CN101092490A - Method for preparing polymer microballons of molecular engram of nitrogen benzyl penicillin - Google Patents
Method for preparing polymer microballons of molecular engram of nitrogen benzyl penicillin Download PDFInfo
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Abstract
This invention discloses a method for preparing ampicillin molecularly imprinted polymer microspheres. The method comprises: preparing 3-6% poly(vinyl alcohol) solution, mixing functional monomers, template molecules, initiator, pore-foaming agent and crosslinker, ultrasonicating, adding into poly(vinyl alcohol) 1788 solution, stirring, stirring in 70 deg.C water for 60 min, filtering, ultrasonicating, washing with double distilled water twice, methanol three times and acetone twice (10 min each time), removing the template molecules, and vacuum-drying at 50 deg.C to obtain ampicillin molecularly imprinted polymer microspheres. The method has such advantages as simple process and high efficiency, and can prepare ampicillin molecularly imprinted polymer microspheres with high molecular recognition ability. When used in solid phase extraction, the ampicillin molecularly imprinted polymer microspheres have such advantages as high column efficiency and high selectivity. The ampicillin molecularly imprinted polymer microspheres can be used for selective separation and high-efficiency enrichment of penicillin in food matrix, such as honey.
Description
Technical field
What the present invention relates to is the method for a kind of chemistry and chemical technology field, is specially a kind of preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin.
Background technology
Penbritin (ampicillin) is the semi-synthetic Broad spectrum antibiotics of beta-lactam, from microbe metabolite, separate first in nineteen forty-seven and to obtain, gram-positive microorganism and Gram-negative bacteria had stronger anti-microbial effect, thereby be widely used in veterinary clinic, it is antibiotics commonly used during agricultural-food such as livestock and poultry are cultured, penbritin residual in food causes allergic reaction easily to the people, but the generation of inducible resistance bacterial strain simultaneously, with tsiklomitsin, chlorpromazine is mixed when using, easily producing precipitin reaction remains in the animal derived food, therefore, penicillin in the animal derived food is residual to have constituted grave danger to human health, bad toxic side effect mainly contains the generation mild nausea, vomiting, diarrhoea etc. Toxicity of Kidney etc. can occur when serious.At present, the penicillin method for detecting residue mainly contains microbial method, immunization, chromatography etc., and has adopted some coupling techniques.Microbial method have poor specificity, sensitivity low, detect limit for height (＞shortcoming such as 3mg/kg).Drug residue in the high effective liquid chromatography for measuring animal derived food must will pass through a series of sample preparation processes, comprises the extraction, deproteinated of sample, centrifugal, chromatography column purification etc.Immunization is suitable for scene, the rapid detection of some tractable samples (urine sample, blood etc.).But when other compound (as ucleosides, peptide class etc.) of containing in the sample with the microbiotic structure similar, false positive results may occur, have a strong impact on the result and judge.Therefore, from complex biological matrix optionally the sample pretreatment process of separation and purification target substance in the food safety detection technology, be very important.
Molecularly imprinted polymer is the tool of the molecular imprinting field of using future in recent years as solid phase extraction filler, the application of molecular imprinting aspect Solid-Phase Extraction, when main based on traditional solid phase extraction techniques, as comprise the post pre-treatment, go up sample, steps such as drip washing, wash-out, mainly concentrate on the analysis of sample in the extraction aspect, particularly biofluid of material in the biological sample.Molecularly imprinted polymer has higher selectivity with respect to traditional solid phase extraction filler, and therefore, the molecular engram solid phase extraction technology not only is used for the enrichment of analyte, and can effectively remove the interference of sample substrate.In recent years, the molecular engram solid phase extraction technology has been successfully applied to the extraction of relevant trace, trace substance in environmental sample (water or soil), food, plant and the tobacco.
Find that through literature search molecular imprinting has begun to be applied in the detection of penicillin in the food at present to prior art.Urraca etc. are at " Analytical Chemistry " (analytical chemistry, 2007,79, " the Direct extraction of penicillin G and derivatives from aqueoussamples using a stoichiometrically imprinted polymer " that delivers 695-701) (use in the molecularly imprinted polymer clump aqueous sample and extract penicillin G and derivative thereof), molecularly imprinted polymer by stoichiometry syncillin G is proposed, directly enrichment β-lactam microbiotic from water sample.Above-described polymkeric substance mainly is to obtain bulk polymer by mass polymerization, and process grinding, screening and sedimentation obtain the amorphous molecularly imprinted polymer of certain particle diameter, therefore time-consuming, effort, and productive rate is also low.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of preparation method of penicillin molecular blotting polymer microsphere is provided, have molecular blotting polymer microsphere advantage simple, that efficient production goes out to have good molecular recognition performance.
