CN1811411A - Process for producing chloromycetin molecular engram polymer microsphere - Google Patents
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Abstract
The present invention relates to a preparation method of chloromycetin molecular engram polymer microsphere, belonging to field of biological engineering technology. Its preparation method includes the following concrete steps: the mole ratio of template molecule, functional monomer and ethylene glycol dimethacrylate is 1:2-8:25; volume ratio of total volume of diluting agent and ethylene glycol dimethacrylate and water is 1:6-14; dissolving polyvinyl alcohol 1788 in water, dissolving functional monomer and template molecule in diluting agent; mixing ethylene glycol dimethacrylate, azobisisobutyronitrile and diluting agent; mixing the above-mentioned three solutions, after the reaction is completed, stirring product in water, cooling and filtering, washing successively by using double-distilled water, methyl alcohol and acetone, utilizing Soxhlet's extraction process to remove template molecule; vacuum drying so as to obtain the invented chloromycetin molecular engram polymer microsphere.
Description
Technical field
What the present invention relates to is a kind of method of technical field of bioengineering, specifically, relates to a kind of preparation method of chloramphenicol molecularly imprinted polymeric microspheres.
Background technology
Chloromycetin (chloramphenicol is called for short CAP) is nineteen forty-seven to separate the broad-spectrum antibiotic that obtains first from microbe metabolite.Yet owing to be with nitro on its phenyl ring, its half life of decomposition is long and have serious toxic and side effect, and therefore, the residual chloromycetin in animal food and the aquatic products has constituted grave danger to human health.At present, the residual chloromycetin detection method 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); Immunization is the analytical technology based on antigen and antibody specificity association reaction, but when other compound of containing in the sample with the chloromycetin structure similar, false positive results may occur, has a strong impact on the result and judges.Therefore, the pre-treatment process of sample is extremely important.Chromatography mainly comprises liquid phase chromatography and vapor-phase chromatography, is the residual chloromycetin quantitative detection method of generally acknowledging in the world, but its have the sample pretreatment process complexity, cost an arm and a leg, analysis speed waits shortcoming slowly, is not suitable for scene, fast detecting analysis.Adopt solid phase extraction techniques (SPE) to help the separation and the detection of complex matrices, but the acting force between its object of traditional Solid-Phase Extraction and the adsorbent is nonspecific, and the separation of different substrates need be selected different column packings with analyte, has limited further developing of solid phase extraction techniques.Molecular imprinting (MIPs) is a kind of technology of preparing for the polymkeric substance that obtains to mate fully with certain a part on space and binding site, at the multiple biosensor technique relevant with biotechnology and synthesize the application in fields such as artificial antibody.Molecular imprinting has three big characteristics: structure is imitated precordainment, specific recognition, extensive practicality.At present, MIPs and applied research thereof are very active, and coverage is very wide.
Find that through literature search molecular imprinting has begun to be applied in the detection of chloromycetin in the food at present to prior art.Levi etc. are at " Analytical Chemistry " (analytical chemistry, 1997,69, propose to use molecularly imprinted polymer among " the Optical Detection of Chloramphenicol UsingMolecularly Imprinted Polymers " that delivers 2017-2021) (using molecularly imprinted polymer chlorine detection mycin) and combine, the detection sensitivity of chloromycetin can be increased to 10-20 μ g/ml with the HPLC detection method; The concrete method of bulk polymerization that adopts makes chloramphenicol molecularly imprinted polymeric, through grinds, sieve, after a series of processing such as wash-out, obtaining size is the molecularly imprinted polymer of 25-63 μ m, by adorning the HPLC post it is carried out evaluation analysis again.Its weak point is to obtain by complicated procedures such as sub-sieves the molecularly imprinted polymer particle of required particle diameter, and it exists shortcomings such as yield is low, particle shape is irregular, bad dispersibility.Also can cause the molecular recognition and the selectivity of molecularly imprinted polymer to descend in the process of lapping.
