CN105498721A - Aflatoxin molecularly imprinted material and preparation method thereof - Google Patents

Aflatoxin molecularly imprinted material and preparation method thereof Download PDF

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CN105498721A
CN105498721A CN201510820896.2A CN201510820896A CN105498721A CN 105498721 A CN105498721 A CN 105498721A CN 201510820896 A CN201510820896 A CN 201510820896A CN 105498721 A CN105498721 A CN 105498721A
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aflatoxin
preparation
molecular engram
engram material
molecularly imprinted
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CN105498721B (en
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方国臻
张璐璐
王俊平
王硕
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Tianjin University of Science and Technology
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26Synthetic macromolecular compounds
    • B01J20/268Polymers created by use of a template, e.g. molecularly imprinted polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/281Sorbents specially adapted for preparative, analytical or investigative chromatography
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30Processes for preparing, regenerating, or reactivating
    • B01J20/305Addition of material, later completely removed, e.g. as result of heat treatment, leaching or washing, e.g. for forming pores
    • B01J20/3057Use of a templating or imprinting material ; filling pores of a substrate or matrix followed by the removal of the substrate or matrix
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0605Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0616Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/26Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00Sampling; Preparing specimens for investigation
    • G01N1/28Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/34Purifying; Cleaning
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N1/00Sampling; Preparing specimens for investigation
    • G01N1/28Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
    • G01N1/40Concentrating samples
    • G01N1/405Concentrating samples by adsorption or absorption
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/40Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/44Materials comprising a mixture of organic materials
    • B01J2220/445Materials comprising a mixture of organic materials comprising a mixture of polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/40Aspects relating to the composition of sorbent or filter aid materials
    • B01J2220/48Sorbents characterised by the starting material used for their preparation
    • B01J2220/4812Sorbents characterised by the starting material used for their preparation the starting material being of organic character
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/50Aspects relating to the use of sorbent or filter aid materials
    • B01J2220/54Sorbents specially adapted for analytical or investigative chromatography
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2220/00Aspects relating to sorbent materials
    • B01J2220/80Aspects related to sorbents specially adapted for preparative, analytical or investigative chromatography
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C08J2379/04Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors

Abstract

The present invention provides an aflatoxin molecularly imprinted material using a supported ionic liquid as a carrier. The present invention also discloses a preparation method of the molecularly imprinted material is as follows: (1) aflatoxin structural analog 1,4-naphthalene dicarboxylic acid as a template molecule is added into a DMF solution, and fully dissolved by stirring, a functional-monomer-supported ionic liquid is added and stirred for 30min, then tetraethoxysilane and catalyst ammonia are added, and incubation is performed for 24h in a water bath at 40 DEG C, and (2) filtering by suction. Advantages are that the supported ionic liquid is introduced to be used as the carrier, a large surface area is provided, and the molecularly imprinted material can be synthesized by surface-sol-gel method. The molecularly imprinted material is low in cost, simple in synthesis process, easy in control of reaction conditions, uniform in particle size, and high in aflatoxin selectivity. The molecularly imprinted material can be used in solid phase extraction enrichment, can be used for separation enrichment of aflatoxin in a variety of food samples by combination with high performance liquid chromatography, and has broad application prospects.

