Advances in Molecularly Imprinted Systems: Materials, Characterization Methods and Analytical Applications

Author(s): Yeşeren Saylan, Adil Denizli*

Journal Name: Current Analytical Chemistry

Volume 16 , Issue 3 , 2020


Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Abstract:

Introduction: A molecular imprinting is one of the fascinating modification methods that employ molecules as targets to create geometric cavities for recognition of targets in the polymeric matrix. This method provides a broad versatility to imprint target molecules with different size, three-dimensional structure and physicochemical features. In contrast to the complex and timeconsuming laboratory surface modification procedures, this method offers a rapid, sensitive, inexpensive, easy-to-use, and selective approach for the diagnosis, screening and monitoring disorders. Owing to their unique features such as high selectivity, physical and chemical robustness, high stability, low-cost and reusability of this method, molecularly imprinted polymers have become very attractive materials and been applied in various applications from separation to detection.

Background: The aims of this review are structured according to the fundamentals of molecularly imprinted polymers involving essential elements, preparation procedures and also the analytical applications platforms. Finally, the future perspectives to increase the development of molecularly imprinted platforms.

Methods: A molecular imprinting is one of the commonly used modification methods that apply target as a recognition element itself and provide a wide range of versatility to replica other targets with a different structure, size, and physicochemical features. A rapid, easy, cheap and specific recognition approach has become one of the investigation areas on, especially biochemistry, biomedicine and biotechnology. In recent years, several technologies of molecular imprinting method have gained prompt development according to continuous use and improvement of traditional polymerization techniques.

Results: The molecularly imprinted polymers with excellent performances have been prepared and also more exciting and universal applications have been recognized. In contrast to the conventional methods, the imprinted systems have superior advantages including high stability, relative ease and low cost of preparation, resistance to elevated temperature, and pressure and potential application to various target molecules. In view of these considerations, molecularly imprinted systems have found application in various fields of analytical chemistry including separation, purification, detection and spectrophotometric systems.

Conclusion: Recent analytical methods are reported to develop the binding kinetics of imprinted systems by using the development of other technologies. The combined platforms are among the most encouraging systems to detect and recognize several molecules. The diversity of molecular imprinting methods was overviewed for different analytical application platforms. There is still a requirement of more knowledge on the molecular features of these polymers. A next step would further be the optimization of different systems with more homogeneous and easily reachable recognition sites to reduce the laborious in the accessibility in the three-dimensional polymeric materials in sufficient recognition features and also better selectivity and sensitivity for a wide range of molecules.

Keywords: Analytical applications, molecular imprinting, polymeric systems, three-dimensional structure, physicochemical features, biochemistry, biomedicine, biotechnology.

