色谱 ›› 2020, Vol. 38 ›› Issue (1): 104-112.DOI: 10.3724/SP.J.1123.2019.06013
何忠禹, 崔亚涵, 黄宁, 杨树良, 陈艳华(), 丁兰()
收稿日期:
2019-06-24
出版日期:
2020-01-08
发布日期:
2020-12-11
通讯作者:
陈艳华,丁兰
作者简介:
丁兰, E-mail:dinglan@jlu.edu.cn基金资助:
HE Zhongyu, CUI Yahan, HUANG Ning, YANG Shuliang, CHEN Yanhua(), DING Lan()
Received:
2019-06-24
Online:
2020-01-08
Published:
2020-12-11
Contact:
CHEN Yanhua,DING Lan
Supported by:
摘要:
β-环糊精(β-CD)及其衍生物作为一种新兴的功能单体在分子印迹技术中得到了越来越多的应用。β-CD及其衍生物能够与许多分子形成主-客体包合物,基于这一包合作用制备的分子印迹聚合物具有稳定性好和选择性高等优点,因此在具有复杂基质的环境和食品样品中目标化合物的选择性分离和富集中得到了重视和发展。该综述主要回顾了2013年以来文献中报道的一些基于β-CD及其衍生物作为功能单体的分子印迹聚合物在环境水和食品样品前处理方面的最新应用,揭示这一分子印迹聚合物在复杂样品前处理中的优势。
何忠禹, 崔亚涵, 黄宁, 杨树良, 陈艳华, 丁兰. 基于β-环糊精的分子印迹聚合物在环境和食品样品前处理中的应用进展[J]. 色谱, 2020, 38(1): 104-112.
HE Zhongyu, CUI Yahan, HUANG Ning, YANG Shuliang, CHEN Yanhua, DING Lan. Progress in application of molecularly imprinted polymers based on β-cyclodextrin to environmental and food sample pretreatment[J]. Chinese Journal of Chromatography, 2020, 38(1): 104-112.
图1 BPA-印迹CD-PLL水凝胶制备示意图[31]
Fig. 1 Preparation scheme of the BPA-imprinted CD-PLL hydrogel by molecular imprinting[31] BPA: bisphenol A; CD-PLL: cyclodextrin-introduced poly(L-lysine); PEGDE: poly-(ethylene glycol) diglycidyl ether.
图2 Fe3O4-MAH-β-CD@MIP的制备方案及外加磁场条件下去除2-氨基吡啶[40]
Fig. 2 Scheme of preparation of Fe3O4-MAH-β-CD@MIP and application for removal of 2-aminopyridine with external magnetic field[40] MAH: maleic anhydride; β-CD: β-cyclodextrin; MIP: molecularly imprinted polymers; 2-AP: 2-aminopyridine; MAA: methacrylic acid; EGDMA: ethyleneglycol dimethacrylate; AIBN: 2, 2′-azobis (2-methylpropionitrile).
Sample type | Target | Functional monomers | Crosslinker | Method for sample pretreatment | Reference |
MAA-β-CD: methacrylic acid functionalized β-cyclodextrin; β-CD-1: mono-(6-N-allylamino-6-deoxy)-β-cyclodextrin; β-CD-2: mono-(6-N-diallylamine-6-deoxy)-β-cyclodextrin; β-CD-3: mono-(6-N-ethylenediamine (N-(2-bis(2-hydroxy-5-hexene))) (N-(2-hydroxy-5-hexene))-6-deoxy)-β-cyclodextrin; β-CD-4: mono-(6-N-ethylenediamine (N-(2-bis (2-hydroxy-7-octene))) (N-(2-hydroxy-7-octene))-6-deoxy)-β-cyclodextrin; β-CD: β-cyclodextrin; MA-β-CD: methylacryloyl-β-cyclodextrin; CTs: chitosan; TRIM: trimethylolpropane trimethacrylate; SPME: solid-phase microextraction; d-SPE: dispersive solid-phase extraction. | |||||
Tap and river waters | 2, 4-dichlorophenol | MAA-β-CD | TRIM | SPE | [ |
River water | p-nitrophenol | β-CD-1, β-CD-2, β-CD-3 | EGDMA | SPME | [ |
and β-CD-4 | |||||
Rain, river, and lake waters | di(2-ethylhexyl) phthalate | MA-β-CD | EGDMA | SPE | [ |
Tap and river waters | 2-aminopyridine | CTs and β-CD | EGDMA | d-SPE | [ |
表1 基于β-CD及其衍生物为功能单体的MIPs在环境水样品前处理中的应用
Table 1 Applications of MIPs based on β-CD and its derivatives as functional monomers for the pretreatment of environmental samples
Sample type | Target | Functional monomers | Crosslinker | Method for sample pretreatment | Reference |
MAA-β-CD: methacrylic acid functionalized β-cyclodextrin; β-CD-1: mono-(6-N-allylamino-6-deoxy)-β-cyclodextrin; β-CD-2: mono-(6-N-diallylamine-6-deoxy)-β-cyclodextrin; β-CD-3: mono-(6-N-ethylenediamine (N-(2-bis(2-hydroxy-5-hexene))) (N-(2-hydroxy-5-hexene))-6-deoxy)-β-cyclodextrin; β-CD-4: mono-(6-N-ethylenediamine (N-(2-bis (2-hydroxy-7-octene))) (N-(2-hydroxy-7-octene))-6-deoxy)-β-cyclodextrin; β-CD: β-cyclodextrin; MA-β-CD: methylacryloyl-β-cyclodextrin; CTs: chitosan; TRIM: trimethylolpropane trimethacrylate; SPME: solid-phase microextraction; d-SPE: dispersive solid-phase extraction. | |||||
Tap and river waters | 2, 4-dichlorophenol | MAA-β-CD | TRIM | SPE | [ |
River water | p-nitrophenol | β-CD-1, β-CD-2, β-CD-3 | EGDMA | SPME | [ |
and β-CD-4 | |||||
Rain, river, and lake waters | di(2-ethylhexyl) phthalate | MA-β-CD | EGDMA | SPE | [ |
Tap and river waters | 2-aminopyridine | CTs and β-CD | EGDMA | d-SPE | [ |
图3 氯吡脲分子印迹聚合物的制备和再结合的示意图[42]
Fig. 3 Schematic demonstration of preparation and re-binding of molecularly imprinted polymer of forchlorfenuron[42] HMDI: 1, 6-hexamethylene diisocyanate.