The present invention is achieved by the following technical solutions, and the present invention specifically may further comprise the steps:
1) compound concentration is 3%～6% polyvinyl alcohol solution, as: polyvinyl alcohol 1788 (commercially available) strength of solution is 3%～6%;
2) then function monomer, template molecule (being penbritin), initiator (being Diisopropyl azodicarboxylate AIBN), pore-creating agent and linking agent are mixed, ultrasonic, add in polyvinyl alcohol 1788 solution of preparing in the step 1), constant speed stirs 24h;
3) after reaction finishes, stir 60min in 70 ℃ of water, filter, sonic oscillation, successively with distilled water washing 2 times, methanol wash 3 times, washing with acetone 2 times, each 10min removes template molecule by soxhlet extraction method (for method of the prior art) at last;
4) will remove polymkeric substance behind the template molecule, vacuum-drying under 50 ℃ of temperature obtains polymer microballons of molecular engram of nitrogen benzyl penicillin.
Step 2) in, described pore-creating agent is methyl-sulphoxide: the mixing solutions of chloroform volume ratio=1: 1.
Step 2) in, described function monomer is methacrylic acid (MAA), or trifluoromethyl acrylate (TFMAA), or 4-vinylpyridine (4-VP), or methacrylic acid N, N-diethylamino ethyl ester (DAM).
Step 2) in, described linking agent is ethylene glycol dimethacrylate (EGDMA), or trimethylolpropane trimethacrylate (TRIM).
Step 2) in, described ultrasonic, its ultrasonic time is 5min～10min.
Step 2) in, described constant speed stirs, and its condition is that temperature is controlled between 60 ℃～80 ℃, and stirring velocity is 400rpm～600rpm.
Described 1), 2), 3), 4) four steps, carry out under the nitrogen atmosphere condition keeping.
Described polymer microballons of molecular engram of nitrogen benzyl penicillin, there are many apertures on its surface, and median size is about 15 μ m～60 μ m.-
Adopt the polymer microballons of molecular engram of nitrogen benzyl penicillin of the present invention's preparation,, penbritin in the food substrate is carried out separation and purification used as the Solid-Phase Extraction material.The present invention is applied to Solid-Phase Extraction, has post and imitates high, good selective, can be directly used in the food substrate (as honey etc.), and the specific selectivity of penicillin separates, efficiently concentrating.The present invention separate to purify uses in Solid-Phase Extraction: (quality is 0.100g～0.200g), the solid phase extraction column of the 10ml that packs into 1. to take by weighing polymer microballons of molecular engram of nitrogen benzyl penicillin; 2. after activating with 5ml methyl alcohol, 1ml aqueous solution coupled columns then, sample solution is crossed post; 3. use eluent solution (eluent solution is 5% acetonitrile solution, and elution volume is 2ml), 3 * 1ml removes impurity; 4. adopt organic solvent as elutriant (methyl alcohol or acetonitrile solution, elution volume are 5ml), collect penbritin.It detects after 0.22 μ m membrane filtration passes through liquid phase chromatography or fluorescence detection method again.
Compared with prior art, the inventive method directly prepares the molecular blotting polymer microsphere of appropriate particle size, be filled in the molecular imprinted solid phase extraction cartridge, directly separation, the residual penbritin of purifying from rich water medium are removed the impurity in the food substrate.
The present invention is template molecule with the penbritin, adopt suspension polymerization to obtain the molecularly imprinted polymer of penbritin, template molecule had stronger recognition capability, very high selectivity and sensitivity are in food substrate, as honey, penbritin separates, purifying, enrichment, adopt high performance liquid chromatography, fluorescent method detects, and sample recovery rate can reach more than 85%.
Embodiment
Below embodiments of the invention are elaborated: present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1
Present embodiment is implemented under following implementation condition and technical requirements condition:
The preparation of the molecular blotting polymer microsphere of penbritin:
At first compound concentration is 3% polyvinyl alcohol 1788 solution; With DAM, penbritin, methyl-sulphoxide and chloroform, EDGMA and AIBN, mix then, ultrasonication 5min joins in 100mL polyvinyl alcohol 1788 solution, and 60 ℃, 400rpm, constant speed stirs 24h; After reaction finishes, stir 60min in 70 ℃ of water, filter, adopt the sonic oscillation method, successively with 50ml distilled water washing 2 times, 50ml methanol wash 3 times, 50ml washing with acetone 2 times (removing organism such as residual dispersion agent, monomer), each 10min, pass through methyl alcohol at last: acetate (90: 10), methyl alcohol (100%) soxhlet extraction are further removed template molecule; To remove the polymkeric substance of template molecule, vacuum-drying (50 ℃) obtains 60 μ m penicillin molecular blotting polymer microspheres.