[1]
Lv, Y.; Tan, T.; Svec, F. Molecular imprinting of proteins in polymers attached to the surface of nanomaterials for selective recognition of biomacromolecules. Biotechnol. Adv., 2013, 31(8), 1172-1186.
[http://dx.doi.org/10.1016/j.biotechadv.2013.02.005] [PMID: 23466364]
[2]
Li, L.; Fan, L.; Dai, Y.; Kan, X. Recognition and determination of bovine hemoglobin using a gold electrode modified with gold nanoparticles and molecularly imprinted self-polymerized dopamine. Mikrochim. Acta, 2015, 182, 2477-2483.
[http://dx.doi.org/10.1007/s00604-015-1594-5]
[3]
Wulff, G.; Sarhan, A. Use of polymers with enzyme analogous structures for the resolution of racemates. Angew. Chem. Int. Ed. Engl., 1972, 11, 341.
[4]
Wulff, G.; Gross, T.; Schonfeld, R. Enzyme models based on molecularly imprinted polymers with strong esterase activity. Angew. Chem. Int. Ed. Engl., 1997, 36, 1962-1964.
[http://dx.doi.org/10.1002/anie.199719621]
[5]
Verma, A.; Nakade, H.; Simard, J.M.; Rotello, V.M. Recognition and stabilization of peptide α-helices using templatable nanoparticle receptors. J. Am. Chem. Soc., 2004, 126(35), 10806-10807.
[http://dx.doi.org/10.1021/ja047719h] [PMID: 15339141]
[6]
Aubin-Tam, M.E.; Hamad-Schifferli, K. Gold nanoparticle-cytochrome C complexes: the effect of nanoparticle ligand charge on protein structure. Langmuir, 2005, 21(26), 12080-12084.
[http://dx.doi.org/10.1021/la052102e] [PMID: 16342975]
[7]
Cabaleiro-Lago, C.; Quinlan-Pluck, F.; Lynch, I.; Lindman, S.; Minogue, A.M.; Thulin, E.; Walsh, D.M.; Dawson, K.A.; Linse, S. Inhibition of amyloid β protein fibrillation by polymeric nanoparticles. J. Am. Chem. Soc., 2008, 130(46), 15437-15443.
[http://dx.doi.org/10.1021/ja8041806] [PMID: 18954050]
[8]
Hoshino, Y.; Urakami, T.; Kodama, T.; Koide, H.; Oku, N.; Okahata, Y.; Shea, K.J. Design of synthetic polymer nanoparticles that capture and neutralize a toxic peptide. Small, 2009, 5(13), 1562-1568.
[http://dx.doi.org/10.1002/smll.200900186] [PMID: 19296557]
[9]
Haupt, K. Molecularly imprinted polymers: the next generation. Anal. Chem., 2003, 75(17), 376A-383A.
[http://dx.doi.org/10.1021/ac031385h] [PMID: 14632031]
[10]
Zimmerman, S.C.; Lemcoff, N.G. Synthetic hosts via molecular imprinting--are universal synthetic antibodies realistically possible? Chem. Commun. , 2004, 1, 5-14.
[http://dx.doi.org/10.1039/B304720B]
[11]
Mosbach, K. The promise of molecular imprinting. Sci. Am., 2006, 295(4), 86-91.
[http://dx.doi.org/10.1038/scientificamerican1006-86] [PMID: 16989485]
[12]
Saylan, Y.; Yilmaz, F.; Özgür, E.; Derazshamshir, A.; Yavuz, H.; Denizli, A. Molecularly imprinting of macromolecules for sensors applications. Sensors (Basel), 2017, 17(4), 898-928.
[http://dx.doi.org/10.3390/s17040898] [PMID: 28422082]
[13]
Piletsky, S.A.; Turner, N.W.; Laitenberger, P. Molecularly imprinted polymers in clinical diagnostics--future potential and existing problems. Med. Eng. Phys., 2006, 28(10), 971-977.
[http://dx.doi.org/10.1016/j.medengphy.2006.05.004] [PMID: 16828327]
[14]
Volkert, A.A.; Haes, A.J. Advancements in nanosensors using plastic antibodies. Analyst (Lond.), 2014, 139(1), 21-31.
[http://dx.doi.org/10.1039/C3AN01725G] [PMID: 24179993]
[15]
Ye, L. Synthetic strategies in molecular imprinting; Advances in biochemical engineering/biotechnology. Mol. Imprint. Polym Biotechnol., 2015, 150, 1-24.
