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Photosensitizer sodium chlorophyllin derivatives and their preparation method and use

A technology of sodium chlorophyllin and chlorophyllin, which is applied in the direction of drug combinations, pharmaceutical formulas, and medical preparations containing active ingredients, etc. It can solve problems such as restrictions on the use of equipment, and achieve high safety, low toxicity, and good curative effect Effect

Inactive Publication Date: 2013-07-10
JINSHAN HOSPITAL FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The difference between photosensitizers and general anticancer drugs is that their use is strictly limited by equipment conditions, because photosensitizers must be used in conjunction with a dedicated photodynamic laser therapy device to produce therapeutic effects on patients

Method used

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  • Photosensitizer sodium chlorophyllin derivatives and their preparation method and use
  • Photosensitizer sodium chlorophyllin derivatives and their preparation method and use
  • Photosensitizer sodium chlorophyllin derivatives and their preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Preparation of chlorophyllin e 6 sodium salt

[0023] Use traditional Chinese medicine silkworm excrement as raw material, pulverize, add 3-5 times the volume of 80% acetone to dissolve, stir in a water bath at 60°C for 2-4 hours, filter, and extract the filter residue twice with 80% acetone, combine the filtrates, evaporate Go to acetone. Adjust the pH of the remaining aqueous solution to 10 with 10% NaOH, extract 3-4 times with an equal volume of purified gasoline, remove impurities, and concentrate to obtain a paste-like crude chlorophyll.

[0024] Take 200g of crude chlorophyll, add 800ml of 80% acetone, stir evenly, add 30ml of 20% NaOH, hydrolyze at 60°C for 60min, evaporate the acetone, let it stand, take alkaline aqueous solution after layering, adjust the pH of the solution with 18% HCl to around 10. Use 400ml of purified gasoline to extract and remove impurities 4 times, filter, and then adjust the pH of the filtrate to 3 with 18% HCl, there is a precipitat...

Embodiment 2

[0031] Preparation of chlorophyllin e 4 sodium salt

[0032] Get the chlorophyllin e that the method described in embodiment 1 makes 6 5g, dissolved in 100ml of pyridine, refluxed with nitrogen in an oil bath at 120°C for 60min, evaporated the pyridine under reduced pressure, added 200ml of water, adjusted the pH to 3 to obtain dark green crystals, dried in vacuum, filtered the precipitate, and obtained chlorophyllin e 4 4.32g.

[0033] chlorophyllin e 4 The TLC identification, the mensuration of HPLC retention time and the result of mass spectrometry are as follows:

[0034] TLC: Rf=0.53

[0035] HPLC: Rt=6.632min

[0036] MS m / z:554(M+H+1) + , 553(M+H) +

[0037] chlorophyllin e 4 5g, prepared chlorophyllin e 4 Sodium salt (e 4 Na), method is the same as embodiment 1, obtains 5.04g.

Embodiment 3

[0039] Preparation of chlorophyllin f sodium salt

[0040] Get the chlorophyllin e that the method described in embodiment 1 makes 6 5g, dissolve in 100ml of pyridine, add 250ml of 25% KOH methanol solution, and let it flow for 60min under the condition of oxygen. Reflux for 60 min under nitrogen, distill off pyridine under reduced pressure, add 200ml of water, adjust the pH to 3 with 18% HCl solution, and precipitate out. The crystals were collected by filtration, washed with water, and dried in vacuum to obtain 4.0 g of chlorophyllin f.

[0041] The TLC identification of chlorophyllin f, the results of HPLC retention time determination and mass spectrometry are as follows:

[0042] TLC: Rf=0.65

[0043]HPLC: Rt=8.532min

[0044] MS m / z:550(M+H+1) + , 539(M+H) + , 538(M+H-1) +

[0045] Take f5g of chlorophyllin to prepare f sodium salt of chlorophyllin (f·Na), and the method is the same as in Example 1 to obtain 5.02g.

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Abstract

The invention relates to photosensitizer sodium chlorophyllin derivatives and their preparation method and novel use in preparation of drugs for treating tumors and especially in preparation of a photosensitizer drug for photodynamic treatment on the bladder cancer. The photosensitizer sodium chlorophyllin derivatives comprise sodium chlorophyllin e4, sodium chlorophyllin e6 and sodium chlorophyllin f compounds shown in the structural formula. An in-vitro human bladder cancer killing effect test on sodium chlorophyllin proves that the photosensitizer sodium chlorophyllin derivatives have obvious effects of killing tumor cells, good effects of treating bladder carcinoma in situ and intractable and repeated superficial bladder cancer, low toxicity and high safety, avoids operation in a dark place in treatment, has a unique advantage and provides an experiment basis for clinic application.

Description

technical field [0001] The present invention relates to photosensitizer chlorophyllin sodium salt derivatives and its preparation method and its new use in pharmacy, in particular to the new use of photosensitizer chlorophyllin sodium salt derivatives in the preparation of drugs for treating tumors, especially in the preparation of therapeutic Use in tumor photosensitizer drugs such as bladder cancer. Background technique [0002] The application of silkworm excrement in traditional Chinese medicine has a long history in my country, and it is usually used for dispelling wind and dampness, and resolving stomach turbidity. Chen Zangqi's "Supplements to Materia Medica" in the Tang Dynasty and Li Shizhen's "Compendium of Materia Medica" in the Ming Dynasty all contained silkworm excrement for the treatment of women with metrorrhagia, anemia and blood stasis. Studies have shown that silkworm excrement is rich in chlorophyll, which is a porphyrin compound, and its acid hydrolyzat...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K41/00A61P35/00A61P13/10
Inventor 张元芳陈刚李斌方杰潘小平
Owner JINSHAN HOSPITAL FUDAN UNIV
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