化工进展 ›› 2021, Vol. 40 ›› Issue (12): 6752-6764.DOI: 10.16085/j.issn.1000-6613.2021-0007
收稿日期:
2021-01-04
修回日期:
2021-02-18
出版日期:
2021-12-05
发布日期:
2021-12-21
通讯作者:
潘建明
作者简介:
卞维柏(1988—),男,博士后,讲师,研究方向为选择性吸附分离。E-mail:基金资助:
BIAN Weibai1,2,3(), CHEN Yifan1, PAN Jianming2,3()
Received:
2021-01-04
Revised:
2021-02-18
Online:
2021-12-05
Published:
2021-12-21
Contact:
PAN Jianming
摘要:
智能印迹聚合物在外部环境刺激下对模板分子具有响应性分子识别吸附能力,在吸附分离、药物传递、检测、固相萃取、催化等应用领域有着广阔的前景。本文首先对分子印迹聚合物进行了综述并指出在外场强化过程中常规分子印迹聚合物很难通过改变结合位点来控制结合特性的问题,针对这个问题进而提出具有柔性位点的智能响应型印迹聚合物。随后以具有不同响应功能的智能印迹聚合物为出发点,对磁、热、光、pH、生物大分子等单因子及双重因子响应功能印迹聚合物在外场强化过程中的响应与识别机制分别进行分析与总结,并综述了近些年来这些智能印迹聚合物在不同应用领域中相关研究工作进展。最后,基于不同响应功能的智能印迹聚合物的现状问题,对智能印迹聚合物在材料制备与理论两方面分别进行了展望。
中图分类号:
卞维柏, 陈一帆, 潘建明. 智能印迹聚合物及其外场强化的识别机制研究进展[J]. 化工进展, 2021, 40(12): 6752-6764.
BIAN Weibai, CHEN Yifan, PAN Jianming. Research progress in intelligent imprinted polymers and their recognition mechanisms under external field enhancement[J]. Chemical Industry and Engineering Progress, 2021, 40(12): 6752-6764.
1 | ZHANG H Q, YE L, MOSBACH K. Non-covalent molecular imprinting with emphasis on its application in separation and drug development[J]. Journal of Molecular Recognition, 2006, 19(4): 248-259. |
2 | FU J Q, CHEN L X, LI J H, et al. Current status and challenges of ion imprinting[J]. Journal of Materials Chemistry A, 2015, 3(26): 13598-13627. |
3 | GUO L H, MA X G, XIE X W, et al. Preparation of dual-dummy-template molecularly imprinted polymers coated magnetic graphene oxide for separation and enrichment of phthalate esters in water[J]. Chemical Engineering Journal, 2019, 361: 245-255. |
4 | MARTÍN-ESTEBAN A. Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation[J]. Trends in Analytical Chemistry, 2013, 45: 169-181. |
5 | PAN Y J, CHEN Y Y, WANG D R, et al. Redox/pH dual stimuli-responsive biodegradable nanohydrogels with varying responses to dithiothreitol and glutathione for controlled drug release[J]. Biomaterials, 2012, 33(27): 6570-6579. |
6 | WU W T, SHEN J, BANERJEE P, et al. Core-shell hybrid nanogels for integration of optical temperature-sensing, targeted tumor cell imaging, and combined chemo-photothermal treatment[J]. Biomaterials, 2010, 31(29): 7555-7566. |
7 | SCHEVE C S, GONZALES P A, MOMIN N, et al. Steric pressure between membrane-bound proteins opposes lipid phase separation[J]. Journal of the American Chemical Society, 2013, 135(4): 1185-1188. |
8 | ZHANG Y Z, ZHANG J W, WANG C Z, et al. Polydopamine-coated magnetic molecularly imprinted polymers with fragment template for identification of pulsatilla saponin metabolites in rat feces with UPLC-Q-TOF-MS[J]. Journal of Agricultural and Food Chemistry, 2018, 66(3): 653-660. |
9 | WU W T, SHEN J, LI Y X, et al. Specific glucose-to-SPR signal transduction at physiological pH by molecularly imprinted responsive hybrid microgels[J]. Biomaterials, 2012, 33(29): 7115-7125. |
10 | OKUTUCU B, ÖNAL S. Molecularly imprinted polymers for separation of various sugars from human urine[J]. Talanta, 2011, 87: 74-79. |
11 | WULFF G. Enzyme-like catalysis by molecularly imprinted polymers[J]. Chemical Reviews, 2002, 102(1): 1-27. |
12 | HAUPT K, MOSBACH K. Molecularly imprinted polymers and their use in biomimetic sensors[J]. Chemical Reviews, 2000, 100(7): 2495-2504. |
13 | OMRANIPOUR H M, SAJADI TABASSI S A, KOWSARI R, et al. Brimonidine imprinted hydrogels and evaluation of their binding and releasing properties as new ocular drug delivery systems[J]. Current Drug Delivery, 2015, 12(6): 717-725. |