[http://dx.doi.org/10.1007/10_2015_313]
[16]
Ramstroem, O.; Andersson, L.I.; Mosbach, K. Recognition sites incorporating both pyridinyl and carboxy functionalities prepared by molecular imprinting. J. Org. Chem., 1993, 58, 7562-7464.
[http://dx.doi.org/10.1021/jo00078a041]
[17]
Siemann, M.; Andersson, L.I.; Mosbach, K. Separation and detection of macrolide antibiotics by HPLC using macrolide-imprinted synthetic polymers as stationary phases. J. Antibiot. (Tokyo), 1997, 50(1), 89-91.
[http://dx.doi.org/10.7164/antibiotics.50.89] [PMID: 9066772]
[18]
Yan, H.; Row, K.R. Characteristic and synthetic approach of molecularly imprinted polymer. Int. J. Mol. Sci., 2006, 7, 155-178.
[http://dx.doi.org/10.3390/i7050155]
[19]
Santora, B.P.; Gagne, M.R.; Moloy, K.G.; Radu, N.S. Porogen and cross-linking effects on the surface area, pore volume distribution, and morphology of macroporous polymers obtained by bulk polymerization. Macromolecules, 2001, 34, 658-661.
[http://dx.doi.org/10.1021/ma0004817]
[20]
Lofgreen, J.E.; Ozin, G.A. Controlling morphology and porosity to improve performance of molecularly imprinted sol-gel silica. Chem. Soc. Rev., 2014, 43(3), 911-933.
[http://dx.doi.org/10.1039/C3CS60276A] [PMID: 24247659]
[21]
Ikegami, T.; Mukawa, T.; Nariai, H.; Takeuchi, T. Bisphenol A-recognition polymers prepared by covalent molecular imprinting. Anal. Chim. Acta, 2004, 504, 131-135.
[http://dx.doi.org/10.1016/j.aca.2003.08.032]
[22]
Arshady, R.; Mosbach, K. Synthesis of substrate-selective polymers by host-guest polymerization. Macromol. Chem. Phys., 1981, 182, 687-692.
[http://dx.doi.org/10.1002/macp.1981.021820240]
[23]
Mosbach, K.; Ye, L.; Cormack, P. Molecular imprinting on microgel spheres. Anal. Chim. Acta, 2001, 435, 187-196.
[http://dx.doi.org/10.1016/S0003-2670(00)01248-4]
[24]
Curcio, P.; Zandanel, C.; Wagner, A.; Mioskowski, C.; Baati, R. Semi-covalent surface molecular imprinting of polymers by one-stage mini-emulsion polymerization: glucopyranoside as a model analyte. Macromol. Biosci., 2009, 9(6), 596-604.
[http://dx.doi.org/10.1002/mabi.200900056] [PMID: 19434676]
[25]
[26]
Chen, L.; Wang, X.; Lu, W.; Wu, X.; Li, J. Molecular imprinting: perspectives and applications. Chem. Soc. Rev., 2016, 45(8), 2137-2211.
[http://dx.doi.org/10.1039/C6CS00061D] [PMID: 26936282]
[27]
Wackerlig, J.; Schirhagl, R. Applications of molecularly imprinted polymer nanoparticles and their advances toward industrial use.: A review. Anal. Chem., 2016, 88(1), 250-261.
[http://dx.doi.org/10.1021/acs.analchem.5b03804] [PMID: 26539750]
[28]
Huang, D.L.; Wang, R.Z.; Liu, Y.G.; Zeng, G.M.; Lai, C.; Xu, P.; Lu, B.A.; Xu, J.J.; Wang, C.; Huang, C. Application of molecularly imprinted polymers in wastewater treatment: a review. Environ. Sci. Pollut. Res. Int., 2015, 22(2), 963-977.
[http://dx.doi.org/10.1007/s11356-014-3599-8] [PMID: 25280502]
[29]
Lan, H.; Gan, N.; Pan, D.; Hu, F.; Li, T.; Long, N.; Qiao, L. An automated solid-phase microextraction method based on magnetic molecularly imprinted polymer as fiber coating for detection of trace estrogens in milk powder. J. Chromatogr. A, 2014, 1331, 10-18.
[http://dx.doi.org/10.1016/j.chroma.2014.01.016] [PMID: 24485038]
[30]
Saylan, Y.; Tamahkar, E.; Denizli, A. Recognition of lysozyme using surface imprinted bacterial cellulose nanofibers. J. Biomater. Sci. Polym. Ed., 2017, 28(16), 1950-1965.
