CN101130580A - Tsiklomitsin molecular engram polyalcohol and uses of the same - Google Patents
Tsiklomitsin molecular engram polyalcohol and uses of the same Download PDFInfo
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- CN101130580A CN101130580A CNA200710070753XA CN200710070753A CN101130580A CN 101130580 A CN101130580 A CN 101130580A CN A200710070753X A CNA200710070753X A CN A200710070753XA CN 200710070753 A CN200710070753 A CN 200710070753A CN 101130580 A CN101130580 A CN 101130580A
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- imprinted polymer
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Abstract
The invention discloses an abricycline molecule stamp polymer, which is characterized by the following: mixing mold fermentmycin molecule, functional monomer methacrylic acid, cross linker dimethyl acroleic acid glycol ester and trigger azobisisobutyronitrile with mass ratio at 1-5 : 2-10 : 80 : 0. 1-0. 5; polymerizing at original position; possessing 'memory' function for the spatial structure of the abricycline mold molecule; possessing high selective separating enriched property for abricycline and oxytetracycline in residue analysis sample solution; filling the product into small column of polypropene shell; getting abricycline molecule stamp solid phase extraction column.
Description
(1) technical field
The present invention relates to the tsiklomitsin molecularly imprinted polymer, and the application in the teracycline antibiotic residues in measuring animal food.
(2) background technology
Cyclomycin family antibiotic comprises that terramycin (0TC), tsiklomitsin (TC), duomycin (CTC), doxycycline (DOXY) are widely used in edible animal and halobiontic breed.Cyclomycin family antibiotic adds in the animal-feed, to promote growth of animal, prevention or to treat certain disease, so just cause inevitably that to contain Cyclomycin family antibiotic in its tissue residual, world Codex Committee on Food and countries in the world are to the residual requirement of limiting the quantity of that strictness is all arranged of Cyclomycin family antibiotic in the poultry, and also it being limited the quantity of in the international trade, there are strict requirements.
At present, the method for Cyclomycin family antibiotic mainly contains microbial method, liquid phase chromatography and liquid chromatography-mass spectrography in the mensuration food.Sample pre-treatments is many to be post with the Solid-Phase Extraction, solid-phase extraction column commonly used is the C18 post, after yet C18 purifies, sample substrate disturbs still bigger, sample recovery rate is low, therefore have still adopt WARETS replaced C18 Solid-Phase Extraction column purification with Oasis HLB solid-phase extraction column or Oasis HLB and the purification of Carboxylic Acid anion-exchange column twin columns, reduced matrix interference, improve decontamination effect improving, improved sensitivity and selectivity.Oasis HLB solid-phase extraction column is a WATERS company product, and price is expensive, not quite is fit to China's national situation.
Molecular imprinting claims molecular imprinting, molecular imprinting technique or molecular template technology again.Molecular imprinting comes from the forties in 20th century the earliest, and Nobel winner Pauling had proposed the formation theory of antibody in immunology research at that time, thinks that the synthetic of antibody is template with antigen.Compare with the sample-pretreating method that tradition is commonly used, molecular imprinting can be realized the separation of purpose component simultaneously, and the selectivity height is applied widely, is easy to suitability for industrialized production, and therefore the application in drug residue detects is more and more wider at present.
(3) summary of the invention
The present invention promptly is for a kind of cross-linked polymer---tsiklomitsin molecularly imprinted polymer that fixing hole size and shape is arranged and definite arranging functional group is arranged is provided, it has " memory " function to the three-dimensional arrangement of tsiklomitsin template molecule, has the characteristic of highly selective separation and concentration for the tsiklomitsin in the retention analysis sample solution, terramycin.
For reaching goal of the invention the technical solution used in the present invention be:
A kind of tsiklomitsin molecularly imprinted polymer, mix according to the ratio 1～5: 2～10: 20～80: 0.1～0.5 of quality by template tetracycline hydrochloride molecule, function monomer methacrylic acid, linking agent Ethylene glycol dimethacrylate, initiator Diisopropyl azodicarboxylate, obtain through in-situ polymerization again.
