分子印迹技术在水环境抗生素富集中的应用进展
Recent advances of molecularly imprinted technology in the enrichment of antibiotics in aquatic environment
-
摘要: 近年来,由于抗生素的大量使用,使得环境中抗生素的残留现象变得十分普遍.这些残留的抗生素通过多种途径进入到水环境中,会对人类健康以及水生生态系统造成危害.分子印迹技术(MIT)因其能选择性识别、有效富集和去除目标分析物,被广泛应用于水环境中抗生素的富集及检测.本文介绍了分子印迹技术的原理以及印迹聚合物的制备方法,并且总结了分子印迹聚合物在水环境抗生素富集中的应用.最后,本文对分子印迹技术在处理水体中抗生素的应用前景进行了展望.Abstract: The overuse of antibiotics in recent years has resulted in widespread of antibiotic residues in the environment. These residual antibiotics can enter the water environment, resulting in harm to human health and the ecosystems. Molecular imprinting technology(MIT) has been widely used in the treatment of antibiotics in water due to its high selectivity and enrichment of targets compounds. This paper introduced the principle of MIT and the preparation method of imprinted polymers. The application of molecular imprinted polymer in aquatic environment as adsorbents for antibiotics enrichment was comprehensively summarized. Finally, the future prospectives of applying MIT in the treatment of antibiotics was discussed.
-
Key words:
- antibiotics /
- molecular imprinting technology(MIT) /
- enrichment
-
[1] KUMMERER K. Antibiotics in the aquatic environment-A review-Part I[J]. Chemosphere, 2009, 75(4):417-434. [2] ZHANG Q Q, JIA A, WAN Y, et al. Occurrences of three classes of antibiotics in a natural river basin:Association with antibiotic-Resistant escherichia coli[J]. Environmental Science & Technology, 2014, 48(24):14317-14325. [3] CYCON M, MROZIK A, PIOTROWSKA-SEGET Z. Antibiotics in the soil environment-degradation and their impact on microbial activity and diversity[J]. Frontiers in Microbiology, 2019, 10:338. [4] LUO Y L, GUO W S, NGO H H, et al. A review on the occurrence of micropollutants in the aquatic environment and their fate and removal during wastewater treatment[J]. Science of the Total Environment, 2014, 473:619-641. [5] CHEN L G, ZHANG X P, XU Y, et al. Determination of fluoroquinolone antibiotics in environmental water samples based on magnetic molecularly imprinted polymer extraction followed by liquid chromatography-tandem mass spectrometry[J]. Analytica Chimica Acta, 2010, 662(1):31-38. [6] CHANG X S, MEYER M T, LIU X Y, et al. Determination of antibiotics in sewage from hospitals, nursery and slaughter house, wastewater treatment plant and source water in Chongqing region of Three Gorge Reservoir in China[J]. Environmental Pollution, 2010, 158(5):1444-1450. [7] FREY S K, TOPP E, KHAN I U H, et al. Quantitative Campylobacter spp., antibiotic resistance genes, and veterinary antibiotics in surface and ground water following manure application:Influence of tile drainage control[J]. Science of the Total Environment, 2015, 532:138-153. [8] BOEHME C C, NABETA P, HILLEMANN D, et al. Rapid molecular detection of tuberculosis and rifampin resistance[J]. New England Journal of Medicine, 2010, 363(11):1005-1015. [9] LUKACISINOVA M, BOLLENBACH T. Toward a quantitative understanding of antibiotic resistance evolution[J]. Current Opinion in Biotechnology, 2017, 46:90-97. [10] HIRSCH R, TERNES T, HABERER K, et al. Occurrence of antibiotics in the aquatic environment[J]. Science of the Total Environment, 1999, 225(1/2):109-118. [11] KUMMERER