Summary of the invention
The objective of the invention is to overcome the deficiency in enrichment that existing molecularly imprinted polymer technology of preparing and chloromycetin relates in the sample pretreatment in detecting, clarification, extraction, the separation and detection method, a kind of preparation method of chloramphenicol molecularly imprinted polymeric microspheres is provided, make it prepare molecular blotting polymer microsphere simply, efficiently with good monodispersity, molecular recognition performance, when being particularly useful for fields such as chromatographic stationary phase, Solid-Phase Extraction, have post and imitate high, good selective, can be directly used in specific selectivity separation, efficiently concentrating chloromycetin.
The present invention is achieved by the following technical solutions, and the preparation method of chloramphenicol molecularly imprinted polymeric microspheres of the present invention specifically may further comprise the steps:
1), the mol ratio of template molecule, function monomer and ethylene glycol dimethacrylate (EGDMA) is 1: 2～8: 25; The cumulative volume of thinning agent and ethylene glycol dimethacrylate and the volume ratio of water are 1: 6～14;
2), with polyvinyl alcohol (PVA) 1788 as in the water, 80 ℃ are stirred 30min to its whole dissolvings; The concentration of polyvinyl alcohol (PVA) 1788 (PVA1788) is 3～6%;
3), function monomer and template molecule are dissolved in the thinning agent ultrasonication 5～10min;
4), with ethylene glycol dimethacrylate, initiating agent and mixing diluents, ultrasonication 5～10min;
5), above-mentioned three kinds of solution are mixed, at 60～70 ℃ of constant temperature 350～400rpm constant speed stirring 20～24h;
6) after reaction finishes, the molecular blotting polymer microsphere of above-mentioned prepared in reaction is stirred 60min in 80 ℃ of water, cooling is filtered then, filter the back with distilled water washing 3 times, use methanol wash again 3 times, washing with acetone 2 times, each 15min further removes template molecule by soxhlet extraction at last;
7), will remove the polymkeric substance of template molecule, vacuum drying (50 ℃) obtains chloramphenicol molecularly imprinted polymeric microspheres.
Described template is chloromycetin.
Described initiating agent is azoisobutyronitrile (AIBN).
Described thinning agent is octanol: the mixed solvent of chloroform volume ratio=5: 1.
Described function monomer is styrene, acrylamide or methacrylic acid N, N-diethylamino ethyl ester.
Keep nitrogen atmosphere in the course of reaction, flow velocity is 0.5ml/min.
Described chloramphenicol molecularly imprinted polymeric microspheres, average pore size are about 40～120 μ m, on the molecular blotting polymer microsphere surface many apertures are arranged.
The present invention prepares chloramphenicol molecularly imprinted polymeric microspheres, is dispersion medium with water in the reaction, and the special molecularly imprinted polymer of prepared chloromycetin is spherical, need not to grind, screening; Usually, the molecularly imprinted polymer that obtains by mass polymerization is bulk, needs to use through grinding and after sieving, and not only subsequent treatment work is loaded down with trivial details, time-consuming, and loss is bigger in grinding the sieve process, and shape of product is irregular, and dispersiveness is relatively poor, and separation efficiency is lower; And the molecular blotting polymer microsphere that suspension polymerization obtains need not grind, and can obtain the polymer microballoon of different-grain diameter by the different proportion of control stirring rate and adjusting spreading agent.This chloramphenicol molecularly imprinted polymeric microspheres will provide good pre-treatment material for the detection of residual chloromycetin in the food, but efficiently concentrating, accurately separate chloromycetin, in conjunction with existing detection method (as ELISA, HPLC etc.), significantly improve the detection sensitivity and the detection efficiency of residual chloromycetin, in food, have bigger application value in the detection of residual chloromycetin.
Description of drawings
The porous molecular blotting polymer microsphere that Fig. 1 makes for the present invention
The porous molecular blotting polymer microsphere surface Electronic Speculum scintigram that Fig. 2 makes for the present invention
Embodiment
Embodiment 1.
The PVA1788 of 100ml 4% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.8ml DAM, the 5ml EDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, ultrasonic mixing 20min adds 120mg AIBN, the 5ml chloroform continues ultrasonic 5min, adds ice cube when ultrasonic, keeps low temperature then.
Keep stirring rate, the monomer for preparing is added to the good monomer dispersion of assurance in the four-hole bottle.Continue logical nitrogen, 70 ℃, 24h.The polymkeric substance of gained is carried out the wash-out processing.
