CN110204711A - The preparation method and application of one type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbent - Google Patents
The preparation method and application of one type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbent Download PDFInfo
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Abstract
The invention discloses type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbents and the preparation method and application thereof, using dopamine as function monomer, Pluronic F-127 and 1,3,5- trimethylbenzenes (TMB) be organic pore-foaming agent and by template molecule trace in the material.Using the method for organic-organic auto polymerization, poly-dopamine (PDA) particle and 1 that auto polymerization based on dopamine is formed, 3, π-π interaction between 5- trimethylbenzene drop obtains the mesoporous type molecularly imprinted polymer that the stereochemical structure to template molecule that the present invention synthesizes has " memory " function.As dispersive solid-phase extraction adsorbent, good effect is achieved in conjunction with HPLC-MS/MS detection with Selective Separation analysans for being enriched with.Preparation method of the invention is simple, and adsorption capacity is high, and mass transfer velocity is fast, and selective good and long service life has broad application prospects in analytical chemistry, environmental analysis field.
Description
Technical field
The present invention relates to analytical chemistry pre-treatment fields, are specifically applied in the big ring in measurement animal derived food
One type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle of the highly selective separation of esters antibiotic residual quantity
The preparation method and application of sub- adsorbent.
Background technique
Macrolide antibiotics (MACs) is a kind of low pole and alkali molecules with macrolide.Macrolides
Antibiotic has most of gram-positive bacteriums, certain gramnegative bacteriums and more uncommon pathogen relatively strong
Antibacterial activity, it has antimicrobial spectrum more wider than beta-Lactam antibiotic, and is not easy to cause allergic reaction.Therefore, it
It is often used as the substitute of beta-Lactam antibiotic, studies have shown that macrolide antibiotics not only has antibacterial activity,
With anti-inflammatory effect and immunoregulation effect, and it is widely used as feed addictive and animal husbandry disease prevention.So
And lasting or illegal drug addition may cause the antibiotic residue in animal derived food.Macrolide antibiotics can
, in people's cylinder accumulation, to generate bacterial drug resistance and toxic side effect to consumer by food chain, such as gastrointestinal reaction, part thorn
Sharp and hepatotoxicity wind agitation.Therefore, developing macrolide antibiotic residues detection method in a kind of effective animal derived food has
Significance.
Currently, high performance liquid chromatography-tandem mass (HPLC-MS/MS) has become trace macrolides in detection food
The main method of antibiotic.But sample pretreatment process is laborious, time-consuming, and is related to relatively great amount of sample.In addition, by
In lacking selectivity, traditional adsorbent is frequently subjected to the interference of Coexisting component, extraction efficiency is caused to reduce.Therefore, in recent years
The research of macrolide antibiotics selectivity sample pretreating method causes the extensive concern of people.
In recent years, the samples such as molecularly imprinted polymer (MIPs) and Solid Phase Extraction, solid phase microextraction and dispersive solid-phase extraction
The combination of technology of preparing has become the new trend of selective extraction and identification target molecule from complex matrices.Although molecule prints
Mark polymer has broad application prospects.But molecularly imprinted polymer is prepared in traditional bulk polymerization and precipitation polymerization
In technology, since recognition site is deeply inserted in polymer, show that accessibility is poor, affinity is low and barrier diffusion properties
The disadvantages of high.In order to overcome these disadvantages, design trace mesoporous material has been attempted, imprinted material is (highly selective and abundant
Binding cavity) the advantages of combine with the advantages of mesoporous material (quickly diffusion and good accessibility).Although trace is mesoporous
The advantage of material is described in the works of many previous publications, but still limits its application there are four principal element:
(1) strong acid reflux or high-temperature heating are indispensable during removing the common pore-foaming agents such as CTAB；(2) traditional polymerized monomer
As silane and methacrylic acid have refractory organics and poor biocompatibility；(3) knot of analyte and internal recognition site
Conjunction is limited by single meso-hole structure；(4) preparation process complexity is tediously long.Therefore, a kind of mild, bio-compatible and extensively is prepared
Applicable trace mesoporous material is still a challenge.
It therefore, is template using erythromycin, TMB is organic pore-foaming agent, and for F-127 as surfactant, dopamine is function
Can monomer prepare a type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbent and be applied to point
The method for dissipating a variety of macrolide antibiotics in Solid Phase Extraction Sync enrichment animal-derived food is suggested.
Summary of the invention
The purpose of the present invention is to provide a type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticles
Preparation method, the molecularly imprinted polymer are equal to the macrolide antibiotics for ten four to ten hexa-atomic lactone ring structures having
There is good recognition performance.
