Molecularly imprinted polymers for the separation of organic compounds in capillary electrochromatography

Current Organic Chemistry

Volumn 15, Issue 11, 2011, Pages 1863-1870

  Huang, Yan Ping ^a   Zheng, Chao ^a   Liu, Zhao Sheng ^a  

^a TIANJIN MEDICAL UNIVERSITY   (China)

Author keywords

Capillary electrochromatography; Chiral separation; Micro separation; Molecularly imprinted polymer; Stationary phase; Template directed synthesis

Indexed keywords

CHIRALITY; ORGANIC POLYMERS; STEREOCHEMISTRY; SUSTAINABLE CHEMISTRY;

APPLICATION AREA; CAPILLARY ELECTROCHROMATOGRAPHY; CHEMICAL FUNCTIONALITY; CHIRAL SEPARATIONS; CHROMATOGRAPHIC SORBENTS; MICRO-SEPARATION; MOLECULAR IMPRINTED POLYMERS; MOLECULARLY IMPRINTED POLYMER; STATIONARY PHASE; TEMPLATE-DIRECTED SYNTHESIS;

SYNTHESIS (CHEMICAL);

EID: 79958735979     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211795656651     Document Type: Review

References (62)

1. Zhang, H.; Ye, L.; Mosbach, K. Non-covalent molecular imprinting with emphasis on its application in separation and drug development. J. Mol. Recognit., 2006, 19, 248-259.
2. Lee, W. C.; Cheng, C. H.; Pan H. H.; Chung, T. H.; Hwang, C. C. Chromatographic characterization of molecularly imprinted polymers. Anal. Bioanal. Chem., 2008, 390, 1101-1109.
3. Wulff, G.; Enzyme-like catalysis by molecularly imprinted polymers. Chem. Rev., 2002, 102, 1-27.
4. McCluskey, A.; Holdsworth, C. I.; Bowyer, M. C. Molecularly imprinted polymers (MIPs): sensing, an explosive new opportunity?. Org. Biomol. Chem., 2007, 5, 3233-3244.
5. Turiel, E.; Martín-Esteban A. Molecularly imprinted polymers for solidphase microextraction. J. Sep. Sci., 2009, 32, 3278-3284.
6. Puoci, F., Iemma, F, Picci, N. Stimuli-responsive molecularly imprinted polymers for drug delivery: a review. Curr. Drug Deliv., 2008, 5, 85-96.
7. Haginaka J. Molecularly imprinted polymers as affinity-based separation media for sample preparation. J. Sep. Sci., 2009, 32, 1548-1565.
8. Lin, J.-M.; Nakagama, T.; Uchiyama, K.; Hobo, T. Temperature effect on chiral recognition of some amino acids with molecularly imprinted polymer filled capillary electrochromatography. Biomed. Chromatogr., 1997, 11, 298-302.
9. Lin, J.-M.; Nakagama, T.; Uchiyama, K.; Hobo, T. Enantioseparation of D, L-phenylalanine by molecularly imprinted polymer particles filled capillary electrochromatography. J. Liq. Chromatogr. Relat. Technol., 1997, 20, 1489-1506.
10. Lin, J.-M.; Uchiyama, K.; Hobo, T. Enantiomeric resolution of dansyl amino acids by capillary electrochromatography based on molecular imprinting method. Chromatographia, 1998, 47, 625-629.
11. Lin, J.-M.; Nakagama, T.; Uchiyama, K.; Hobo, T. Molecularly imprinted polymer as chiral selector for enantioseparation of amino acids by capillary gel electrophoresis. Chromatographia, 1996, 43, 585-591.
12. Chirica, G.; Remcho, V. T. Silicate entrapped columns-new columns designed for capillary electrochromatography. Electrophoresis, 1999, 20, 50-56.
13. Quaglia, M.; De Lorenzi, E.; Sulitzky, C.; Massolini, G.; Sellergren, B. Surface initiated molecularly imprinted polymer films: a new approach in chiral capillary electrochromatography. Analyst, 2001, 126, 1495-1498.
14. Quaglia, M.; De Lorenzi, E.; Sulitzky, C.; Caccialanza, G.; Sellergren, B. Molecularly imprinted polymer films grafted from porous or nonporous silica: Novel affinity stationary phases in capillary electrochromatography. Electrophoresis, 2003, 24, 952-957.