The molecular blotting polymer microsphere advantage that present embodiment has simply, efficient production goes out to have good molecular recognition performance.Present embodiment can be applicable to solid phase extraction column penbritin is had single-minded selectivity, can selectivity separation and purification penbritin from animal derived food matrix.
Embodiment 2
Present embodiment is implemented under following implementation condition and technical requirements condition:
The preparation of the molecular blotting polymer microsphere of penbritin:
At first compound concentration is 6% polyvinyl alcohol 1788 solution; With MAA, penbritin, methyl-sulphoxide and chloroform, EDGMA and AIBN, mix then, ultrasonication 10min joins in 100mL polyvinyl alcohol 1788 solution, and 80 ℃, 600rpm, constant speed stirs 24h; After reaction finishes, stir 60min in 70 ℃ of water, filter, adopt the sonic oscillation method, successively with 50ml distilled water washing 2 times, 50ml methanol wash 3 times, 50ml washing with acetone 2 times (removing organism such as residual dispersion agent, monomer), each 10min, pass through methyl alcohol at last: acetate (90: 10), methyl alcohol (100%) soxhlet extraction are further removed template molecule; To remove the polymkeric substance of template molecule, vacuum-drying (50 ℃) obtains 15 μ m penicillin molecular blotting polymer microspheres.
The molecular blotting polymer microsphere advantage that present embodiment has simply, efficient production goes out to have good molecular recognition performance.Present embodiment can be applicable to solid phase extraction column penbritin is had single-minded selectivity, can selectivity separation and purification penbritin from animal derived food matrix.
Embodiment 3
Present embodiment is implemented under following implementation condition and technical requirements condition:
The preparation of the molecular blotting polymer microsphere of penbritin:
At first compound concentration is 4% polyvinyl alcohol 1788 solution; With TFMAA, penbritin, methyl-sulphoxide and chloroform, EDGMA and AIBN, mix then, ultrasonication 8min joins in 100mL polyvinyl alcohol 1788 solution, and 70 ℃, 500rpm, constant speed stirs 24h; After reaction finishes, stir 60min in 70 ℃ of water, filter, adopt the sonic oscillation method, successively with 50ml distilled water washing 2 times, 50ml methanol wash 3 times, 50ml washing with acetone 2 times (removing organism such as residual dispersion agent, monomer), each 10min, pass through methyl alcohol at last: acetate (90: 10), methyl alcohol (100%) soxhlet extraction are further removed template molecule; To remove the polymkeric substance of template molecule, vacuum-drying (50 ℃) obtains 40 μ m penicillin molecular blotting polymer microspheres.
The molecular blotting polymer microsphere advantage that present embodiment has simply, efficient production goes out to have good molecular recognition performance.Present embodiment can be applicable to solid phase extraction column penbritin is had single-minded selectivity, can selectivity separation and purification penbritin from animal derived food matrix.
Embodiment 4
Present embodiment is implemented under following implementation condition and technical requirements condition:
The preparation of the molecular blotting polymer microsphere of penbritin:
At first compound concentration is 3% polyvinyl alcohol 1788 solution; With 4-VP, penbritin, methyl-sulphoxide and chloroform, EDGMA and AIBN, mix then, ultrasonication 5min joins in 100mL polyvinyl alcohol 1788 solution, and 60 ℃, 400rpm, constant speed stirs 24h; After reaction finishes, stir 60min in 70 ℃ of water, filter, adopt the sonic oscillation method, successively with 50ml distilled water washing 2 times, 50ml methanol wash 3 times, 50ml washing with acetone 2 times (removing organism such as residual dispersion agent, monomer), each 10min, pass through methyl alcohol at last: acetate (90: 10), methyl alcohol (100%) soxhlet extraction are further removed template molecule; To remove the polymkeric substance of template molecule, vacuum-drying (50 ℃) obtains 60 μ m penicillin molecular blotting polymer microspheres.
The molecular blotting polymer microsphere advantage that present embodiment has simply, efficient production goes out to have good molecular recognition performance.Present embodiment can be applicable to solid phase extraction column penbritin is had single-minded selectivity, can selectivity separation and purification penbritin from animal derived food matrix.
