Molecularly imprinted polymer based enantioselective sensing devices: A review

Analytica Chimica Acta

Volumn 853, Issue 1, 2015, Pages 1-18

  Tiwari, Mahavir Prasad ^a   Prasad, Amrita ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

Chiral recognition; Electrochemical chiral sensors; Enantio sensing; Molecularly imprinted polymers; Optical sensors; Piezoelectric devices

Indexed keywords

BACTERIOPHAGES; BIOLOGY; BIOSYNTHESIS; ENANTIOMERS; MOLECULAR MODELING; OPTICAL SENSORS; PIEZOELECTRIC DEVICES; PIEZOELECTRICITY; POLYMERIZATION; POLYMERS;

CHIRAL RECOGNITION; CHIRAL SENSOR; ENANTIO; ENANTIO-DIFFERENTIATING; MOLECULAR IMPRINTING TECHNOLOGY; MOLECULARLY IMPRINTED POLYMER; PHARMACEUTICAL ANALYSIS; THREE DIMENSIONAL CAVITY;

STEREOCHEMISTRY;

MOLECULARLY IMPRINTED POLYMER; NANOMATERIAL; METAL; POLYMER; THYROXINE;

ARTICLE; BINDING AFFINITY; CHIRALITY; ELECTROCHEMICAL DETECTION; ENANTIOMER; ENANTIOSELECTIVITY; MOLECULAR IMPRINTING; MOLECULAR RECOGNITION; NANOFABRICATION; PIEZOELECTRICITY; POLYMERIZATION; SENSOR; CHEMISTRY; ELECTROCHEMICAL ANALYSIS; QUARTZ CRYSTAL MICROBALANCE; STEREOISOMERISM;

ELECTROCHEMICAL TECHNIQUES; METALS; MOLECULAR IMPRINTING; NANOSTRUCTURES; POLYMERS; QUARTZ CRYSTAL MICROBALANCE TECHNIQUES; STEREOISOMERISM; THYROXINE;

EID: 84922537467     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2014.06.011     Document Type: Article

References (103)