K, HENNINGER A. Promoting resistance by the emission of antibiotics from hospitals and households into effluent[J]. Clinical Microbiology and Infection, 2003, 9(12):1203-1214. [12] SARMAH A K, MEYER M T, BOXALL A B A. A global perspective on the use, sales, exposure pathways, occurrence, fate and effects of veterinary antibiotics (VAs) in the environment[J]. Chemosphere, 2006, 65(5):725-759. [13] BAGUER A J, JENSEN J, KROGH P H. Effects of the antibiotics oxytetracycline and tylosin on soil fauna[J]. Chemosphere, 2000, 40(7):751-757. [14] KUMAR K, GUPTA S C, BAIDOO S K, et al. Antibiotic uptake by plants from soil fertilized with animal manure[J]. Journal of Environmental Quality, 2005, 34(6):2082-2085. [15] HARTIG C, STORM T, JEKEL M. Detection and identification of sulphonamide drugs in municipal waste water by liquid chromatography coupled with electrospray ionisation tandem mass spectrometry[J]. Journal of Chromatography A, 1999, 854(1/2):163-173. [16] PENG X, TAN J, TANG C, et al. Multiresidue determination of fluoroquinolone, sulfonamide, trimethoprim, and chloramphenicol antibiotics in urban waters in China[J]. Environmental Toxicology and Chemistry, 2008, 27(1):73-79. [17] YU R, ZHAO J, ZHAO Z, et al. Copper substituted zinc ferrite with abundant oxygen vacancies for enhanced ciprofloxacin degradation via peroxymonosulfate activation[J]. Journal of Hazardous Materials, 2020, 390:121998. [18] MICHAEL I, HAPESHI E, MICHAEL C, et al. Solar Fenton and solar TiO2 catalytic treatment of ofloxacin in secondary treated effluents:Evaluation of operational and kinetic parameters[J]. Water Research, 2010, 44(18):5450-5462. [19] ZHAO C, DENG H P, LI Y, et al. Photodegradation of oxytetracycline in aqueous by 5A and 13X loaded with TiO2 under UV irradiation[J]. Journal of Hazardous Materials, 2010, 176(1/3):884-892. [20] SHEN X T, ZHU L H, WANG N, et al. Molecular imprinting for removing highly toxic organic pollutants[J]. Chemical Communications, 2012, 48(6):788-798. [21] LAVIGNAC N, ALLENDER C J, BRAIN K R. Current status of molecularly imprinted polymers as alternatives to antibodies in sorbent assays[J]. Analytica Chimica Acta, 2004, 510(2):139-145. [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] MORELLI I, CHIONO V, VOZZI G, et al. Molecularly imprinted submicronspheres for applications in a novel model biosensor-film[J]. Sensors and Actuators B-Chemical, 2010, 150(1):394-401. [24] HAUPT K, MOSBACH K. Molecularly imprinted polymers and their use in biomimetic sensors[J]. Chemical Reviews, 2000, 100(7):2495-2504. [25] ADVINCULA R C. Engineering molecularly imprinted polymer (MIP) materials:Developments and challenges for sensing and separation technologies[J]. Korean Journal of Chemical Engineering, 2011, 28(6):1313-1321. [26] BOSSI A, BONINI F, TURNER A P F, et al. Molecularly imprinted polymers for the recognition of proteins:The state of the art[J]. Biosensors & Bioelectronics, 2007, 22(6):1131-1137. [27] OKUTUCU B, ONAL S. Molecularly imprinted polymers for separation of various sugars from human urine[J]. Talanta, 2011, 87:74-79. [28] XU Z F, KUANG D Z, ZHANG F X, et al. Fluorogenic molecularly imprinted polymers with double recognition abilities synthesized via click chemistry[J]. Journal of Materials Chemistry B, 2013, 1(13):1852-1859. [29] MARTIN-ESTEBAN A. Molecularly-imprinted polymers as a versatile, highly selective tool in sample preparation[J]. Trac-Trends in Analytical Chemistry, 2013, 45:169-181. [30] TAMAYO F G, TURIEL E, MARTIN-ESTEBAN A. Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction:Recent developments and future trends[J]. Journal of Chromatography A, 2007, 1152(1/2):32-40. [31] BERGMANN N M, PEPPAS N A. Molecularly imprinted polymers with specific recognition for macromolecules and proteins[J]. Progress in Polymer Science, 2008, 33(3):271-288. [32] WHITCOMBE M J, RODRIGUEZ M E, VILLAR P, et al. A new method for the introduction of recognition site functionality into polymers prepared by molecular imprinting-synthesis and characterization of polymeric receptors for cholesterol[J]. Journal of the American Chemical Society, 1995, 117(27):7105-7111. [33] FUCHS Y, SOPPERA O, HAUPT K. Photopolymerization and photostructuring of molecularly imprinted polymers for sensor applications-A review[J]. Analytica Chimica Acta, 2012, 717:7-20. [34] SOLEDAD-RODRIGUEZ B, FERNANDEZ-HERNANDO P, GARCINUNO-MARTINEZ R M, et al. Effective determination of ampicillin in cow milk using a molecularly imprinted polymer as sorbent for sample preconcentration[J]. Food Chemistry, 2017, 224:432-438. [35] GUO X C, XIA Z Y, WANG H H, et al. Molecularly imprinted solid phase extraction method for simultaneous determination of seven nitroimidazoles from honey by HPLC-MS/MS[J]. Talanta, 2017, 166:101-108. [36] LIU X J, OUYAN C B, ZHAO R, et al. Monolithic molecularly imprinted polymer for sulfamethoxazole and molecular recognition properties in aqueous mobile phase[J]. Analytica Chimica Acta, 2006, 571(2):235-241. [37] 黄镭, 熊舟翼, 和平生, 等. 磁性分子印迹聚合物微球的制备及吸附特性研究[J]. 高分子学报, 2011(1):120-124. HUANG L, XIONG Z Y, HE P S, et al.Preparation and adsorption characteristics of magnetic molecularly imprinted polymer microspheres[J]. Acta Polymerica Sinica, 2011 (1):120-124(in Chinese).
[38] 魏丹, 苏立强, 栾田. 加替沙星分子印迹聚合物的制备及其性能研究[J]. 化工时刊, 2013, 27(1):10-13. WEI D, SU L Q, LUAN T. Preparation and performance research of the gatifloxacin molecularly imprinted polymer[J]. Chemical Industry Times, 2013, 27(1):10-13(in Chinese).
[39] 宋任远, 胡小玲, 管萍, 等. 红霉素分子印迹聚合物微球的制备及性能研究[J]. 离子交换与吸附, 2013, 29(2):97-107. SONG R Y, HU X L, GUAN P, et al.Preparation and properties of molecularly imprinted polymer microspheres for erythromycin[J]. Ion Exchange and Adsorption, 2013, 29(2):97-107(in Chinese).
[40] KAN X W, GENG Z R, ZHAO Y, et al. Magnetic molecularly imprinted polymer for aspirin recognition and controlled release[J]. Nanotechnology, 2009, 20(16):165601. [41] LI H P, CHEN J L, TAN L J, et al. Solid-phase extraction using a molecularly imprinted polymer for the selective purification and preconcentration of norfloxacin from seawater[J]. Analytical Letters, 2019, 52(18):2896-2913. [42] 赵娜, 胡小玲, 管萍, 等. 乳液聚合法制备红霉素分子印迹聚合物微球及其吸附性能[J]. 物理化学学报, 2014, 30(1):121-128. ZHAO N, HU X L, GUAN P, et al. Preparation of erythromycin-imprinted polymeric microspheres by emulsion polymerization and their adsorption properties[J]. Acta Physica-Chimica Sinica, 2014, 30(1):121-128(in Chinese).