图4 刚果红分子印迹聚合物制备过程[43]
Fig. 4 Preparation procedure of molecularly imprinted polymer[43] DMC: [2-(methacryloyloxy) ethyl] trimethylammonium chloride; MBA: N, N-methylenebisacryl amide; APS: ammonium persulfate.
图5 MIM的制备过程[50]
Fig. 5 Preparation processes of molecularly imprinted materials[50]Thiol-SBA-15: thiol-modified SBA-15; acrolyl-β-CD: acrolyl-modified β-cyclodextrin.
Sample type | Target | Functional monomers | Crosslinker | Method for sample pretreatment | Reference |
allyl-β-CD: allyl-β-cyclodextrin; β-CD-MA: β-cyclodextrin-maleic anhydride; DMC: [2-(methacryloyloxy) ethyl]trimethylammonium chloride; AN: acrylonitrile; AM: acrylamide; 4-VP: 4-vinylpyridine; A-β-CD: acryloyl-β-cyclodextrin; HMDI: 1, 6-hexamethylene diisocyanate; MBA: N, N-methylenebisacryl amide; TEOS: tetraethoxysilane; EDMA: ethylene glycol dimethacrylate. | |||||
Vegetables | pirimicarb | allyl-β-CD and MAA | EGDMA | SPE | [ |
Strawberry | forchlorfenuron | β-CD | HMDI | QuEChERS | [ |
Pork, beef, jelly, and | congo red | β-CD-MA and DMC | MBA | SPE | [ |
hawthorn volumes | |||||
Pig livers | clenbuterol hydrochloride | allyl-β-CD and MAA | EGDMA | SPE | [ |
Infant formula | di(2-ethylhexyl) phthalate | allyl-β-CD and AN | EGDMA | SPE | [ |
Infant formula | di(2-ethylhexyl) phthalate | allyl-β-CD and AN | EGDMA | SPE | [ |
Cinnamon and peppers | chlorpyrifos | β-CD and AM | TEOS | SPME | [ |
Milk | bisphenol A | 4-VP and β-CD | TRIM | SPE | [ |
Citrus | benzimidazole | A-β-CD and MAA | EDMA | SPE | [ |
表2 基于β-CD及其衍生物为功能单体的MIPs在食品样品前处理中应用
Table 2 Applications of MIPs with β-CD and its derivatives as functional monomers for the pretreatment of food samples
Sample type | Target | Functional monomers | Crosslinker | Method for sample pretreatment | Reference |
allyl-β-CD: allyl-β-cyclodextrin; β-CD-MA: β-cyclodextrin-maleic anhydride; DMC: [2-(methacryloyloxy) ethyl]trimethylammonium chloride; AN: acrylonitrile; AM: acrylamide; 4-VP: 4-vinylpyridine; A-β-CD: acryloyl-β-cyclodextrin; HMDI: 1, 6-hexamethylene diisocyanate; MBA: N, N-methylenebisacryl amide; TEOS: tetraethoxysilane; EDMA: ethylene glycol dimethacrylate. | |||||
Vegetables | pirimicarb | allyl-β-CD and MAA | EGDMA | SPE | [ |
Strawberry | forchlorfenuron | β-CD | HMDI | QuEChERS | [ |
Pork, beef, jelly, and | congo red | β-CD-MA and DMC | MBA | SPE | [ |
hawthorn volumes | |||||
Pig livers | clenbuterol hydrochloride | allyl-β-CD and MAA | EGDMA | SPE | [ |
Infant formula | di(2-ethylhexyl) phthalate | allyl-β-CD and AN | EGDMA | SPE | [ |
Infant formula | di(2-ethylhexyl) phthalate | allyl-β-CD and AN | EGDMA | SPE | [ |
Cinnamon and peppers | chlorpyrifos | β-CD and AM | TEOS | SPME | [ |
Milk | bisphenol A | 4-VP and β-CD | TRIM | SPE | [ |
Citrus | benzimidazole | A-β-CD and MAA | EDMA | SPE | [ |
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