亲水性分子印迹聚合物的制备及其在喹乙醇检测中的应用
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摘要
喹乙醇（2-[N-(2-羟基-乙基)-氨基甲酰]-3-甲基-喹喔啉-1,4-二氧化物），属喹喔啉类抑菌促生长剂。喹乙醇作为一种抗菌促生长剂被广泛应用于畜禽及水产品的养殖中以提高饲料利用率。然而，由于不合理使用，出现残留问题。对此世界各国针对喹乙醇会对动物产生致癌、致突变和光敏反应，从1998年开始禁止将喹乙醇作为饲料添加剂使用。基于以上原因，找到一种准确可靠检测动物饲料中残留喹乙醇技术对于消费者健康来说至关重要。本论文主要研究用水相分子印迹技术对喹乙醇进行富集检测。分子印迹技术是一种发展较快的分析检测技术，主要利用“钥匙－锁”的原理，以喹乙醇为模板，采用不同的功能单体和交联剂，制备有较高识别喹乙醇的聚合物，与高效液相技术或酶联免疫技术联用后能高效检测饲料中痕量喹乙醇含量。
1.喹乙醇分子印迹聚合物的制备及其与固相萃取-高效液相色谱联用检测技术
以喹乙醇作为模板分子，甲基丙烯酸为功能单体，乙二醇二甲基丙烯酸酯为交联剂，水/乙腈（4：6，v/v）为溶剂，偶氮二异丁腈为引发剂，采用本体聚合法制备分子印迹聚合物。通过红外光谱、扫描电镜、吸附动力学实验、吸附平衡实验、选择性实验对制备的聚合物进行表征，实验结果表明此聚合物具有较高识别选择能力，对喹乙醇具有快速吸附效果。将聚合物作为固相萃取材料与高效液相色谱联用进行离线富集检测饲料中喹乙醇，在上样流速为1.6mL min~(-1)，预富集63min条件下，富集倍数为80，最低检测限(S/N=3)为38.0ng L~(-1)，连续在线富集5次的精密度(相对标准偏差，RSD)为4.9%。对添加有喹乙醇浓度为1.0μg g~(-1)和5.0μg g~(-1)的饲料进行检测，其回收率分别为89.8%~97.4%。
2.以壳聚糖为载体制备水相识别分子印迹聚合物及其表征
以离子交联法制备壳聚糖微球，以乙酸乙酯为致孔剂，环氧氯丙烷为交联剂，通过交联法制备出交联化壳聚糖微球。以交联化壳聚糖微球为表面载体，以水和乙腈为混合溶剂，将模板分子（喹乙醇），功能单体（AA）及交联剂（MBA）采用表面分子印迹与溶胶-凝胶法合成喹乙醇分子印迹聚合物。并对新型水相分子印迹聚合进行红外光谱、扫描电镜、吸附动力学实验、吸附平衡实验、选择性实验的表征。实验结果表明以壳聚糖为载体的分子印迹聚合物对喹乙醇的吸附容量为10.14mg g~(-1)，对喹烯酮的分离因子为2.29，乙酰甲喹的分离因子为2.22。以壳聚糖为载体的分子印迹聚合物具有较高识别选择能力，对喹乙醇具有快速吸附效果。
3.亲水性磁性分子印迹聚合物的制备及与固相萃取-高效液相色谱联用检测技术
采用溶胶一凝胶法制备二氧化硅包覆壳的磁性四氧化三铁纳米粒子，以喹乙醇为模板，以水和乙腈为反应溶剂，硅烷化Fe_3O_4为载体，将模板分子（喹乙醇），功能单体（AA）及交联剂（EGDMA）按1:2:4比例采用表面分子印迹技术制得分子印迹聚合物。通过对磁性纳米粒子和分子印迹聚合物进行红外光谱、热重分析、扫描电镜、聚合物吸附动力学实验、吸附平衡实验、选择性实验表征，实验结果表明此聚合物具有较高识别选择能力，对喹乙醇具有快速吸附效果。将聚合物作为固相萃取材料与高效液相色谱联用进行离线富集检测饲料中喹乙醇，在上样流速为2.0mL min~(-1)，预富集50min条件下，富集倍数为95，最低检测限（S/N=3）为32.0ng L~(-1)，连续在线富集5次的精密度（相对标准偏差，RSD）为4.7%。对添加有喹乙醇浓度为1.0μg g~(-1)和5.0μg g~(-1)的饲料进行检测，其回收率分别为90.2%~98.2%。
4.新型可控水相分子印迹膜的制备及在仿生酶联免疫检测中应用
该方法通过本体聚合法直接在96孔酶标板孔穴表面上合成了喹乙醇水相分子印迹膜，该聚合物膜对喹乙醇具有很好的结合能力和特异性识别能力。以制备的印迹膜作为仿生抗体，建立了仿生酶联免疫分析（BELISA）方法。在最佳的条件下，该BELISA方法的灵敏度(IC_(50))和最低检测限(IC_(15))分别为700±60μg L~(-1)和17±1.6μg L~(-1)。对结构类似物的交叉反应率为12%和6.2%；该方法的添加回收率在89%~96%范围内。
Olaquindox as an antimicrobial growth accelerant, is usually added into chick feed tocontrol chick dysentery and bacterial enteritis in young chick. However, due to the possiblecarcinogenic, mutagenic, and photoallergenic effects, its use as an additive in animalfeedstuffs have been prohibited in the European Union and many other countries. In order toprotect human health, an accurate and reliable analytical method for the determination ofolaquindox in the feed samples is required. The aim of this paper is to study the determinationof preconcentration of olaquindox using molecular imprinting technology in aqueous phase.MIT is one of the most promising approaches whose principle came from “Key-Lock”. In thepresent work, we prepared four new hydrophilic functionalized materials in aqueous solutionby a series of molecular imprinting techniques in combination with high pressure liquidchromatography or enzyme-linked immunospot assay.