[43] ANDRADE-EIROA A, CANLE M, LEROY-CANCELLIERI V, et al. Solid-phase extraction of organic compounds:A critical review (Part I)[J]. Trac-Trends in Analytical Chemistry, 2016, 80:641-654. [44] LIAN Z R, WANG J T. Determination of ciprofloxacin in Jiaozhou Bay using molecularly imprinted solid-phase extraction followed by high-performance liquid chromatography with fluorescence detection[J]. Marine Pollution Bulletin, 2016, 111(1/2):411-417. [45] ZHANG Z, CAO X L, ZHANG Z P, et al. Synthesis of dummy-template molecularly imprinted polymer adsorbents for solid phase extraction of aminoglycosides antibiotics from environmental water samples[J]. Talanta, 2020, 208:120385. [46] WEI S L, LI J W, LIU Y, et al. Development of magnetic molecularly imprinted polymers with double templates for the rapid and selective determination of amphenicol antibiotics in water, blood, and egg samples[J]. Journal of Chromatography A, 2016, 1473:19-27. [47] LI G Y, ZHA J, NIU M C, et al. Bifunctional monomer molecularly imprinted sol-gel polymers based on the surface of magnetic halloysite nanotubes as an effective extraction approach for norfloxacin[J]. Applied Clay Science, 2018, 162:409-417. [48] CHEN H Y, ZHANG Y Q, GAO B, et al. Fast determination of sulfonamides and their acetylated metabolites from environmental water based on magnetic molecularly imprinted polymers[J]. Environmental Science and Pollution Research, 2013, 20(12):8567-8578. [49] FIZIR M, WEI L, MUCHUAN N, et al. QbD approach by computer aided design and response surface methodology for molecularly imprinted polymer based on magnetic halloysite nanotubes for extraction of norfloxacin from real samples[J]. Talanta, 2018, 184:266-276. [50] BAEZA-FONTE A N, GARCES-LOBO I, LUACES-ALBERTO M D, et al. Determination of cephalosporins by UHPLC-DAD using molecularly imprinted polymers[J]. Journal of Chromatographic Science, 2018, 56(2):187-193. [51] BELTRAN A, MARCE R M, CORMACK P A G, et al. Selective solid-phase extraction of amoxicillin and cephalexin from urine samples using a molecularly imprinted polymer[J]. Journal of Separation Science, 2008, 31(15):2868-2874. [52] ZHU G F, CHENG G H, WANG P Y, et al. Water compatible imprinted polymer prepared in water for selective solid phase extraction and determination of ciprofloxacin in real samples[J]. Talanta, 2019, 200:307-315. [53] QIN D, ZHAO M, WANG J T, et al. Selective extraction and detection of norfloxacin from marine sediment and seawater samples using molecularly imprinted silica sorbents coupled with HPLC[J]. Marine Pollution Bulletin, 2020, 150:110677. [54] NIU M C, SUN C, ZHANG K, et al. A simple extraction method for norfloxacin from pharmaceutical wastewater with a magnetic core-shell molecularly imprinted polymer with the aid of computer simulation[J]. New Journal of Chemistry, 2017, 41(7):2614-2624. [55] WU X, WU L T. Molecularly imprinted polymers for the solid-phase extraction of four fluoroquilones from milk and lake water samples[J]. Journal of Separation Science, 2015, 38(20):3615-3621. [56] QIN S L, SU L Q, WANG P, et al. Mixed templates molecularly imprinted solid-phase extraction for the detection of sulfonamides in fish farming water[J]. Journal of Applied Polymer Science, 2015, 132(8):41491. [57] LIAN Z R, WANG J T. Selective detection of chloramphenicol based on molecularly imprinted solid-phase extraction in seawater from Jiaozhou Bay, China[J]. Marine Pollution Bulletin, 2018, 133:750-755. [58] QIN S L, DENG S, SU L Q, et al. Simultaneous determination of five sulfonamides in wastewater using group-selective molecularly imprinted solid-phase extraction coupled with HPLC-DAD[J]. Analytical Methods, 2012, 4(12):4278-4283. [59] BARAHONA F, ALBERO B, TADEO J L, et al. Molecularly imprinted polymer-hollow fiber microextraction