Technical solution of the present invention is as follows:
The preparation method of one type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbent, feature
It is to carry out as follows:
(1) step 1, synthetic molecules trace poly-dopamine particle: first by the surfactant of 1~5g and 2~5mL
TMB is dissolved in the mixture of ultrapure water (100~600mL) and EtOH (100~500mL), is then ultrasonically treated 5~30 points
Clock.Then, under stiring plus the template molecule of 50~100mg.After 10~50 minutes, 250~600mg TRIS is dissolved in 20
In~100mL ultrapure water, and add it in reaction solution.It is eventually adding 100~500mg Dopamine hydrochloride.It stirs at room temperature
It mixes 12~48 hours, by being centrifugated product grain.
(2) synthesis of step 2, class pomegranate structure hollow mesoporous molecular trace poly-dopamine particle: organic pore-foaming agent is used
Extract liquor under ultrasonic treatment the resulting particle of washing step 1 to remove organic pore template.Then, with imprinted templates molecule
Eluent washs imprinted templates molecule under ultrasonic treatment.Final product is dried in vacuo at 20~100 DEG C for further
It uses.
TMB be joined in the reaction system as organic pore-foaming agent, and remove organic pore-foaming agent.
The imprinted templates molecule, it is any organic for that can interact with poly-dopamine formation hydrogen bond, hydrophobic, π-π
Object.
Surfactant be joined in the reaction system to stablize TMB, can for cationic surfactant, sun from
Sub- surfactant, nonionic surfactant any one.
The template molecule: the molar ratio of function monomer will affect the structure and active site quantity of the nanoparticle,
It can be adjusted in 1: 1.6~16 ranges according to demand when practical preparation
Organic pore-foaming agent: the mass ratio of surfactant will affect the structure snd size of the nanoparticle, practical
It can be adjusted in 1: 1~5 ranges according to demand when preparation.
The eluent of the imprinted templates molecule: organic pore-foaming agent extract liquor is the mixed solution of ethyl alcohol and acetone, print
Mark template molecule elution liquid is that sour (such as: formic acid, acetic acid) or alkali (such as: ammonium hydroxide) are any with organic solvent mixed liquor.
Compared with the prior art, the invention has the advantages that:
1. the advantages of molecularly imprinted polymer and dispersive solid-phase extraction (DSPE) is effectively combined, make the adsorbent not
It is only highly selective with molecularly imprinted polymer, while there is few DSPE amount of samples, short processing time, easy to operate, examination
The advantages that agent consumption is few.
2. being successively eluant, eluent, imprinted templates eluant, eluent with organic pore-foaming agent, the core of no any recognition site is removed
(TMB core) and imprinted templates, obtained hollow mesoporous molecular imprinted polymer have particular cavity structure, increase absorption
Capacity further improves the mass transfer velocity of imprinted material and the ability of unit mass combining target molecule.
3. dopamine can auto polymerization be without crosslinking in alkalinity or aqueous oxidizing solutions, so using dopamine
Novel hollow mesoporous molecular trace poly-dopamine nanoparticle as monomer can simplify experimentation and reduce chemicals
It uses.And compared with conventional polymeric monomer, poly-dopamine is degradable, good biocompatibility.
4. the molecularly imprinted polymer has the macrolide antibiotics with ten four to ten hexa-atomic lactone ring structures
Good recognition performance, extraction recovery is high, can detect, add to plurality of target molecule simultaneously with HPLC-MS/MS combination
The wide detection range of target molecule.
Detailed description of the invention
Fig. 1 prepares the poly- DOPA of class pomegranate structure hollow mesoporous molecular trace in the case where existing and TMB being not present respectively
The schematic diagram of the mechanism of amine nanoparticle adsorbent (a) and molecularly imprinted polymer (b)
Fig. 2 is molecular engram poly-dopamine nanoparticle MIPDA (A), hollow mesoporous non-trace poly-dopamine nanoparticle
The transmission electron microscope picture of NIMPDA (B) and class pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle MIMPDA (C) (D)
Picture.(B)/(C) illustration shows the images of transmissive electron microscope of the amplification of single NIMPDA/MIMPDA particle.(B) in/(D)
Arrow indicates that hollow structure is formed
Fig. 3 is that (A) is used to extract the MIMPDA adsorbent of seven kinds of macrolide antibiotics and the ratio of NIMPDA adsorbent
Compared with.Condition: mark-on is horizontal, 40 μ gkg-1.(B) AZI, SPI, SDA, STR, ENR and OTC are 100 μ gmL in concentration-1When
To the adsorbance of MIMPDA adsorbent and NIMPDA adsorbent
Fig. 4 is analysis of the MIMPDA to 7 kinds of macrolide antibiotic residues objects in true milk sample
Specific embodiment
Technical solution of the present invention is described further below by way of specific embodiment.Test procedure and examination in embodiment
Product and test equipment used are tested, is unless otherwise noted conventional technical means in the art, commercially available conventional products and known instrument
Device.
