大环化合物在高选择性分子印迹识别体系中的研究进展

doi:10.19894/j.issn.1000-0518.220142

摘要/Abstract

摘要：

分子印迹技术（Molecular Imprinting Technology，MIT）因其预定性、专一性和适用性而被广泛应用于色谱分离、固相萃取、药物分析以及手性识别等领域。近些年来，研究者们将大环化合物引入MIT中，在增加识别位点的同时，有效改善了印迹聚合物材料的结构和性能，提高了对模板分子的选择性识别能力。本文重点综述了近10年来环糊精、杯芳烃、柱芳烃、冠醚和葫芦脲等大环化合物在分子印迹技术中的研究进展及应用，并对该领域的发展前景进行了展望。

关键词: 大环化合物, 分子印迹, 选择性

Abstract:

Molecular imprinting technology（MIT） has predetermination， recognition and usability， and has been widely used in chromatographic separation， solid phase extraction， drug analysis， chiral recognition and other fields. In recent years， researchers have introduced macrocyclic compounds into MIT， which not only increases the types of functional monomers， but also effectively improves the specificity of molecularly imprinted polymers and the selectivity of target molecules. In this paper， the research progress and application of macrocyclic compounds such as cyclodextrin， calixarene， pillararene， crown ether， cucurbituril and other supramolecular compounds in MIT in the past ten years are reviewed and its development prospects are prospected.

Key words: Microcylic compound, Molecular imprinting, Selectivity

中图分类号:

O654

高静霞, 王子安, 张连明, 李建平. 大环化合物在高选择性分子印迹识别体系中的研究进展[J]. 应用化学, 2023, 40(1): 24-39.

Jing-Xia GAO, Zi-An WANG, Lian-Ming ZHANG, Jian-Ping LI. Research Progress of Macrocyclic Compounds in Highly Selective Molecular Imprinting Recognition System[J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 24-39.

图/表 18

图1 MIT示意图［46］

Fig.1 Schematic diagram of MIT［46］

图2 CD的一般化学结构（a）和三维结构的示意图（b），以及α-、 β-和γ-CD的化学结构和尺寸（分别为n=6、7和8）（c）［50］

Fig.2 Schematic representations of the general chemical structure（a）， the tridimensional structure of CD （b）， and chemical structure and dimensions for α-， β- and γ-CD （n=6， 7 and 8， respectively）（c）［50］

图3 β-CD的MIPs合成用于多菌灵测定示意图［55］

Fig.3 Schematic illustration of synthesis of β-CD based MIPs for carbendazim etermination［55］

图4 β-CD-MIPs的合成［58］

Fig.4 Synthesis of derived β-CD-MIPs［58］

图5 以CD基离子液体为功能单体制备MMIPs用于高选择性和有效富集细胞色素c［64］

Fig.5 Preparation of MMIPs using CD-based ionic liquids as functional monomer for highly selective and effective enrichment of cytochrome c［64］

图6 深共熔溶剂基磁性β-CD-MIPs对蛋白质的特异性识别［69］

Fig.6 Specific recognition of protein by deep eutectic solvent-based magnetic β-CD-MIPs［69］

图7 CD超分子水凝胶的MIPs改善药物装载和递送［71］

Fig.7 MIPs of CD supramolecular hydrogels improves drug loading and delivery［71］

图8 CA功能化结构的示意图［72］

Fig.8 Schematic representation of functionalized structures of CA［72］

图9 CA分子印迹纤维固相微萃取水果中4种有机磷农药［79］

Fig.9 Molecularly imprinted calixarene fiber for solid-phase microextraction of four organophosphorous pesticides in fruits［79］

图10 基于Pt-In催化纳米颗粒和溴酚蓝掺杂MIPs膜双放大的新烟碱类杀虫剂吡虫啉超分子印迹电化学传感器［80］

Fig.10 Supramolecular imprinted electrochemical sensor for the neonicotinoid insecticide imidacloprid based on double amplification by Pt-In catalytic nanoparticles and a Bromophenol blue doped molecularly imprinted film［80］

图11 杯［4］芳烃衍生物MIPs识别乙酰苯胺［81］

Fig.11 MIPs with calix［4］arene derivative forthe recognition of acetanilide［81］

图12 常用CE结构式［82］

Fig.12 Structure of commonly CE［82］

图13 Fe3O4@SiO2@IIPs制备过程［86］

Fig.13 The detailed illustration of the preparation of Fe3O4@SiO2@IIPs［86］

图14 基于12-冠-4和聚醚砜协同作用的高Li+选择性多层IIPs［87］

Fig.14 Multilayered IIPs with high selectivity towards Li+ based on the synergistic effect of 12-crown-4 and polyether sulfone［87］

图15 CB［n］（n=5~8）的X射线晶体结构［93］

Fig.15 X-ray crystal structures of CB［n］（n=5~8）［93］

图16 基于单羟基CB［7］尿嘧啶-百草枯复合物的分子印迹搅拌棒特异性吸附环境水和蔬菜样品中的百草枯［96］

Fig.16 Specific recognition of cationic paraquat in environmental water and vegetable samples by molecularly imprinted stir-bar sorptive extraction based on monohydroxylcucurbit［7］uril-paraquat inclusion complex［96］

图17 柱［6］芳烃多层膜：对甲基紫精客体分子的可逆摄取和释放［113］

Fig.17 Pillar［6］arene containing multilayer films： reversible uptake and release of guest molecules with methyl viologen moieties［113］

表1 大环化合物在MIT中的应用

Table 1 Application of macrocyclic compounds in MIT

Macrocyclic compounds	Application mode	Reported applications	Deficiency
CD	Functional monomer， carrier	Metal ions， steroid molecules， pesticide residues， porphyrins， amino acids， oligopeptides， proteins， etc.	As anion receptors， CD and its derivatives are not easy to directly coated inorganic anions or positively charged receptors. It is difficult to maintain the activity of oligopeptides， proteins and other biological macromolecules in the elution process^{［54-71，115］}
CA	Functional monomer	Acetanilide， α-tocopherol， L-dopa and other chiral drugs， organic phosphorus pesticides such as methyl parathion and imidacloprid etc.	Because the structure of CA is wide at the top and narrow at the bottom， molecules are easy to fall off in the recognition process， and CA has poor water solubility^{［79-81， 116-117］}
CE	Functional monomer，Assisted recognition unit	K⁺， Rb⁺， Li⁺ and other alkali metal ions.	CE does not bind to anions. Due to the size of ring structure， CE is difficult to be applied to molecular recognition^{［86-92，118-120］}
CB	Functional monomer	Paraquat， melamine， quaternary ammonium salt and other pesticide molecules	CB has poor solubility and strong structural rigidity， so it cannot change its shape to suit the guest molecules. The separation and purification of CB［n］ is very difficult and not easy to be functionalized^［95-97］
PA	Assisted recognition unit	Methylviologen， 2-naphthoic acid pyrene， etc.	PA molecule has electron-rich cavity， highly symmetrical structure and strong rigidity^{［113-114］}

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