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Unsaturated fatty acid-Cu/Zn-SOD modifier and preparation method thereof

A technology of unsaturated fatty acid and superoxide, which is applied in the field of unsaturated fatty acid-Cu/Zn-superoxide dismutase modification and its preparation, can solve the problem of no physiological activity, inability to exert the synergistic effect of fatty acid and SOD, Cu/Zn The Zn-SOD activity retention rate is not very high, and achieves high activity retention rate, good use effect and range of use, and increased stability.

Active Publication Date: 2013-04-24
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still the following deficiencies: the activity retention rate of Cu / Zn-SOD after modification is not very high, only 85%. In addition, lauric acid belongs to saturated fatty acid itself and has no physiological activity, so it cannot exert the synergistic effect of fatty acid and SOD

Method used

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  • Unsaturated fatty acid-Cu/Zn-SOD modifier and preparation method thereof
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  • Unsaturated fatty acid-Cu/Zn-SOD modifier and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Example 1: Synthesis of unsaturated fatty acid-Cu / Zn-superoxide dismutase modification by thionyl chloride activation method

[0020] Install a mechanical stirrer, reflux condenser, dropping funnel and thermometer in a four-neck flask, add 6ml of petroleum ether, 2ml of thionyl chloride, pass in nitrogen, cool down to below 0°C in an ice bath, and slowly add unsaturated fatty acid dropwise (linoleic acid, linolenic acid, eicosapentaenoic acid, docosapentaenoic acid or docosahexaenoic acid) 1.8 grams, maintain the temperature at about 5°C during the dropwise addition, after the dropwise addition, the room temperature The reaction was carried out for 3 hours. Distill petroleum ether and excess thionyl chloride to obtain unsaturated fatty acid chlorides. Take 1.2g Cu / Zn-SOD and dissolve it in weakly alkaline phosphate buffer solution, stir and dissolve at 20°C. Slowly add activated unsaturated fatty acid under the protection of nitrogen, and add a small amount of sodium ...

Embodiment 2

[0023] Embodiment 2: Synthesis of unsaturated fatty acid-Cu / Zn-superoxide dismutase modification by N-hydroxysuccinimide method

[0024] Take 1g of unsaturated fatty acid (linoleic acid, linolenic acid, eicosapentaenoic acid, docosapentaenoic acid or docosahexaenoic acid) dissolved in 8ml 1,4-dioxane, and then Add 200mg of N-hydroxysuccinimide and 400mg of N',N'-dicyclohexylcarbimide, and react at 25°C for 24 hours. The filtrate was filtered and evaporated to obtain a white solid, and the activated unsaturated fatty acid ester was obtained by separation on a silica gel column with ethyl acetate: ether = 10:1. Weigh 500mg of Cu / Zn-superoxide dismutase and dissolve it in 10ml of 0.1mol / L phosphate buffer solution (pH8.0), add N-hydroxysuccinimide unsaturated fatty acid ester under stirring, and stir at 25°C 24 hours. The reaction solution was poured into 20ml of pre-cooled acetone (-20°C), centrifuged and the precipitate was separated by a Sephadex G-100 column, with water as ...

Embodiment 3

[0025] Embodiment 3: the Cu / Zn-SOD performance comparison of saturated fatty acid and unsaturated fatty acid modification

[0026] The present invention adopts the saturated fatty acid-Cu / Zn oxide dismutase knot modifier (lauric acid-Cu / Zn-SOD) synthesized in Comparative Example 1 and the unsaturated fatty acid-Cu / Zn oxide dismutase modified in Example 1. substances (linoleic acid-Cu / Zn-SOD, linolenic acid-Cu / Zn-SOD). Its performance is shown in Table 1:

[0027] Table 1 Performance comparison of lauric acid-Cu / Zn-SOD modification and unsaturated fatty acid-Cu / Zn-SOD modification

[0028] sample

[0029] It can be seen from Table 1 that under the condition that the amino modification rate is basically the same, the activity recovery rates of linoleic acid-Cu / Zn-SOD and linolenic acid-Cu / Zn-SOD are as high as 104% and 98%, which are significantly higher than the saturated Fatty acid (lauric acid) modified Cu / Zn-SOD. Also significantly higher than the macromolecular...

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Abstract

The invention discloses an unsaturated fatty acid-Cu / Zn-superoxide dismutase (SOD) modification and a preparation method thereof. Free amino groups on the Cu / Zn-SOD bond with carboxyls on the unsaturated fatty acid in an amido link mode; one Cu / Zn-SOD bonds with not more than 20 unsaturated fatty acid molecules; and the carbochain length of the unsaturated fatty acid is 16-26. The preparation method comprises the following steps: adopting a thionyl chloride activation method or an N-hydroxysuccinimide activation method to activate the carboxyls on the unsaturated fatty acid to obtain an activation product of the unsaturated fatty acid; adding the activation products of the Cu / Zn-SOD and the unsaturated fatty acid to a buffer solution with a pH value of 6.0-9.0; reacting while stirring at 0-30 DEG C to prepare a destination product. The unsaturated fatty acid-Cu / Zn-SOD modification fully executes the synergism of the unsaturated fatty acid and the Cu / Zn-SOD, improves the stability of the Cu / Zn-SOD, decreases the immunogenicity thereof and has better application effect and wider application range.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to an unsaturated fatty acid-Cu / Zn-superoxide dismutase modified product and a preparation method thereof. Background technique [0002] Superoxide dismutase (SOD) is an important class of superoxide anion free radical scavenger, which can be used to prevent and treat diseases and body damage caused by excessive superoxide anion free radicals, such as diabetes, arthritis, autoimmune diseases, radiation damage , Ischemia and then focus on injury, etc. So far, scientists have isolated SOD from organisms such as bacteria, fungi, protozoa, algae, insects, fish, plants and mammals. Based on different metal prosthetic groups, these SODs can be classified into at least three types: Cu / Zn-SOD, Mn-SOD, and Fe-SOD. Generally speaking, Fe-SOD is a type of SOD that is considered to exist in more primitive biological groups; Mn-SOD is a type of protein that evolved on the basis of Fe-SOD...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12N9/96
Inventor 单伟光占扎君周志刚李成平于海宁唐岚侯晓蓉王建伟
Owner ZHEJIANG UNIV OF TECH
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