15. Walshe, M.; Garcia, E.; Howarth, J.; Smyth, M. R.; Kelly, M. T. Separation of the Enantiomers of Propranolol by Incorporation of Molecularly Imprinted Polymer Particles as Chiral Selectors in Capillary Electrophoresis. Anal. Commun., 1997, 34, 119-121.
16. Schweitz, L.; Spégel, P.; Nilsson, S. Molecularly imprinted microparticles for capillary electrochromatographic enantiomer separation of propranolol. Analyst, 2000, 125, 1899-1901.
17. Spégel, P.; Schweitz, L.; Nilsson, S. Molecularly imprinted microparticles for capillary electrochromatography: studies on microparticle synthesis and electrolyte composition. Electrophoresis, 2001, 22, 3833-3841.
18. Spégel, P.; Nilsson, S. A new approach to capillary electrochromatography: Disposable molecularly imprinted nanoparticles. Am. Lab., 2002, 34, 29-33.
19. Spégel, P.; Schweitz, L.; Nilsson, S. Selectivity toward multiple predetermined targets in nanoparticle capillary electrochromatography. Anal. Chem., 2003, 75, 6608-6613.
20. de Boer, T.; Mol, R.; de Zeeuw, R. A.; de Jong, G. J.; Sherrington, D. C.; Cormack, P. A. G.; Ensing, K. Spherical molecularly imprinted polymer particles: A promising tool for molecular recognition in capillary electrokinetic separations. Electrophoresis, 2002, 23, 1296-1300.
21. Priego-Capote, F.; Ye, L.; Shakil, S.; Shamsi, S. A.; Nilsson, S. Monoclonal Behaviour of Molecularly Imprinted Polymer Nanoparticles in Capillary Electrochromatography. Anal. Chem., 2008, 80, 2881-2887.
22. Brüggemann, O.; Freitag, R.; Whitcombe, M. J.; Vulfson, E. N. Comparison of polymer coatings of capillaries for capillary electrophoresis with respect to their applicability to molecular imprinting and electrochromatography. J. Chromatogr. A, 1997, 781, 43-53.
23. Zaidi, S. A.; Cheong, W. J. Preparation of an open-tubular capillary column with a monolithic layer of S-ketoprofen imprinted and 4-styrenesulfonic acid incorporated polymer and its enhanced chiral separation performance in capillary electrochromatography. J. Chromatogr. A, 2009, 1216, 2947-2952.
24. Zaidi S. A.; Cheong W. J. Long open tubular molecule imprinted polymer capillary columns with excellent separation efficiencies in chiral and nonchiral separation by capillary electrochromatography. Electrophoresis, 2009, 30, 1603-1607.
25. Zaidi S. A.; Han K. M.; Kim S. S.; Hwang D. G.; Cheong W. J. Open tubular layer of S-ofloxacin imprinted polymer fabricated in silica capillary for chiral CEC separation. J. Sep. Sci., 2009, 32, 996-1001.
26. Tan, J. Z.; Remcho, V. T. Molecular imprint polymers as highly selective stationary phases for open tubular liquid chromatography and capillary electrochromatography. Electrophoresis, 1998, 19, 2055-2060.
27. Huang, Y.-C.; Lin, C.-C.; Liu, C.-Y. Preparation and evaluation of molecularly imprinted polymers based on 9-ethyladenine for the recognition of nucleotide bases in capillary electrochromatography. Electrophoresis, 2004, 25, 554-561.
28. Schweitz, L. Molecularly imprinted polymer coatings for open-tubular capillary electrochromatography prepared by surface initiation. Anal. Chem., 2002, 74, 1192-1196.
29. Nilsson, K.; Lindell, J.; Norrlöw, G.; Sellergren, B. Imprinted polymers as antibody mimetics and new affinity gels for selective separations in capillary electrophoresis. J. Chromatogr. A, 1994, 680, 57-61.