Described in-situ polymerization can carry out under 65～85 ℃ of temperature, polymerization time 6～24 hours.
Described in-situ polymerization also can carry out polymerization time 6～24 hours under the ultraviolet light irradiation.
Described tsiklomitsin molecularly imprinted polymer can be used for measuring teracycline antibiotic residues in the animal tissues.
Described tetracycline antibiotics is one of following or its mixture: 1. terramycin, 2. tsiklomitsin.
Described application method is as follows: the tsiklomitsin molecularly imprinted polymer is filled in the post of polypropylene shell, obtains the tsiklomitsin molecularly imprinted solid phase extraction column, animal tissues's sample was carried out post handle.
Concrete, described to cross the post treatment process as follows: (1) with the rubbing of tested animal tissue, homogenate after, add trichoroacetic acid(TCA), get supernatant liquor behind the 20000rpm high speed centrifugation 10min, be testing sample; (2) get the tsiklomitsin molecularly imprinted solid phase extraction column, cross post activation pillar with methyl alcohol, water, EDTA-2Na solution earlier, then with the whole posts of crossing of testing sample, washing again, vacuum is drained water in the pillar, collects with methanol-eluted fractions at last, and methyl alcohol dries up at 50 ℃ of following nitrogen, add the dissolving of EDTA-2Na solution, cross 0.22 μ m filter membrane rear filtrate instrumental analysis.
Beneficial effect of the present invention is mainly reflected in: tsiklomitsin molecularly imprinted polymer of the present invention, three-dimensional arrangement to the tsiklomitsin template molecule has " memory " function, has the characteristic of highly selective separation and concentration for the tsiklomitsin in the retention analysis sample solution, terramycin; Be filled in the pillar of polypropylene shell with tsiklomitsin molecularly imprinted polymer of the present invention, the tsiklomitsin molecularly imprinted solid phase extraction column that obtains, more simpler, quick than Oasis HLB solid-phase extraction column, efficient, enrichment, purification efficiency are higher.
(4) description of drawings
Fig. 1 adds tsiklomitsin, terramycin for the pork sample after color atlas behind the Oasis HLB Solid-Phase Extraction column purification;
Fig. 2 adds tsiklomitsin, terramycin after the tsiklomitsin molecularly imprinted solid phase extraction column purifies the back color atlas for the pork sample.
(5) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
Delivery plate tetracycline hydrochloride molecule 2.0g (Chinese medicine bioassay institute), function monomer methacrylic acid (MAA) 4.0g (analytical pure, Tianjin section close europeanized reagent center), linking agent Ethylene glycol dimethacrylate (EDMA) 60.0g (Fluka company), add 0.20g initiator Diisopropyl azodicarboxylate again, above-mentioned reaction mixture is dissolved in the 50KHz Ultrasonic Cleaners, mixes evenly, join in the reactor, carry out in-situ polymerization, polymerization temperature is controlled between 75～80 ℃, reaction times is 20 hours, obtains hard bulk yellow polymer.
After polyreaction finishes, synthetic tsiklomitsin molecularly imprinted polymer is taken out from reactor, grind the back and cross 100 eye mesh screens, the powder that obtains utilizes 80% methanol eddy extracting to remove template tetracycline hydrochloride molecule (till not hydrochloric tsiklomitsin molecule in the liquid chromatographic detection 80% methanol eddy liquid, approximately need 12 hours), the tsiklomitsin molecularly imprinted polymer powder after will refluxing again is positioned in the moisture eliminator stand-by 80 ℃ of dryings after 2 hours.This tsiklomitsin molecularly imprinted polymer is a white, and water insoluble, methylene dichloride, methyl alcohol have very strong absorption save power to tsiklomitsin, terramycin.
