A kind of fullerene phthalocyanine derivative and its preparation method and application

A technology of fullerene phthalocyanine derivatives and derivatives, which is applied in the field of fullerene phthalocyanine derivatives and their preparation, and can solve problems such as poor stability, low solubility, and easy photodegradation

Active Publication Date: 2020-07-21
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the problems of poor stability, easy photodegradation and photobleaching, and low solubility of existing phthalocyanine photosensitizers used in photodynamic therapy, the purpose of the present invention is to provide a fullerene phthalocyanine derivative and a preparation method thereof and application

Method used

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  • A kind of fullerene phthalocyanine derivative and its preparation method and application
  • A kind of fullerene phthalocyanine derivative and its preparation method and application
  • A kind of fullerene phthalocyanine derivative and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0081] When fullerene is C 70 , M is zinc (Zn), n=15, the fullerene phthalocyanine derivatives are as shown in formula 1-1, and the preparation method includes:

[0082] (1) Add 0.12 millimoles of C 70 , 1.4 millimoles of N-ethylglycine (purchased from Alfa; as a reaction material), 1.4 millimoles of p-carboxybenzaldehyde (purchased from Alfa; as a reaction material) were dissolved in 150 ml of toluene solution (purchased from Bailingwei; As the solvent), under the protection of argon atmosphere, the reaction was stirred at 110°C for 6 hours, and most of the solvent was removed by rotary evaporation. The compound was separated by silica gel column to obtain the compound represented by formula 4-1. The compound and 10 microliters of N,N-dimethylformamide (purchased from Bailingwei; as a catalyst) were added to 20 ml of anhydrous dichloromethane (purchased from Bailingwei; as a solvent), and at 0°C, 2.3 millimoles of grass were added Acyl chloride (purchased from Inokia; used as an...

Embodiment 2

[0097] The photodegradation stability test of the fullerene phthalocyanine derivatives represented by formula 1-1 obtained in Example 1 is as follows:

[0098] (1) Prepare a DMSO solution of the fullerene phthalocyanine derivative represented by formula 1-1 obtained at 10 micromol / liter in Example 1 (a) and 10 micromol / liter tetracarboxylic acid phthalein represented by formula 2-1 The DMSO solution of cyanine (b) was exposed to 650 nm red light for different times (0, 10, 20, 30, 40, 50, 60, 90 minutes), and then measured its UV-Vis absorption spectrum and UV-Vis The characteristic absorption intensity at 685nm in the absorption spectrum changes with the illumination time, and the results are shown in Figure 5(a), Figure 5(b) and Figure 5(c) respectively.

[0099] As the illumination time increases, if the change in UV-Vis absorption intensity is smaller, the sample is more stable and the ability to resist photobleaching is stronger. It can be seen from Figure 5(b) and Figure 5(c...

Embodiment 3

[0101] The dark toxicity test was performed on the fullerene phthalocyanine derivatives represented by formula 1-1 obtained in Example 1. The steps and results are as follows:

[0102] (1) Resuscitate Hela cells (Cell Resource Center, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences), and adjust the cell density to 5×10 when the cells enter the log phase and the growth is stable. 4 / Ml, planted in 96-well plate, 37℃, 5% CO 2 , Incubate for 24 hours;

[0103] (2) After the cells adhere to the wall, replace the DMEM solution (Corning R10-013-CV, purchase company: Baierdi) with 200 microliters of 0 (as a control), 4.5, 9, 13.5, 18, 22.5 , 27 micromol / L of the DMEM solution of the fullerene phthalocyanine derivatives obtained in Example 1, 37 ℃, 5% CO 2 , Incubate for 24 hours in the dark;

[0104] (3) Discard the DMEM solution containing the fullerene phthalocyanine derivatives obtained in Example 1, add 10% CCK-8 (Dojindo Molecular Technologies, Inc) colorless D...

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Abstract

The embodiment of the invention discloses a fullerene phthalocyanine derivative as well as a preparation method and application thereof. The fullerene phthalocyanine derivative has the advantages of novel structure, small possibility of generating photobleaching, light degradation and aggregation, high phototoxicity and low dark toxicity and is more stable under an illumination condition.

Description

Technical field [0001] The invention relates to the field of fullerene derivatives, in particular to a fullerene phthalocyanine derivative, and a preparation method and application thereof. Background technique [0002] Malignant tumors are invasive, easily metastatic, and easy to relapse. The current traditional cancer treatment methods still cannot guarantee the radical cure of various types of tumors or improve the quality of life of patients. Therefore, the development of new cancer treatment methods is still of practical significance. [0003] Compared with traditional cancer treatment methods (such as surgery, radiotherapy, chemotherapy), photodynamic therapy (Photodynamic therapy, referred to as PDT) has high selectivity, low toxicity, low side effects, less trauma, wide application range, and easy comparison with other tumor treatment methods. Combined with other advantages, it has been widely used in tumor and other clinical treatment fields in recent years. Among them, p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/325C08G65/337A61K41/00A61K47/22A61K51/06A61P35/00
CPCA61K41/0071A61K47/22A61K51/06A61P35/00C08G65/325C08G65/337C08G2650/04
Inventor 王春儒赵佳佳舒春英孙笛关密荣刘帅白春礼
Owner INST OF CHEM CHINESE ACAD OF SCI
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