[http://dx.doi.org/10.1080/09205063.2017.1364099] [PMID: 28784017]
[31]
Jha, S.K.; Liu, C.; Hayashi, K. Molecular imprinted polyacrylic acids based QCM sensor array forrecognition of organic acids in body odor. Sens. Actuators B Chem., 2014, 204, 74-87.
[http://dx.doi.org/10.1016/j.snb.2014.07.098]
[32]
Rodríguez-Fernández, R.; Peña-Vázquez, E.; Bermejo-Barrera, P. Synthesis of an imprinted polymer for the determination of methylmercury in marine products. Talanta, 2015, 144, 636-641.
[http://dx.doi.org/10.1016/j.talanta.2015.06.028] [PMID: 26452871]
[33]
Tokonami, S.; Shiigi, H.; Nagaoka, T. Review: micro- and nanosized molecularly imprinted polymers for high-throughput analytical applications. Anal. Chim. Acta, 2009, 641(1-2), 7-13.
[http://dx.doi.org/10.1016/j.aca.2009.03.035] [PMID: 19393361]
[34]
Ansari, S.; Karimi, M. Novel developments and trends of analytical methods for drug analysis in biological and environmental samples by molecularly imprinted polymers. Trends Analyt. Chem., 2017, 89, 146-162.
[http://dx.doi.org/10.1016/j.trac.2017.02.002]
[35]
Aşır, S.; Sarı, D.; Derazshamshir, A.; Yılmaz, F.; Şarkaya, K.; Denizli, A. Dopamine-imprinted monolithic column for capillary electrochromatography. Electrophoresis, 2017, 38(22-23), 3003-3012.
[http://dx.doi.org/10.1002/elps.201700228] [PMID: 28786521]
[36]
Urraca, J.L.; Huertas-Pérez, J.F.; Cazorla, G.A.; Gracia-Mora, J.; García-Campaña, A.M.; Moreno-Bondi, M.C. Development of magnetic molecularly imprinted polymers for selective extraction: determination of citrinin in rice samples by liquid chromatography with UV diode array detection. Anal. Bioanal. Chem., 2016, 408(11), 3033-3042.
[http://dx.doi.org/10.1007/s00216-016-9348-8] [PMID: 26873195]
[37]
Soleimani, M.; Ghaderi, S.; Afshar, M.G.; Soleimani, S. Synthesis of molecularly imprinted polymer as a sorbent for solid phase extraction of bovine albumin from whey, milk, urine and serum. Microchem. J., 2012, 100, 1-7.
[http://dx.doi.org/10.1016/j.microc.2011.06.026]
[38]
Su, X.; Li, X.; Li, J.; Liu, M.; Lei, F.; Tan, X.; Li, P.; Luo, W. Synthesis and characterization of core-shell magnetic molecularly imprinted polymers for solid-phase extraction and determination of Rhodamine B in food. Food Chem., 2015, 171, 292-297.
[http://dx.doi.org/10.1016/j.foodchem.2014.09.024] [PMID: 25308672]
[39]
Davoodi, D.; Hassanzadeh-Khayyat, M.; Rezaei, M.A.; Mohajeri, S.A. Preparation, evaluation and application of diazinon imprinted polymers as the sorbent in molecularly imprinted solid-phase extraction and liquid chromatography analysis in cucumber and aqueous samples. Food Chem., 2014, 158, 421-428.
[http://dx.doi.org/10.1016/j.foodchem.2014.02.144] [PMID: 24731364]
[40]
Xie, J.; Zhou, B.; Zhang, T.; Zeng, X.; Yang, M.; Wang, W.; Yang, J. Preparation of nicotine surface molecularly imprinted polymers for selective solid-phase extraction of nicotine from zero-level refill liquids of electronic cigarettes. Anal. Methods, 2018, 10, 3637-3645.
[http://dx.doi.org/10.1039/C8AY00616D]
[41]
Haupt, K. Molecularly imprinted polymers in analytical chemistry. Analyst (Lond.), 2001, 126(6), 747-756.
[http://dx.doi.org/10.1039/b102799a] [PMID: 11445931]
[42]
Saylan, Y.; Denizli, A. Molecular fingerprints of hemoglobin on a nanofilm chip. Sensors (Basel), 2018, 18(9), 1-13.