1. Rouhi A.M. Chiral business. Chem. Eng. News 2003, 81:45-55.
2. Aboul-Enein H.Y., Stefan R.I. Enantioselective sensors and biosensors in the analysis of chiral drugs. Crit. Rev. Anal. Chem. 1998, 28:259-266.
3. Stefan R.I., van Staden J.F., Aboul-Enein H.Y. Molecular recognition in chiral discrimination. Cryst. Eng. 2001, 4:113-118.
4. Stefan R.I., van Staden J.F., Aboul-Enein H.Y. Design and use of electrochemical sensors in enantioselective high throughput screening of drugs. Comb. Chem. High Throughput Screen. 2000, 6:445-454.
5. Stefan R.I., van Staden J.F., Aboul-Enein H.Y. Analysis of chiral drugs with enantioselective biosensors. An overview. Electroanalysis 1999, 11:1233-1235.
6. Aboul-Enein H.Y., Stefan R.I., van Staden J.F. Analysis of several angiotensin converting enzyme inhibitors using potentiometric, enantioselective membrane electrodes. Anal. Lett. 1999, 32:623-632.
7. Stefan R.I., Radu G.L., Aboul-Enein H.Y., Baiulescu G.E. The opportunity to use amperometric biosensors for enantioselective analysis of angiotensin converting enzyme inhibitors. Curr. Trends Anal. Chem. 1998, 1:135-138.
8. Zhang L., Song M., Tian Q., Min S. Chiral separation of l,d-tyrosine and l,d-tryptophan by ctDNA. Sep. Purif. Technol. 2007, 55:388-391.
9. Whitcombe M.J., Alexander C., Vulfson E.N. Imprinted polymers: versatile new tools in synthesis. Synlett 2000, 2000:911-923.
10. Wulff G. Enzyme-like catalysis by molecularly imprinted polymers. Chem. Rev. 2002, 102:1-28.
11. Haupt K., Mosbach K. Molecularly imprinted polymers and their use in biomimetic sensors. Chem. Rev. 2000, 100:2495-2504.
12. Ye L., Haupt K. Molecularly imprinted polymers as antibody and receptor mimics for assays, sensors and drug discovery. Anal. Bioanal. Chem. 2004, 378:1887-1897.
13. Alexander C., Andersson H.S., Andersson L.I., Ansell R.J., Kirsch N., Nicholls I.A., O'Mahony J., Whitcombe M.J. Molecular imprinting science and technology: a survey of the literature for the years up to and including. J. Mol. Recognit. 2003, 19:106-180.
14. Ansell R.J. Molecularly imprinted polymers for the enantioseparation of chiral drugs. Adv. Drug Delivery Rev. 2005, 57:1809-1835.
15. Sellergren B. Imprinted chiral stationary phases in high-performance liquid chromatography. J. Chromatogr. A 2001, 906:227-252.
16. Kempe M. Antibody-mimicking polymers as chiral stationary phases in HPLC. Anal. Chem. 1996, 68:1948-1953.
17. Ramstrom O., Nicholls I.A., Mosbach K. Synthetic peptide receptor mimics: highly stereoselective recognition in non-covalent molecularly imprinted polymers. Tetrahedron: Asym. 1994, 5:649-656.
18. Cheong W.J., Ali F., Choi J.H., Lee J.O., Sung K.Y. Recent applications of molecular imprinted polymers for enantioselective recognition. Talanta 2013, 106:45-59.
19. Kaniewska M., Trojanowicz M. Chiral sensors based on molecularly imprinted polymers. Mol. Imprint. Sens. 2012, 175-194.
20. Trojanowicz M., Wcislo M. Electrochemical and piezoelectric enantioselective sensors and biosensors. Anal. Lett. 2005, 38:523-547.
21. Prasad B.B., Tiwari M.P. Molecularly Imprinted Nanomaterial-Based Highly Sensitive and Selective Medical Devices, Biomedical Materials and Diagnostic Devices 2012, 337-390. Wiley.
22. Wulff G., Sarhan A. The use of polymers with enzyme-analogous structures for the resolution of racemates. Angew. Chem. Int. Ed. 1972, 11:341.
23. Sellergren B., Lepisto M., Mosbach K. Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition. J. Am. Chem. Soc. 1988, 110:5853-5860.
24. Ramstrom O., Ansell R.J. Molecular imprinting technology: challenges and prospects for the future. Chirality 1998, 10:195-209.
25. Maier N.M., Franco P., Lindner W. Separation of enantiomers: needs, challenges, perspectives. J. Chromatogr. A 2001, 906:3-33.