Description

A kind of aflatoxin molecular engram material and preparation method thereof
Technical field
The invention belongs to technical field of polymer materials, especially relate to a kind of enriched with trace aflatoxin (B 1, B 2, G 1, G 2) molecular engram material and preparation method thereof.
Background technology
Aflatoxin (AFT) is the compound that one group of chemical constitution is similar, has been separated at present and has identified 12 kinds, and main molecules pattern is containing B 1, B 2, G 1, G 2, M 1, M 2deng.It is 1 class carcinogenic substance that aflatoxin delimited by the Agency for Research on Cancer of the World Health Organization (WHO), is the extremely strong extremely toxic substance of a kind of toxicity.Aflatoxin is present in soil, animals and plants, various nut, particularly peanut and walnut.Also often aflatoxin is found in soybean, paddy, corn, macaroni, flavouring, milk, dairy produce, edible wet goods goods.
Along with people are to the quick rising of food security attention rate, the quick detection of toxin has become the development trend of research both at home and abroad.But it is long that thin film chromatography, liquid chromatography, gold test strip method and immune affinity column method have sense cycle, and needed for program complexity, reagent is various, testing cost crosses the shortcomings such as high, can not meet modern measure requirement far away.Along with the development of molecular imprinting and improving constantly of mycotoxin testing requirement, the application of molecular imprinting in mycotoxin detects is more and more extensive.Be filled in by molecularly imprinted polymer in solid phase extraction column, can be used for the separation of sample, purifying and concentrated, compared with antibody, molecularly imprinted polymer preparation process is simple, good stability, long service life.But at present owing to there is no suitable molecule marking material aflatoxin to very strong recognition function, so also do not widely use molecular engram method to detect aflatoxin.
Summary of the invention
In view of this, the invention is intended to propose one to aflatoxin (B 1, B 2, G 1, G 2) there is the molecular engram material of high selectivity.
The present invention utilizes function monomer load-type ion liquid for carrier, and surface sol-gel method synthesizes a kind of for selective enrichment trace aflatoxin (B 1, B 2, G 1, G 2) sorbing material.This material can be used as SPE material, can overcome the preprocessing process of environmental sample system complexity, and for the enrichment of sample provides great convenience with being separated, compared with immune affinity column, cost is also low.Play an important role in the trace analysis of field of food, there is usability.
For achieving the above object, the technical scheme of the invention is achieved in that
Adopt function monomer load-type ion liquid as carrier, synthesize a kind of aflatoxin (B 1, B 2, G 1, G 2) molecular engram material.
Molecular engram material of the present invention is to aflatoxin (B 1, B 2, G 1, G 2) there is very strong recognition function.
The invention also discloses the preparation method of this molecular engram material:
A preparation method for aflatoxin molecular engram material, comprises the steps:
(1) the analogue DMC of aflatoxin is joined in DMF solution as template molecule, stirring makes it fully dissolve, and adds function monomer load-type ion liquid, stirs 30min, add tetraethoxysilane and catalyst again, 40 DEG C of water-bath hatching 24h;
(2) step (1) products therefrom is first used DMF drip washing, then remove unreacted reactant with methyl alcohol drip washing, 50 DEG C of aging 8h of vacuum drying; Product after aging is put in soxhlet's extractor, washes away template molecule; 50 DEG C of vacuum drying, obtain molecular engram material aflatoxin to high selectivity.
Further, in step (1), the mass ratio of DMC and load-type ion liquid is 0.5-1:1; The volume ratio of tetraethoxysilane and catalyst is 5-6:1.
Further, step (1) described catalyst is ammoniacal liquor.
Further, washing away template molecule in step (2) is use volume ratio for after 8-10:1 methyl alcohol and glacial acetic acid mixed solution surname extraction 48h, then uses methyl alcohol surname extraction 12h, till detecting without DMC in extract.Obtain molecularly imprinted polymer of the present invention (MIP).
With function monomer load-type ion liquid for support, synthesize molecular engram material aflatoxin to high selectivity; The class material that the function monomer load-type ion liquid used is core is imidazole ring, structural formula be:
X -=Br -、NTf 2 -、BF 4 -、PF 6 -
According to the method described above, but do not add template molecule DMC, the non-imprinted polymer (NIP) that preparation the present invention is corresponding.
Aflatoxin molecular engram material of the present invention, for the quick detection of aflatoxin in food.
Relative to prior art, the preparation method of the aflatoxin molecular engram material described in the invention and be applied in during aflatoxin detects there is following advantage:
The molecular engram material that the present invention utilizes surface sol-gel method to synthesize, has mass transfer velocity fast, and specific area is large, the advantage that grain diameter is homogeneous.This material can quick adsorption aflatoxin, has strong selective to object; This material is chemically prepared, and has good stability, longer service life.The present invention is with low cost, and experimental implementation is simple, easy control of reaction conditions, and obtained aflatoxin molecularly imprinted polymer, as the filler of SPE and liquid chromatogram coupling, is applicable to the separation and consentration of trace aflatoxin in food.Compared with commercial immune affinity column, this material has easy to prepare, selective height, the advantage that cost is low.
Accompanying drawing explanation
The accompanying drawing of the part of formation the invention is used to provide the further understanding to the invention, and the schematic description and description of the invention, for explaining the invention, does not form the improper restriction to the invention.
Accompanying drawing explanation
Fig. 1 molecularly imprinted polymer and non-imprinted polymer dynamic experiment;
Fig. 2 ochratoxin A (OTA) is aflatoxin (B 1, B 2, G 1, G 2) competitor, study the selectivity of this molecular engram material.
Detailed description of the invention
In order to make the above-mentioned feature and advantage of the present invention clearly and easy understand, below in conjunction with accompanying drawing, embodiments of the present invention are described in further detail.
Load-type ion liquid described in following embodiment is oneself synthesis, other (DMC, aflatoxin (B 1, B 2, G 1, G 2), tetraethoxysilane, ammoniacal liquor, DMF, methyl alcohol, glacial acetic acid) be commercially available, use before without any process.
Embodiment 1
A kind of aflatoxin (B 1, B 2, G 1, G 2) preparation of molecular engram material:
(1) 0.6mmolDMC is joined in 1.7mlDMF, stir 15min to dissolving completely, add 100mg load-type ion liquid, continue to stir 30min, add 9mmol tetraethoxysilane subsequently, stirring reaction 30min, then add 0.4ml ammoniacal liquor (3.0mol/L), stirring reaction 20min, 40 DEG C of water-bath hatching 24h;
(2) suction filtration, first uses DMF drip washing, then washes away unreacted reactant further with methyl alcohol, and 50 DEG C of aging 8h in vacuum drying chamber, repeatedly extract 48h by the methanol acetic acid that volume ratio is 9:1, then use methanol extraction 12h, till detecting without DMC in extract.50 DEG C of vacuum drying, obtain aflatoxin (B 1, B 2, G 1, G 2) there is the molecular engram material of high selectivity.
According to the method described above, do not add DMC, the non-imprinted polymer that preparation the present invention is corresponding.
Embodiment 2
Study the absorption property of this molecular engram material.The molecularly imprinted polymer of 4mg is placed in 2ml centrifuge tube, add respectively 1.5ml variable concentrations (10,20,30,40,50,60,80,100,120,150,200mg/L) DMC methyl alcohol standard liquid, at room temperature vibrate 4h, and under 15 DEG C and 4000r/min centrifugal 15min.The supernatant accurately pipetting 400 μ l is diluted to 4ml, measures the absorbance of DMC at ultraviolet-visible spectrophotometer (λ=327nm) place, calculates the concentration of DMC, finally calculate adsorption capacity according to calibration curve.Simultaneously parallelly do non-imprinted polymer and test the adsorptive selectivity of DMC, wherein molecularly imprinted polymer and non-imprinted polymer all need to do blank assay, and the molecularly imprinted polymer by 4mg is placed in 2ml centrifuge tube, add the methyl alcohol of 1.5mlDMC respectively.Along with the rising of DMC concentration, adsorption capacity increases gradually, finally keeps balance gradually.Under same concentrations, the adsorption capacity of molecularly imprinted polymer is greater than the adsorption capacity (Fig. 1) of non-imprinted polymer.
Embodiment 3
Study the dynamic performance of this molecular engram material.The molecularly imprinted polymer of 4mg is placed in 2ml centrifuge tube, add the DMC methyl alcohol standard liquid of 1.5ml100mg/L, at room temperature vibrate 10 respectively, 20,30,40,60,90,120,160,200,300,360min, centrifugal 15min under 15 DEG C and 4000r/min condition.The supernatant accurately pipetting 400 μ l is diluted to 4ml, measures the absorbance of DMC at ultraviolet-visible spectrophotometer (λ=327nm) place, calculates the concentration of DMC, finally calculate adsorption capacity according to calibration curve.Simultaneously parallelly do non-imprinted polymer and test the adsorptive selectivity of DMC, wherein molecularly imprinted polymer and non-imprinted polymer all need to do blank assay, and the molecularly imprinted polymer by 4mg is placed in 2ml centrifuge tube, add the methyl alcohol of 1.5mlDMC respectively.Imprinted polymer to object be adsorbed on 60min time almost reach balance.
Embodiment 4
Ochratoxin A (OTA) is selected to be aflatoxin (B 1, B 2, G 1, G 2) competitor, study the selectivity of this molecular engram material.Compound concentration is OTA and the aflatoxin (B of 1.0 μ g/L respectively 1, B 2, G 1, G 2) list mark solution.The solution prepared by 4mL, by solid phase extraction column, by methanol-eluted fractions, detects with high performance liquid chromatography.(Fig. 2)
The foregoing is only the preferred embodiment of the invention; not in order to limit the invention; within all spirit in the invention and principle, any amendment done, equivalent replacement, improvement etc., within the protection domain that all should be included in the invention.