14 | GE Y, BUTLER B, MIRZA F, et al. Smart molecularly imprinted polymers: recent developments and applications[J]. Macromolecular Rapid Communications, 2013, 34(11): 903-915. |
15 | LE NOIR M, GUIEYSSE B, MATTIASSON B. Removal of trace contaminants using molecularly imprinted polymers[J]. Water Science and Technology, 2006, 53(11): 205-212. |
16 | MENG Z H, CHEN W, MULCHANDANI A. Removal of estrogenic pollutants from contaminated water using molecularly imprinted polymers[J]. Environmental Science & Technology, 2005, 39(22): 8958-8962. |
17 | SUN H W, QIAO F X. Recognition mechanism of water-compatible molecularly imprinted solid-phase extraction and determination of nine quinolones in urine by high performance liquid chromatography[J]. Journal of Chromatography A, 2008, 1212(1/2): 1-9. |
18 | FANG G Z, TAN J, YAN X P. An ion-imprinted functionalized silica gel sorbent prepared by a surface imprinting technique combined with a sol-gel process for selective solid-phase extraction of cadmium(Ⅱ)[J]. Analytical Chemistry, 2005, 77(6): 1734-1739. |
19 | TAN J, WANG H F, YAN X P. A fluorescent sensor array based on ion imprinted mesoporous silica[J]. Biosensors and Bioelectronics, 2009, 24(11): 3316-3321. |
20 | ZHANG Z T, SAENGKERDSUB S, DAI S. Intersurface ion-imprinting synthesis on layered magadiite hosts[J]. Chemistry of Materials, 2003, 15(15): 2921-2925. |
21 | MINOURA N, IDEI K, RACHKOV A, et al. Preparation of azobenzene-containing polymer membranes that function in photoregulated molecular recognition[J]. Macromolecules, 2004, 37(25): 9571-9576. |
22 | CHEN L X, WANG X Y, LU W H, et al. Molecular imprinting: perspectives and applications[J]. Chemical Society Reviews, 2016, 45(8): 2137-2211. |
23 | BYRNE M E, PARK K, PEPPAS N A. Molecular imprinting within hydrogels[J]. Advanced Drug Delivery Reviews, 2002, 54(1): 149-161. |
24 | BELBRUNO J J. Molecularly imprinted polymers[J]. Chemical Reviews, 2019, 119(1): 94-119. |
25 | WANG Y F, MA Y, ZHOU J J, et al. Thermo-sensitive surface molecularly imprinted magnetic microspheres based on bio-macromolecules and their specific recognition of bovine serum albumin[J]. Journal of Separation Science, 2020, 43(5): 996-1002. |
26 | ZHOU J J, WANG Y F, MA Y, et al. Surface molecularly imprinted thermo-sensitive polymers based on light-weight hollow magnetic microspheres for specific recognition of BSA[J]. Applied Surface Science, 2019, 486: 265-273. |
27 | LIU X Y, ZHOU T, DU Z W, et al. Recognition ability of temperature responsive molecularly imprinted polymer hydrogels[J]. Soft Matter, 2011, 7(5): 1986. |
28 | TAKEUCHI T, AKEDA K, MURAKAMI S, et al. Photoresponsive porphyrin-imprinted polymers prepared using a novel functional monomer having diaminopyridine and azobenzene moieties[J]. Organic & Biomolecular Chemistry, 2007, 5(15): 2368. |
29 | GOMY C, SCHMITZER A R. Synthesis and photoresponsive properties of a molecularly imprinted polymer[J]. Organic Letters, 2007, 9(20): 3865-3868. |
30 | MINOURA N, IDEI K, RACHKOV A, et al. Molecularly imprinted polymer membranes with photoregulated template binding[J]. Chemistry of Materials, 2003, 15(25): 4703-4704. |
31 | ANSARI S. Application of magnetic molecularly imprinted polymer as a versatile and highly selective tool in food and environmental analysis: recent developments and trends[J]. Trends in Analytical Chemistry, 2017, 90: 89-106. |
