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Tildipirosin hapten and artificial antigen as well as preparation methods thereof

A new technology of Tidelotide and artificial antigen, applied in the field of immunology, can solve the problems of cumbersome operation process, complex equipment, unsuitable for on-site monitoring, etc., achieve high sensitivity, easy to be recognized by animal organisms, and suitable for high-throughput screening Effect

Inactive Publication Date: 2012-12-12
河北远征药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] At present, the method for detecting the residual amount of Tedirosin is mainly solid-phase extraction liquid-mass spectrometry (SPE-HPLC-MS / MS). Leads to unsuitable on-site monitoring and screening of large numbers of samples

Method used

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  • Tildipirosin hapten and artificial antigen as well as preparation methods thereof
  • Tildipirosin hapten and artificial antigen as well as preparation methods thereof
  • Tildipirosin hapten and artificial antigen as well as preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment １

[0037] Example 1 Tedirosin hapten, artificial antigen and their preparation method

[0038] ① A kind of tedirosine hapten and its preparation method

[0039] Its structure of a kind of tediroxin hapten is as follows:

[0040] ;

[0041] A kind of preparation method of above-mentioned tedirosine hapten is carried out according to the following sequence of steps:

[0042] (11) in dry N 2 Under certain conditions, dissolve 1 part of tedirosin with 10 parts of acetone to make solution A1;

[0043] (12) While stirring, continue to feed N 2 , and added dropwise 1.5 parts of succinic anhydride in acetone solution to solution A1, and stirred and reacted at 25°C for 15 h after the dropwise addition, until the reaction was complete to obtain a transparent solution;

[0044] (13) Remove the solvent by rotary evaporation under reduced pressure to obtain a light yellow amorphous powder, then add dichloromethane to dissolve, wash with water, adjust the pH value to 10 with 1mol / L s...

Embodiment 2

[0061] Example 2 A preparation method of Tedirosin artificial antigen

[0062] Tedirosin artificial antigen as described in Example 1, it adopts the mixed anhydride method to prepare, and it carries out according to the following sequence of steps:

[0063] (21) Dissolve 1.0 mmol of the above tedirosine hapten and an equivalent of tri-n-butylamine in 15 mL of dioxane, stir for 30 min, add an equivalent of isobutyl chloroformate, and use 1 mol / L NaOH solution Adjust the pH to 7.5, stir and react for 1 h to obtain solution B1;

[0064] (22) Add solution B1 dropwise to 70 mL of 10 mg / mL chicken ovalbumin (OVA) in dioxane and phosphate buffer, and stir at 5°C for 24 h to prepare solution C1;

[0065] (23) Dialyze solution C1 with distilled water at 4°C for 3 days, change the solution 4 times a day, freeze-dry to obtain tedirosin artificial antigen M11, and store at -20°C.

[0066] Dissolve haptens, chicken ovalbumin (OVA) and artificial antigens in phosphate buffer, dilute the...

Embodiment 3

[0069] Example 3 A kind of tedirosine hapten, artificial antigen and their preparation method

[0070] ① A tedirosine hapten and its preparation method

[0071] Its structure of a kind of tediroxin hapten is as follows:

[0072] ;

[0073] The preparation method of above-mentioned tedirosine hapten, it carries out according to the following steps:

[0074] (11) in dry N 2 Under certain conditions, dissolve 1 part of Tedirosin with 15 parts of methanol to make solution A2;

[0075] (12) While stirring, continue to feed N 2 , and dropwise added 1.0 parts of methanol solution of phthalic anhydride to solution A2, after the dropwise addition was completed, stirred and reacted at 25°C for 15 h, and it was a transparent solution;

[0076] (13) Remove the solvent by rotary evaporation under reduced pressure to obtain a light yellow amorphous powder, then add dichloromethane to dissolve, wash with water, adjust the pH value to 10 with 1mol / L sodium hydroxide solution, separ...

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Abstract

The invention discloses a tildipirosin hapten and an artificial antigen as well as preparation methods thereof, wherein the preparation method of the tildipirosin hapten comprises the following step of: introducing 3-carboxyl propionyl or 2-carboxyl benzoyl on the base of the base structure of the tildipirosin, so that the prepared tildipirosin hapten not only keeps the base structure of the tildipirosin but also is beneficial to the coupling of a carrier protein, is used for preparing the artificial antigen, and can be easily identified by an animal body; and the artificial antigen of the tildipirosin takes the tildipirosin hapten as a base, and is prepared by a mixed anhydride method or an active ester method, and the prepared tildipirosin hapten can be used for detecting the ELISA (enzyme-linked immuno sorbent assay) residual of the tildipirosin. Compared with the existing detection method for the joint use of solid phase extraction liquid-mass (SPE-HPLC-MS / MS) (solid phase extraction-high performance liquid chromatography-memory system / memory system), the preparation method has the advantages of being simple and convenient, quick, high in sensitivity, suitable for high throughput screening. The preparation method provided by the invention is used for preparing the tildipirosin hapten and the artificial antigen.

Description

technical field [0001] The invention belongs to the field of immunology, and in particular relates to a tydirosin hapten, an artificial antigen and a preparation method thereof. Background technique [0002] Tildipirosin is a new macrolide animal-specific antibiotic developed by Intervet-Schering-Plough Animal Health. The CAS registration number is: 328898-40-4, and the chemical name is: 20-Deoxo -23-deoxy-5-O-[3,6-dideoxy-3-(dimethylamino)-β-D-glucopyranosyl]-20,23-di-1-piperidinyltylonolide, the structural formula is as follows: [0003] . [0004] On March 8, 2011, the European Commission for Veterinary Medicines (CVMP) approved the market authorization application for a sterile injection solution (trade name: Zuprevo) with Tedirosin as the main ingredient. In veterinary medicine, it is mainly used for the treatment of bovine respiratory tract infection caused by Mannheimia haemolytica, Pasteurella multocida and Haemophilus somnus and by Actinobacillus pleuropneumonia...

Claims

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Application Information

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IPC IPC(8): C07H17/08C07H1/00C07K14/765C07K14/77C07K1/113
Inventor 岳永波李伟岭杨芳郭鸿志刘波刘毅刘海亮陈玲魏占勇杨国辉
Owner 河北远征药业有限公司
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