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Water-soluble molecular target porphin photosensitizer and preparation method thereof

A technology of molecular targeting and photosensitizers, which is applied in the direction of organic active ingredients, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve the problem of unsatisfactory photodynamic activity of targeted photosensitizers Difficulty in intravenous administration of photosensitizers, low photodynamic activity and other problems, to achieve the effects of prolonging the circulation time in the body, improving bioavailability, and strong reproducibility

Inactive Publication Date: 2013-01-30
INST OF FIELD OPERATION SURGERY NO 3 MILITARY MEDICL UNIV PLA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low photodynamic activity of porphyrin molecules themselves, the photodynamic activity of folic acid-porphyrin targeted photosensitizers is not ideal; in addition, porphyrins are mostly fat-soluble macrocyclic compounds, which are difficult to dissolve in water, while folic acid The solubility of porphyrin-folic acid conjugates is extremely limited, especially in the physiological environment, so the porphyrin-folate conjugates linked by these fatty short chains have extremely poor solubility in the physiological environment, resulting in the intravenous administration of these targeted photosensitizers very difficult

Method used

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  • Water-soluble molecular target porphin photosensitizer and preparation method thereof
  • Water-soluble molecular target porphin photosensitizer and preparation method thereof
  • Water-soluble molecular target porphin photosensitizer and preparation method thereof

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preparation example Construction

[0051] The preparation method of the water-soluble molecular targeting photosensitizer of the present invention is carried out as follows:

[0052] (1), first use polyethylene glycol diamine (NH 2 PEGNH 2 , PEG) and folic acid under the catalysis of the condensation agent to avoid light condensation reaction, control the temperature and time of the reaction, and purify to obtain the PEG amine substituted by monofolate;

[0053] (2) Folate PEG amine and the carboxyl group or acid anhydride on the porphin are condensed under the catalysis of the condensing agent in the dark, and the temperature and time of the reaction are controlled and purified to obtain a water-soluble porphin-PEG-folate target-targeting photosensitizer

[0054] A better method in the preparation process is:

[0055] (1) The average molecular weight of PEG is 1000-10000, preferably 1000-5000. The reaction temperature is 0°C-100°C, preferably 20°C-50°C; the reaction time is 0.5-100 hours, preferably 5-50...

Embodiment 1

[0061] Example 1: Folic acid-PEG (3350) NH 2 Synthesis

[0062] Weigh 221 mg folic acid and dissolve it in 5 ml DMSO, add 20 ml pyridine and 110 mg DCC, add 1.68 g H 2 N-PEG-NH 2 (3350), react at room temperature in the dark for 30 h, add 10 ml of deionized water, use deionized water as a medium to remove small molecular impurities such as DMSO and pyridine, lyophilize, and use anion exchange resin to separate and purify to obtain folic acid-PEG ( 3350) NH 2 , yield 25%. UV-vis(λ): 281(0.2431), 347(0.0534); HPLC(8.7, 98%).

Embodiment 2

[0063] Example 2: Folic acid-PEG (2000) NH 2 Synthesis

[0064] Weigh 442 mg folic acid and dissolve in 12 ml DMSO, add 35 ml pyridine, 250 mg DCC and 130 mg NHS, add 2.0 g H 2 N-PEG-NH 2 (2000), after reacting at 50°C in the dark for 12 h, add 30 ml of deionized water, dialyze with deionized water to remove small molecular impurities such as DMSO and pyridine, lyophilize, and separate and purify with anion exchange resin to obtain folic acid-PEG (2000) NH 2 , yield 22%. UV-vis(λ): 281(0.2237), 347(0.0555); HPLC(8.4, 97%).

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Abstract

The invention relates to a water-soluble molecular target porphin photosensitizer and a preparation method thereof. The photosensitizer is characterized in that the two bridged ends of polyethylene glycol (PEG) diamine are respectively connected with folic acid and porphin with substituent groups, wherein other substituent groups can be connected with the porphin, and the average molecular weight of PEG is 1000-10000. According to the preparation method of the water-soluble molecular target porphin photosensitizer, PEG diamine reacts with folic acid so as to produce PEG amine which is obtained from single folic acid, and the PEG amine has amidation with carboxyl, acyl chloride or anhydride substituent group on the porphin so as to obtain the porphin-PEG-folic acid target photosensitizer. The photosensitizer has good photodynamic activity, tumor target performance and good water solubility and is applicable to intravenous administration; the phagocytosis of macrophage to the photosensitizer can be reduced, the body circulation time of the photosensitizer is prolonged and the bioavailability of the photosensitizer is improved. Moreover, the preparation method of the water-soluble molecular target photosensitizer is simple to operate, has moderate conditions and has strong repeatability.

Description

Technical field [0001] The present invention involves a molecular targeting photoretically sensitive agent and its preparation method, especially a photochemical agent and its preparation method for tumor -targeted photovoltaic therapy by folic acid body. Background technique [0002] The annual incidence of tumors in my country is 2.3 million, with an average of 3 people dying from the tumor per minute, which has seriously threatened human health.Tumor light therapy (PDT) is the development direction of modern tumor minimally invasive or non -invasive therapy.Because the photoretinizer itself is safe to the human body when there is no light, and the PDT fully uses the dual -selection effect of laser selective irradiation of lesions and photoresistid agents to kill tumor cells, which is small to damage to health tissues.In the past two decades, PDT has been formally approved by governments of various countries to enter the clinic, becoming a conventional means to treat a variety ...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K41/00A61K31/409A61P35/00A61K47/60
Inventor 李东红李鹏熙
Owner INST OF FIELD OPERATION SURGERY NO 3 MILITARY MEDICL UNIV PLA
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