26. Matsui J., Kato T., Takeuchi T., Suzuki M., Yokoyama K., Tamiya E., Karube I. Molecular recognition in continuous polymer rods prepared by a molecular imprinting technique. Anal. Chem. 1993, 65:2223-2224.
27. Yin J., Yang G., Chen Y.J. Rapid and efficient chiral separation of nateglinide and its l-enantiomer on monolithic molecularly imprinted polymers. J. Chromatogr. A 2005, 1090:68-75.
28. Kempe H., Kempe M. Development and evaluation of spherical molecularly imprinted polymer beads. Anal. Chem. 2006, 78:3659-3666.
29. Ansell R.J., Mosbach K. Molecularly imprinted polymers by suspension polymerisation in perfluorocarbon liquids, with emphasis on the influence of the porogenic solvent. J. Chromatogr. A 1997, 787:55-66.
30. Kempe H., Kempe M. Novel method for the synthesis of molecularly imprinted polymer bead libraries. Macromol. Rapid Commun. 2004, 25:315-320.
31. Haginaka J., Sanbe H., Takehira H. Uniform-sized molecularly imprinted polymer for (S)-ibuprofen: retention properties in aqueous mobile phases. J. Chromatogr. A 1999, 857:117-125.
32. Haginaka J., Takehira H., Hosoya K., Tanaka N. Molecularly imprinted uniform-sized polymer-based stationary phase for naproxen. Chem. Lett. 1997, 6:555-556.
33. Haginaka J., Kagawa C. Retentivity and enantioselectivity of uniformly sized molecularly imprinted polymers for d-chlorpheniramine and -brompheniramine in hydro-organic mobile phases. J. Chromatogr. B 2004, 804:19-24.
34. Fu Q., Sanbe H., Kagawa C., Kunimoto K.K., Haginaka J. Uniformly sized molecularly imprinted polymer for (S)-nilvadipine. comparison of chiral recognition ability with HPLC chiral stationary phases based on a protein. Anal. Chem. 2003, 75:191-198.
35. Sulitzky C., Rueckert B., Hall A.J., Lanza F., Unger K., Sellergren B. Grafting of molecularly imprinted polymer films on silica supports containing surface-bound free radical initiators. Macromolecules 2002, 35:79-91.
36. Titirici M.M., Sellergren B. Thin molecularly imprinted polymer films via reversible addition-fragmentation chain transfer polymerization. Chem. Mater. 2006, 18:1773-1779.
37. Maier N.M., Lindner W. Chiral recognition applications of molecularly imprinted polymers: a critical review. Anal. Bioanal. Chem. 2007, 389:377-397.
38. Gübitz G., Schmid M.G. Chiral separation by capillary electromigration techniques. J. Chromatogr. A 2008, 1204:140-156.
39. Mangelings D., Heyden Y.V. Enantioselective capillary electrochromatography: recent developments and new trends. Electrophoresis 2011, 32:2583-2601.
40. Ward T.J., Ward K.D. Chiral separations: a review of current topics and trends. Anal. Chem. 2012, 84:626-635.
41. Izake E.L. Chiral discrimination and enantioselective analysis of drugs: an overview. J. Pharm. Sci. 2007, 96:1659-1676.
42. Hofstetter O., Hofstetter H., Wilchek M., Schurig V., Green B.S. Chiral discrimination using an immunosensor. Nat. Biotechnol. 1999, 17:371-374.
43. Cao L., Zhou X.C., Li S.F.Y. Enantioselective sensor based on microgravimetric quartz crystal microbalance with molecularly imprinted polymer film. Analyst 2001, 126:184-188.
44. Levi R., McNiven S., Piletsky S.A., Cheong S.H., Yano K., Karube I. Optical detection of chloramphenicol using molecularly imprinted polymers. Anal. Chem. 1997, 69:2017-2021.
45. Fukuda T., Maeda Y., Kitano H. Stereoselective inclusion of dopa derivatives by a self-assembled monolayer of thiolated cyclodextrin on a gold electrode. Langmuir 1999, 15:1887-1890.
46. Paolesse R., Monti D., La Monica L., Venanzi M., Froiio A., Nardis S., Di Natale C., Martinelli E., D'Amico A. Preparation and self-assembly of chiral porphyrin diads on the gold electrodes of quartz crystal microbalances: a novel potential approach to the development of enantioselective chemical sensors. Chem. -Eur. J. 2002, 8:2476-2483.
47. Lough W.J., Wainer I.W. Chirality in Natural and Applied Science 2002, 91. CRC Press.