Get 200～500mg tsiklomitsin molecularly imprinted polymer and be loaded in the pillar of 6ml polypropylene shell, cover the polyethylene filter plate, obtain the tsiklomitsin molecularly imprinted solid phase extraction column.
Embodiment 2:
Delivery plate tetracycline hydrochloride molecule 4.0g (analytical pure, Chinese medicine bioassay institute), function monomer methacrylic acid (MAA) 6.0g (analytical pure, Tianjin section close europeanized reagent center), linking agent Ethylene glycol dimethacrylate (EDMA) 80.0g (Fluka company), add 0.4g initiator Diisopropyl azodicarboxylate again, above-mentioned reaction mixture is dissolved in the 50KHz Ultrasonic Cleaners, mixes evenly, join in the reactor, under the irradiation of 366nm ultra-violet lamp, carry out in-situ polymerization, reaction times is 24 hours, obtains hard bulk yellow polymer.
After polyreaction finishes, synthetic tsiklomitsin molecularly imprinted polymer is taken out from reactor, grind the back and cross 100 eye mesh screens, the powder that obtains utilizes 80% methanol eddy extracting to remove template tetracycline hydrochloride molecule (till not hydrochloric tsiklomitsin molecule in the liquid chromatographic detection 80% methanol eddy liquid, approximately need 12 hours), the tsiklomitsin molecularly imprinted polymer powder after will refluxing again is positioned in the moisture eliminator stand-by 80 ℃ of dryings after 2 hours.This tsiklomitsin molecularly imprinted polymer is a white, and water insoluble, methylene dichloride, methyl alcohol have very strong absorption save power to tsiklomitsin, terramycin.
Get 200～500mg tsiklomitsin molecularly imprinted polymer and be loaded in the pillar of 6ml polypropylene shell, cover the polyethylene filter plate, obtain the tsiklomitsin molecularly imprinted solid phase extraction column.
Embodiment 3:
It is as follows with embodiment 1,2 gained tsiklomitsin molecularly imprinted solid phase extraction columns tsiklomitsin, terramycin mark-on pork to be carried out sample pre-treatments:
1, gets 5.0g after tsiklomitsin, the terramycin mark-on pork (tsiklomitsin, each 0.1mg/kg of terramycin) of rubbing are used 20mL0.01mol/L EDTA-2Na homogenate, add 2mL1: 1 (V: V) trichloroacetic acid solution, get supernatant liquor behind the 20000rpm high speed centrifugation 10min, be testing sample.
2, get tsiklomitsin molecularly imprinted solid phase extraction column (200mg/6mL), cross post activation pillar with 5mL methyl alcohol, 5mL water, 5mL0.01mol/LEDTA-2Na solution earlier, then with the whole posts of crossing of above-mentioned testing sample, wash with 5mL again, vacuum is drained water in the pillar, collects with the 5mL methanol-eluted fractions at last, and methyl alcohol dries up at 50 ℃ of following nitrogen, add the dissolving of 1mL0.01mol/LEDTA-2Na solution, cross 0.22 μ m filter membrane rear filtrate for instrumental analysis.
Use Oasis HLB solid-phase extraction column (200mg/6ml) to carry out sample pre-treatments (method is with the tsiklomitsin molecularly imprinted solid phase extraction column) then equally, scavenging solution compares after with liquid chromatogram measuring, the results are shown in Figure 1, Fig. 2.
By Fig. 1, Fig. 2 color atlas more as can be known, the pork sample add tsiklomitsin, terramycin standard after the tsiklomitsin molecularly imprinted solid phase extraction column purify back color atlas (Fig. 2) than Oasis HLB Solid-Phase Extraction column purification after color atlas (Fig. 1) impurity lack, and sample mark-on 0.1mg/kg, rate of recovery tsiklomitsin, terramycin are respectively 85.5% and 83.4%, be higher than 78.9% and 75.4% of Oasis HLB, the tsiklomitsin molecularly imprinted solid phase extraction column can satisfy tsiklomitsin in the animal tissues, the residual mensuration requirement of terramycin fully.