Pour in the 200ml beaker after after polyreaction finishes the polymkeric substance that obtains being leached water flushing three times, 80 ℃ of distilled waters stir 60min, with 50ml methanol wash three times, twice of 50ml washing with acetone (organism such as flush away sweller, remaining organic monomer), methyl alcohol: acetate (80: 20) soxhlet extraction 24h, wash-out is removed template molecule, methyl alcohol (100%) 24h, (40 μ m) sieves, last 50 ℃ of vacuum drying 6h are to weight, obtaining the mean grain size size at last is the microballoon that there are a lot of apertures on 80 μ m, surface, and its invention effect as shown in Figure 1, 2.
Embodiment 2.
The PVA1788 of 100ml 4% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.8ml St, the 5ml EGDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, other operation and embodiment 1 with.The microballoon that obtain the mean grain size size at last and be about 120 μ m, there are a lot of apertures on the surface, its invention effect is equal to shown in Fig. 1,2 substantially.
Embodiment 3.
The PVA1788 of 100ml 4% is added in the four-hole bottle, and logical nitrogen 10min stirs 350rpm simultaneously.
In another container, will remove 0.8ml DAM, the 5ml EGDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, ultrasonic mixing 20min adds 120mg AIBN, the 5ml chloroform continues ultrasonic 5min, adds ice cube when ultrasonic, keeps low temperature then.
Keep stirring rate, the monomer for preparing is added to the good monomer dispersion of assurance in the four-hole bottle.Continue logical nitrogen, 70 ℃, 24h.Other operation and embodiment 1 are together.The microballoon that obtain the mean grain size size at last and be about 90 μ m, there are a lot of apertures on the surface, its invention effect is equal to shown in Fig. 1,2 substantially.
Embodiment 4.
The PVA1788 of 100ml 3% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.8ml DAM, the 5ml EGDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, other operation and embodiment 1 with.The microballoon that obtain the mean grain size size at last and be about 120 μ m, there are a lot of apertures on the surface, its invention effect is equal to shown in Fig. 1,2 substantially.
Embodiment 5.
The PVA1788 of 100ml 5% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.8ml DAM, the 5ml EGDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, other operation and embodiment 1 with.The microballoon that obtain the mean grain size size at last and be about 60 μ m, there are a lot of apertures on the surface, its invention effect is equal to shown in Fig. 1,2 substantially.
Embodiment 6.
The PVA1788 of 100ml 6% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.8ml DAM, the 5ml EGDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, other operation and embodiment 1 with.The microballoon that obtain the mean grain size size at last and be about 40 μ m, there are a lot of apertures on the surface, its invention effect is equal to shown in Fig. 1,2 substantially.
Embodiment 7.
The PVA1788 of 100ml 4% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.4ml DAM, the 5ml EDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, ultrasonic mixing 20min adds 120mg AIBN, the 5ml chloroform continues ultrasonic 5min, adds ice cube when ultrasonic, keeps low temperature then.
Keep stirring rate, the monomer for preparing is added to the good monomer dispersion of assurance in the four-hole bottle.Continue logical nitrogen, 70 ℃, 24h.The polymkeric substance of gained is carried out the wash-out processing.
Pour in the 200ml beaker after after polyreaction finishes the polymkeric substance that obtains being leached water flushing three times, 80 ℃ of distilled waters stir 60min, with 50ml methanol wash three times, twice of 50ml washing with acetone (organism such as flush away sweller, remaining organic monomer), methyl alcohol: acetate (80: 20) soxhlet extraction 24h, wash-out is removed template molecule, methyl alcohol (100%) 24h, (40 μ m) sieves, last 50 ℃ of vacuum drying 6h are to weight, obtaining the mean grain size size at last is the microballoon that there are a lot of apertures on 80 μ m, surface, and its invention effect as shown in Figure 1, 2.
Embodiment 8.
The PVA1788 of 100ml 4% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.2ml DAM, the 5ml EDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, ultrasonic mixing 20min adds 120mg AIBN, the 5ml chloroform continues ultrasonic 5min, adds ice cube when ultrasonic, keeps low temperature then.