The preparation method of 1. class pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle of embodiment
(1) Step 1: the synthesis of macrolides molecular engram poly-dopamine particle: first by the F-127 of 0.18g and
The TMB of 0.2085mL is dissolved in the mixture of ultrapure water (30mL) and EtOH (30mL), is then ultrasonically treated 30 minutes.With
Afterwards, the erythromycin of 7.4mg is added under mechanical stirring.After 30 minutes, 45mg TRIS is dissolved in be formed in 5mL ultrapure water and is mixed
Solution is closed, and is added in mixture.Then 30mg dopamine hydrochloride is added.It is small that reaction mixture is stirred at room temperature 24
When, then pass through centrifuge separation product grain.The particle being centrifuged using ethyl alcohol and acetone washing.
(2) Step 2: the synthesis of the hollow porous poly-dopamine particle of macrolides molecular engram: being had by extraction
The removal of machine pore-foaming agent, wherein sample is surpassed in the mixed solution of ethyl alcohol and acetone (volume ratio of ethyl alcohol and acetone is 2: 1)
Sonication (three times, 30 minutes every time).Then, with 20mL eluent (volume ratio of methanol and ammonium hydroxide is 95: 5) supersound washing
Erythromycin imprinted templates molecule 1.5 hours (every 30 minutes update eluents).Final product is dried in vacuo at 60 DEG C for
It further uses.
Embodiment 2.MIMPDA is to macrolides enrichment concentrated effect verifying
(1) electromicroscopic photograph of MIMPDA and NIMPDA
The projection electron microscopic picture of MIMPDA and NIMPDA material is as shown in Figure 2.It can be seen that MIMPDA is through ethyl alcohol and acetone
Mixed liquor eliminate and show hollow porous structure after TMB core, therefore there is biggish specific surface area and aperture body
Product, to have higher adsorption capacity and mass transfer rate.
(2) there are traces in the class pomegranate structure hollow mesoporous molecular trace poly-dopamine nano material in order to verify preparation
Site, respectively using MIMPDA and NIMPDA as dispersive solid-phase extraction material, respectively dissolved with the azithromycin of 40 μ g/kg
(AZI), spiramvcin (SPI), Tilmicosin (TILM), clarithromycin (CLA), josamycin (JOS), roxithromycin
(ROX), the milk sample of tylosin (TYL) is the parallel comparative experiments that sample solution carries out recovery of extraction, and eluent is used
The method of HPLC-MS/MS carries out analysis detection.As a result as shown in Fig. 3, MIMPDA is examined to azithromycin, spiramvcin, for rice
Star, clarithromycin, josamycin, roxithromycin, the enriching and recovering rate of seven kinds of macrolide antibiotics of tylosin are respectively
103.2%, 110.7%, 104.8%, 94.3%, 80.7%, 92.0% and 82.2%.NIMPDA is mould to azithromycin, spiral
The enrichment of element, Tilmicosin, clarithromycin, josamycin, seven kinds of roxithromycin, tylosin macrolide antibiotics is returned
Yield is 11.9%, 12.0%, 20.0%, 7.5%, 6.4%, 6.5% and 7.0% respectively.This shows class pomegranate structure hollow
The matrix effect of actual sample is lower than hollow mesoporous non-trace after the processing of mesoporous molecular trace poly-dopamine nanoparticle adsorbent
Poly-dopamine nanoparticle adsorbent treated matrix effect.It confirmed exist on MIMPDA adsorbent to a certain extent
Specific recognition site, it is seen that MIMPDA has better effect of extracting to macrolide antibiotics.
Embodiment 3. is used to analyze the class pomegranate structure hollow mesoporous molecular trace poly-dopamine of macrolide antibiotics
The method validation of nanoparticle adsorbent
(1) DSPE-HPLC- of the class pomegranate structure hollow mesoporous molecular trace poly-dopamine nano adsorber based on preparation
A series of mixed model macrolide antibiotics building that the linearity of MS/MS method is prepared in milk sample product.Such as one institute of table
Show, in the range of linearity of 0.8-80 μ gkg-1, DSPE-HPLC-MS/MS program is to all 7 macrolide antibiotics
Show good linear, related coefficient (R2) is higher than 0.992.In antibiotic residue analysis, the sensitivity of this method is usual
It is expressed as detection limit (LOD) and quantitative limit (LOQ).During this investigation it turned out, LOD and LOQ are estimated as signal-to-noise ratio (S/N) respectively
Three times and ten times.Data are as shown in Table 1, and the LOD range of 7 macrolide antibiotics is 0.009-0.043 μ g.kg-1,
And LOQ range is 0.030-0.144 μ g.kg-1.We are newly developed to be inhaled based on the mesoporous poly-dopamine nanoparticle of molecular engram
Attached dose of DSPE-HPLC-MS/MS method allows simultaneously and 7 kinds of macrolide antibiotics of Selective Separation, and is used to survey
The detection limit of macrolide antibiotics residue in food matrix is determined far below other analysis methods.Therefore, the advantages of this method
It is set to be more suitable for conventional analysis.
