Metal complex of chlorophyll degradation product chlorin e6 derivatives as well as preparation method and applications of metal complex

A chlorophyll degradation and metal complex technology is applied in the field of metal complexes of chlorin e6 derivatives, which are chlorophyll degradation products, and their preparation, and can solve the problems of poor stability, limited application, complex components and the like

Active Publication Date: 2015-01-14
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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  • Metal complex of chlorophyll degradation product chlorin e6 derivatives as well as preparation method and applications of metal complex
  • Metal complex of chlorophyll degradation product chlorin e6 derivatives as well as preparation method and applications of metal complex
  • Metal complex of chlorophyll degradation product chlorin e6 derivatives as well as preparation method and applications of metal complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-methoxymethyl-17-methoxyethyl-17,18- Preparation of Chlorin

[0040]

[0041] Chlorin e 6 (1.0g, 1.7mmol) was added to methanol (30ml), stirred at room temperature and added dropwise with 98% concentrated sulfuric acid (1ml), and reacted at 55°C for 5h under nitrogen protection. The reaction solution was cooled, diluted with dichloromethane (90ml), poured into ice water (150ml) for extraction, left to stand and separated, the organic phase was concentrated to dryness by rotary evaporation, washed with water and suction filtered, and the filter cake was vacuum-dried and then chromatographed on a silica gel column to obtain 0.75g black fine particle product, yield: 75%. LC-MS (ESI): [M+H] + = 625.

Embodiment 2

[0042] Example 2: 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-methoxymethyl-17-methoxyethyl-17,18- Preparation of Zinc Complex of Chlorin

[0043]

[0044] 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-methoxymethyl-17-methoxyethyl-17,18-chlorine The dried sample of phenene (1.0g, 1.6mmol) was finely ground, dissolved in dichloromethane (100ml), and zinc acetate (0.5g, 2.3mmol) was completely dissolved in methanol (20ml). 2 Mix well under protection, stir and react at room temperature for 1 h. The reaction solution changed from yellow-brown to blue-green. After the reaction solution was extracted with 2 times the volume of dichloromethane, 5 times the volume of ice water was added and stirred slowly until the organic phase precipitated a solid. After static until liquid separation, the organic phase was suction-filtered, washed with water until the filtrate was clear and transparent, and the filter cake was dried to obtain 0.68 g of black fine particle compo...

Embodiment 3

[0045] Example 3: 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-methoxymethyl-17-methoxyethyl-17,18- Preparation of Copper Complex of Chlorin

[0046]

[0047] 2,7,12,18-tetramethyl-3-vinyl-8-ethyl-13-carboxy-15-methoxymethyl-17-methoxyethyl-17,18-chlorine The dried sample of phenene (1.0g, 1.6mmol) was pulverized, dissolved in 100ml methylene chloride, (0.4g, 2.0mmol) copper acetate was dissolved in 50 ml methanol, and the two were dissolved in N 2 Mix well under protection, and stir the reaction at room temperature for 0.5h. The reaction solution changed from yellowish brown to bright green. After the reaction solution was extracted with 2 times the volume of dichloromethane, 5 times the volume of deionized water was added to slowly stir to wash away free copper ions. After static liquid separation, the lower organic phase was concentrated to dryness by rotary evaporation, soaked in water, stirred and washed several times with water until the filtrate was clear a...

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Abstract

The invention discloses a metal complex of chlorophyll degradation product chlorin e6 derivatives as well as a preparation method and applications of the metal complex. The metal complex of the chlorin e6 derivatives is shown in the formula I (shown in the specification), wherein R1 and R2 are H or CH3, CH2CH3, CH2CH2CH3, n-C4H9 and other common alkane groups, M is common divalent metal ions such as Cu<2+>, Zn<2+>, Fe<2+>, Mn<2+>, Ni<2+>, Co<2+> and Pd<2+>. The compound is clear in structure and excellent in activity, and has potential for developing anti-gastric ulcer and liver protection drugs. The metal complex is low in sources of raw materials, the preparation method is simple and fast to react, and suitable for large-scale industrial production. The formula is shown in the specification.

Description

technical field [0001] The invention belongs to the field of chlorophyll compounds, in particular to metal complexes of chlorophyll degradation products chlorin e6 derivatives, their preparation methods and their application in the field of medicine. Background technique [0002] Studies have found that silkworm excrement is rich in chlorophyll (0.6%~1.0% in dry products), and the crude silkworm excrement chlorophyll is first subjected to acid degradation reaction to obtain stable degradation products of chlorophyll a, pheophorbide a and pyropheophytin Acid a and pheophorbide a can be further alkaline degraded into stable derivatives such as chlorin e6, chlorin e4, purpurin-18 and chlorin p6. [0003] 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 t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22A61P1/04A61P1/16
CPCC07D487/22
Inventor 沈凤明余建鑫吴一书
Owner 海宁凤鸣叶绿素有限公司
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