(1) Separation and determination of olaquindox using molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography
A new and hydrophilic molecularly imprinted polymer (MIP), selective for olaquindox,was prepared by bulk polymerization technique using olaquindox as the template, methacrylicacid as the functional monomer, and ethylene glycoldimethacrylate as the cross-linker. Thesynthesized polymer was characterized by Fourier transform infrared and static adsorptionexperiments, and the results showed that the MIP had good recognition and selective abilityfor olaquindox. A novel method of molecularly imprinted solid-phase extraction coupled withhigh-performance liquid chromatography (HPLC) was developed for separation anddetermination of trace olaquindox in feed samples. Under the selected experimental condition,the detection limit (S/N=3) was38.0ng L~(-1), and the RSD for five replicate extractions of50μg L~(-1)olaquindox was4.9%. This method was employed for quantitative determination ofolaquindox in fish feed with recoveries ranging from89.8~97.4%.
(2) Chitosan beads as molecularly imprinted polymer matrix for selectiveseparation of olaquindox in aqueous phase
A simple molecularly imprinted polymer (MIP) was prepared using olaquindox as theimprinted molecule and acrylamide as the functional monomer. The MIP was achieved bygrafting of the selective soft polyacrylamide gel to the chitosan beads by letting the monomers and the template molecule diffuse into the pores of the chitosan matrix before starting thepolymerization. This prepared material was evaluated by FT-IR spectra, SEM images, andstatic adsorption experiments. The adsorption test indicated that the imprinted polymerexhibited higher selectivity and adsorption capacity toward olaquindox than that ofstructurally related compounds. The adsorption capacity of the imprinted polymer were10.14mg g~(-1). The MIP has much higher adsorption capacity for OLA than the non-imprintedpolymer with the same chemical composition, and also has a higher selectivity for theimprinted molecule.
