and application of axially substituted silicon phthalocyanine to photodynamic therapy

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Experimental program
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Effect test

Embodiment 1

[0031] Under nitrogen protection, in a 50mL three-necked flask equipped with a reflux device, phthalocyanine silicon dichloride (purchased from Sigma-Aldrich, USA, purity 85%) 50mg, 4-piperidinemethanol 37.67mg and catalyst NaH 30mg were added to In 15mL of toluene, heated to 110°C and refluxed for 24h. After the reaction, the organic solvent was evaporated under reduced pressure, and the product was dissolved in dichloromethane and washed to obtain 30.2 mg of 4-piperidinemethoxy-substituted silicon phthalocyanine, with a yield of 68%.

[0032] 1 H NMR (400MHz, CDCl 3 ,ppm): δ9.65(m,8H,Pc-Ha),8.35(m,8H,Pc-Hb),1.2-1.88(m,8H,CH 2 ),1.19(t,2H,NH).-1.10-1.56(m,8H,CH 2 ),-1.8,(m,2H,CH),-2.3(d,4H.CH 2 );

[0033] 13 C NMR: δ149.2, 135.9, 130.7, 123.66, 60.6, 45.0, 35.2, 27.8; IR: 3439, 2964, 2896, 1630, 1548, 1438, 1418, 1369, 1342, 1246, 1074, 1012, 909, 799cm -1 .

Embodiment 2

[0035]Under nitrogen protection, in a 50 mL three-necked flask equipped with a reflux device, 50 mg of silicon phthalocyanine dichloride, 47.09 mg of 4-piperidine methanol and 30 mg of catalyst NaH were added to 15 mL of toluene, and heated to 110 °C for reflux reaction for 24 h. After the reaction, the organic solvent was evaporated under reduced pressure, and the product was dissolved in dichloromethane and washed to obtain 26.8 mg of the product, 4-piperidinemethoxy-substituted silicon phthalocyanine, with a yield of 60.6%.

Embodiment 3

[0037] Under nitrogen protection, in a 50 mL three-necked flask equipped with a reflux device, 50 mg of silicon phthalocyanine dichloride, 75.34 mg of 4-piperidine methanol and 40 mg of catalyst NaH were added to 15 mL of toluene, and heated to 110 °C for reflux reaction for 24 h. After the reaction, the organic solvent was evaporated under reduced pressure, and the product was dissolved in dichloromethane and washed to obtain 21,2 mg of the product, 4-piperidinemethoxy-substituted silicon phthalocyanine, with a yield of 47.9%.

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Abstract

The invention discloses novel axially substituted silicon phthalocyanine, a method for preparing the same and application of the axially substituted silicon phthalocyanine to photodynamic therapy. The axially substituted silicon phthalocyanine is a 4-piperidine methoxy axially substituted silicon phthalocyanine derivative. The method includes adding silicon phthalocyanine dichloride, 4-piperidinemethanol and alkaline catalysts into organic solvents in a reactor with a reflux device in nitrogen atmosphere, and carrying out heating reflux reaction to obtain the 4-piperidine methoxy substituted silicon phthalocyanine. The novel axially substituted silicon phthalocyanine, the method and the application have the advantages that the axially substituted silicon phthalocyanine structurally contains 4-piperidine methoxy, synergistic effects can be realized by the axially substituted silicon phthalocyanine which is used as a photosensitizer during photodynamic therapy, the method for synthesizing the novel axially substituted silicon phthalocyanine is simple, and the problem of easiness in aggregation of phthalocyanine in physiological environments can be solved (owing to the low aggregation degree of the axially substituted silicon phthalocyanine); the axially substituted silicon phthalocyanine is good in photostability, is high in absorption in phototherapy windows (with the sizes of 600-900 nm), is high in singlet oxygen quantum yield and has PDT (photodynamic therapy) application potential.

Description

technical field [0001] The invention belongs to the technical field of photosensitizers with photodynamic activity, and relates to a silicon phthalocyanine, in particular to an axially substituted silicon phthalocyanine and its synthesis method and application. Background technique [0002] Photodynamic therapy (PDT for short) is a treatment method based on the photochemical reaction principle of specific chemical substances. The chemical substances used are called tumor chemical diagnosis and treatment drugs (photosensitizer, Photosensitizer, referred to as PS). The treatment process of PDT therapy is as follows: the photosensitizer is injected into the body through intravenous injection, and after a certain period of time, the tumor tissue is irradiated with light of a specific wavelength. The photosensitizer enriched in the tumor tissue produces a series of photodynamic reactions under the excitation of light. Thereby killing cancer cells and destroying tumor tissue. Co...

Claims

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Application Information

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IPC IPC(8): C07F7/10A61K41/00A61P35/00A61P29/00
CPCA61K41/0071C07F7/10
Inventor 魏少华张权权王越周林周家宏林云
Owner NANJING NORMAL UNIVERSITY
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