Chemical modification method capable of improving producing ability of reactive oxygen species (ROS) of rheum emodin

A technology of chemical modification and emodin, which is applied in the field of chemical modification, can solve the problem that the anticancer activity is not enough to make medicine directly

Inactive Publication Date: 2014-05-28
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Emodin has broad-spectrum anticancer activity, but its anticancer activity is not enough to be directly used as a drug, and chemical modification is needed to improve its anticancer activity

Method used

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  • Chemical modification method capable of improving producing ability of reactive oxygen species (ROS) of rheum emodin
  • Chemical modification method capable of improving producing ability of reactive oxygen species (ROS) of rheum emodin
  • Chemical modification method capable of improving producing ability of reactive oxygen species (ROS) of rheum emodin

Examples

Experimental program
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Effect test

Embodiment 1

[0024] 1. Not de-monobrominated 2 Synthesis of (1,3,8-trimethoxy-6-bromomethyl-9,10-anthraquinone):

[0025] Get 3.0g (11.0mmol) emodin and dissolve in 200ml acetone, add 15g (109mmol) anhydrous potassium carbonate, slowly add dropwise 10ml (109mmol) of (CH 3 O) 2 SO 2 , refluxed for 24h, cooled to room temperature, concentrated, added 150ml of water and stirred for 30min, suction filtered, washed with acetone to obtain a yellow powder crude product, separated by silica gel column chromatography (dichloromethane elution) to obtain 1,3,8-trimethoxy Base-6-methyl-9,10-anthraquinone 2.8g (8.9mmol), yield 81%. Take 1.21g (3.88mmol) of 1,3,8-trimethoxy-6-methyl-9,10-anthraquinone, 2.2g N-bromosuccinimide (NBS) (12.4mmol), 0.20g Benzoyl peroxide (BPO, initiator) and 90ml CCl 4 Add it into a three-necked flask, heat to reflux for 24h, cool to room temperature, filter, and use CCl 4 , H 2 Washed with O and acetone, and separated by silica gel column chromatography (eluted with...

Embodiment 2

[0063] Emodin quaternary ammonium salt 7a - 7l In vitro cell viability test

[0064] Adjust the cell density of 3 cancer cells including skin cancer A375, gastric cancer AGS and liver cancer HepG2 and normal human embryonic lung fibroblast HELF to 1.5×10 5 / ml, inoculated in 96-well culture plate, 100 μl per well, placed at 37°C, 5% CO 2 Cultivate in an incubator for 24 hours; remove the old medium, and add the test derivative (dilute the stock solution of the test derivative with the medium to set different action concentrations), 100 μL per well. After 24 hours of drug action, discard the drug-containing medium, add 100 μL of serum-free and phenol red-free 1640 medium to each well, then add 10 μL of MTT solution, continue to incubate for 4 hours, and terminate the culture; carefully aspirate and discard 96 wells Add 150 μL DMSO to each well of the supernatant in the plate well, shake for 10 min, measure the light absorbance (OD value) of each well on a microplate reader a...

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Abstract

The invention relates to a chemical modification method capable of improving the anti-cancer activity of reactive oxygen species (ROS) through improving the producing ability of the ROS of rheum emodin. Experiments prove that a series of rheum emodin hyamines obtained by chemical modification to the rheum emodin have better anti-cancer activity on three kinds of cancer cells such as skin cancer A375, liver cancer HepG2 and stomach cancer AGS, and the anti-cancer activity and the producing ability of the ROS far exceeds those of the rheum emodin; moreover, experiments prove that the producing ability of the ROS and the anti-cancer activity of rheum emodin derivates are in positive correlation. The drug chemically modified by the chemical modification method has a certain selective killing effect on the cancer cells, and has a better prospect for development as an anti-cancer drug.

Description

technical field [0001] The invention relates to a chemical modification method capable of improving the production capacity of emodin active oxygen (ROS). Background technique [0002] Emodin has broad-spectrum anticancer activity, but its anticancer activity is not enough to be directly used as a medicine, and chemical modification is needed to improve its anticancer activity. The anticancer activity of emodin itself comes from its ability to intercalate into DNA and generate reactive oxygen species (ROS). Since reactive oxygen species are a major factor in inducing apoptosis in cancer cells, it is an important research content of chemical modification of emodin to improve its anti-cancer activity by improving the reactive oxygen species generation ability of emodin. Active oxygen is produced in mitochondria, so one way to increase the ability to produce active oxygen is to enable emodin derivatives to enter the mitochondria of cancer cells smoothly. It is known that the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/24C07C221/00A61P35/00
Inventor 王文峰李圆芳姜美红邵敬伟郑艳艳赵文娜
Owner FUZHOU UNIV
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