Keep stirring rate, the monomer for preparing is added to the good monomer dispersion of assurance in the four-hole bottle.Continue logical nitrogen, 70 ℃, 24h.The polymkeric substance of gained is carried out the wash-out processing.
Pour in the 200ml beaker after after polyreaction finishes the polymkeric substance that obtains being leached water flushing three times, 80 ℃ of distilled waters stir 60min, with 50ml methanol wash three times, twice of 50ml washing with acetone (organism such as flush away sweller, remaining organic monomer), methyl alcohol: acetate (80: 20) soxhlet extraction 24h, wash-out is removed template molecule, methyl alcohol (100%) 24h, (40 μ m) sieves, last 50 ℃ of vacuum drying 6h are to weight, obtaining the mean grain size size at last is the microballoon that there are a lot of apertures on 80 μ m, surface, and its invention effect as shown in Figure 1, 2.
Embodiment 9.
The PVA1788 of 100ml 4% is added in the four-hole bottle, and logical nitrogen 10min stirs 400rpm simultaneously.
In another container, will remove 0.8ml DAM, the 5ml EDMA of polymerization inhibitor and 10ml octanol, 0.32g chloromycetin, ultrasonic mixing 20min adds 120mg AIBN, the 5ml chloroform continues ultrasonic 5min, adds ice cube when ultrasonic, keeps low temperature then.
Keep stirring rate, the monomer for preparing is added to the good monomer dispersion of assurance in the four-hole bottle.Continue logical nitrogen, 60 ℃, 24h.The polymkeric substance of gained is carried out the wash-out processing.
Pour in the 200ml beaker after after polyreaction finishes the polymkeric substance that obtains being leached water flushing three times, 80 ℃ of distilled waters stir 60min, with 50ml methanol wash three times, twice of 50ml washing with acetone (organism such as flush away sweller, remaining organic monomer), methyl alcohol: acetate (80: 20) soxhlet extraction 24h, wash-out is removed template molecule, methyl alcohol (100%) 24h, (40 μ m) sieves, last 50 ℃ of vacuum drying 6h are to weight, obtaining the mean grain size size at last is the microballoon that there are a lot of apertures on 80 μ m, surface, and its invention effect as shown in Figure 1, 2.
Claims (10)
1, a kind of preparation method of chloramphenicol molecularly imprinted polymeric microspheres is characterized in that may further comprise the steps:
1) mol ratio of template molecule, function monomer and ethylene glycol dimethacrylate is 1: 2～8: 25; The cumulative volume of thinning agent and ethylene glycol dimethacrylate and the volume ratio of water are 1: 6～14;
2) with polyvinyl alcohol (PVA) 1788 as in the water, be stirred to its whole dissolvings;
3) function monomer and template molecule are dissolved in the thinning agent ultrasonication;
4) with ethylene glycol dimethacrylate, azoisobutyronitrile and mixing diluents, ultrasonication;
5) above-mentioned three kinds of solution are mixed, the constant temperature constant speed stirs;
6) after reaction finishes, the molecular blotting polymer microsphere of above-mentioned prepared in reaction is stirred in water, cooling is filtered then, after the filtration successively with distilled water wash, methyl alcohol, washing with acetone, further remove template molecule by soxhlet extraction at last;
7) will remove the polymkeric substance of template molecule, vacuum drying obtains chloramphenicol molecularly imprinted polymeric microspheres.
2, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1, it is characterized in that described 2) in, with polyvinyl alcohol (PVA) 1788 as in the water, 80 ℃ are stirred 30min to its whole dissolvings, and the concentration of described polyvinyl alcohol (PVA) 1788 is 3～6%.
3, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, described 3) and 4) in, the ultrasonication time is 5～10min.
4, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, described 5) in, the constant temperature constant speed stirs, and is meant: stir 20～24h 60～70 ℃ of constant temperature 350～400rpm constant speed.
5, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1, it is characterized in that, described 6) in, molecular blotting polymer microsphere is stirred 60min in 80 ℃ of water, cooling is filtered then, filters the back with distilled water washing 3 times, uses methanol wash again 3 times, washing with acetone 2 times, each 15min.
6, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, described 7) in, the vacuum drying temperature is 50 ℃.
7, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, described template is chloromycetin; Described function monomer is styrene, acrylamide or methacrylic acid N, N-diethylamino ethyl ester.
8, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, described thinning agent is octanol: the mixed solvent of chloroform volume ratio=5: 1.
9, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, keeps nitrogen atmosphere in the course of reaction, and flow velocity is 0.5ml/min.
10, the preparation method of chloramphenicol molecularly imprinted polymeric microspheres according to claim 1 is characterized in that, described chloramphenicol molecularly imprinted polymeric microspheres, and average pore size is 40～120 μ m, on the molecular blotting polymer microsphere surface many apertures is arranged.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101507916B (en) * | 2009-02-16 | 2011-01-19 | 西北工业大学 | Preparation method of macrolide antibiotics molecular engram polymer microsphere |
| CN101591412B (en) * | 2009-06-03 | 2011-05-18 | 中国农业科学院农业质量标准与检测技术研究所 | Method for preparing chloramphenicol molecularly imprinted polymeric microspheres |
| CN101628955B (en) * | 2009-07-31 | 2011-07-27 | 宁波大学 | Method for preparing molecular imprinted polymer for recognizing chloromycetin, thiamphenicol and florfenicol simultaneously |
| CN102336871A (en) * | 2010-07-16 | 2012-02-01 | 中国科学院过程工程研究所 | Chloramphenicol molecular imprinting polymer microballoon with uniformity in size as well as preparation method and application thereof |
| CN101387617B (en) * | 2008-10-16 | 2012-07-04 | 上海交通大学 | Silk-screen printing electrode and method for synthesizing chloramphenicol molecular imprinting film |
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| CN101387617B (en) * | 2008-10-16 | 2012-07-04 | 上海交通大学 | Silk-screen printing electrode and method for synthesizing chloramphenicol molecular imprinting film |
| CN101507916B (en) * | 2009-02-16 | 2011-01-19 | 西北工业大学 | Preparation method of macrolide antibiotics molecular engram polymer microsphere |
| CN101591412B (en) * | 2009-06-03 | 2011-05-18 | 中国农业科学院农业质量标准与检测技术研究所 | Method for preparing chloramphenicol molecularly imprinted polymeric microspheres |
| CN101628955B (en) * | 2009-07-31 | 2011-07-27 | 宁波大学 | Method for preparing molecular imprinted polymer for recognizing chloromycetin, thiamphenicol and florfenicol simultaneously |
| CN102336871A (en) * | 2010-07-16 | 2012-02-01 | 中国科学院过程工程研究所 | Chloramphenicol molecular imprinting polymer microballoon with uniformity in size as well as preparation method and application thereof |
| CN102336871B (en) * | 2010-07-16 | 2013-11-06 | 中国科学院过程工程研究所 | Chloramphenicol molecular imprinting polymer microballoon with uniformity in size as well as preparation method and application thereof |
| CN109232823A (en) * | 2018-08-14 | 2019-01-18 | 桂林理工大学 | A kind of preparation method of abietyl TDI type polyurethane molecular engram microsphere |
| CN109265727A (en) * | 2018-08-14 | 2019-01-25 | 桂林理工大学 | A kind of preparation method of abietyl HDI type polyurethane molecular engram microsphere |
| CN109369951A (en) * | 2018-08-14 | 2019-02-22 | 桂林理工大学 | A kind of preparation method of abietyl IPDI type polyurethane molecular engram microsphere |
| CN109369951B (en) * | 2018-08-14 | 2020-11-24 | 桂林理工大学 | Preparation method of rosin-based IPDI polyurethane molecularly imprinted microspheres |
| CN109265727B (en) * | 2018-08-14 | 2020-11-24 | 桂林理工大学 | Preparation method of rosin-based HDI polyurethane molecularly imprinted microspheres |
| CN109232823B (en) * | 2018-08-14 | 2020-11-24 | 桂林理工大学 | Preparation method of rosin-based TDI (toluene diisocynate) type polyurethane molecularly imprinted microspheres |
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