Lauroyl arginine ethyl ester derivative and application thereof as animal antibacterial agent

A technology of lauroyl arginine ethyl ester and derivatives, which is applied in antibacterial drugs, animal feed, applications, etc., can solve the problems of unstudied antibacterial effect of LAE alone, and has not been taught, so as to improve the survival rate of ducklings, Risk reduction, no effect on survival

Active Publication Date: 2018-12-11
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method involves multiple antibacterial components including LAE, and the antibacterial effect of LAE alone was not studied
At the same time, the invention only teaches that the composition is used for daily products, cleaning agents, wound care compositions, various foods, various medical cleaning products, etc., and does not teach how to use a single LAE component for poultry Use of antibacterial feed for aquatic products

Method used

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  • Lauroyl arginine ethyl ester derivative and application thereof as animal antibacterial agent
  • Lauroyl arginine ethyl ester derivative and application thereof as animal antibacterial agent
  • Lauroyl arginine ethyl ester derivative and application thereof as animal antibacterial agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Example 1: Preparation method of synthetic ion-pair compound of lauroyl arginine ethyl ester hydrochloride and nicotinic acid

[0079] Dissolve 2.0 g of sodium nicotinic acid (purchased from Tixiai (Shanghai) Chemical Industry Development Co., Ltd.) in 50 mL of water to prepare sodium nicotinic acid salt solution (A); 6.8 g of lauroyl arginine ethyl ester hydrochloride Dissolve in 40mL of water and heat to 90°C until all lauroyl arginine ethyl ester hydrochloride is dissolved to prepare an aqueous solution of lauroyl arginine ethyl ester hydrochloride (B); The saline solution (A) is slowly added to the lauroyl arginine ethyl ester hydrochloride solution (B), stirring constantly, reacting for 2 hours, cooling to room temperature, filtering, fully washing the precipitate with purified water, and drying the precipitate in vacuum at 60°C. 7.6 g of niacin ion pair compound is obtained.

Embodiment 2

[0080] Example 2: Analysis of the molecular formula and molecular weight of the compound of the nicotinic acid ion of ethyl lauroyl arginine

[0081] By mass spectrometry, 1 H-NMR, 13 The molecular formula of the compound obtained by C-NMR spectrum analysis is:

[0082] 1. Mass spectrometry (ESI) analysis

[0083] Cation B + The m / z of the molecular ion peak = 385.3, see figure 1 ;

[0084] Mass spectrometry detection ESI+ is 124.2, see figure 2 . Then ESI- is 122.2, which is anion A - The m / z of the molecular ion peak is 122.2.

[0085] The theoretical calculated value of the cation of the niacin ion pair compound is 507.4, and the measured value is consistent with the theoretical value.

[0086] 2.NMR analysis

[0087] Lauroyl arginine ethyl ester hydrochloride (see image 3 ), niacin 1 H-NMR (see Figure 4 ) And ion pair compound 1 H-NMR (see Figure 5 )Compared. Since the LAE ion-pair compound is in the process of salt formation, the peak shape and chemical shift of the ion-pair c...

Embodiment 3

[0088] Example 3: Preparation method of synthetic ion-pair compound of lauroyl arginine ethyl ester hydrochloride and tartaric acid

[0089] Dissolve 2.0 g of tartaric acid (purchased from Tixiai (Shanghai) Chemical Industry Development Co., Ltd.) in 50 mL of methanol, add equivalent NaOH, stir at room temperature until a white solid precipitates, filter with suction and wash with 30 mL of methanol three times to obtain sodium tartrate . Sodium tartrate is dissolved in 50mL of water to prepare a sodium tartrate solution (A); 5.6 g of lauroyl arginine ethyl ester hydrochloride is dissolved in 40 mL of water and heated to 90°C until the lauroyl arginine ethyl ester salt The acid salt is completely dissolved to prepare an aqueous solution of lauroyl arginine ethyl ester hydrochloride (B); the sodium tartrate aqueous solution (A) is slowly added to the aqueous solution of lauroyl arginine ethyl ester hydrochloride ( In B), continue to stir, react for 2 hours, cool to room temperatur...

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Abstract

The invention relates to a novel veterinary antibacterial agent and in particular relates to a lauroyl arginine ethyl ester ion pair compound derivative which is prepared from lauroyl arginine ethyl ester LAE and an organic acid through reactions. As a livestock aquatic animal antibacterial agent, the derivative is capable of preventing and treating duckling riemerella anatipestifer diseases caused by riemerella anatipestifer, is capable of treating peritonitis diseases caused by escherichia coli and staphylococcus aureus, is capable of preventing and treating fish septicemia caused by aeromonas sobria, and has remarkably improved prevention and treatment effects when being compared with a conventional LAE veterinary antibacterial agent. The derivative can be completely degraded in human bodies and animal bodies and is small in toxic and side effect, environment drug resistance bacteria caused by residual antibacterial agents discharged into the environment can be avoided, and small adverse environment influence can be caused while an effective antibacterial effect is achieved.

Description

[0001] This invention application requires Chinese invention patent application 201711071006.8, the invention name is "lauroyl arginine" "Use of ethyl ester and its derivatives as veterinary antibacterial agents" priority application. Technical field [0002] The invention relates to an ion-pair compound derivative of ethyl lauroylarginine and a preparation method, and the application of the derivative in the treatment and prevention of animal pathogenic bacteria diseases. Especially the use of the derivative to prepare an antibacterial agent for animals. Background technique [0003] Riemerella anatipestifer is a contact infectious disease caused by Riemerella anatipestifer (RA), also known as infectious duck serositis, duck sepsis, duck disease syndrome, duck disease Bacillosis and so on. It is more common in ducklings of 1-8 weeks of age, and ducklings of 2-4 weeks are the most susceptible. Acute or chronic sepsis, the main clinical manifestations are increased secretions fr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C279/14C07C65/10C07C53/06C07C53/10C07C53/122C07C53/124C07C59/08C07C63/08C07C57/10C07C57/15C07C59/265C07C59/255C07C59/245C07C55/07C07D233/64A61K31/155A61K31/4164A61K31/223A61P1/12A61P31/04A61P11/06A61P7/10A61P1/00A61P31/06
CPCA23K20/142A61K31/223A23K20/195
Inventor 易正芳邵婷仇文卫刘明耀
Owner EAST CHINA NORMAL UNIV
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