30. Lin, J.-M.; Nakagama, T.; Wu, X. Z.; Uchiyama, K.; Hobo, T. Capillary electrochromatographic separation of amino acid enantiomers with molecularly imprinted polymers as chiral recognition agents. Fresenius' J. Anal. Chem., 1997, 357, 130-132.
31. Lin, J.-M.; Nakagama, T.; Uchiyama, K.; Hobo, T. Capillary electrochromatographic separation of amino acid enantiomers using on-column prepared molecularly imprinted polymer. J. Phamaceut. Biomed. Anal., 1997, 15, 1351-1358.
32. Schweitz, L.; Andersson, L. I.; Nilsson, S. Capillary electrochromatography with predetermined selectivity obtained through molecular imprinting. Anal. Chem., 1997, 69, 1179-1183.
33. Nilsson, S.; Schweitz, L.; Petersson, M. Three approaches to enantiomer separation of β-adrenergic antagonists by capillary electrochromatography. Electrophoresis, 1997, 18, 884-890.
34. Schweitz, L.; Andersson, L. I.; Nilsson, S. Capillary electrochromatography with molecular imprint-based selectivity for enantiomer separation of local anaesthetics. J. Chromatogr. A, 1997, 792, 401-409.
35. Schweitz, L.; Andersson L. I.; Nilsson S. Rapid electrochromatographic enantiomer separations on short molecularly imprinted polymer monoliths. Anal. Chim. Acta, 2001, 435, 43-47.
36. Schweitz, L.; Andersson, L. I.; Nilsson, S. Molecularly imprinted CEC sorbents: investigations into polymer preparation and electrolyte composition. Analyst, 2002, 127, 22-28.
37. Cacho, C.; Schweitz, L.; Turiel, E.; Perez-Conde, C. Molecularly imprinted capillary electrochromatography for selective determination of thiabendazole in citrus samples. J. Chromatogr. A, 2008, 1179, 216-223.
38. Ou, J.; Dong, J.; Tian, T.; Hu, J.; Ye, M.; Zou, H. Enantioseparation of tetrahydropalmatine and Tröger's base by molecularly imprinted monolith in capillary electrochromatography. J. Biochem. Biophys. Methods, 2007, 70, 71-76.
39. Szumski, M.; Buszewski, B. Molecularly imprinted polymers: A new tool for separation of steroid isomers. J. Sep. Sci., 2004, 27, 837-842.
40. Liu, Z.-S.; Xu, Y.-L.; Wang, H.; Yan, C.; Gao, R.-Y. Chiral separation of binaphthol enantiomers on molecularly imprinted polymer monolith by capillary electrochromatography. Anal. Sci., 2004, 20, 673-678.
41. Liu, Z.-S.; Xu, Y.-L.; Yan, C.; Gao, R.-Y. Preparation and characterization of molecularly imprinted monolithic column based on 4-hydroxybenzoic acid for the molecular recognition in capillary electrochromatography. Anal. Chim. Acta, 2004, 523, 243-250.
42. Xu, Y.-L.; Liu, Z.-S; Wang, H.-F.; Yan, C.; Gao, R.-Y. Chiral recognition ability of an (S)-naproxen-imprinted monolith by capillary electrochromatography. Electrophoresis, 2005, 26, 804-811.
43. Liu, Z.-S.; Xu, Y.-L.; Yan, C.; Gao, R.-Y. Mechanism of molecular recognition on molecular imprinted monolith by capillary electrochromatography. J. Chromatogr. A, 2005, 1087, 20-28.
44. Deng, Q.; Lun, Z.; Shao, H.; Yan, C.; Gao, R. Molecularly imprinted polymers as tools for the screening of felodipine from dihydropyridine calcium antagonists by pressurized capillary electrochromatography. Anal. Bioanal. Chem., 2005, 382, 51-58.
45. Lun, Z.-H.; Deng, Q.-L.; Yan C.; Gao, R.-Y. Molecularly imprinted polymer monolithic column separation of isomers and analogues of vanillin by capillary electrochromatography. Chin. J. Chem., 2006, 24, 442-444.