Claims (7)
1. tsiklomitsin molecularly imprinted polymer, by template tetracycline hydrochloride molecule, function monomer methacrylic acid, linking agent Ethylene glycol dimethacrylate, initiator Diisopropyl azodicarboxylate according to mass ratio 1～5: mix at 2～10: 20～80: 0.1～0.5, obtains through in-situ polymerization again.
2. tsiklomitsin molecularly imprinted polymer as claimed in claim 1 is characterized in that described in-situ polymerization carries out, polymerization time 6～24 hours under 65～85 ℃ of temperature.
3. tsiklomitsin molecularly imprinted polymer as claimed in claim 1 is characterized in that described in-situ polymerization carries out polymerization time 6～24 hours under the ultraviolet light irradiation.
4. as the application in the teracycline antibiotic residues in measuring animal tissues of the described tsiklomitsin molecularly imprinted polymer of one of claim 1～3.
5. application as claimed in claim 4 is characterized in that described tetracycline antibiotics is one of following or its mixture: 1. terramycin, 2. tsiklomitsin.
6. application as claimed in claim 4 is characterized in that described application method is as follows: the tsiklomitsin molecularly imprinted polymer is filled in the post of polypropylene shell, obtains the tsiklomitsin molecularly imprinted solid phase extraction column, animal tissues's sample was carried out post handle.
7. application as claimed in claim 6 is characterized in that described to cross the post treatment process as follows: (1) with the rubbing of tested animal tissue, homogenate after, add trichoroacetic acid(TCA), get supernatant liquor behind the 20000rpm high speed centrifugation 10min, be testing sample; (2) get the tsiklomitsin molecularly imprinted solid phase extraction column, cross post activation pillar with methyl alcohol, water, EDTA-2Na solution earlier, then with the whole posts of crossing of testing sample, washing again, vacuum is drained water in the pillar, collects with methanol-eluted fractions at last, and methyl alcohol dries up at 50 ℃ of following nitrogen, add the dissolving of EDTA-2Na solution, cross 0.22 μ m filter membrane rear filtrate and carry out liquid chromatogram measuring.
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Cited By (19)
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| CN101402706B (en) * | 2008-11-13 | 2010-06-09 | 上海交通大学 | Method for preparing tsiklomitsin molecular engram polymer used for water environment |
| CN101857664A (en) * | 2010-06-21 | 2010-10-13 | 湖北出入境检验检疫局检验检疫技术中心 | Preparation method of molecular imprinting polymer with specific recognition capability to tetracycline family |
| CN101246150B (en) * | 2008-03-28 | 2010-12-08 | 南开大学 | Tsiklomitsin molecular engram integral column preparation method |
| CN102012372A (en) * | 2010-11-10 | 2011-04-13 | 吉林大学 | Method for detecting medicinal molecules by magnetic imprinting surface enhanced Raman spectroscopy technology |
| CN102116759A (en) * | 2009-12-30 | 2011-07-06 | 宁波大学 | Selective electrode of tetracycline drugs and preparation method thereof |
| CN101324541B (en) * | 2008-07-18 | 2011-08-03 | 大连理工大学 | Abricycline molecular imprinting polymer membrane electrode and preparation and application thereof |
| CN101723505B (en) * | 2009-09-14 | 2011-09-14 | 陕西科技大学 | Method for removing azo acid dye waste water by utilizing molecular imprinting method |
| CN101710116B (en) * | 2009-11-10 | 2012-11-07 | 桂林理工大学 | Method for determining trace terramycin by utilizing molecularly imprinted immunosensor |