48. Andersson L.I., Miyabayashi A., O'Shannessy D.J., Mosbach K. Enantiomeric resolution of amino acid derivatives on molecularly imprinted polymers as monitored by potentiometric measurements. J. Chromatogr. 1990, 516:323-331.
49. 2 films associated with field-effect transistors: novel functionalized devices for chiroselective and chirospecific analyses. Chem. -Eur. J. 2001, 7:3992-3997.
50. Okuno H., Kitano T., Yakabe H., Kishimoto M., Deore B.A., Siigi H., Nagaoka T. Characterization of overoxidized polypyrrole colloids imprinted with l-lactate and their application to enantioseparation of amino acids. Anal. Chem. 2002, 74:4184-4190.
51. Kirchner R., Seidel J., Wolf G., Wulff G. Calorimetric investigation of chiral recognition processes in a molecularly imprinted polymer. Inclusion Phenom. Macrocyclic Chem. 2002, 43:279-283.
52. Zhou Y.X., Yu B., Levon K. Potentiometric sensing of chiral amino acids. Chem. Mater. 2003, 15:2774-2779.
53. Liang H.-J., Ling T.-R., Rick J.F., Chou T.-C. Molecularly imprinted electrochemical sensor able to enantroselectivly recognize d and l-tyrosine. Anal. Chim. Acta 2005, 542:83-89.
54. Sekine S., Watanabe Y., Yoshimi Y., Hattori K., Sakai K. Influence of solvents on chiral discriminative gate effect of molecularly imprinted poly(ethylene glycol dimethacrylate-co-methacrylic acid). Sens. Actuators, B 2007, 127:512-517.
55. Ouyang R., Lei J., Ju H., Xue Y. A molecularly imprinted copolymer designed for enantioselective recognition of glutamic acid. Adv. Funct. Mater. 2007, 17:3223-3230.
56. Kong Y., Huang G.T., Chen Z.D., Wang W.C. Molecular-imprinted electrochemical sensor for recognization of enantiomorphs of d-tyrosine and l-tyrosine. Phys. Test. Chem. Anal. Part B: Chem. Anal. 2007, 43:997-999.
57. Huang J., Wei Z., Chen J. Molecular imprinted polypyrrole nanowires for chiral amino acid recognition. Sens. Actuators, B 2008, 134:573-578.
58. Granot E., Tel-Vered R., Lioubashevski O., Willner I. Stereoselective and enantioselective electrochemical sensing of monosaccharides using imprinted boronic acid-functionalized polyphenol films. Adv. Funct. Mater. 2008, 18:478-484.
59. Qu P., Lei J., Ouyang R., Ju H. Enantioseparation and amperometric detection of chiral compounds by in situ molecular imprinting on the microchannel wall. Anal. Chem. 2009, 81:9651-9656.
60. Luo X.H., Liu K., Huang H.Y. Determination of l-serine with self-assembled molecular imprinted monolayer modified electrode. J. Instrum. Anal. 2009, 28:349-353.
61. Zhang Z., Hu Y., Zhang H., Luo L., Yao S. Layer-by-layer assembly sensitive electrochemical sensor for selectively probing l-histidine based on molecular imprinting sol-gel at functionalized indium tin oxide electrode. Biosens. Bioelectron. 2010, 26:696-702.
62. Prasad B.B., Tiwari M.P., Madhuri R., Sharma P.S. Enatioselective quantitative separation of d- and l-thyroxine by molecularly imprinted micro-solid phase extraction silver fiber coupled with complementary molecularly imprinted polymer-sensor. J. Chromatogr. A 2010, 1217:4255-4266.
63. Prasad B.B., Madhuri R., Tiwari M.P., Sharma P.S. Layer-by-layer assembled molecularly imprinted polymer modified silver electrode for enantioselective detection of d- and l-thyroxine. Anal. Chim. Acta 2010, 681:16-26.
64. Prasad B.B., Madhuri R., Tiwari M.P., Sharma P.S. Enantioselective recognition of d- and l-tryptophan by imprinted polymer-carbon composite fiber sensor. Talanta 2010, 81:187-196.
65. Prasad B.B., Tiwari M.P., Madhuri R., Sharma P.S. Enantioselective separation and electrochemical sensing of d- and l-tryptophan at ultratrace level using molecularly imprinted micro-solid phase extraction fiber coupled with complementary molecularly imprinted polymer-fiber sensor. J. Chromatogr. B 2011, 879:364-370.
66. Prasad B.B., Kumar D., Madhuri R., Tiwari M.P. Metal ion mediated imprinting for electrochemical enantioselective sensing of l-histidine at trace level. Biosens. Bioelectron. 2011, 28:117-126.
