Towards the rational development of molecularly imprinted polymers: 1H NMR studies on hydrophobicity and ion-pair interactions as driving forces for selectivity

Biosensors and Bioelectronics

Volumn 20, Issue 9, 2005, Pages 1884-1893

  O'Mahony, J ^a   Molinelli, A ^b   Nolan, K ^a   Smyth, M R ^a   Mizaikoff, B ^b  

^a DUBLIN CITY UNIVERSITY   (Ireland)

^b GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

2,4 Dichlorophenoxyacetic acid (2,4 D); Complexation; Molecularly imprinted polymer (MIP); NMR; Non covalent imprinting; Norephedrine (NEP)

Indexed keywords

HYDROPHOBICITY; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POLYMERS; SEPARATION; SORPTION;

HIGH-AFFINITY BINDING SITES; MOLECULARLY IMPRINTED POLYMERS (MIP); NON-COVALENT INTERACTIONS; SORBENT MATERIALS;

BIOELECTRIC PHENOMENA;

ION; MONOMER; POLYMER; SORBENT;

ARTICLE; BINDING AFFINITY; CORRELATION ANALYSIS; EXTRACELLULAR MATRIX; FORCE; HYDROPHOBICITY; MATERIALS; MOLECULAR IMPRINTING; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OBSERVATION; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SEPARATION TECHNIQUE;

COATED MATERIALS, BIOCOMPATIBLE; HYDROPHOBICITY; IONS; MAGNETIC RESONANCE SPECTROSCOPY; MATERIALS TESTING; POLYMERS; PROTONS; SURFACE PROPERTIES;

EID: 12844261785     PISSN: 09565663     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bios.2004.07.036     Document Type: Article

References (28)

1. R.J. Abrahams, J. Fisher, and P. Loftus Introduction to NMR Spectroscopy 1st ed. 1988 Wiley New York
2. H.S. Andersson, and I.A. Nicholls Spectroscopic evaluation of molecular imprinting polymerization systems Bioorg. Chem. 25 1997 203 211
3. L.I. Andersson, and K. Mosbach Enantiomeric resolution on molecularly imprinted polymers prepared with only non-covalent and non-ionic interactions J. Chromatogr. 516 2 1990 313 322
4. L.I. Andersson, B. Sellergren, and K. Mosbach Imprinting of amino acid derivatives in macroporous polymers Tetrahedron Lett. 25 1984 5211 5214
5. J.L. Atwood Comprehensive Supramolecular Chemistry, vol. 8 1st ed. 1996 Pergamon Press New York
6. W.Y. Chen, C.S. Chen, and F.Y. Lin Molecular recognition in imprinted polymers: thermodynamic investigation of analyte binding using microcalorimetry J. Chromatogr. A 923 2001 1 6
7. X. Dong, H. Sun, X. Lu, H. Wang, S. Liu, and N. Wang Separation of ephedrine stereoisomers by molecularly imprinted polymers - influence of synthetic conditions and mobile phase composition on the chromatographic performance Analyst 127 2002 1427 1432
8. K. Haupt, A. Dzgoev, and K. Mosbach Assay system for the herbicide 2,4-dichlorophenoxyacetic acid using a molecularly imprinted polymer as an artificial recognition element Anal. Chem. 70 1998 628 631
9. M. Jakusch, M. Janotta, B. Mizaikoff, K. Mosbach, and K. Haupt Molecularly imprinted polymers and infrared evanescent wave spectroscopy. A chemical sensors approach Anal. Chem. 71 1999 4786 4791
10. M. Janotta, R. Weiss, B. Mizaikoff, O. Brüggemann, L. Yei, and K. Mosbach Molecularly imprinted polymers for nitrophenols: an advanced separation material for environmental analysis Int. J. Environ. Anal. Chem. 80 2 2001 75 86
11. A. Katz, and M.E. Davis Investigations into the mechanisms of molecular recognition with imprinted polymers Macromolecules 32 1999 4113 4121
12. G. Lancelot Hydrogen bonding between nucleic acid bases and carboxylic acids J. Am. Chem. Soc. 99 1977 7037 7042
13. N. Lavignac, C.J. Allender, and K.R. Brain Current status of molecularly imprinted polymers as alternatives to antibodies in sorbent assays Anal. Chim. Acta 510 2004 139 145
14. L. Liu, and R. Breslow Dendrimeric pyridoxamine enzyme mimics J. Am. Chem. Soc. 125 2003 12110 12111
15. A. Molinelli, R. Weiss, and B. Mizaikoff Advanced solid phase extraction using molecularly imprinted polymers for the determination of quercetin in red wine J. Agric. Food Chem. 50 2002 1804 1808
16. S.A. Piletsky, S. Alcock, and A.P.F. Turner Molecular imprinting: at the edge of the third millennium Trends Biotechnol. 19 1 2001 9 12
17. M. Quaglia, K. Chenon, A.J. Hall, E. De Lorenzi, and B. Sellergren Target analogue imprinted polymers with affinity for folic acid and related compounds J. Am. Chem. Soc. 123 2001 2146 2154
18. B. Sellergren Direct drug determination by selective sample enrichment on an imprinted polymer Anal. Chem. 66 1994 1578 1582
19. B. Sellergren, M. Lepisto, and K. Mosbach 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. 110 1988 5853 5860
20. 13C CP/MAS NMR and FT-IR spectroscopy J. Am. Chem. Soc. 113 1991 4109 4120
21. B.H.M. Snellink-Ruel, M.M.G. Antonisse, J.F.J. Engbersen, P. Timmerman, and D.N. Reinhoudt Neutral anion receptors with multiple urea-binding sites Eur. J. Org. Chem. 2000 165 170
22. R. Suedee, T. Srichana, J. Saelim, and T. Thavornpibulbut Chiral determination of various adrenergic agents by thin-layer chromatography using molecularly imprinted chiral stationary phases prepared with α-agonists Analyst 124 1999 1003 1009
23. D.S. Terekhov, K.J.M. Nolan, C.R. McArthur, and C.C. Leznoff Synthesis of 2,3,9,10,16,17,23,24-octaalkynylphthalocyanines and the effects of concentration and temperature on their 1H-NMR spectra J. Org. Chem. 61 1996 3034 3040
24. G. Vlatkis, L.I. Andersson, R. Müller, and K. Mosbach Drug assay using antibody mimics made by molecular imprinting Nature 361 1993 645 647
25. M.J. Whitcombe, L. Martin, and E.N. Vulfson Predicting the selectivity of imprinted polymers Chromatographia 47 1998 457 464
26. D.H. Williams, J.P.L. Cox, A.J. Doig, M. Gardner, U. Gerhard, P.T. Kaye, A.R. Lal, I.A. Nicholls, C.J. Salter, and R.C. Mitchell Toward the semiquantitative estimation of binding constants. Guides for peptide-peptide binding in aqueous solution J. Am. Chem. Soc. 113 1991 7020 7030
27. G. Wulff Molecular imprinting in cross-linked materials with the aid of molecular templates - a way towards artificial antibodies Angew. Chem. Int. Ed. Engl. 34 1995 1812 1832
28. A. Zander, P. Finlay, T. Renner, B. Sellergren, and A. Swietlow Analysis of nicotine and its oxidation products in nicotine chewing gum by a molecularly imprinted solid phase extraction Anal. Chem. 70 1998 3304 3314