(3) Core-shell magnetic molecularly imprinted solid phase extraction coupled withhigh-performance liquid chromatography for recognition of olaquindox.
The magnetic nanoparticles were synthesized by the chemical coprecippitation of Fe2+and Fe3+in an ammonia solution. Subsequently, silica was coated on the Fe_3O_4nanoparticlesusing a sol-gel method to obtain silica shell magnetic nanoparticles. Subsequently,acrylamide(AA) as the functional monomer, and ethylene glycoldimethacrylate(EGDMA) asthe cross-linker. The synthesized polymer was coated onto the silica-modified Fe_3O_4surfacethrough oxidation with AIBN in an aqueous solution. The polymer was characterized byFourier transform infrared spectra, static adsorption experiments and thermogtavimetricanalysis. The results showed that the MIP had good recognition and selective ability forolaquindox. A novel method of molecularly imprinted solid-phase extraction coupled withhigh-performance liquid chromatography (HPLC) was developed for separation anddetermination of trace olaquindox in feed samples. Under the selected experimental condition,the detection limit (S/N=3) was32.0ng L~(-1), and the RSD for five replicate extractions of50μg L~(-1)olaquindox was4.7%. This method was employed for quantitative determination ofolaquindox in fish feed with recoveries ranging from90.2%~98.2%.
(4) Development of a biomimetic Enzyme-Linked Immunosorbent Assay Methodbased on a hydrophilic molecularly imprinted polymer film for determination ofolaquindox
We developed a fast and new competitive biomimetic enzyme-linked immunosorbentassay (BELISA) method for the determination of olaquindox in chick feed based on a novelmolecularly imprinted film as an artificial antibody. The imprinted film was directlysynthesized on the well surface of Maxisorp polystyrene96-well plate by bulk polymerizationwith molecular imprinting technique. Then the experimental conditions which areconcentration of enzyme conjugate, diluent choice and pH values were optimized through theexperiments followed by the establishment of the standard curve. Using it as the recognition element, a fast and new direct competitive biomimetic enzyme-linked immunosorbent assay(BELISA) method for the determination of olaquindox in feed was developed. This BELISAmethod had low cross-reactivities of6.2%and12%for two analogues. Under the optimalconditions, the sensitivity (IC_(50)) and the limit of detection (IC_(15)) were700±60μgL~(-1)and17±1.6μg L~(-1), respectively. The blank chick feed samples spiked with olaquindox at threelevels were determined by this developed method with recoveries ranging from89.0%~96.0%