| CN103554363A (en) * | 2013-10-10 | 2014-02-05 | 安徽农业大学 | Preparation and application of nano silica-based doxycycline molecularly imprinted polymer |
| CN104341562A (en) * | 2014-10-28 | 2015-02-11 | 武夷学院 | Magnetic molecularly-imprinted polymer for identifying and enriching varieties of trace antibiotics and preparation method and application thereof |
| CN104458858A (en) * | 2014-12-12 | 2015-03-25 | 广西科技大学 | Method for preparing molecularly imprinted membrane modified glass carbon electrode from PEDOT/methacrylic acid |
| CN104592446A (en) * | 2015-01-15 | 2015-05-06 | 宁波大学 | Preparation method and application of nano fiber molecularly-imprinted polymer of tetracycline antibiotics |
| CN106526175A (en) * | 2016-11-30 | 2017-03-22 | 百奥森（江苏）食品安全科技有限公司 | Method and card for detecting tetracyclines in poultry meat |
| CN106868622A (en) * | 2017-01-13 | 2017-06-20 | 东南大学成贤学院 | Can be used to detect nanofiber and its preparation and the application of tetracycline |
| CN107913682A (en) * | 2017-11-08 | 2018-04-17 | 常州大学 | A kind of method for preparing porous temperature sensitive molecular imprinting adsorbing agent |
| CN111268814A (en) * | 2020-01-07 | 2020-06-12 | 昆明理工大学 | Anthracycline wastewater treatment method combining porous carbon nanosphere-based surface molecularly imprinted filter material and ultrafiltration molecularly imprinted membrane |
| CN111363185A (en) * | 2020-03-27 | 2020-07-03 | 江苏大学 | Preparation method and application of molecularly imprinted composite membrane initiated by surface functional monomer prepolymerization system |
| CN113368706A (en) * | 2021-06-02 | 2021-09-10 | 江苏大学 | Preparation method and application of bionic suction filtration type double-layer molecularly imprinted nanofiber composite membrane based on poly-dopamine imprinting strategy |
| CN114878657A (en) * | 2022-04-18 | 2022-08-09 | 陕西科技大学 | Molecularly imprinted electrochemical sensor based on magnetic mesoporous titanium dioxide material and preparation method and application thereof |
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2007
- 2007-08-10 CN CNA200710070753XA patent/CN101130580A/en active Pending
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| CN101246150B (en) * | 2008-03-28 | 2010-12-08 | 南开大学 | Tsiklomitsin molecular engram integral column preparation method |
| CN101324541B (en) * | 2008-07-18 | 2011-08-03 | 大连理工大学 | Abricycline molecular imprinting polymer membrane electrode and preparation and application thereof |
| CN101402706B (en) * | 2008-11-13 | 2010-06-09 | 上海交通大学 | Method for preparing tsiklomitsin molecular engram polymer used for water environment |
| CN101723505B (en) * | 2009-09-14 | 2011-09-14 | 陕西科技大学 | Method for removing azo acid dye waste water by utilizing molecular imprinting method |
| CN101710116B (en) * | 2009-11-10 | 2012-11-07 | 桂林理工大学 | Method for determining trace terramycin by utilizing molecularly imprinted immunosensor |
| CN102116759A (en) * | 2009-12-30 | 2011-07-06 | 宁波大学 | Selective electrode of tetracycline drugs and preparation method thereof |
| CN102116759B (en) * | 2009-12-30 | 2013-07-24 | 宁波大学 | Selective electrode of tetracycline drugs and preparation method thereof |
| CN101857664A (en) * | 2010-06-21 | 2010-10-13 | 湖北出入境检验检疫局检验检疫技术中心 | Preparation method of molecular imprinting polymer with specific recognition capability to tetracycline family |
| CN102012372A (en) * | 2010-11-10 | 2011-04-13 | 吉林大学 | Method for detecting medicinal molecules by magnetic imprinting surface enhanced Raman spectroscopy technology |