[http://dx.doi.org/10.3390/s18093016] [PMID: 30205614]
[43]
Saylan, Y.; Akgönüllü, S.; Çimen, D.; Derazshamshir, A.; Bereli, N.; Yılmaz, F.; Denizli, A. Surface plasmon resonance nanosensors based on molecularly imprinted nanofilm for detection of pesticides. Sensor. Actuat. B., 2017, 241, 446-454.
[http://dx.doi.org/10.1016/j.snb.2016.10.017]
[44]
Battal, D.; Akgönüllü, S.; Yalcin, M.S.; Yavuz, H.; Denizli, A. Molecularly imprinted polymer based quartz crystal microbalance sensor system for sensitive and label-free detection of synthetic cannabinoids in urine. Biosens. Bioelectron., 2018, 111, 10-17.
[http://dx.doi.org/10.1016/j.bios.2018.03.055] [PMID: 29631158]
[45]
Dibekkaya, H.; Saylan, Y.; Yılmaz, F.; Derazshamshir, A.; Denizli, A. Surface plasmon resonance sensors for real-time detection of cyclic citrullinated peptide antibodies. J. Macromol. Sci. Pure Appl. Chem., 2016, 53(9), 585-594.
[http://dx.doi.org/10.1080/10601325.2016.1201756]
[46]
Liang, Y.; Yu, L.; Yang, R.; Li, X.; Qu, L.; Li, J. High sensitive and selective graphene oxide/molecularly imprinted polymer electrochemical sensor for 2,4-dichlorophenol in water. Sens. Actuat. B., 2017, 240, 1330-1335.
[http://dx.doi.org/10.1016/j.snb.2016.08.137]
[47]
Zhang, T.; Liu, J.; Wang, J.P. Preparation of a molecularly imprinted polymer based chemiluminescence sensor for the determination of amantadine and rimantadine in meat. Anal. Methods, 2018, 10, 5025-5032.
[http://dx.doi.org/10.1039/C8AY01900B]
[48]
Wang, Q.; Zhang, D. A novel fluorescence sensing method based on quantum dot-graphene and a molecular imprinting technique for the detection of tyramine in rice wine. Anal. Methods, 2018, 10, 3884-3890.
[http://dx.doi.org/10.1039/C8AY01117F]
[49]
Ansari, S. Application of magnetic molecularly imprinted polymer as a versatile and highly selective tool in food and environmental analysis: Recent developments and trends. Trends Analyt. Chem., 2017, 90, 89-106.
[http://dx.doi.org/10.1016/j.trac.2017.03.001]
[50]
Bazrafshan, A.A.; Ghaedi, M.; Rafiee, Z.; Hajati, S.; Ostovan, A. Nano-sized molecularly imprinted polymer for selective ultrasound-assisted microextraction of pesticide Carbaryl from water samples: Spectrophotometric determination. J. Colloid Interface Sci., 2017, 498, 313-322.
[http://dx.doi.org/10.1016/j.jcis.2017.03.076] [PMID: 28343129]
[51]
Ozkütük, E.B.; Ersöz, A.; Denizli, A.; Say, R. Preconcentration of phosphate ion onto ion-imprinted polymer. J. Hazard. Mater., 2008, 157(1), 130-136.
[http://dx.doi.org/10.1016/j.jhazmat.2007.12.118] [PMID: 18313219]
[52]
Yilmaz, V.; Arslan, Z.; Hazer, O.; Yilmaz, H. Selective solid phase extraction of copper using a new Cu(II)-imprinted polymer and determination by inductively coupled plasma optical emission spectroscopy (ICP-OES). Microchem. J., 2014, 114, 66-72.
[http://dx.doi.org/10.1016/j.microc.2013.12.002] [PMID: 24511158]
[53]
Chen, Y.; Li, D.; Bie, Z.; He, X.; Liu, Z. Coupling of phosphate-imprinted mesoporous silica nanoparticles-based selective enrichment with matrix-assisted laser desorption ionization-time-of-flight mass spectrometry for highly efficient analysis of protein phosphorylation. Anal. Chem., 2016, 88(2), 1447-1454.
[http://dx.doi.org/10.1021/acs.analchem.5b04343] [PMID: 26684413]
[54]