1.喹乙醇分子印迹聚合物的制备及其与固相萃取-高效液相色谱联用检测技术
以喹乙醇作为模板分子，甲基丙烯酸为功能单体，乙二醇二甲基丙烯酸酯为交联剂，水/乙腈（4：6，v/v）为溶剂，偶氮二异丁腈为引发剂，采用本体聚合法制备分子印迹聚合物。通过红外光谱、扫描电镜、吸附动力学实验、吸附平衡实验、选择性实验对制备的聚合物进行表征，实验结果表明此聚合物具有较高识别选择能力，对喹乙醇具有快速吸附效果。将聚合物作为固相萃取材料与高效液相色谱联用进行离线富集检测饲料中喹乙醇，在上样流速为1.6mL min~(-1)，预富集63min条件下，富集倍数为80，最低检测限(S/N=3)为38.0ng L~(-1)，连续在线富集5次的精密度(相对标准偏差，RSD)为4.9%。对添加有喹乙醇浓度为1.0μg g~(-1)和5.0μg g~(-1)的饲料进行检测，其回收率分别为89.8%~97.4%。
2.以壳聚糖为载体制备水相识别分子印迹聚合物及其表征
以离子交联法制备壳聚糖微球，以乙酸乙酯为致孔剂，环氧氯丙烷为交联剂，通过交联法制备出交联化壳聚糖微球。以交联化壳聚糖微球为表面载体，以水和乙腈为混合溶剂，将模板分子（喹乙醇），功能单体（AA）及交联剂（MBA）采用表面分子印迹与溶胶-凝胶法合成喹乙醇分子印迹聚合物。并对新型水相分子印迹聚合进行红外光谱、扫描电镜、吸附动力学实验、吸附平衡实验、选择性实验的表征。实验结果表明以壳聚糖为载体的分子印迹聚合物对喹乙醇的吸附容量为10.14mg g~(-1)，对喹烯酮的分离因子为2.29，乙酰甲喹的分离因子为2.22。以壳聚糖为载体的分子印迹聚合物具有较高识别选择能力，对喹乙醇具有快速吸附效果。
3.亲水性磁性分子印迹聚合物的制备及与固相萃取-高效液相色谱联用检测技术
采用溶胶一凝胶法制备二氧化硅包覆壳的磁性四氧化三铁纳米粒子，以喹乙醇为模板，以水和乙腈为反应溶剂，硅烷化Fe_3O_4为载体，将模板分子（喹乙醇），功能单体（AA）及交联剂（EGDMA）按1:2:4比例采用表面分子印迹技术制得分子印迹聚合物。通过对磁性纳米粒子和分子印迹聚合物进行红外光谱、热重分析、扫描电镜、聚合物吸附动力学实验、吸附平衡实验、选择性实验表征，实验结果表明此聚合物具有较高识别选择能力，对喹乙醇具有快速吸附效果。将聚合物作为固相萃取材料与高效液相色谱联用进行离线富集检测饲料中喹乙醇，在上样流速为2.0mL min~(-1)，预富集50min条件下，富集倍数为95，最低检测限（S/N=3）为32.0ng L~(-1)，连续在线富集5次的精密度（相对标准偏差，RSD）为4.7%。对添加有喹乙醇浓度为1.0μg g~(-1)和5.0μg g~(-1)的饲料进行检测，其回收率分别为90.2%~98.2%。
4.新型可控水相分子印迹膜的制备及在仿生酶联免疫检测中应用
该方法通过本体聚合法直接在96孔酶标板孔穴表面上合成了喹乙醇水相分子印迹膜，该聚合物膜对喹乙醇具有很好的结合能力和特异性识别能力。以制备的印迹膜作为仿生抗体，建立了仿生酶联免疫分析（BELISA）方法。在最佳的条件下，该BELISA方法的灵敏度(IC_(50))和最低检测限(IC_(15))分别为700±60μg L~(-1)和17±1.6μg L~(-1)。对结构类似物的交叉反应率为12%和6.2%；该方法的添加回收率在89%~96%范围内。
Olaquindox as an antimicrobial growth accelerant, is usually added into chick feed tocontrol chick dysentery and bacterial enteritis in young chick. However, due to the possiblecarcinogenic, mutagenic, and photoallergenic effects, its use as an additive in animalfeedstuffs have been prohibited in the European Union and many other countries. In order toprotect human health, an accurate and reliable analytical method for the determination ofolaquindox in the feed samples is required. The aim of this paper is to study the determinationof preconcentration of olaquindox using molecular imprinting technology in aqueous phase.MIT is one of the most promising approaches whose principle came from “Key-Lock”. In thepresent work, we prepared four new hydrophilic functionalized materials in aqueous solutionby a series of molecular imprinting techniques in combination with high pressure liquidchromatography or enzyme-linked immunospot assay.
