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Asymmetric dendritic metalloporphyrin as well as preparation method and application thereof

A dendritic metal, asymmetric technology, applied in the direction of medical preparations containing active ingredients, pharmaceutical formulations, organic chemistry, etc., can solve the problems of photodynamic therapy effect to be improved, preparation process is complicated, reaction is not easy to control, etc., to achieve Easy operation, simple process, and mild conditions

Inactive Publication Date: 2015-02-18
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process of symmetrical dendritic metalloporphyrins is relatively complicated, the reaction is not easy to control, and the effect of photodynamic therapy needs to be improved.

Method used

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  • Asymmetric dendritic metalloporphyrin as well as preparation method and application thereof
  • Asymmetric dendritic metalloporphyrin as well as preparation method and application thereof
  • Asymmetric dendritic metalloporphyrin as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] G 2 - Preparation of ZnPor:

[0054] Dissolve 28 mg (ie 0.038 mol) of 5-p-hydroxyphenyl-10, 15, 20-trichlorophenylporphyrin in 10 ml of chloroform and stir;

[0055] Dissolve 21 mg (0.114 mol) of zinc acetate in a mixture of 10 ml of chloroform and 20 ml of methanol to obtain a zinc acetate solution;

[0056] The zinc acetate solution is placed in the constant pressure funnel; the zinc acetate solution in the constant pressure funnel is added dropwise to the 5-p-hydroxyphenyl-10,15,20-trichlorophenylporphyrin solution; the dropping time is controlled About 15 minutes; after the dropwise addition, stir for 16 hours at a temperature of 25°C;

[0057] Take 30 ml of distilled water and add it to the reaction solution, stir and let it stand. After the layers are separated, the organic phase of the lower layer is dried with anhydrous sodium sulfate and evaporated to dryness to obtain 5-p-hydroxyphenyl-10, 15, 20-trichloro Crude phenyl zinc porphyrin;

[0058] Dissolv...

Embodiment 2

[0063] G 3 - Preparation of ZnPor:

[0064] Dissolve 30 mg (ie 0.038 mol) of 5-p-hydroxyphenyl-10, 15, 20-trichlorophenyl zinc porphyrin prepared in Example 1 and 33 mg (ie 0.041 mol) of [G-3]Br in 20 ml of dry acetone; then add 2.4 mg (ie 0.017 mol) of potassium carbonate and 9.5 mg (ie 0.036 mol) of 18-crown-6 ether as a catalyst; under the temperature condition of 56 ℃, in nitrogen atmosphere, stir the reaction for 60 h .

[0065] Then, the reaction solution is post-treated. First add 30 ml of distilled water to the reaction solution, stir, and let stand to separate layers; then take the lower organic phase and extract with 20 ml of dichloromethane, spin the extract to dryness, and remove the solvent under reduced pressure; then use dichloromethane as the eluent liquid, purified with a silica gel column to obtain G 3 -ZnPor Crude. Will G 3 - Dissolve the crude ZnPor in 20 ml of chloroform, carefully inject 120 ml of methanol, and let it stand, the precipitated crystal...

Embodiment 3

[0068] G 4 - Preparation of ZnPor:

[0069] Dissolve 30 mg (ie 0.038 mol) of 5-p-hydroxyphenyl-10, 15, 20-trichlorophenyl zinc porphyrin prepared in Example 1 and 77 mg (ie 0.044 mol) of [G-4]Br in 10 ml of dry 2.0 mg (ie 0.015 mol) of potassium carbonate and 9.0 mg (ie 0.035 mol) of 18-crown-6 ether were added as catalysts; at 56°C, in a nitrogen atmosphere, the reaction was stirred for 42 h.

[0070] Then, the reaction solution is post-treated. First add 20 ml of distilled water to the reaction solution, stir, and let stand to separate layers; then take the lower organic phase and extract with 20 ml of dichloromethane, spin the extract to dryness, and remove the solvent under reduced pressure; then use dichloromethane as the eluent , Purify with silica gel column to get G 4 -ZnPor Crude. Will G 4 - Dissolve the crude ZnPor in 20 ml of chloroform, carefully inject 120 ml of methanol, and let it stand, the precipitated crystal is G 4 -ZnPor, yield 60%.

[0071] NMR spec...

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Abstract

The invention relates to asymmetric dendritic metalloporphyrin as well as a preparation method and an application thereof and belongs to the technical field of photodynamic treatment. The asymmetric dendritic metalloporphyrin is firstly prepared from 5-p-hydroxyl phenyl-10,15,20-trichlorophenylporphyrin through coordination reaction and substitution reaction. Compared with symmetric dendritic metalloporphyrin, the asymmetric dendritic metalloporphyrin has a larger decorative space; the introduction of functional groups including halogen and the like enables porphyrin to have higher three-line-state quantum yield and single-line-state oxygen quantum yield so as to greatly improve the photodynamic treatment effect; and meanwhile, the asymmetric dendritic metalloporphyrin molecule has very strong light cytotoxicity and is a promising photodynamic treatment medicine. The structure of the asymmetric dendritic metalloporphyrin is shown as the specification, wherein R is a dendritic polyphenyl ether substituent.

Description

technical field [0001] The invention relates to an asymmetric dendritic metalloporphyrin, a preparation method and application thereof, and belongs to the technical field of photodynamic therapy. Background technique [0002] Photodynamic therapy (Photodynamic Therapy, PDT), also known as photochemotherapy, is a new method of treating cancer that has been established and developed in recent years. Photosensitizers are the key to photodynamic therapy. In order to obtain high quantum yield and achieve effective energy absorption, photosensitizers generally need to have a large π-conjugated system, and porphyrin is a good photosensitizer. Hematoporphyrin derivatives (HpD) are the first generation of photodynamic therapy drugs. In 1993, Canada first approved the clinical application of this drug (the trade name is photofrin, Photofrin). At present, hematoporphyrin derivatives have been widely used in the treatment of cancer, especially in the treatment of brain tumors, but the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C08G65/48A61K41/00A61K31/409A61K31/787A61P35/00
Inventor 朱沛华马玉翔王红研尹慧阚玲玲陈学伟任明亮
Owner UNIV OF JINAN
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