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Method for synthesizing swainsonine antigen

A technology of swainsonine and antigen, applied in the fields of toxicology, immunology and organic chemistry, can solve the problems of time delay in poisoning, limited research and application, low yield, etc., achieve stable reaction system, simple synthetic route, avoid poisoning effect

Inactive Publication Date: 2011-11-23
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It has been proved that by preparing SW-BSA antigen to immunize goats, the poisoning time of goats after eating locoweed can be significantly delayed, showing its application prospect in the prevention and treatment of livestock poisoning, but the preparation method used is cumbersome and difficult to detect during the reaction process , the yield is low, the cost of the antigen is too high, and the immunogenicity of the antigen is not satisfactory, which limits its further research and application

Method used

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  • Method for synthesizing swainsonine antigen
  • Method for synthesizing swainsonine antigen
  • Method for synthesizing swainsonine antigen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The synthesis of embodiment 1 artificial antigen

[0032] The method is carried out according to the following technical route: firstly, the halogenated aryl fatty acid is reacted with alcohol to form a halogenated aryl fatty acid ester, and the latter is reacted with swainsonin to form a quaternary ammonium salt of equine toxin with an aromatic ring structure. The resulting product undergoes ester hydrolysis with sodium hydroxide to generate SW-aryl fatty acid conjugates, and finally condenses with bovine serum albumin (BSA) or ovalbumin (OVA) to form SW-BSA conjugates containing aromatic ring bridges ( SW artificial antigen).

[0033]

[0034] Wherein, X=Cl, Br, I, Y=O(CH 2 ) m , (CH 2 ) m , Z=CH 2 , CH 2 CO 2 , n, m=0, 1, 2, . . .

[0035] The first step, the synthesis of compound 1

[0036] Reaction formula:

[0037]

[0038] The operating procedure is:

[0039] Take 60mL of anhydrous methanol, add about 40ml of acetyl chloride dropwise while stirri...

Embodiment 2

[0057] Embodiment 2 animal immunity test

[0058] 1. Antigen Preparation

[0059] Weigh SW-BSA freeze-dried powder, add physiological saline to dissolve, add an equal amount of Freund's adjuvant or incomplete Freund's adjuvant, fully mix and emulsify with a micro mixer, and use it as an immune antigen.

[0060] 2. Animal immunization

[0061] Six mice were taken, five of which were immunized with SW-BSA, and the remaining one was injected with PBS as a control. Immunization was performed once every 2 weeks, and 0.2 mL (100 μg) of immunogen was subcutaneously injected at 3 points each time at the nape of each dog. Antigens were used in complete Freund's adjuvant for the first immunization, and antigens in Freund's incomplete adjuvant for subsequent immunizations. One week after the third immunization, blood was collected from the orbital venous plexus of each mouse, the serum was separated, and the antibody titer was determined by indirect ELISA. The ratio P / N of the OD valu...

Embodiment 3

[0074] This embodiment provides the test results and data in Example 1.

[0075] 1.1 Compound 1 (SW-methyl chloromethylbenzoate), reference Figure 1 to Figure 3 ;

[0076] Compound 1 is a light yellow powder after purification, with strong water absorption, dark red on TLC at 254nm, positive SW color reaction (blue spots) reference Figure 10 a.

[0077] Its molecular weight was determined to be 322 by spectroscopic analysis, and compared with the literature, it was proved that the structure of the synthesized product was completely consistent with the theoretical results, and the results of the Pope analysis were as follows:

[0078] ESI MS m / z 322 (M + ): 13 C NMR (125MHz, CD 3 OD): δ167.6 (C-10), 134.6 (C-1′), 134.3 (C-3′), 133.3 (C-4′), 131.2 (C-2′), 77.4 (C-δa) , 71.6(C-2), 69.4(C-1), 68.8(C-3), 65.3(C-8), 65.1(C-9), 59.2(C-5), 52.9(OCH 3 ), 28.3(C-7), 16.6(C-6). 1 H NMR (400MHz, CD 3 OD): δ8.13(d, J=8.8Hz, 2H, H-3′), 7.78(d, J=8.8Hz, 2H, H-2′), 3.93(s, 3H, OCH ...

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Abstract

The invention discloses a method for synthesizing a swainsonine antigen, comprising the following steps of: firstly performing a reaction between halo alkyl aryl fatty acid and alcohol to generate halo alkyl aryl fatty acid ester, followed by a reaction between halo alkyl aryl fatty acid ester and swainsonine to generate a quaternary ammonium salt with a structure of aromatic nucleus, performing a reaction between the quaternary ammonium salt and sodium hydroxide for deesterification to generate a sodium salt, adjusting the pH value by the use of hydrochloric acid to generate SW-halo alkyl aryl fatty acid; condensing SW-halo alkyl aryl fatty acid with bovine serum albumin (BSA) to produce SW-BSA, sieving through a glucan gel column chromatography for desalination, freeze drying, determining the proportion of BSA and SW, and adding an immunoadjuvant for emulsification to obtain the SW immune antigen. The antigen is white and oily with the effective content being 5mg / mL and the effective immune period being 12 months. The effective protection rate reaches more than 90%.

Description

technical field [0001] The invention relates to a method for biochemically synthesizing swainsonine antigen, which belongs to the technical fields of organic chemistry, toxicology, immunology and the like. Background technique [0002] Swainsonine (SW) is the main toxic alkaloid in locoweed, and it is the main cause of mass poisoning and death of horses, cattle, sheep and other livestock after eating locoweed. The crude protein content of the leguminous plant locoweed is as high as 11% to 12%, which is equivalent to that of alfalfa, and has the potential to be used as an excellent forage grass. At the same time, it plays an important role in sand control and sand fixation. Studies in recent years have shown that SW has significant anticancer activity, which provides a broader prospect for the in-depth research and application of locoweed. Therefore, how to solve the contradiction between correct and effective prevention and treatment of livestock poisoning and full utilizat...

Claims

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Application Information

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IPC IPC(8): C07K14/765
Inventor 王建华王爱华靳亚平周乐宋毓民
Owner NORTHWEST A & F UNIV
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