Diosmin-copper complex and preparation method and application thereof

A technology of diosmin and complexes, which is applied in the field of medicine, can solve the problems of weak anti-oxidation and anti-tumor activities, and achieve the effects of easy-to-obtain raw materials, simple preparation methods, and low cost

Active Publication Date: 2019-10-25
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the antioxidant and antitumor activities of diosmin are relatively weak, so there are few applications in this area.

Method used

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  • Diosmin-copper complex and preparation method and application thereof
  • Diosmin-copper complex and preparation method and application thereof
  • Diosmin-copper complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Dissolve 0.5mmol of diosmin in 5mL of dimethyl sulfoxide, then add a certain amount of sodium hydroxide to adjust the pH to 5-8, then add 0.5mL of 0.5mol / L copper chloride aqueous solution, at 60°C React for 3 hours. After the reaction, cool down to room temperature, filter, wash with ethanol and deionized water until neutral, and obtain the target product with a yield of 80%.

[0031] The complex has the following properties:

[0032] The complex was analyzed by elements, and the values ​​are as follows: theoretical value (%): C, 50.13; H, 5.55; Cu, 4.76; measured value (%): C, 50.40; H, 5.18; Cu, 4.73;

[0033] The complex was analyzed by infrared spectroscopy (such as figure 1 ): (KBr,cm -1 ): 3408ν (O-H); 1628ν (C=O); 639ν (Cu-O). Depend on figure 1 It can be seen that diosmin at 3400cm -1 There is a sharp hydroxyl stretching vibration peak on the left and right, 1670cm -1 There is a strong peak of carbonyl stretching vibration at the diosmin-copper complex at...

Embodiment 2

[0038] Using Fe 2+ Inducing vitellolipoprotein lipid peroxidation and salicylic acid method to scavenge hydroxyl free radicals to study the ability of diosmin and its complexes to scavenge free radicals, the steps are as follows:

[0039] (1) to Fe 2+ Inhibition of Induced Vitellin Lipid Peroxidation

[0040] Egg yolk suspension configuration: take the yolk of fresh eggs, add an equal volume of phosphate buffer (pH=7.4) and stir evenly, then dilute 25 times with phosphate buffer, and store in the refrigerator at 4°C.

[0041] Take 0.25ml egg yolk suspension and add it to a 5ml centrifuge tube, then add 0.1ml sample solution (DMSO is the solvent, the sample concentration is 20μM, 40μM, 60μM, 80μM, 100μM), 0.25ml FeSO 4 Solution aqueous solution (25mmol / L) and 2.4ml phosphate buffer solution, heat and shake in a water bath at 37°C for 15min, then add 0.5mL trichloroacetic acid aqueous solution (0.2g / mL), 0.5mL thiobarbituric acid aqueous solution (8mg / mL ), heated at 90°C for...

Embodiment 3

[0054] MTT method was used to study the effects of diosmin and its copper (Ⅱ) complex on mouse melanoma cells (B16, purchased from Shanghai Cell Bank, Chinese Academy of Sciences) and cervical cancer cells (Hela, purchased from Shanghai Cell Bank, Chinese Academy of Sciences) Inhibition of two cancer cells. Proceed as follows:

[0055] The cancer cells in the logarithmic growth phase were prepared into a cell solution with a concentration of 50,000 cells / mL in DMEM medium, and the cell suspension was inoculated in a 96-well plate, and 90uL was added to each well, at 37°C, 5% CO 2 cultured in an incubator for 24 h. After the cancer cells grow and adhere to the wall, the DMSO solution of the complex of the present invention is added to make the concentrations respectively 1.56 μM, 3.12 μM, 6.25 μM, 12.5 μM, 25.0 μM, 50.0 μM, and 100 μM. After dosing, put in 37°C, 5% CO 2 Continue culturing in the incubator for 44 hours, then add 20uL 5mg / mL MTT solution to each well, put it b...

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Abstract

The invention belongs to the field of medicine and discloses a diosmin-copper(II) complex and a preparation method and application thereof. The diosmin-copper(II) complex has a chemical formula of [Cu(DM)2(H2O)2] 1.5H2O, wherein DM is diosmin; the specific structural formula is shown in the description. The antitumor activity of the diosmin-copper(II) complex is studied by means of a MTT (methyl thiazolyl tetrazolium) process; the results show that the diosmin-copper(II) complex can inhibit B16 (mouse melanoma cells) and Hela (cervical cancer cells) more effectively than diosmin; anti-lipid peroxidation experiments and experiments of removing hydroxyl radicals by a salicylic acid method show that the diosmin-copper(II) complex has better capacity to remove free radicals than diosmin.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a diosmin-copper (II) complex and a preparation method and application thereof. Background technique [0002] Diosmin is a natural flavonoid glycoside compound that widely exists in fruits. It was first extracted and isolated from Scrophularia nodosa in 1925. It was used as a medicine in 1969. It was launched in 1987 under the trade name Amiron . Diosmin can enhance venous tone, promote lymphatic return, and promote microcirculation, thereby treating hemorrhoids and venous insufficiency. However, the antioxidant and antitumor activities of diosmin are relatively weak, so there are few applications in this regard. [0003] The molecular structure of diosmin has carbonyl oxygen and hydroxyl oxygen containing lone pairs of electrons. According to the basic principles of coordination chemistry, compounds with this structure may coordinate with metal ions to form metal complexes....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H23/00C07H1/00A61P35/00A61P39/06
CPCA61P35/00A61P39/06C07H1/00C07H23/00
Inventor 乐学义马玲龙朱丽付银莲熊亚红陈实
Owner SOUTH CHINA AGRI UNIV
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