Dihydroporphin photosensitizer as well as preparation method and application thereof

A technology of photosensitizer and chlorin, which is applied in the field of chlorin photosensitizer and its preparation and application, can solve the problems of affecting the effect of photodynamic therapy, less distribution, easy to be oxidized and damaged, and achieve significant killing effect, Enhanced stability and simple preparation method

Inactive Publication Date: 2011-07-20
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantage of this compound is that the surrounding substituent group is phenol, which is easily damaged by oxidation, and because it contains 4 hydroxyl groups, the polarity is relatively high, and it is less distributed in hydrophobic tissue lesions (such as skin cancer), which affects the effect of photodynamic therapy.

Method used

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  • Dihydroporphin photosensitizer as well as preparation method and application thereof
  • Dihydroporphin photosensitizer as well as preparation method and application thereof
  • Dihydroporphin photosensitizer as well as preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0028] Meso-tetra[3-(N,N-diethylaminomethyl)-4-methoxyphenyl]chlorin (meso-tetra[3-(N,N-diethylaminomethyl)-4-methoxyphenyl] Chlorine) synthesis:

[0029] Add 1184g (1.047mmol) meso-tetrakis[3-(N,N-diethylaminomethyl)-4-methoxyphenyl]porphine to a 250mL three-necked flask, add 0.318g (1.696mmol) p-toluenesulfonate hydrazide, and added 0.977g (7.080mmol) of anhydrous potassium carbonate. Evacuate and fill with nitrogen. Finally, add 48mL of pyridine to the three-necked flask, stir evenly, keep heating and reflux in the oil bath under the protection of nitrogen, and add 0.318g (1.696mmol) p-toluenesulfonylhydrazide in the 2nd, 4th, 6th, and 8th hours of the reaction , TLC detection reaction. After the reaction was over, the heating was stopped and allowed to cool naturally. Then it was stirred overnight at room temperature (25°C). Afterwards, 90 mL of ethyl acetate and 40 mL of water were added to the reaction solution, and the mixture was kept at 100° C. in an oil bath for...

Embodiment 2

[0034] Meso-tetra[3-(N,N-diethylaminomethyl)-4-methoxyphenyl]chlorin (meso-tetra[3-(N,N-diethylaminomethyl)-4-methoxyphenyl] Chlorine) synthesis:

[0035]Add 1193g (1.055mmol) meso-tetrakis[3-(N,N-diethylaminomethyl)-4-methoxyphenyl]porphine to a 250mL three-necked flask, add 0.087g (1.72mmol) hydrazine hydrate, And add 0.994g (7.200mmol) of anhydrous potassium carbonate. Evacuate and fill with nitrogen. Finally, 48 mL of pyridine was added to the three-necked flask, stirred evenly, under the protection of nitrogen, kept under heating and reflux in an oil bath, and 0.087 g (1.72 mmol) of hydrazine hydrate was added during the 2nd, 4th, 6th, and 8th hours of the reaction, and detected by TLC reaction. After the reaction was over, the heating was stopped and allowed to cool naturally. It was then stirred overnight at room temperature (25°C). Afterwards, 110 mL of ethyl acetate and 60 mL of water were added to the reaction liquid, and the mixture was kept at 100° C. in an oi...

Embodiment 3

[0037] Photodynamic Antiproliferation Experiment of Photosensitizers on Colon Cancer SW480 Cells

[0038] Tested cells: colon cancer cells SW480

[0039] Test drug: photosensitizer, hematoporphyrin derivative HpD (produced by Beijing Institute of Pharmaceutical Industry).

[0040] Light source: MTZ-1 pulse laser cancer treatment machine; SD2490 laser power measuring instrument.

[0041] Photodynamic anti-tumor cell proliferation experiment: cells in the logarithmic growth phase were digested with trypsin, and the complete medium was resuspended into a cell suspension, which was then inoculated in a 96-well plate, 100 μl per well, placed at 37 ℃5%CO 2 Culture in an incubator, add two different photosensitizers at the same concentration after 24 hours; replace with fresh medium after 48 hours, and then light (XD-635AB photodynamic PDT laser therapy instrument, power 15mW / cm 2 , wavelength 630mm, radiation cells 20min, light dose 18J / cm 2 ); MTT detection was carried out at 7...

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Abstract

The invention relates to a dihydroporphin photosensitizer as well as a preparation method and an application thereof. The dihydroporphin photosensitizer is meso-4(3-N,N-diethylaminemethyl)-4-metoxyphenyl)-dihydroporphin, and the chemical structural formula thereof is provided. The photosensitizer is prepared by the following steps: reducing meso-4(3-N,N-diethylaminemethyl)-4-metoxyphenyl)-dihydroporphin through a reducer in the presence of nitrogen gas and eluting through silica gel column chromatography. The dihydroporphin photosensitizer provided by the invention is used for preparing medicines for treating tumors and photoactivated insecticides. The preparation method is simple. The dihydroporphin photosensitizer can be made into hydrochloride injections to use, and has wide application prospects.

Description

technical field [0001] The invention belongs to the field of photosensitizers and their preparation and application, in particular to a chlorinated photosensitizer and its preparation and application. Background technique [0002] Photodynamic therapy is one of the most promising new technologies developed in the past 20 years. Since entering clinical research in the 1970s, breakthroughs have been made in the treatment of tumors. At present, photodynamic therapy is not only limited to the treatment of malignant tumors, but also shows good prospects in the treatment of many other diseases. [0003] In photodynamic therapy, photosensitizers play a decisive role as energy carriers and reaction bridges. The first generation photosensitizer is represented by photofrin II, the first photosensitizer listed in the Netherlands in 1993, which is a complex mixture of hematoporphyrin derivatives, and its indication is tumor; the second generation photosensitizer is porphyrin II These ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/409A61K41/00C07D487/22A61P35/00A01N43/90A01P7/04
Inventor 陈志龙曾坤张薇莉张丹萍郑皓徐少俊
Owner DONGHUA UNIV
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