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Chitosan oligosaccharide-antibiotic conjugate as well as preparation method and application thereof

A technology of chitosan oligosaccharide and antibiotics, applied in the field of antibacterial agents, can solve problems such as serious antibiotic resistance, and achieve the effects of good inhibitory effect, wide sterilization range and strong destructive effect

Active Publication Date: 2018-09-04
ZHONGKE RUNXIN SUZHOU BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Mainly address the growing problem of antibiotic resistance in existing technologies

Method used

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  • Chitosan oligosaccharide-antibiotic conjugate as well as preparation method and application thereof
  • Chitosan oligosaccharide-antibiotic conjugate as well as preparation method and application thereof
  • Chitosan oligosaccharide-antibiotic conjugate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] The preparation of embodiment 1 chitosan oligosaccharide-Florfenicol chemical conjugate

[0041] The reaction equation for the chemical coupling of chitosan and florfenicol is shown in Scheme 1. Compound 1 is Florfenicol, which reacts with succinic anhydride to obtain Compound 2, and the carboxyl group on Compound 2 reacts with the amino group of Compound 3 (oligochitosan) to obtain Compound 4, which is the oligochitosan-Florfenicol conjugate .

[0042]

[0043] The concrete implementation steps of chemical coupling reaction are as follows:

[0044] (1) Florfenicol and succinic anhydride are dissolved in organic solvents such as acetone at a molar ratio of 1:1 to 1:1.5, and the catalyst 4-dimethylaminopyridine is added to react at 40 to 70°C for 2 to 5 hours, 20 to 30 Rotary evaporation under reduced pressure at ℃, recrystallization under the condition of ethanol and water volume 1:1 to obtain a white solid.

[0045] (2) Mix the product obtained in step (1) with chi...

Embodiment 2

[0059] Embodiment 2 Chitosan oligosaccharide-florfenicol conjugate inhibits bacterial growth

[0060] In this example, the effect of the prepared oligochitosan-florfenicol conjugate on inhibiting the growth of Streptococcus suis was studied. The Streptococcus suis used was from the China General Microorganism Culture Collection and Management Center. Streptococcus suis was shaken and cultured overnight at 37°C in MRS liquid medium, diluted to 4mL about 1×10 5 CFU bacteria liquid, add florfenicol (abbreviated as Flo), chitosan oligosaccharide (COS), chitosan-florfenicol conjugate (abbreviated as F-COS) and florfenicol and chitosan oligosaccharide mixture ( Abbreviated as Flo+COS) (mixed mass ratio is 1:1), cultured dynamically at 37°C respectively, and counted the number of bacteria at different times.

[0061] see figure 2 , is the bar graph of the inhibitory effect of Flo, COS, F-COS and Flo+COS on Streptococcus suis. The experimental results showed that: Flo group and F...

Embodiment 3

[0062] Example 3 Oligochitosan-Florfenicol Conjugate Destructive Effect on Streptococcus suis Biofilm

[0063] In this example, the effect of F-COS, a COS chemically modified product of Flo, on destroying the biofilm of Streptococcus suis was studied. The Streptococcus suis used was from the China General Microorganism Culture Collection and Management Center. After Streptococcus suis was shaken and cultured overnight at 37°C in MRS liquid medium, take 100 μL ~ 2×10 7 The CFU bacterial solution was added to a 96-well plate and cultured statically at 37°C for 24 hours to form a mature biofilm.

[0064] Prepare samples of Flo, COS, F-COS, and Flo and COS mixture Flo+COS (mixing mass ratio 1:1) for this study. After the biofilm matures, remove the supernatant and add 100 μL of 1 mg / mL MRS broth for the above samples. Add 100 μL MRS liquid medium to the untreated group. After acting at 37°C for 24 hours, the biofilm destruction effect was detected by MTT staining.

[0065] se...

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Abstract

The invention discloses a chitosan oligosaccharide-antibiotic conjugate as well as a preparation method and application thereof. The chitosan oligosaccharide-antibiotic conjugate is a covalent complexof chitosan oligosaccharide and an antibiotic, and the antibiotic is a chloramphenicol antibiotic; and the chloramphenicol antibiotic is florfenicol, and the conjugate is a chitosan oligosaccharide-florfenicol conjugate. The chitosan oligosaccharide-florfenicol conjugate disclosed by the invention has a good inhibitory effect on pathogenic bacteria, especially has a strong destroying effect on deep bacteria which form a biofilm, and has a wide sterilization range and a good inhibitory effect on formation of the biofilm; and compared with the florfenicol, the chitosan oligosaccharide-florfenicol conjugate disclosed by the invention has significantly-improved bacteriostatic activity.

Description

technical field [0001] The invention belongs to the technical field of antibacterial agents, and in particular relates to a chitosan oligosaccharide-antibiotic conjugate and a preparation method and application thereof. Background technique [0002] The overuse of antibiotics by humans has led to the increasing resistance of bacteria to existing antibiotics. In addition, the causes of clinical persistent infection and hospital-acquired infection are mostly related to the formation of biofilm (Biofilm) by pathogenic bacteria on the surface of the host or medical materials. Biofilm is a bacterial community and its extracellular matrix complex with a special microenvironment. Bacterial or fungal colonies attach to surfaces or gas-liquid boundaries and secrete large amounts of exopolysaccharides, proteins, and DNA to form biofilm colonies. The tolerance of biofilm pathogenic bacteria to antibacterial agents is often hundreds to thousands of times higher than that of planktonic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/06C07H1/00A61K31/165A61K31/722A61K31/702A61K47/55A61P31/04C08B37/08
CPCA61K31/165A61K31/702A61K31/722A61K47/552A61P31/04C07H1/00C07H13/06C08B37/003
Inventor 杜昱光王倬刘静孙明
Owner ZHONGKE RUNXIN SUZHOU BIOLOGICAL TECH CO LTD
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