32 | TANG Q, NIE Y T, GONG C B, et al. Photo-responsive molecularly imprinted hydrogels for the detection of melamine in aqueous media[J]. Journal of Materials Chemistry, 2012, 22(37): 19812. |
33 | BAI W, GARIANO N A, SPIVAK D A. Macromolecular amplification of binding response in superaptamer hydrogels[J]. Journal of the American Chemical Society, 2013, 135(18): 6977-6984. |
34 | WOLSKA J, KUJAWSKA M, CYGANOWSKI P. pH-responsive molecularly imprinted polymer for sorption and rapid desorption of dibutyl phthalate[J]. Separation Science and Technology, 2018, 53(7): 1076-1087. |
35 | ALVAREZ-LORENZO C, GUNEY O, OYA T, et al. Reversible adsorption of calcium ions by imprinted temperature sensitive gels[J]. The Journal of Chemical Physics, 2001, 114(6): 2812-2816. |
36 | ZHANG M L, ZHANG Z H, LIU Y N, et al. Preparation of core-shell magnetic ion-imprinted polymer for selective extraction of Pb(Ⅱ) from environmental samples[J]. Chemical Engineering Journal, 2011, 178: 443-450. |
37 | LUO X B, ZHAN Y C, HUANG Y N, et al. Removal of water-soluble acid dyes from water environment using a novel magnetic molecularly imprinted polymer[J]. Journal of Hazardous Materials, 2011, 187(1/2/3): 274-282. |
38 | XIE C S, HUANG X J, WEI S L, et al. Novel dual-template magnetic ion imprinted polymer for separation and analysis of Cd2+ and Pb2+ in soil and food[J]. Journal of Cleaner Production, 2020, 262: 121387. |
39 | KONG X J, ZHENG C, LAN Y H, et al. Synthesis of multirecognition magnetic molecularly imprinted polymer by atom transfer radical polymerization and its application in magnetic solid-phase extraction[J]. Analytical and Bioanalytical Chemistry, 2018, 410(1): 247-257. |
40 | ZHANG W, HE X W, LI W Y, et al. Thermo-sensitive imprinted polymer coating CdTe quantum dots for target protein specific recognition[J]. Chemical Communications, 2012, 48(12): 1757. |
41 | CHEN Y P, LUAN J B, SHEN W J, et al. Injectable and thermosensitive hydrogel containing liraglutide as a long-acting antidiabetic system[J]. ACS Applied Materials & Interfaces, 2016, 8(45): 30703-30713. |
42 | DEMIREL G, ÖZÇETIN G, TURAN E, et al. pH/temperature-sensitive imprinted ionic poly(N-tert-butylacrylamide-co-acrylamide/maleic acid) hydrogels for bovine serum albumin[J]. Macromolecular Bioscience, 2005, 5(10): 1032-1037. |
43 | SUEDEE R, SEECHAMNANTURAKIT V, CANYUK B, et al. Temperature sensitive dopamine-imprinted (N,N-methylene-bis-acrylamide cross-linked) polymer and its potential application to the selective extraction of adrenergic drugs from urine[J]. Journal of Chromatography A, 2006, 1114(2): 239-249. |
44 | LIU X Y, DING X B, GUAN Y, et al. Fabrication of temperature-sensitive imprinted polymer hydrogel[J]. Macromolecular Bioscience, 2004, 4(4): 412-415. |
45 | PAN G Q, GUO Q P, CAO C B, et al. Thermo-responsive molecularly imprinted nanogels for specific recognition and controlled release of proteins[J]. Soft Matter, 2013, 9(14): 3840. |
46 | TOKUYAMA H, KANAZAWA R, SAKOHARA S. Equilibrium and kinetics for temperature swing adsorption of a target metal on molecular imprinted thermosensitive gel adsorbents[J]. Separation and Purification Technology, 2005, 44(2): 152-159. |
47 | XIONG H H, WU X Q, LU W H, et al. Switchable zipper-like thermoresponsive molecularly imprinted polymers for selective recognition and extraction of estradiol[J]. Talanta, 2018, 176: 187-194. |
