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Chlorins e6 metal salt compound and preparing method and application thereof

A technology of chlorin and compound, which is applied in the field of chlorin e6 metal salt compound and its preparation, can solve the problems of complex composition, limited application, poor stability, etc., and achieve the effect of clear structure and remarkable activity

Active Publication Date: 2016-07-06
海宁凤鸣叶绿素有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have found that copper chlorophyllin sodium salt made from silkworm excrement has a good hepatoprotective effect, but its complex composition and poor stability greatly limit its application in this field

Method used

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  • Chlorins e6 metal salt compound and preparing method and application thereof
  • Chlorins e6 metal salt compound and preparing method and application thereof
  • Chlorins e6 metal salt compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: Preparation of chlorin e6 trisodium salt

[0030]

[0031] (1) Dissolve 100g of crude silkworm excrement chlorophyll in 300ml of ether, add 600ml of hydrochloric acid, stir for 2 hours, let stand, remove the lower layer of acid solution, add 500ml of water to dilute, add dropwise 10mol / L sodium hydroxide solution to pH 5-6, A dark green precipitate was precipitated and dried under reduced pressure to obtain about 20 g of pheophorbide a.

[0032]

[0033] (2) Take about 5g of pheophorbide a, dissolve it in 200ml of methanol, add 500ml of 0.5% sodium hydroxide methanol solution, stir for 5h, add 3g of sodium hydroxide and 30ml of water, reflux in the water bath for 2h, add hydrochloric acid dropwise To pH 5-6, add three times the volume of water, precipitate out after standing still, filter under reduced pressure and go through silica gel column chromatography (300-400 mesh, eluent: dichloromethane, methanol, acetone, formic acid = 10:1 :1:0.7), colle...

Embodiment 2

[0036] Embodiment 2: Preparation of chlorin e6 tripotassium salt

[0037]

[0038] The sodium hydroxide used in step (3) in Example 1 was replaced by potassium hydroxide to obtain chlorin e6 tripotassium salt, MS (ESI+) M / Z: 599(M+2).598( M+1), 1H-NMR (δPPM, CDCL3): 1.63(3H), 1.75(3H), 2.25-2.30(4H), 3.29(3H), 3.47(3H), 3.62(3H), 3.73-3.77(2H ), 3.80(3H), 4.56(2H), 5.01(2H), 6.15(1H), 6.34(1H), 8.05(1H), 8.86(1H), 9.59(1H), 9.77(1H).

Embodiment 3

[0039] Example 3: Chlorin e6 Metal Salt Stability

[0040] Take chlorin e6 metal salt (taking sodium salt as an example) and chlorin e6 (purchased from Maya Reagent Co., Ltd.), respectively, take 1.0 g and place them in a refrigerator at room temperature and at 0-4 °C. Sampling at regular intervals measures the purity of the two by HPLC, and the results are as follows: figure 1 , figure 2 shown.

[0041] Compared with chlorin e6, the stability of chlorin e6 metal salt (taking sodium salt as an example) at room temperature and at 0-4°C is more stable, and the rate of change is slower.

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Abstract

The invention relates to a chlorins e6 metal salt compound.The chemical structure is shown in the formula (I) in the description, wherein R is common metal ions such as K+ or Na+.A preparing method comprises the following steps that firstly, silkworm excrement crude product chlorophyll serves as a raw material and is dissolved in diethyl ether, concentrated hydrochloric acid is added, and magnesium-removed chlorophyllin a is generated; secondly, magnesium-removed chlorophyllin a is reacted in a strong-base methanol solution, a little of water is added later to generate chlorins e6 mono-methyl ester; thirdly, obtained chlorins e6 mono-methyl ester is reacted in a strong-base alcoholic solution reaction reagent, and a compound (I) is obtained through separation and purification.The chlorins e6 metal salt compound is a raw material in the study field of medicine for resisting gastric ulcers, resisting anemia and protecting the liver and promoting leucopoiesis.

Description

technical field [0001] The invention belongs to the field of chlorin compounds, in particular to a kind of chlorin e 6 Metal salt compound and its preparation method and application. Background technique [0002] It has been proved that chlorophyll degradation products and their derivatives have various biological activities such as sterilization, anti-mutagenesis, promotion of wound tissue healing, anti-ulcer, liver protection, promotion of hematopoietic function and photodynamic therapy. Therefore, the in-depth development of chlorophyll is expected to become a new family of medicine and health products. However, so far, biomedical science and technology circles at home and abroad, especially pharmaceutical circles, have not paid attention to it, and chlorophyll is still a blank in today's medicinal chemistry research. [0003] The development of anti-ulcer drugs at home and abroad is mainly achieved by controlling gastric acid secretion, killing Helicobacter pylori and ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K31/409A61P1/04A61P7/06A61P1/16A61P7/00
CPCC07D487/22
Inventor 沈凤明余建鑫李晔晨邱振伟
Owner 海宁凤鸣叶绿素有限公司
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