(1) Separation and determination of olaquindox using molecularly imprinted solid-phase extraction coupled with high-performance liquid chromatography
A new and hydrophilic molecularly imprinted polymer (MIP), selective for olaquindox,was prepared by bulk polymerization technique using olaquindox as the template, methacrylicacid as the functional monomer, and ethylene glycoldimethacrylate as the cross-linker. Thesynthesized polymer was characterized by Fourier transform infrared and static adsorptionexperiments, and the results showed that the MIP had good recognition and selective abilityfor olaquindox. A novel method of molecularly imprinted solid-phase extraction coupled withhigh-performance liquid chromatography (HPLC) was developed for separation anddetermination of trace olaquindox in feed samples. Under the selected experimental condition,the detection limit (S/N=3) was38.0ng L~(-1), and the RSD for five replicate extractions of50μg L~(-1)olaquindox was4.9%. This method was employed for quantitative determination ofolaquindox in fish feed with recoveries ranging from89.8~97.4%.
(2) Chitosan beads as molecularly imprinted polymer matrix for selectiveseparation of olaquindox in aqueous phase
A simple molecularly imprinted polymer (MIP) was prepared using olaquindox as theimprinted molecule and acrylamide as the functional monomer. The MIP was achieved bygrafting of the selective soft polyacrylamide gel to the chitosan beads by letting the monomers and the template molecule diffuse into the pores of the chitosan matrix before starting thepolymerization. This prepared material was evaluated by FT-IR spectra, SEM images, andstatic adsorption experiments. The adsorption test indicated that the imprinted polymerexhibited higher selectivity and adsorption capacity toward olaquindox than that ofstructurally related compounds. The adsorption capacity of the imprinted polymer were10.14mg g~(-1). The MIP has much higher adsorption capacity for OLA than the non-imprintedpolymer with the same chemical composition, and also has a higher selectivity for theimprinted molecule.
(3) Core-shell magnetic molecularly imprinted solid phase extraction coupled withhigh-performance liquid chromatography for recognition of olaquindox.
The magnetic nanoparticles were synthesized by the chemical coprecippitation of Fe2+and Fe3+in an ammonia solution. Subsequently, silica was coated on the Fe_3O_4nanoparticlesusing a sol-gel method to obtain silica shell magnetic nanoparticles. Subsequently,acrylamide(AA) as the functional monomer, and ethylene glycoldimethacrylate(EGDMA) asthe cross-linker. The synthesized polymer was coated onto the silica-modified Fe_3O_4surfacethrough oxidation with AIBN in an aqueous solution. The polymer was characterized byFourier transform infrared spectra, static adsorption experiments and thermogtavimetricanalysis. The results showed that the MIP had good recognition and selective ability forolaquindox. A novel method of molecularly imprinted solid-phase extraction coupled withhigh-performance liquid chromatography (HPLC) was developed for separation anddetermination of trace olaquindox in feed samples. Under the selected experimental condition,the detection limit (S/N=3) was32.0ng L~(-1), and the RSD for five replicate extractions of50μg L~(-1)olaquindox was4.7%. This method was employed for quantitative determination ofolaquindox in fish feed with recoveries ranging from90.2%~98.2%.
(4) Development of a biomimetic Enzyme-Linked Immunosorbent Assay Methodbased on a hydrophilic molecularly imprinted polymer film for determination ofolaquindox
We developed a fast and new competitive biomimetic enzyme-linked immunosorbentassay (BELISA) method for the determination of olaquindox in chick feed based on a novelmolecularly imprinted film as an artificial antibody. The imprinted film was directlysynthesized on the well surface of Maxisorp polystyrene96-well plate by bulk polymerizationwith molecular imprinting technique. Then the experimental conditions which areconcentration of enzyme conjugate, diluent choice and pH values were optimized through theexperiments followed by the establishment of the standard curve. Using it as the recognition element, a fast and new direct competitive biomimetic enzyme-linked immunosorbent assay(BELISA) method for the determination of olaquindox in feed was developed. This BELISAmethod had low cross-reactivities of6.2%and12%for two analogues. Under the optimalconditions, the sensitivity (IC_(50)) and the limit of detection (IC_(15)) were700±60μgL~(-1)and17±1.6μg L~(-1), respectively. The blank chick feed samples spiked with olaquindox at threelevels were determined by this developed method with recoveries ranging from89.0%~96.0%
引文
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