48 | KHOURY J M EL, ZHOU X L, QU L T, et al. Organo-soluble photoresponsive azo thiol monolayer-protected gold nanorods[J]. Chemical Communications, 2009(16): 2109-2111. |
49 | HUANG Y, WANG R. Green recovery of lithium from water by a smart imprinted adsorbent with photo-controlled and selective properties[J]. Chemical Engineering Journal, 2019, 378: 122084. |
50 | GUANG S J, SHI A Z, LAN C, et al. Synthesis of molecularly imprinted organic-inorganic hybrid azobenzene materials by sol-gel for radiation induced selective recognition of 2,4-dichlorophenoxyacetic acid[J]. Radiation Physics and Chemistry, 2011, 80(2): 130-135. |
51 | GONG C B, WONG K L, LAM M H W. Photoresponsive molecularly imprinted hydrogels for the photoregulated release and uptake of pharmaceuticals in the aqueous media[J]. Chemistry of Materials, 2008, 20(4): 1353-1358. |
52 | MOHAJERI S A, MALAEKEH-NIKOUEI B, SADEGH H. Development of a pH-responsive imprinted polymer for diclofenac and study of its binding properties in organic and aqueous media[J]. Drug Development and Industrial Pharmacy, 2012, 38(5): 616-622. |
53 | MIYATA T, NAKAMAE K, HOFFMAN A S, et al. Stimuli-sensitivities of hydrogels containing phosphate groups[J]. Macromolecular Chemistry and Physics, 1994, 195(4): 1111-1120. |
54 | KANEKIYO Y, NAGANAWA R, TAO H. pH-responsive molecularly imprinted polymers[J]. Angewandte Chemie International Edition, 2003, 42(26): 3014-3016. |
55 | ZHAO W F, FANG B H, LI N, et al. Fabrication of pH-responsive molecularly imprinted polyethersulfone particles for bisphenol-A uptake[J]. Journal of Applied Polymer Science, 2009, 113(2): 916-921. |
56 | MIYATA T, HAYASHI T, KURIU Y, et al. Responsive behavior of tumor-marker-imprinted hydrogels using macromolecular cross-linkers[J]. Journal of Molecular Recognition, 2012, 25(6): 336-343. |
57 | HOSHINO Y, OHASHI R C, MIURA Y. Rational design of synthetic nanoparticles with a large reversible shift of acid dissociation constants: proton imprinting in stimuli responsive nanogel particles[J]. Advanced Materials, 2014, 26(22): 3718-3723. |
58 | WATANABE M, AKAHOSHI T, TABATA Y, et al. Molecular specific swelling change of hydrogels in accordance with the concentration of guest molecules[J]. Journal of the American Chemical Society, 1998, 120(22): 5577-5578. |
59 | CHEN Z Y, HUA Z D, XU L, et al. Protein-responsive imprinted polymers with specific shrinking and rebinding[J]. Journal of Molecular Recognition, 2008, 21(1): 71-77. |
60 | MIYATA T, JIGE M, NAKAMINAMI T, et al. Tumor marker-responsive behavior of gels prepared by biomolecular imprinting[J]. Proceedings of the National Academy of Sciences of the United States of America, 2006, 103(5): 1190-1193. |
61 | LIU W F, QIN L, AN Z L, et al. Thermo-responsive ion imprinted polymer on the surface of magnetic carbon microspheres for identification and removal of low-concentrations of Cu2+[J]. Environmental Chemistry, 2018, 15(5): 306. |
62 | ZHANG Y Z, QIN B, ZHANG B, et al. Specific enrichment of caffeic acid from Taraxacum mon-golicum Hand.-Mazz. by pH and magnetic dual-responsive molecularly imprinted polymers[J]. Analytica Chimica Acta, 2020, 1096: 193-202. |
63 | CHEN F F, DONG Y H, ZHAO Y X. Synthesis and characterization of photo-responsive magnetic molecularly imprinted microspheres for the detection of sulfonamides in aqueous solution[J]. Journal of Separation Science, 2016, 39(24): 4866-4875. |
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