Claims (8)

1. an aflatoxin molecular engram material, is characterized in that, using function monomer charge type ionic liquid is carrier.
2. the preparation method of a kind of aflatoxin molecular engram material described in claim 1, is characterized in that, comprise the steps:
(1) the analogue DMC of aflatoxin is joined in DMF solution as template molecule, stirring makes it fully dissolve, and adds function monomer load-type ion liquid, stirs 30min, add tetraethoxysilane and catalyst again, 40 DEG C of water-bath hatching 24h;
(2) step (1) products therefrom is first used DMF drip washing, then remove unreacted reactant with methyl alcohol drip washing, 50 DEG C of aging 8h of vacuum drying; Product after aging is put in soxhlet's extractor, washes away template molecule; 50 DEG C of vacuum drying, obtain molecular engram material aflatoxin to high selectivity.
3. the preparation method of a kind of aflatoxin molecular engram material according to claim 2, is characterized in that: in step (1), the mass ratio of DMC and load-type ion liquid is 0.5-1:1; The volume ratio of tetraethoxysilane and catalyst is 5-6:1.
4. the preparation method of a kind of aflatoxin molecular engram material according to claim 2, is characterized in that: in step (1), the mass ratio of DMC and load-type ion liquid is 0.97:1; The volume ratio of tetraethoxysilane and catalyst is 5.01:1.
5. the preparation method of a kind of aflatoxin molecular engram material according to the arbitrary claim of claim 2-4, is characterized in that, step (1) described catalyst is ammoniacal liquor.
6. the preparation method of a kind of aflatoxin molecular engram material according to claim 2, it is characterized in that: washing away template molecule in step (2) is use volume ratio for after 8-10:1 methyl alcohol and glacial acetic acid mixed solution surname extraction 48h, use methyl alcohol surname extraction 12h again, till detecting without DMC in extract.
7. the preparation method of a kind of aflatoxin molecular engram material according to claim 2, it is characterized in that: washing away template molecule in step (2) is use volume ratio for after 9:1 methyl alcohol and glacial acetic acid mixed solution surname extraction 48h, use methyl alcohol surname extraction 12h again, till detecting without DMC in extract.
8. according to a kind of aflatoxin molecular engram material prepared by the preparation method of the arbitrary claim of claim 1-7, it is characterized in that, for the quick detection of aflatoxin in food.
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CN107179367A (en) * 2017-06-15 2017-09-19 青岛斯比密科学仪器有限公司 A kind of SPE columns in series and preparation method for Mycotoxin identification
CN107955171A (en) * 2017-12-26 2018-04-24 珠海健帆生物科技股份有限公司 A kind of preparation method and adsorbent equipment of protein binding toxin imprinted silica gel adsorbent
CN109293938A (en) * 2018-10-11 2019-02-01 河南工业大学 Prepare the composite material of metallic framework compound binding molecule imprinted polymer
CN110183594A (en) * 2019-06-12 2019-08-30 河南工业大学 Aflatoxin surface imprinted polymer and its application based on SBA-15
CN113262766A (en) * 2021-05-17 2021-08-17 河南水利与环境职业学院 Aflatoxin porous aromatic skeleton PAF-6 molecularly imprinted material and application thereof

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107179367A (en) * 2017-06-15 2017-09-19 青岛斯比密科学仪器有限公司 A kind of SPE columns in series and preparation method for Mycotoxin identification
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CN107955171A (en) * 2017-12-26 2018-04-24 珠海健帆生物科技股份有限公司 A kind of preparation method and adsorbent equipment of protein binding toxin imprinted silica gel adsorbent
CN107955171B (en) * 2017-12-26 2021-01-05 健帆生物科技集团股份有限公司 Preparation method and adsorption device of protein-bound toxin imprinted silica gel adsorbent
CN109293938A (en) * 2018-10-11 2019-02-01 河南工业大学 Prepare the composite material of metallic framework compound binding molecule imprinted polymer
CN110183594A (en) * 2019-06-12 2019-08-30 河南工业大学 Aflatoxin surface imprinted polymer and its application based on SBA-15
CN113262766A (en) * 2021-05-17 2021-08-17 河南水利与环境职业学院 Aflatoxin porous aromatic skeleton PAF-6 molecularly imprinted material and application thereof
CN113262766B (en) * 2021-05-17 2023-03-21 河南水利与环境职业学院 Aflatoxin porous aromatic skeleton PAF-6 molecularly imprinted material and application thereof

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