67. Prasad B.B., Pandey I., Srivastava A., Kumar D., Tiwari M.P. Multiwalled carbon nanotubes-based pencil graphite electrode modified with an electrosynthesized molecularly imprinted nanofilm for electrochemical sensing of methionine enantiomers. Sens. Actuators, B: Chem. 2012, 176:863-874.
68. Prasad B.B., Srivastava A., Pandey I., Tiwari M.P. Electrochemically grown imprinted polybenzidine nanofilm on multiwalled carbon nanotubes anchored pencil graphite fibers for enantioselective micro-solid phase extraction coupled with ultratrace sensing of d- and l-methionine. J. Chromatogr. B 2012, 912:65-74.
69. Prasad B.B., Pandey I. Electrochemically imprinted molecular recognition sites on multiwalled carbon-nanotubes/pencil graphite electrode surface for enantioselective detection of d- and l-aspartic acid. Electrochim. Acta 2013, 88:24-34.
70. Prasad B.B., Srivastava A., Tiwari M.P. Molecularly imprinted polymer-matrix nanocomposite for enantioselective electrochemical sensing of d- and l-aspartic acid. Mater. Sci. Eng. C 2013, 33:4071-4080.
71. Prasad B.B., Srivastava A., Tiwari M.P. Highly sensitive and selective hyphenated technique (molecularly imprinted polymer solid-phase microextraction-molecularly imprinted polymer sensor) for ultra trace analysis of aspartic acid enantiomers. J. Chromatogr. A 2013, 1283:9-19.
72. Prasad B.B., Pandey I. Metal incorporated molecularly imprinted polymer-based electrochemical sensor for enantio-selective analysis of pyroglutamic acid isomers. Sens. Actuators, B 2013, 186:407-416.
73. Basozabal I., Gómez-Caballero A., Unceta N., Goicolea M.A., Barrio R.J. Voltammetric sensors with chiral recognition capability: the use of a chiral inducing agent in polyaniline electrochemical synthesis for the specific recognition of the enantiomers of the pesticide dinoseb. Electrochim. Acta 2011, 58:729-735.
74. Chen Y., Chen L., Bi R., Xu L., Liu Y. A potentiometric chiral sensor for l-Phenylalanine based on crosslinked polymethylacrylic acid-polycarbazole hybrid molecularly imprinted polymer. Anal. Chim. Acta 2012, 754:83-90.
75. Hu Y.-F., Zhang Z.-H., Zhang H.-B., Luo L.-J., Yao S.-Z. Electrochemical determination of l-phenylalanine at polyaniline modified carbon electrode based on β-cyclodextrin incorporated carbon nanotube composite material and imprinted sol-gel film. Talanta 2011, 84:305-313.
76. Sulaiman Y., Kataky R. Chiral acid selectivity displayed by PEDOT electro-polymerized in the presence of chiral molecules. Analyst 2012, 137:2386-2393.
77. Wen X., Xiao L., Weiying Z., Xiaoguang Y. Electrochemical sensors for l-tryptophan based on molecularly imprinted polymers. Adv. Mater. Res. 2012, 499:434-438.
78. Liao Y., Wang W., Wang B. Building fluorescent sensors by template polymerization: the preparation of a fluorescent sensor for l-tryptophan. Bioorg. Chem. 1999, 27:463-476.
79. Nopper D., Lammershop O., Wulff G., Gauglitz G. Amidine-based molecularly imprinted polymers-new sensitive elements for chiral chemosensors. Anal. Bioanal. Chem. 2003, 377:608-613.
80. Hu X., An Q., Li G., Tao S., Liu J. Imprinted photonic polymers for chiral recognition. Angew. Chem. Int. Ed. 2006, 45:8145-8148.
81. Wang L., Zhang Z., Huang L. Molecularly imprinted polymer based on chemiluminescence imaging for the chiral recognition of dansyl-phenylalanine. Anal. Bioanal. Chem. 2008, 390:1431-1436.
82. Nguyen T.H., Ansell R.J. Fluorescent imprinted polymer sensors for chiral amines. Org. Biomol. Chem. 2009, 7:1211-1220.
83. Paik P., Gedanken A., Mastai Y. Chiral-mesoporous-polypyrrole nanoparticles: its chiral recognition abilities and use in enantioselective separation. J. Mater. Chem. 2010, 20:4085-4093.
84. Kong Y., Yao C., Ni J., Junhua, Zhou Y., Chen Z. Identification of aspartic acid enantiomers based on molecularly imprinted polyaniline. Chin. J. Chem. 2011, 29:2659-2663.