| CN102012372B (en) * | 2010-11-10 | 2012-03-28 | 吉林大学 | Method for detecting medicinal molecules by magnetic imprinting surface enhanced Raman spectroscopy technology |
| CN103554363B (en) * | 2013-10-10 | 2015-11-25 | 安徽农业大学 | The preparations and applicatio of nano silicon butyldoxycycline molecularly imprinted polymer |
| CN103554363A (en) * | 2013-10-10 | 2014-02-05 | 安徽农业大学 | Preparation and application of nano silica-based doxycycline molecularly imprinted polymer |
| CN104341562A (en) * | 2014-10-28 | 2015-02-11 | 武夷学院 | Magnetic molecularly-imprinted polymer for identifying and enriching varieties of trace antibiotics and preparation method and application thereof |
| CN104458858A (en) * | 2014-12-12 | 2015-03-25 | 广西科技大学 | Method for preparing molecularly imprinted membrane modified glass carbon electrode from PEDOT/methacrylic acid |
| CN104592446A (en) * | 2015-01-15 | 2015-05-06 | 宁波大学 | Preparation method and application of nano fiber molecularly-imprinted polymer of tetracycline antibiotics |
| CN104592446B (en) * | 2015-01-15 | 2016-11-23 | 宁波大学 | The preparation method and application of the nanofiber molecularly imprinted polymer of tetracycline antibiotics |
| CN106526175B (en) * | 2016-11-30 | 2018-08-31 | 百奥森（江苏）食品安全科技有限公司 | Tetracyclines detection method and detection card in a kind of poultry |
| CN106526175A (en) * | 2016-11-30 | 2017-03-22 | 百奥森（江苏）食品安全科技有限公司 | Method and card for detecting tetracyclines in poultry meat |
| CN106868622A (en) * | 2017-01-13 | 2017-06-20 | 东南大学成贤学院 | Can be used to detect nanofiber and its preparation and the application of tetracycline |
| CN106868622B (en) * | 2017-01-13 | 2020-04-03 | 东南大学成贤学院 | Nanofiber capable of being used for detecting tetracycline and preparation and application thereof |
| CN107913682A (en) * | 2017-11-08 | 2018-04-17 | 常州大学 | A kind of method for preparing porous temperature sensitive molecular imprinting adsorbing agent |
| CN111268814A (en) * | 2020-01-07 | 2020-06-12 | 昆明理工大学 | Anthracycline wastewater treatment method combining porous carbon nanosphere-based surface molecularly imprinted filter material and ultrafiltration molecularly imprinted membrane |
| CN111268814B (en) * | 2020-01-07 | 2022-05-24 | 昆明理工大学 | Anthracycline wastewater treatment method combining porous carbon nanosphere-based surface molecularly imprinted filter material and ultrafiltration molecularly imprinted membrane |
| CN111363185A (en) * | 2020-03-27 | 2020-07-03 | 江苏大学 | Preparation method and application of molecularly imprinted composite membrane initiated by surface functional monomer prepolymerization system |
| CN111363185B (en) * | 2020-03-27 | 2022-04-26 | 江苏大学 | Preparation method and application of molecularly imprinted composite membrane initiated by surface functional monomer prepolymerization system |
| CN113368706A (en) * | 2021-06-02 | 2021-09-10 | 江苏大学 | Preparation method and application of bionic suction filtration type double-layer molecularly imprinted nanofiber composite membrane based on poly-dopamine imprinting strategy |
| CN113368706B (en) * | 2021-06-02 | 2022-05-20 | 江苏大学 | Preparation method and application of bionic suction filtration type double-layer molecularly imprinted nanofiber composite membrane based on poly-dopamine imprinting strategy |
| CN114878657A (en) * | 2022-04-18 | 2022-08-09 | 陕西科技大学 | Molecularly imprinted electrochemical sensor based on magnetic mesoporous titanium dioxide material and preparation method and application thereof |
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