46. Zheng C.; Liu, Z.-S.; Gao, R.-Y.; Zhang, Y.-K. Mechanism of molecular recognition on tetrapetide-imprinted monolith by capillary electrochromatography. Chin. J. Chem., 2008, 26, 1857-1862.
47. Lin, C.-C.; Wang, G.-R.; Liu, C.-Y. A novel monolithic column for capillary electrochromatographic separation of oligopeptides. Anal. Chim. Acta, 2006, 572, 197-204.
48. Spégel, P.; Schweitz, L.; Andersson, L. I.; Nilsson, S. Novel Vinylpyridine Based Cationic MIP Monoliths for Enantiomer Separation in CEC. Chromatographia, 2009, 69, 277-285.
49. Zheng, C.; Liu, Z.; Gao, R.; Zhang, L.; Zhang, Y. Recognition of oxytocin by capillary electrochromatography with monolithic tetrapeptide-imprinted polymer used as the stationary phase. Anal. Bioanal. Chem., 2007, 388, 1137-1145.
50. Wang, H. F.; Zhu, Y. Z.; Yan, X. P.; Gao, R. Y.; Zheng, J. Y. A room temperature ionic liquid (RTIL)-mediated, non-hydrolytic sol-gel methodology to prepare molecularly imprinted, silica-based hybrid monoliths for chiral separation. Adv. Mater., 2006, 18, 3266-3270.
51. Wang, H. F.; Zhu, Y. Z.; Lin, J. P.; Yan, X. P. Fabrication of molecularly imprinted hybrid monoliths via a room temperature ionic liquid-mediated nonhydrolytic sol-gel route for chiral separation of zolmitriptan by capillary electrochromatography. Electrophoresis, 2008, 29, 952-959.
52. Ou, J.; Li, X.; Feng, S.; Dong, J.; Dong, X.; Kong, L.; Ye, M.; Zou, H. Preparation and evaluation of a molecularly imprinted polymer derivatized silica monolithic column for capillary electrochromatography and capillary liquid chromatography. Anal. Chem., 2007, 79, 639-646.
53. Deng, Q. L.; Lun, Z. H.; Gao, R.Y.; Zhang, L. H.; Zhang, W. B.; Zhang, Y. K. (S)-Ibuprofen-imprinted polymers incorporating γ-methacryloxypropyl trimethoxysilane for CEC separation of ibuprofen enantiomers. Electrophoresis, 2006, 27, 4351-4358.
54. Zhang, Y.-P.; Zuo, G.-Q.; Xu, G.-R.; Li, Q.-M.; Yuan, Z. B. Rapid preparation of molecularly imprinted capillary monolithic column by microwave polymerization. Chem. J. Chin. Univ., 2007, 28, 1654-1656.
55. Li, M.; Lin, X.; Xie, Z. Investigation of enantiomer recognition of molecularly imprinted polymeric monoliths in pressurized capillary electrochromatography screening the amino acids and their derivatives. J. Chromatogr. A, 2009, 1216, 5320-5326.
56. Yan, W.; Gao, R.; Zhang, Z.; Wang, Q.; Jiang, C. W.; Yan, C. Capillary electrochromatographic separation of ionizable compounds with a molecular imprinted monolithic cationic exchange column. J. Sep. Sci., 2003, 26, 555-561.
57. Ye, L.; Cormack, P. A. G.; Mosbach, K. Molecularly imprinted monodisperse microspheres for competitive radioassay. Anal. Commun., 1999, 36, 35-38.
58. Svec, F.; Fréchet, J. M. J. New designs of macroporous polymers and supports: From separation to biocatalysis. Science, 1996, 273, 205-211.
59. Jiang, Z.; Thorogate, R.; Smith, N. W. Highlighting the role of the hydroxyl position on the alkyl spacer of hydroxypropyl-β-cyclodextrin for enantioseparation in capillary electrophoresis. J. Sep. Sci., 2008, 31, 177-187.
60. Wu, X.; Wei, Z.-H.; Huang, Y.-P.; Liu, Z.-S. Preparation of molecularly imprinted coatings with ternary porogen for CEC. Chromatographia, 2010, 47, 625-629.
61. Vallano, P. T.; Remcho V. T. Highly selective separations by capillary electrochromatography: molecular imprint polymer sorbents. J. Chromatogr. A, 2000, 887, 125-135.
62. 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.