85. 2 nano-thin films. Anal. Chim. Acta 2011, 694:142-150.
86. Qiu H., Luo C., Sun M., Lu F., Fan L., Li X. Determination of l-tryptophan based on graphene oxide-magnetite-molecularly imprinted polymers and chemiluminescence. Talanta 2012, 98:226-230.
87. Zhang Y.-X., Zhao P.-Y., Yu L.-P. Highly-sensitive and selective colorimetric sensor for amino acids chiral recognition based on molecularly imprinted photonic polymers. Sens. Actuators, B 2013, 181:850-857.
88. Haupt K., Noworyta K., Kutner W. Imprinted polymer-based enantioselective acoustic sensor using a quartz crystal microbalance. Anal. Commun. 1999, 36:391-393.
89. Deore B., Chen Z., Nagaoka T. Potential-induced enantioselective uptake of amino acid into molecularly imprinted overoxidized polypyrrole. Anal. Chem. 2000, 72:3989-3994.
90. Percival C.J., Stanley S., Galle M., Braithwaite A., Newton M.I., McHale G., Hayes W. Molecular-imprinted, polymer-coated quartz crystal microbalances for the detection of terpenes. Anal. Chem. 2001, 73:4225-4228.
91. Liu Y., Peng H., Nie L., Yao S. Enantioseparation of dl-phenylalanine, based on a continuous molecularly imprinted rod, using a series quartz crystal sensor as the detector. Instrum. Sci. Technol. 2002, 30:455-464.
92. Stanley S., Percival C.J., Morel T., Rraithwaite A., Newton M.I., McHale G., Hayes W. Enantioselective determination of l-serine. Sens. Actuators, B 2003, 89:103-106.
93. Liao H., Zhang Z., Nie L., Yao S. Electrosynthesis of imprinted polyacrylamide membranes for the stereospecific l-histidine sensor and its characterization by AC impedance spectroscopy and piezoelectric quartz crystal technique. J. Biochem. Biophys. Methods 2004, 59:75-87.
94. Piachama T., Josell A., Arwin H., Prachayasittikul V., Ye L. Molecularly imprinted polymer thin films on quartz crystal microbalance using a surface bound photo-radical initiator. Anal. Chim. Acta 2005, 536:191-196.
95. Liu F., Liu X., Ng S.-C., Chan H.S.-O. Enantioselective molecular imprinting polymer coated QCM for the recognition of l-tryptophan. Sens. Actuators, B 2006, 113:234-240.
96. Syritski V., Reut J., Menaker A., Gyurcsanyi R.E., Opik A. Electrosynthesized molecularly imprinted polypyrrole films for enantioselective recognition of l-aspartic acid. Electrochim. Acta 2008, 53:2729-2736.
97. Kong Y., Zhao W., Yao S., Xu J., Wang W., Chen Z. Molecularly imprinted polypyrrole prepared by electrodeposition for the selective recognition of tryptophan enantiomers. J. Appl. Polym. Sci. 2010, 115:1952-1957.
98. Kong Y., Li X., Ni J., Yao C., Chen Z. Enantioselective recognition of glutamic acid enantiomers based on poly(aniline-co-m-aminophenol) electrode column. Electrochem. Commun. 2012, 14:17-20.
99. Arenas L.F., Ebarvia B.S., Sevilla F.B. Enantioselective piezoelectric quartz crystal sensor for d-methamphetamine based on a molecularly imprinted polymer. Anal. Bioanal. Chem. 2010, 397:3155-3158.
100. Pernites R.B., Venkata S.K., Tiu B.D.B., Yago A.C.C., Advincula R.C. Nanostructured, molecularly imprinted, and template-patterned polythiophenes for chiral sensing and differentiation. Small 2012, 8:1669-1674.
101. Prasad B.B., Pandey I. Molecularly imprinted polymer-based piezoelectric sensor for enantio-selective analysis of malic acid isomers. Sens. Actuators, B 2013, 181:596-604.
102. Riskin M., Tel-Vered R., Frasconi M., Yavo N., Willner I. Stereoselective and chiroselective surface plasmon resonance (SPR) analysis of amino acids by molecularly imprinted Au-nanoparticle composites. Chemistry 2010, 16:7114-7120.
103. Ben-Amram Y., Riskin M., Willner I. Selective and enantioselective analysis of mono- and disaccharides using surface plasmon resonance spectroscopy and imprinted boronic acid-functionalized Au nanoparticle composites. Analyst 2010, 135:2952-2959.