Roushani, M.; Abbasi, S.; Khani, H. Synthesis and application of ion-imprinted polymer nanoparticles for the extraction and preconcentration of mercury in water and food samples employing cold vapor atomic absorption spectrometry. Environ. Monit. Assess., 2015, 187(9), 601-614.
[http://dx.doi.org/10.1007/s10661-015-4820-z] [PMID: 26318321]
[55]
Liu, X.; Zhu, L.; Gao, X.; Wang, Y.; Lu, H.; Tang, Y.; Li, J. Magnetic molecularly imprinted polymers for spectrophotometric quantification of curcumin in food. Food Chem., 2016, 202, 309-315.
[http://dx.doi.org/10.1016/j.foodchem.2016.02.015] [PMID: 26920299]
[56]
Minaberry, Y.S.; Tudino, M. An ion imprinted amino-functionalized mesoporous sorbent for the selective minicolumn preconcentration of cadmium ions and determination by GFAAS. Anal. Methods, 2018, 10, 5305-5313.
[http://dx.doi.org/10.1039/C8AY01496E]
[57]
Shakerian, F.; Kim, K.H.; Kwon, E.; Szulejko, J.E.; Kumar, P.; Dadfarnia, S.; Shabani, A.M.H. Advanced polymeric materials: Synthesis and analytical application of ion imprinted polymers as selective sorbents for solid phase extraction of metal ions. Trends Analyt. Chem., 2016, 83, 55-69.
[http://dx.doi.org/10.1016/j.trac.2016.08.001]
[58]
Rutkowska, M.; Płotka-Wasylka, J.; Morrison, C.; Wieczorek, P.P.; Namiesnik, J.; Marc, M. Application of molecularly imprinted polymers in analytical chiral separations and analysis. Trends Anal. Chem., 2018, 102, 91-102.
[http://dx.doi.org/10.1016/j.trac.2018.01.011]
[59]
Uzun, L.; Turner, A.P.F. Molecularly-imprinted polymer sensors: realising their potential. Biosens. Bioelectron., 2016, 76, 131-144.
[http://dx.doi.org/10.1016/j.bios.2015.07.013] [PMID: 26189406]
[60]
Çetin, K.; Alkan, H.; Bereli, N.; Denizli, A. Molecularly imprinted cryogel as a pH-responsive delivery system for doxorubicin. J. Macromol. Sci. Pure Appl. Chem., 2017, 54(8), 502-508.
[61]
Inanan, T.; Tüzmen, N.; Akgöl, S.; Denizli, A. Selective cholesterol adsorption by molecular imprinted polymeric nanospheres and application to GIMS. Int. J. Biol. Macromol., 2016, 92, 451-460.
[http://dx.doi.org/10.1016/j.ijbiomac.2016.07.007] [PMID: 27411294]
[62]
Yang, F.; Wang, R.; Na, G.; Yan, Q.; Lin, Z.; Zhang, Z. Preparation and application of a molecularly imprinted monolith for specific recognition of domoic acid. Anal. Bioanal. Chem., 2018, 410(6), 1845-1854.
[http://dx.doi.org/10.1007/s00216-017-0843-3] [PMID: 29313078]
[63]
Li, D.; Tu, T.; Wu, X. Efficient preparation of template immobilization based boronate affinity surface-imprinted silica nanoparticles using poly(4-aminobenzyl alcohol) as an imprinting coating for glycoprotein recognition. Anal. Methods, 2018, 10, 4419-4430.
[http://dx.doi.org/10.1039/C8AY00632F]
[64]
Wang, B.; Deng, H.; Wu, M.; Xiang, S.; Ma, Q.; Shi, S.; Xie, L.; Guo, Y. Magnetic surface molecularly imprinted polymeric microspheres using gallic acid as a segment template for excellent recognition of ester catechins. Anal. Methods, 2018, 10, 3317-3325.
[http://dx.doi.org/10.1039/C8AY00903A]
[65]
Yao, R.; Yu, Z.; Wu, M.; Yu, H. Preparation and evaluation of molecularly imprinted membrane of teicoplanin. Anal. Methods, 2018, 10, 5416-5423.
[http://dx.doi.org/10.1039/C8AY01623B]


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 16
ISSUE: 3
Year: 2020
Published on: 14 May, 2020
Page: [196 - 207]
Pages: 12
DOI: 10.2174/1573411015666181214155042
Price: $65

Article Metrics

PDF: 29
HTML: 4