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Lipid-water amphiphilic benzylidene cyclopentanone dye and preparation method and application in photodynamic therapy thereof

A technology of groups and methyl groups is applied in the field of preparation of lipid-water amphiphilic benzylidene cyclopentanone dyes, which can solve the problems of slow metabolism in vivo, low killing efficiency, unclear effective components, etc.

Active Publication Date: 2011-11-23
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These photosensitizers have different degrees of shortcomings such as unclear effective components, low purity, low killing efficiency, and slow metabolism in the body.

Method used

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  • Lipid-water amphiphilic benzylidene cyclopentanone dye and preparation method and application in photodynamic therapy thereof
  • Lipid-water amphiphilic benzylidene cyclopentanone dye and preparation method and application in photodynamic therapy thereof
  • Lipid-water amphiphilic benzylidene cyclopentanone dye and preparation method and application in photodynamic therapy thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] (i) Add 8 grams (0.2 mol) of NaOH and 40 milliliters of water into a 250 milliliter three-neck flask, stir to make it dissolve evenly. 14.42 g (0.12 mol) of dipolyethylene glycol monomethyl ether was added into 30 ml of tetrahydrofuran (THF) to dissolve evenly, and then added to the above-mentioned three-necked flask and mixed evenly with NaOH solution. Mix 22.88 grams (0.12 mol) of p-toluenesulfonyl chloride and 40 milliliters of THF evenly, and then slowly drop them into the above-mentioned three-necked flask. During the dropping process, keep the temperature of the reaction solution not exceeding 10°C. After the dropwise addition, continue to stir and react for 4 hours. Stop responding. The reaction solution was extracted three times with diethyl ether, the extract was washed with water until it was neutral, then dried by adding anhydrous sodium sulfate, filtered and rotary evaporated to remove diethyl ether to obtain 30.2 g (yield: 92%) of the corresponding p-toluen...

Embodiment 2

[0101] (i) Add 8 grams (0.2 mol) of NaOH and 80 milliliters of water into a 250 milliliter three-neck flask, stir to make it dissolve evenly. 19.7 g (0.12 mol) of tripolyethylene glycol monomethyl ether was added into 50 ml of THF to dissolve evenly, and then added to the above-mentioned three-necked flask and mixed evenly with NaOH solution. Mix 22.88 grams (0.12 mol) of p-toluenesulfonyl chloride and 40 milliliters of THF evenly, and then slowly drop them into the above-mentioned three-necked flask. During the dropping process, keep the temperature of the reaction solution not exceeding 10°C. After the dropwise addition, continue to stir and react for 6 hours. Stop responding. The reaction solution was extracted three times with diethyl ether, the diethyl ether extract was washed with water until it was neutral, and then dried by adding anhydrous magnesium sulfate. The diethyl ether was removed by filtration and rotary evaporation to obtain 34.7 g (yield: 91%) of the corresp...

Embodiment 3

[0110] (i) With reference to the operation of (v) in Example 1, use p-toluenesulfonate Al and 4-(N-methyl-N-(2-hydroxyl-ethyl)amino)benzene with a molar weight of 1:1 formaldehyde reaction to prepare the corresponding benzaldehyde derivative E3 with a PEG group, the yield is 75%, 1 HNMR (400MHz CDCl 3 ): δ(ppm) 3.07(s, 3H), 3.34(s, 3H), 3.51~3.65(m, 12H), 6.71(d, J=9Hz, 2H), 7.69(d, J=9Hz, 2H) , 9.70 (s, 1H).

[0111]

[0112] (ii) With reference to the operation of (vi) in Example 1, the target dye H3 was prepared by reacting E3 with a molar mass of 2:1 with cyclopentanone, with a yield of 72%, 1 HNMR (400MHz CDCl 3 ): δ (ppm) 3.05 (s, 6H) 3.08 (s, 4H) 3.37 (s, 6H) 3.51 ~ 3.67 (m, 24H) 6.73 (d, J = 8.6Hz, 4H) 7.51 (d, J = 8.6 Hz, 6H). HR-MS (ESI): m / z Calcd for C 35 h 51 N 2 o 7 [M+H] + 611.36908; found 611.36926.

[0113]

[0114] (iii) Use PBS (pH=7.4) buffer solution to detect the solubility of the target dye H3 in the water system, and its maximum solubil...

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Abstract

The invention relates to a lipid-water amphiphilic benzylidene cyclopentanone dye, a preparation method and an application in photodynamic therapy thereof. The invention provides a compound with a general formula (I), wherein R1 is a -(C2H4O)m-R5 group; and the definitions of R2, R3, R4 are as defined in the specification. The compound with the general formula (I) of the invention has a simple structure, a low molecular weight, a determined chemical structure, and a lipid-water amphiphilic property, is easy to prepare, purify and further modify, and meets basic requirements of clinical medication. The lipid-water amphiphilic benzylidene cyclopentanone dye of the invention can generate singlet oxygen and superoxide anions under the irradiation of a light source with a wave band range of 350-600 nm, and has good application prospects in the aspect of photodynamic medicament preparation.

Description

technical field [0001] The invention belongs to the field of photodynamic therapy, and in particular relates to a preparation method of a class of lipid-water amphiphilic benzylidene cyclopentanone dye and its application in photodynamic therapy. technical background [0002] Photodynamic therapy is an emerging tumor treatment method. Its treatment principle is to generate phototoxic substances such as singlet oxygen by systemically or locally applying a photosensitizer and then irradiating it with laser light of a specific wavelength, which can be realized in situ. The selective killing of target tissues has the advantages of good selectivity, less trauma, high safety, and repeatable treatment. It can protect the appearance and maintain the functions of important organs to the greatest extent. It has achieved many remarkable results in clinical tumor treatment. Notable achievements. In recent years, photodynamic therapy has also been widely used in the treatment of many be...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00C09B23/14A61K41/00
Inventor 吴飞鹏赵榆霞王维佳施盟泉杨威邹千里
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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