Claims (9)
1. the preparation method of a polymer microballons of molecular engram of nitrogen benzyl penicillin is characterized in that, specifically may further comprise the steps:
1) compound concentration is 3%～6% polyvinyl alcohol solution;
2) then function monomer, template molecule, initiator, pore-creating agent and linking agent are mixed, ultrasonic, in the polyvinyl alcohol solution, constant speed stirs 24h in the adding step 1);
3) after reaction finishes, stir 60min in 70 ℃ of water, filter, sonic oscillation, successively with distilled water washing 2 times, methanol wash 3 times, washing with acetone 2 times, each 10min removes template molecule by soxhlet extraction at last;
4) will remove polymkeric substance behind the template molecule, vacuum-drying under 50 ℃ of temperature obtains polymer microballons of molecular engram of nitrogen benzyl penicillin.
2. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 1 is characterized in that step 2) in, described function monomer is methacrylic acid, or trifluoromethyl acrylate, or 4 one vinylpyridines, or methacrylic acid N, N-diethylamino ethyl ester.
3. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 1 is characterized in that step 2) in, described pore-creating agent is the mixing solutions of methyl-sulphoxide and chloroform.
4. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 3 is characterized in that, described mixing solutions, and its volume ratio is: methyl-sulphoxide: chloroform=1: 1.
5. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 1 is characterized in that step 2) in, described linking agent is ethylene glycol dimethacrylate, or trimethylolpropane trimethacrylate.
6. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 1 is characterized in that step 2) in, described ultrasonic, its ultrasonic time is 5min～10min.
7. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 1 is characterized in that step 2) in, described constant speed stirs, and its condition is that temperature is controlled between 60 ℃～80 ℃.
8. as the preparation method of claim 1 or 7 described polymer microballons of molecular engram of nitrogen benzyl penicillin, it is characterized in that described constant speed stirs, its stirring velocity is 400rpm～600rpm.
9. the preparation method of polymer microballons of molecular engram of nitrogen benzyl penicillin as claimed in claim 1 is characterized in that, described 1), 2), 3), 4) four steps, carry out under the nitrogen atmosphere condition keeping.
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| CN102174138A (en) * | 2011-01-25 | 2011-09-07 | 尹小英 | Preparation method and application of codonopsis lactone molecularly imprinted solid phase extraction column |
| CN102924645A (en) * | 2012-11-21 | 2013-02-13 | 安徽农业大学 | Preparation method and application of molecularly imprinted polymer of penicillin antibiotics and intermediate of penicillin antibiotics |
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| CN102174138A (en) * | 2011-01-25 | 2011-09-07 | 尹小英 | Preparation method and application of codonopsis lactone molecularly imprinted solid phase extraction column |
| CN103293302A (en) * | 2012-02-29 | 2013-09-11 | 华中农业大学 | Sulfadimidine molecular imprinting bionic recognition kit, and preparation method and application thereof |
| CN103293302B (en) * | 2012-02-29 | 2015-10-28 | 华中农业大学 | The bionical identification agent box of sulfadimidine molecular engram and preparation method and application |
| CN102924645B (en) * | 2012-11-21 | 2014-03-26 | 安徽农业大学 | Preparation method and application of molecularly imprinted polymer of penicillin antibiotics and intermediate of penicillin antibiotics |
| CN102924645A (en) * | 2012-11-21 | 2013-02-13 | 安徽农业大学 | Preparation method and application of molecularly imprinted polymer of penicillin antibiotics and intermediate of penicillin antibiotics |
| CN103626938B (en) * | 2013-11-05 | 2016-03-30 | 西安交通大学 | A kind of preparation method of mezlocillin sodium silica gel surface molecularly imprinted polymer |
| CN103626938A (en) * | 2013-11-05 | 2014-03-12 | 西安交通大学 | Preparation method of mezlocillin sodium silica gel surface molecularly imprinted polymer |
| CN103626937A (en) * | 2013-11-05 | 2014-03-12 | 西安交通大学 | Preparation method of penicillin sodium surface molecularly imprinted polymer |
| CN103626937B (en) * | 2013-11-05 | 2016-06-08 | 西安交通大学 | The preparation method of benzylpenicillin sodium molecular imprinted polymer on surface |
| CN104759117A (en) * | 2015-03-25 | 2015-07-08 | 上海交通大学 | Domoic acid molecularly-imprinted solid-phase extraction cartridge, and preparation method and application thereof |
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| CN108178810B (en) * | 2016-12-07 | 2020-05-19 | 中国科学院大连化学物理研究所 | Preparation and application of reversed phase/anion exchange mixed mode polymer |
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| CN114917881A (en) * | 2022-05-19 | 2022-08-19 | 中国烟草总公司郑州烟草研究院 | Heterocyclic amine molecularly imprinted composite material and preparation method and application thereof |
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