of hydrophilic fluoroquinolone antibiotics in environmental waters and urine samples[J]. Journal of Chromatography A, 2019, 1587:42-49. [60] LIU X, WANG X C, TAN F, et al. An electrochemically enhanced solid-phase microextraction approach based on molecularly imprinted polypyrrole/multi-walled carbon nanotubes composite coating for selective extraction of fluoroquinolones in aqueous samples[J]. Analytica Chimica Acta, 2012, 727:26-33. [61] ROZAINI M N H, SEMAIL N F, SAAD B, et al. Molecularly imprinted silica gel incorporated with agarose polymer matrix as mixed matrix membrane for separation and preconcentration of sulfonamide antibiotics in water samples[J]. Talanta, 2019, 199:522-531. [62] BASHIR K, LUO Z M, CHEN G N, et al. Development of surface molecularly imprinted polymers as dispersive solid phase extraction coupled with HPLC method for the removal and detection of griseofulvin in surface water[J]. International Journal of Environmental Research and Public Health, 2020, 17(1):134. [63] CHEN X W, YE N S. A graphene oxide surface-molecularly imprinted polymer as a dispersive solid-phase extraction adsorbent for the determination of cefadroxil in water samples[J]. Rsc Advances, 2017, 7(54):34077-34085. [64] LU W H, LIU J, LI J H, et al. Dual-template molecularly imprinted polymers for dispersive solid-phase extraction of fluoroquinolones in water samples coupled with high performance liquid chromatography[J]. Analyst, 2019, 144(4):1292-1302. [65] CHEN X H, ZHAO Y G, ZHANG Y, et al. Ethylenediamine-functionalized superparamagnetic carbon nanotubes for magnetic molecularly imprinted polymer matrix solid-phase dispersion extraction of 12 fluoroquinolones in river water[J]. Analytical Methods, 2015, 7(14):5838-5846. [66] XU Z G, DU Z, HU Y L, et al. Preparation of trimethoprim molecularly imprinted stir bar sorptive extraction and its application for trace analysis of trimethoprim and sulfonamides in complex samples[J]. Chinese Journal of Analytical Chemistry, 2012, 40(7):1002-1009. [67] SONG S Q, WU A B, SHI X Z, et al. Development and application of molecularly imprinted polymers as solid-phase sorbents for erythromycin extraction[J]. Analytical and Bioanalytical Chemistry, 2008, 390(8):2141-2150. [68] HU S G, LI L, HE X W. Comparison of trimethoprim molecularly imprinted polymers in bulk and in sphere as the sorbent for solid-phase extraction and extraction of trimethoprim from human urine and pharmaceutical tablet and their determination by high-performance liquid chromatography[J]. Analytical Chimica Acta, 2005, 537(1-2):215-222. [69] SONG X Q, ZHOU T, LI J F, et al. Determination of ten macrolide drugs in environmental water using molecularly imprinted solid-Phase extraction coupled with liquid chromatography-tandem mass spectrometry[J]. Molecules, 2018, 23(5):1172. [70] DE LEON-MARTINEZ L D, RODRIGUEZ-AGUILAR M, OCAMPO-PEREZ R, et al. Synthesis and evaluation of a molecularly imprinted polymer for the determination of metronidazole in water samples[J]. Bulletin of Environmental Contamination and Toxicology, 2018, 100(3):395-401. [71] GAO D M, ZHANG Z P, WU M H, et al. A surface functional monomer-directing strategy for highly dense imprinting of TNT at surface of silica nanoparticles[J]. Journal of the American Chemical Society, 2007, 129(25):7859-7866. [72] GAO B J, WANG J A, AN F Q, et al. Molecular imprinted material prepared by novel surface imprinting technique for selective adsorption of pirimicarb[J]. Polymer, 2008, 49(5):1230-1238. [73] ZHENG C, HUANG Y P, LIU Z S. Synthesis and theoretical study of molecularly imprinted monoliths for HPLC[J]. Analytical and Bioanalytical Chemistry, 2013, 405(7):2147-2161. [74] YOSHIMATSU K, REIMHULT K, KROZER A, et al. Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization:The control of particle size suitable for different analytical applications[J]. Analytica Chimica Acta, 2007, 584(1):112-121. [75] TAN F, SUN D M, GAO J S, et al. Preparation of molecularly imprinted polymer nanoparticles for selective removal of fluoroquinolone antibiotics in aqueous solution[J]. Journal of Hazardous Materials, 2013, 244:750-757. [76] HE Y H, HUANG Y Y, JIN Y L, et al. Well-defined nanostructured surface-imprinted polymers for highly selective magnetic separation of fluoroquinolones in human urine[J]. Acs Applied Materials & Interfaces, 2014, 6(12):9634-9642. [77] FAN Y M, ZENG G L, MA X G. Multi-templates surface molecularly imprinted polymer for rapid separation and analysis of quinolones in water[J]. Environmental Science and Pollution Research, 2020, 27(7):7177-7187. [78] KAREUHANON W, LEE V S, NIMMANPIPUG P, et al. Synthesis of molecularly imprinted polymers for nevirapine by dummy template imprinting approach[J]. Chromatographia, 2009, 70(11/12):1531-1537. [79] YIN J F, MENG Z H, DU M J, et al. Pseudo-template molecularly imprinted polymer for selective screening of trace beta-lactam antibiotics in river and tap water[J]. Journal of Chromatography A, 2010, 1217(33):5420-5426. [80] HU Y F, WANG C, LI X D, et al. Preparation and application of epitope magnetic molecularly imprinted polymers for enrichment of sulfonamide antibiotics in water[J]. Electrophoresis, 2017, 38(19):2462-2467. [81] XU Y, LI J N, JIANG L Y, et al. Simultaneous determination of sulfonamides and fluoroquinolones from environmental water based on magnetic double-template molecularly imprinting technique[J]. Environmentai Science and Pollution Research, 2018, 25(16):16121-16134. [82] 廖素兰, 陈少云, 刘奇琳, 等. 双功能单体法制备磁性奥硝唑分子印迹聚合物及应用[J]. 分析化学, 2018, 46(1):100-106. LIAO S L, CHEN S Y, LIU Q L, et al. Preparation and application of ornidazole magnetic imprinted polymers with dual functional monomers[J]. Chinese Journal of Analytical Chemistry, 2018, 46(1):100-106(in Chinese).
[83] HU Z H, WANG Y F, OMER A M, et al. Fabrication of ofloxacin imprinted polymer on the surface of magnetic carboxylated cellulose nanocrystals for highly selective adsorption of fluoroquinolones from water[J]. International Journal of Biological Macromolecules, 2018, 107:453-462. [84] TOUDESHKI R M, DADFARNIA S, SHABANI A M H. Chemiluminescence determination of furazolidone in poultry tissues and water samples after selective solid phase microextraction using magnetic molecularly imprinted polymers[J]. New Journal of Chemistry, 2018, 42(13):10751-10760. [85] XU L C, PAN J M, DAI J D, et al. Preparation of thermal-responsive magnetic molecularly imprinted polymers for selective removal of antibiotics from aqueous solution[J]. Journal of Hazardous Materials, 2012, 233:48-56. [86] XU Y, ZHAO Q, JIANG L Y, et al. Selective determination of sulfonamides from environmental water based on magnetic surface molecularly imprinting technology[J]. Environmental Science and Pollution Research, 2017, 24(10):9174-9186. [87] ZHUANG J M, GORDON M R, VENTURA J, et al. Multi-stimuli responsive macromolecules and their assemblies[J]. Chemical Society Reviews, 2013, 42(17):7421-7435. [88] 陈光浩, 欧红香, 余沛霖, 等. 多孔温敏四环素分子印迹吸附剂的制备及性能[J]. 环境化学, 2018, 37(7):1619-1627. CHEN G H, OU H X, YU P L, et al. Preparation and properties of temperature sensitiveporous tetracycline molecularly imprinted adsorbent[J]. Environmental Chemistry, 2018, 37(7):1619-1627(in Chinese).
[89] 欧红香, 陈群汇, 朱晓莉,等. 中空硅球表面分子印迹温敏聚合物吸附溶液中的四环素[J]. 环境化学, 2016, 35(5):901-909. OU H X,CHEN Q H,ZHU X L, et al. Hollow silica sphere surface molecularly imprinted temperature-sensitive polymers for adsorption of tetracycline in solution[J]. Environmental Chemistry, 2016, 35(5):901-909(in Chinese).
计量
- 文章访问数: 3471
- HTML全文浏览数: 3471
- PDF下载数: 160
- 施引文献: 0