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Application of NDGA analogue to preparation of antioxidant drug

An analog, antioxidant technology, applied in drug combinations, antidote, pharmaceutical formulations, etc., can solve the problems of unseen and unseen Chinese patents on the antioxidant activity of NDGA derivatives, achieve a good dose-response relationship, inhibit ROS and other problems. Aggregate effect

Active Publication Date: 2018-03-06
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no Chinese patents on the research on the antioxidant activity of NDGA derivatives, and there is no dual-mechanism anti-oxidation of the present invention that simultaneously has the ability to directly scavenge active oxygen free radicals and activate antioxidant signaling pathways to indirectly scavenge oxygen free radicals

Method used

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  • Application of NDGA analogue to preparation of antioxidant drug
  • Application of NDGA analogue to preparation of antioxidant drug
  • Application of NDGA analogue to preparation of antioxidant drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The synthesis of embodiment 1 compound

[0030] Dissolve 3,4-dihydroxybenzaldehyde (10mmoL) and appropriate ketone (5mmoL) in ethanol, stir at room temperature, and inject HCl (gas) into the solution as a catalyst. Wherein 4-piperidone hydrochloride hydrate (1f) and 3,4-dihydroxybenzaldehyde are dissolved in a mixed solvent of ethanol:water (10:1). The progress of the reaction was monitored by thin-layer chromatography. After the reaction, the crude mixture was cooled and poured into ice water (20mL), the precipitate was precipitated, filtered by suction, and after vacuum drying, purified by silica gel column chromatography to obtain the desired product 3a- 3m, these compounds and their physicochemical properties are described below:

[0031] Effective compound 3a: (2Z,5E)-2,5-bis(3,4-dihydroxybenzylidene)cyclopentano ne(3a): Green powder, 53.6% yield, mp>300℃. 1H-NMR (600MHz, d-DMSO), δ: 9.563(s, 2H, 3-OH×2), 9.211(s, 2H, 4-OH×2), 7.238(s, 2H, Ar-CH=C ×2), 7.113(d, ...

Embodiment 2

[0045] The scavenging ability of embodiment 2 compound to DPPH

[0046] The compound's ability to scavenge DPPH·free radicals was used to initially test the in vitro antioxidant activity of the compound, and the specific method was as follows: NDGA analog solution (20 mg / mL) was prepared with ethanol. DPPH·solution (0.15 mM) was also prepared in ethanol. 80 μL of NDGA analog solution was added to 120 μL of DPPH·solution (0.15 mM) (Ai). The control group was 80 μL NDGA analogue solution added to 120 μL ethanol solution (Aj). In the blank group, 120 μL DPPH·solution (Ac) was added to 80 μL ethanol solution. These mixtures were incubated at 25°C for 30 min before absorbance was measured at 517 nm. Experiments were repeated three times. Calculation of the scavenging capacity of DPPH: %=[1-(Ai-Aj) / Ac]×100. The positive drug NDGA was used as a control during the test. For the scavenging ability of compounds on DPPH, see figure 1 . It can be found that all the compounds from ...

Embodiment 3

[0047] Example 3 compound to H 2 o 2 Protective effect of induced PC12 cell injury model and cytotoxicity of three active compounds in PC12 cells

[0048] to H 2 o 2 Protective effect method for inducing PC12 cell damage: PC12 cells (5 × 10 3 cells / well) were seeded in a 96-well plate, cultured in DMEM medium in a 37°C incubator, and left overnight. After adding the compound for 24 h, additional H was added 2 o 2 (400μM) injury for 24h. After 24 hours, the cells were treated with MTT solution (5 mg / mL) at 37° C. for 4 hours. Finally, formazan crystals were dissolved in 120 μL DMSO, and the OD value was measured at 490 nm. Cell viability is the percentage of the OD value of the DMSO control group. Each compound was repeatedly tested 3 times, and the average value and error value were calculated. For the experimental data, see figure 2 a.

[0049] The cytotoxicity detection method of the compound: the method is basically the same as before, the cells are also inocula...

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Abstract

The invention belongs to the field of pharmaceutical chemistry and particularly relates to application of a specific NDGA analogue to the preparation of an antioxidant drug and an anti-ischemic apoplexy treatment drug. The NDGA analogue not only can protect H2O2-induced PC12 cell injury and inhibit MDA and ROS production, but also can obviously activate a Keap1 / Nrf2 / ARE antioxidant pathway; through in-vivo experiment, the infarct size of a rat MCAO model can be obviously reduced, and nerve scores can be improved.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry, specifically, the present invention relates to the application of specific NDGA analogues in the preparation of antioxidant drugs and the prevention or treatment of various organ ischemic diseases caused by oxidative stress. The dual-mechanism antioxidation of directly scavenging active oxygen free radicals and activating antioxidant signaling pathways to indirectly scavenge oxygen free radicals plays a significant role in in vitro and in vivo antioxidation. Background technique [0002] Oxidative stress is closely related to the occurrence of various diseases, and antioxidant drugs can play a good therapeutic role in related diseases. Active natural products are still an important way to discover new drugs because of their less toxic and side effects. Nordihydroguaiaretic acid (NDGA) is a natural product isolated from Larrea tridentate shrub, which has various biological activities su...

Claims

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Application Information

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IPC IPC(8): A61K31/122A61K31/351A61K31/44A61K45/06A61P39/06A61P9/10A61P25/16
CPCA61K31/122A61K31/351A61K31/44A61K45/06
Inventor 吴建章仇佩虹黄丽丽汪佳兵李物兰王嗣岑
Owner WENZHOU MEDICAL UNIV
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