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Tetrahydroporphin compound and preparation method and application thereof

A technology of tetrahydroporphin and compound, which is applied in the field of tetrahydroporphin compound and its preparation and application, can solve problems such as the listing of tetrahydroporphine PDT drugs, and achieve good application prospects, clear structure and simple preparation Effect

Inactive Publication Date: 2014-02-26
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There is not yet a tetrahydroporphine PDT drug on the market

Method used

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  • Tetrahydroporphin compound and preparation method and application thereof
  • Tetrahydroporphin compound and preparation method and application thereof
  • Tetrahydroporphin compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation method of 2,3-cis-12,13-tetrahydro-2,3,12,13-(tetracarboxymethyl)-5,10,15,20-tetraphenylporphin specifically comprises the following steps:

[0038] (1) Synthesis of 2,3-dihydro-2,3-bis(dicyanomethyl)-5,10,15,20-tetraphenylporphine

[0039] In a 500mL three-neck flask, add 3.38g (24.4mmol) K 2 CO 3and 2.86mL (30.4mmol) of malononitrile, under the protection of nitrogen, inject 100mL of freshly distilled tetrahydrofuran with a syringe, and stir and reflux for 1h. Then 2g (3.04mmol) of 2-nitro-5,10,15,20-tetraphenylporphin was added to the mixture, the mixture was continued to reflux and stirred, and the reaction was monitored by TLC. After 48 hours, the reaction was almost complete. Add 2L dichloromethane to the reaction solution for extraction, wash with water 3 times, and wash with saturated NaCl for 3 times, then anhydrous NaCl 2 SO 4 Dry and concentrate. The crude product was separated by column chromatography, using 300-400 mesh silica gel as th...

Embodiment 2

[0049] Photodynamic Antiproliferation Experiment of Photosensitizers on Colon Cancer SW480 Cells

[0050] Tested cells: colon cancer cells SW480

[0051] Test drug: 2,3-cis-12,13-tetrahydro-2,3,12,13-(tetracarboxymethyl)-5,10,15,20-tetraphenylporphine (hereinafter referred to as photosensitizer 1), hematoporphyrin derivative HpD (produced by Beijing Institute of Pharmaceutical Industry).

[0052] Light source: MTZ-1 pulse laser cancer treatment machine; SD2490 laser power measuring instrument.

[0053] 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 Cultivate in an incubator, add five different photosensitizers at the same concentration after 24 hours; replace with fresh medium after 48 hours, and then carry out light (XD-635AB photodynamic PDT laser therap...

Embodiment 3

[0057] photosensitizer on mouse S 180 Photodynamic therapy experiment of sarcoma

[0058] Test animals: Outbred Kunming strain mice with an average weight of 18-24 g, S180 sarcoma mice (provided by the Institute of Materia Medica, Chinese Academy of Sciences)

[0059] Test drug: 2,3-cis-12,13-tetrahydro-2,3,12,13-(tetracarboxymethyl)-5,10,15,20-tetraphenylporphine (hereinafter referred to as photosensitizer 1) Under aseptic conditions, the above-mentioned medicine was dissolved in a minimum amount of Tween-80 in normal saline and diluted to a 0.5mg / mL solution for later use, hematoporphyrin derivative HpD (produced by Beijing Pharmaceutical Industry Research Institute).

[0060] Light source: MTZ-1 pulse laser cancer treatment machine; SD2490 laser power measuring instrument.

[0061] Photodynamic injury experiment of mouse S180 sarcoma: S180 sarcoma was inoculated subcutaneously in the anterior chest of mice under aseptic conditions. Litters of the same sex were randomly d...

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Abstract

The invention relates to a tetrahydroporphin compound and a preparation method and an application thereof. The structural formula of the compound is shown in the specifications. The preparation method comprises the following steps of: synthesizing 2,3-dihydro-2,3-di(dicyan methyl)-5,10,15,20-tetraphenyl porphin; synthesizing 2,3-dihydro-2,3-di(dicyan methyl)-12-nitro-5,10,15,20-tetraphenyl; synthesizing 2,3-cis-12,13-tetralin-2,3-di(dicyan)-[12:13]-[di(methoxycarbonyl group), di(cyan)methylene]-5,10,15,20-tetraphenyl; and synthesizing 2,3-cis-12,13-tetralin-2,3,12,13-(tetra-carboxymethyl)-5,10,15,20-tetraphenyl porphin. The tetrahydroporphin compound is applied to the preparation of a photosensitizer medicament for treating tumor diseases, and has a definite structure and a wide application prospect, and is easy to prepare.

Description

technical field [0001] The invention belongs to the field of porphine compounds and their preparation and application, in particular to a tetrahydroporphine compound and its preparation and application. Background technique [0002] Photodynamic therapy (PDT) 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22A61K41/00A61K31/409A61P35/00
Inventor 陈志龙丁海林王密刘子雁乜永艳王劲严懿嘉叶颖袁文博孙剑辉夏娇
Owner DONGHUA UNIV
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