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Synthesis of ciprofloxacin propionate antigen

A technology of ciprofloxacin and propionic acid, which is applied in the field of ciprofloxacin hapten and its preparation method and application, and can solve problems such as drug residues and threats to human health

Inactive Publication Date: 2016-06-01
HEBEI NORTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, excessive use or abuse can cause the drug to remain in food of animal origin, thus posing a serious threat to human health

Method used

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  • Synthesis of ciprofloxacin propionate antigen
  • Synthesis of ciprofloxacin propionate antigen
  • Synthesis of ciprofloxacin propionate antigen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1, the preparation of ciprofloxacin propionate

[0046] Take ciprofloxacin hydrochloride 0.33g (1mmol), dissolve it in 10ml of DMF solution, stir to dissolve at 80°C, add 0.18g (1.2mmol) of 3-bromopropionic acid hydrobromide dropwise, stir at 80°C for 3h, after the reaction The solvent is evaporated off from the reaction solution under reduced pressure to obtain the crude product of ciprofloxacin propionate shown in formula (I). By preparing the liquid phase (Column: Sunfire, (3.5um, 150*4.6mm) mobile phase A: H 2 O(0.01%TFA)‐B: Acetonitrile (0.01%TFA) 1‐9min 5%B—95%B, 9‐14min, 95%B, 14‐15min95%B—5%B, flow rate 1.0mL / min, column temperature 40°C) to obtain pure ciprofloxacin propionate.

[0047] It was identified by infrared spectroscopic scanner, ESI‐MS and nuclear magnetic resonance.

[0048]

[0049] The infrared spectrum of formula (I) ciprofloxacin propionate shows that wavenumber 3373cm ‐1 The broad absorption peak is the absorption peak of the c...

Embodiment 2

[0053] Embodiment 2: Synthesis of ciprofloxacin-propionic acid-bovine serum albumin (CIP-C) by glutaraldehyde method 2 h 4 -COO-BSA)

[0054] Weigh 0.10 g of ciprofloxacin propionate prepared in Example 1 with an analytical balance, dissolve it in 5 mL of 0.6 mol / L HCl solution, add 30 mg of zinc powder, and heat in a water bath at 80° C. for 30 min to obtain solution A. Weigh 100 mg bovine serum albumin (BSA) and dissolve it in 2 mL of 0.02 mol / L PBS solution to obtain solution B. Slowly add solution A to solution B dropwise and mix well, add 0.1ml of 25% glutaraldehyde dropwise, and stir at room temperature for 6h. Put the mixed solution into a dialysis bag and dialyze with 0.01mol / L PBS solution (pH7.4) for 72 hours at 4°C to obtain ciprofloxacin-propionic acid-bovine serum albumin CIP-C 2 h 4 -COO-BSA. Store at -20°C.

[0055] Simultaneously to the formula (I) ciprofloxacin propionate (CPLX‐C) prepared by embodiment 1 2 h 4 ‐COOH), ciprofloxacin‐propionic acid‐bovi...

Embodiment 3

[0057] Embodiment 3 carbodiimide method synthesis ciprofloxacin-propionic acid-ovalbumin (CPLX-C 2 h 4 -COO-OVA)

[0058] Get ciprofloxacin propionate 0.10g prepared in Example 1, dissolve in N,N-dimethylformamide (DMF), obtain solution C, take 1-(3-dimethylaminopropyl)-3- Ethylcarbodiimide hydrochloride (EDC) 30 mg was fully dissolved in 4 mL of distilled water, slowly added dropwise to solution C, and stirred at room temperature for 24 hours to obtain solution D. After centrifugation, the supernatant was slowly added dropwise to 5 mL of sodium carbonate buffer solution (0.1 mol / L) containing 50 mg ovalbumin (OVA). Stir in a refrigerator at 4°C for 72 hours to obtain the ciprofloxacin-propionic acid-ovalbumin antigen (CIP-C 3 h 7 -NH 2 ‐OVA)), stored at ‐20°C.

[0059] Simultaneously to the formula (I) ciprofloxacin propionate (CPLX‐C) prepared by embodiment 1 2 h 4 -COOH), ciprofloxacin-propionic acid-ovalbumin (CPLX-C) prepared in embodiment 3 2 h 4 ‐COO‐OVA), ova...

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Abstract

The invention provides a ciprofloxacin propionate hapten, a preparation method of the ciprofloxacin propionate hapten, application of the ciprofloxacin propionate hapten, and a ciprofloxacin antigen prepared from the ciprofloxacin hapten. A New Zealand rabbit is immunized with the ciprofloxacin antigen, so that an antibody with high specificity can be obtained.

Description

technical field [0001] The invention belongs to the field of biochemical technology, and specifically relates to a ciprofloxacin hapten, a preparation method and application thereof, and an antigen prepared from the hapten. Background technique [0002] Ciprofloxacin (CIP) belongs to the third-generation fluoroquinolones and is a commonly used broad-spectrum antibiotic drug. It is often used as an antibacterial agent and widely used in the prevention and treatment of bacterial infectious diseases in livestock and poultry. However, excessive use or abuse can lead to the residue of the drug in animal-derived food, which poses a serious threat to human health. Therefore, the residue limits of ciprofloxacin and other fluoroquinolones are becoming more and more stringent in countries all over the world. The latest revision of the Ministry of Agriculture of my country's "Maximum Residue Limits of Veterinary Drugs in Foods of Animal Origin" stipulates that the milk of cattle, sheep...

Claims

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Application Information

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IPC IPC(8): C07D215/56C07K14/765C07K14/77C07K16/44
CPCC07D215/56C07K14/765C07K14/77C07K16/44C07K19/00
Inventor 张明柱班秀萍黄智鸿冯亭亭魏东梁淑珍李迎春罗飞
Owner HEBEI NORTH UNIV
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