The calibration curve (LODs and LOQ) of one macrolides of table
(2) actual sample analyzes the DSPE-HPLC-MS/ based on the mesoporous poly-dopamine nanoparticle adsorbent of molecular engram
MS program is successfully applied to 7 kinds of macrolide antibiotic residues objects from the true milk sample that local groceries are bought
Analysis.As shown in figure 4, comparing the chromatogram of blank and mark-on milk sample, peak value is not found in blank milk sample.Knot
Fruit shows the concentration of 7 kinds of macrolide antibiotics in true milk sample lower than LOD value.Due to macrolide antibiotics
Low concentration, based on the DSPE of the mesoporous poly-dopamine nanoparticle adsorbent of molecular engram pretreatment before, in mark-on sample
In be unable to the macrolide antibiotics of quantitative detection trace.Based on the mesoporous poly-dopamine nanoparticle absorption of molecular engram
After the DSPE pretreatment of agent, the interference of milk sample is eliminated, the amount of macrolide antibiotics is concentrated and target is big
Cyclic lactone class antibiotic can quantitatively determine.These show that this method is applicable to trace macrolides antibiosis in actual sample
The measurement of element.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
Member, various improvements and modifications may be made without departing from the principle of the present invention, these improvements and modifications should also regard
For protection scope of the present invention.
Claims (7)
1. the preparation method and application of a type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbent,
It is characterized in that carrying out as follows:
(1) step 1, synthetic molecules trace poly-dopamine particle: first that the TMB of the surfactant of 1~5g and 2~5mL is molten
Then solution is ultrasonically treated 5~30 minutes in the mixture of ultrapure water (100~600mL) and EtOH (100~500mL).With
Afterwards, under stiring plus the template molecule of 50~100mg.After 10~50 minutes, 250~600mg TRIS is dissolved in 20~
In 100mL ultrapure water, and add it in reaction solution.It is eventually adding 100~500mg Dopamine hydrochloride.It is stirred at room temperature
12~48 hours, by being centrifugated product grain.
(2) it the synthesis of step 2, class pomegranate structure hollow mesoporous molecular trace poly-dopamine particle: is extracted using organic pore-foaming agent
Liquid under ultrasonic treatment the resulting particle of washing step 1 to remove organic pore-foaming agent.Then, with imprinted templates eluent in ultrasound
Processing is lower to wash imprinted templates molecule.Final product is dried in vacuo at 20~100 DEG C for further use.
2. being inhaled according to any type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle of patent requirements 1
Attached dose of preparation method, it is characterised in that joined TMB in the reaction system as organic pore-foaming agent, and it is organic to remove this
Pore-foaming agent.
3. being inhaled according to any type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle of patent requirements 1
Attached dose of preparation method, it is characterised in that the surfactant being added in the reaction system is the sun that can stablize TMB molecule
Ionic surface active agent, cationic surfactant, nonionic surfactant any one.
4. being inhaled according to any type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle of patent requirements 1
Attached dose of preparation method, it is characterised in that the imprinted templates molecule is that can form hydrogen bond, hydrophobic, π-π phase with poly-dopamine
Any organic matter of interaction.
5. type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle according to claim 1 to 4
The preparation method of adsorbent, it is characterised in that the template molecule: the molar ratio of function monomer will affect the knot of the nanoparticle
Structure and active site quantity can be adjusted in 1: 1.6~16 ranges according to demand when prepared by reality.
6. type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle according to claim 1 to 4
The preparation method of adsorbent, it is characterised in that organic pore-foaming agent: the mass ratio of surfactant will affect the nanoparticle
Structure snd size, when practical preparation can adjust in 1: 1~5 ranges according to demand.
7. type pomegranate structure hollow mesoporous molecular trace poly-dopamine nanoparticle adsorbent according to claim 1
Preparation method and application, it is characterised in that in step (2) organic pore-foaming agent extract liquor be ethyl alcohol and acetone mixed solution, print
Mark template molecule elution liquid is that sour (such as: formic acid, acetic acid) or alkali (such as: ammonium hydroxide) are any with organic solvent mixed liquor.
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