Application of biphenyl compound in preparing medicines for treating oxidative stress induced diseases

A technology of oxidative stress and compounds, applied in the field of medicine, can solve the problems of various and complex components, achieve the effect of inhibiting cell damage and apoptosis, and increasing the level of GSH

Inactive Publication Date: 2017-12-22
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, camphor contains aliphatic compounds, monoterpenoids, sesquiterpenoids, phenolic acids, aromatic compounds, biphenyls, tetralones, benzopyrans, lignans Compounds such as ketones, chromo...

Method used

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  • Application of biphenyl compound in preparing medicines for treating oxidative stress induced diseases
  • Application of biphenyl compound in preparing medicines for treating oxidative stress induced diseases
  • Application of biphenyl compound in preparing medicines for treating oxidative stress induced diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: Preparation and structure confirmation of 3,3',4,4'-tetrahydroxybiphenyl

[0055] The method for obtaining 3,3',4,4'-tetrahydroxybiphenyl is as follows: extract the aerial part of Cinnamomum camphora with 95% ethanol to obtain an ethanol extract, and then sequentially extract with petroleum ether and ethyl acetate. The ethyl acetate fraction was eluted with petroleum ether-ethyl acetate gradient to obtain 19 fractions (A-S). Part N was separated by Sephadex LH-20 chromatographic column to obtain 3,3',4,4'-tetrahydroxybiphenyl.

[0056] Using the prepared 3,3',4,4'-tetrahydroxybiphenyl as raw material, slowly add triethylamine (4mmol) to 3,3',4,4 '-Tetrahydroxybiphenyl (1mmol), carbon tetrabromide (4.4mmol) and dibenzyl phosphite (5mmol) in anhydrous acetonitrile solution, followed by stirring at room temperature for 2 hours, after the reaction was completed, the solvent was evaporated under reduced pressure, The resultant was dissolved in ethyl acetate, was...

Embodiment 2

[0060] Example 2: Evaluation of NQO1-inducing activity of 3,3',4,4'-tetrahydroxybiphenyl

[0061] (1) Culture of mouse hepatocarcinoma hepa 1c1c cell line

[0062] The mouse hepatocarcinoma hepa 1c1c cell line was purchased from the American Type Culture Collection (ATCC), using MEM medium containing 10% fetal bovine serum (FBS), placed at 37°C, 5% CO 2 cultured in an incubator.

[0063] (2) NQO-inducing activity test

[0064] Hepa 1c1c cells were seeded on a 96-well plate, and different concentrations of 3,3',4,4'-tetrahydroxybiphenyl (confirmed in Example 1) were added after the cells adhered to the wall, and treated for 24 hours, using 0.8% digitonin The solution was used to lyse the cells, and the detection solution (1.0mL 0.5M Tris-hydrochloric acid (Tris-HCl), 15mg bovine serum albumin, 6mg MTT, 150μL Tween-20, 150μL 150mM D-glucose-6-phosphate, 15 μL 7.5 mM flavin adenine dinucleotide, 27 μL 50 mM nicotinamide adenine dinucleotide phosphate, 20 μL 50 mM menadione), l...

Embodiment 3

[0066] Example 3: 3,3',4,4'-Tetrahydroxybiphenyl can up-regulate Nrf2, γGCS and NQO1 protein levels

[0067] Method: Western blot analysis (Western blot) to detect changes in protein levels in cells

[0068] Beas-2B cells were inoculated in a 35 mm diameter petri dish, cultured until the density reached 70%-80%, and then treated with different concentrations of compounds to be tested for 16 h, washed twice with PBS, added cell lysate (50 μg / ml aprotinin , 0.5mM phenylmethylsulfonyl fluoride, 1mM sodium orthovanadate, 10mM sodium fluoride, 10mMβ-glycerol phosphate), the protein was collected and the protein concentration was determined by Bradford method. Each sample protein (100 μg) was loaded on the sample, and the protein components were separated by SDS-PAGE, and the protein bands were transferred to the nitrocellulose membrane by electrotransfer method. After the film was sealed with 5% skimmed milk powder solution prepared in TBS at room temperature for 1 hour, it was in...

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Abstract

The invention discloses an application of a biphenyl compound in preparing medicines for treating oxidative stress induced diseases. The chemical formula of the biphenyl compound is shown as Formula (as shown in the Description), wherein R1 is -H, -CH3, Formula (as shown in the Description) or Formula (as shown in the Description); R2 is -H, -CH3, Formula (as shown in the Description) or Formula (as shown in the Description); X1 is -H, Na<+>, K<+> or NH4<+>; X2 is -H, Na<+>, K<+> or NH4<+>; and X3 is -H, Na<+>, K<+> or NH4<+>. With the application of the biphenyl compound, the protein levels of Nrf2 and antioxidase [gamma]GCS and II-phase detoxification enzyme NQO1 regulated and controlled by the Nrf2 can be up-regulated; the GSH level of a cell endogenous antioxidant can be improved, and arsenic-induced Beas-2B cell injury and apoptosis can be inhibited; and a similar cytoprotection effect can be achieved on glomerular mesangial cells SV40MES13, human nerve SHSY5Y cells and human breast carcinoma MDA-MB-231 cells.

Description

technical field [0001] The invention belongs to the field of medicine and relates to the application of biphenyl compounds, in particular to the application of biphenyl compounds in the preparation of medicines or health care products for preventing or treating oxidative stress-induced diseases. Background technique [0002] The rapid development of social industrialization has led to serious air, water, soil, and food pollution, such as carbon, sulfur, and nitrogen oxides (CO, SO 2 , NO 2 etc.), heavy metals (lead, chromium, arsenic, etc.), smog formed by construction mineral dust; water pollution and soil pollution caused by industrial and domestic sewage, and food pollution caused by it. These pollutants invade human tissues and organs, leading to increased active oxygen and nitrogen in the human body, causing damage to nucleotides, proteins, and lipids in the human body, and inducing chronic obstructive pulmonary disease, chronic kidney disease, respiratory inflammation...

Claims

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Application Information

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IPC IPC(8): A61K31/663A61K31/255A61K9/20A61P11/00A61P13/12A61P29/00A61P3/10A61P25/00A61P35/00C07F9/38C07F9/48C07C301/00C07C303/08C07C309/11A23L33/105A23L33/10
CPCA61K31/663A23L33/10A23L33/105A23V2002/00A61K9/2054A61K9/2059A61K31/255C07C301/00C07C303/08C07C309/11C07F9/3808C07F9/4816A23V2200/314A23V2200/308A23V2200/322A23V2200/328A23V2250/21A23V2250/30
Inventor 沈涛周明星孙斌王小宁任冬梅娄红祥徐有伟
Owner SHANDONG UNIV
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