4, 6-diamino-2-mercaptopyrimidine copper (I) sensitizer capable of generating singlet oxygen

A technology of mercaptopyrimidine and singlet oxygen, which is applied in the field of synthesis of photoluminescent transition metal complex sensitized materials, can solve the problems of visible light sensitivity, time-consuming treatment, and is still in the initial stage, and achieves simple preparation methods, leaching Low efficiency and stable luminous effect

Inactive Publication Date: 2021-08-06
HUNAN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, photodynamic therapy (PDT) has been clinically used in the treatment of superficial skin cancer, but only as an auxiliary method, because the photosensitizer 5-aminolevulinic acid (5-ALA) used is sensitive to visible light, and the treatment The disadvantage of time-consuming; microwave thermal therapy (MTT), which uses the thermal effect of microwaves to ablate tumors, has also been clinically used, but microwave thermal therapy has the disadvantages of limited ablation area and high tumor recurrence rate; the anti-tumor effect of microwave dynamic therapy (MDT) Research on tumor effects is still in its infancy

Method used

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  • 4, 6-diamino-2-mercaptopyrimidine copper (I) sensitizer capable of generating singlet oxygen
  • 4, 6-diamino-2-mercaptopyrimidine copper (I) sensitizer capable of generating singlet oxygen
  • 4, 6-diamino-2-mercaptopyrimidine copper (I) sensitizer capable of generating singlet oxygen

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Example 1: Synthesis of Cu-dapy luminescent powder

[0026] Add 40 mL of 1.5 mmol·L to a 250 mL three-neck round bottom flask -1 An aqueous solution of cetyl ammonium bromide and 7.4 mg (0.03 mmol) of copper sulfate pentahydrate (CuSO 4 ·5H 2 O), stirred at room temperature until the copper source was completely dissolved, then added 4.2 mg (0.03 mmol) of 4,6-diaminomercapto-2-pyrimidine (dapyH) under nitrogen atmosphere, stirred vigorously for 30 minutes, and then added 10 mL , 3 mmol·L -1 Stannous chloride (SnCl 2 ) solution, and continued to stir for 4 hours. After fully reacting, the resulting solution was centrifuged (11000 rpm) for 10 min and washed three times with ultrapure water. Finally, the centrifuged precipitate was completely dried in a vacuum oven at 40°C to obtain the final pale yellow product Cu(dapy)·4H 2 O(Cu-dapy). The Cu-dapy solution used in subsequent experiments was obtained by redispersing the vacuum-dried powder in deionized water.

[00...

Embodiment 2

[0030] Example 2: Photoluminescence properties of Cu-dapy

[0031] Such as Figure 4 The fluorescence spectrogram of the suspension prepared by the Cu-dapy prepared in Example 1 with water as a solvent. Cu-dapy was dispersed with deionized water at room temperature to obtain a light yellow suspension (1mg.mL -1 ), which emits intense orange-yellow light under the irradiation of a 365 nm ultraviolet lamp. 368 nm was selected as the excitation wavelength, and Cu-dapy had the strongest emission peak at 580 nm. This strong orange-yellow light emission was caused by ligand-to-metal charge transfer (LMCT).

Embodiment 3

[0032] Embodiment 3: Luminescence stability of Cu-dapy under different pH conditions

[0033] Such as Figure 5 The relationship between the fluorescence intensity and the pH value of the Cu-dapy aqueous solution prepared in Example 1. In the range of pH = 2~7, Cu-dapy showed strong and stable fluorescence emission; in the environment of pH = 6~7, its fluorescence intensity reached the highest; when the pH increased to 8, the Cu-dapy The fluorescence intensity begins to drop sharply because in an alkaline environment, copper ions combine with hydroxide ions to form non-luminescent basic copper salts. The luminescent stability of Cu-dapy under neutral or acidic conditions lays the foundation for its application under physiological conditions.

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Abstract

The invention relates to the technical field of synthesis of photoluminescence transition metal complex sensitized materials, and in particular, relates to a preparation method of a photoluminescence material capable of generating singlet oxygen with ultraviolet and microwave response performance. The preparation method comprises the steps: fully reacting 4,6-diamino-2-mercaptopyrimidine, copper sulfate pentahydrate, stannous chloride, hexadecyl ammonium bromide and an aqueous solution in a nitrogen atmosphere to obtain a white suspension; and carrying out centrifugal separation on the obtained suspension, washing the milk white precipitate, and carrying out vacuum drying to obtain the light yellow 4,6-diamino-2-mercaptopyrimidine copper (I) (Cu-dapy) photoinduced strong orange yellow light-emitting powder material. The material can generate singlet oxygen under the excitation of microwaves and ultraviolet light, and is expected to become a sensitizer in microwave-induced anti-tumor and photodynamic anti-tumor therapies.

Description

technical field [0001] The invention relates to the technical field of synthesis of photoluminescent transition metal complex sensitized materials, in particular to a 4,6-diamino-2-mercaptopyrimidine copper (I) (Cu -dapy) preparation method of sensitizer. Background technique [0002] Malignant tumors have become a major problem threatening human health and the second leading cause of population death. In the process of tumor treatment, chemotherapy drugs used in clinic have systemic toxicity and low drug resistance; surgical resection has high recurrence rate and distant metastasis; radiotherapy has radiation dose limitation and the risk of damage to normal cells. Therefore, on the basis of traditional cancer treatment methods, designing and developing more practical, more effective, more economical, and more comfortable cancer treatment methods is an opportunity and a challenge for anti-tumor researchers. Photodynamic therapy refers to the use of specific wavelengths of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/48A61K41/00A61P35/00C09K11/06
CPCC07D239/48A61K41/0057A61K41/0052A61P35/00C09K11/06C09K2211/188
Inventor 张漫波谢仕安胡瑞祥
Owner HUNAN NORMAL UNIVERSITY
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