Noncovalent molecular imprinting: antibody-like molecular recognition in polymeric network materials

Abstract Molecular imprinting techniques allow the preparation of polymeric receptors which bind small molecules with affinities and selectivities of the same order as those observed in the binding of antigens by antibodies. The molecular imprinting technology has now reached a stage where the commercial use of imprinted materials is being assessed, notably for separations requiring strong and selective binding of small molecules. This development is driven by the potential advantages of polymeric receptors over biological in terms of stability, capacity, cost and ease of preparation. In this short review the state of the art of noncovalent imprinting is summarised indicating a few areas in analytical chemistry where the technique may have future impact.

[1]  M. Muldoon,et al.  Polymer synthesis and characterization of a molecularly imprinted sorbent assay for atrazine , 1995 .

[2]  Klaus Mosbach,et al.  Drug assay using antibody mimics made by molecular imprinting , 1993, Nature.

[3]  Linus Pauling,et al.  "A Theory of the Structure and Process of Formation of Antibodies" (pages 26-32) , 1940 .

[4]  K Mosbach,et al.  Molecularly imprinted polymer beads:  suspension polymerization using a liquid perfluorocarbon as the dispersing phase. , 1996, Analytical chemistry.

[5]  J. Rebek.  Molecular recognition and biophysical organic chemistry , 1990 .

[6]  Frances H. Arnold,et al.  Specific Protein Attachment to Artificial Membranes via Coordination to Lipid-Bound Copper(II) , 1994 .

[7]  D. Sasaki,et al.  An analysis of small-molecule binding to functionalized synthetic polymers by 13C CP/MAS NMR and FT-IR spectroscopy , 1991 .

[8]  D. Sherrington,et al.  Molecular imprinting of flat polycondensed aromatic molecules in macroporous polymers , 1993 .

[9]  Börje Sellergren,et al.  Molecular imprinting by noncovalent interactions: enantioselectivity and binding capacity of polymers prepared under conditions favoring the formation of template complexes , 1989 .

[10]  Takaomi Kobayashi,et al.  Molecular imprint membranes prepared by the phase inversion precipitation technique , 1996 .

[11]  Frances H. Arnold,et al.  Towards Materials for the Specific Recognition and Separation of Proteins , 1994 .

[12]  Klaus Mosbach,et al.  Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition , 1988 .

[13]  Börje Sellergren,et al.  Use of silane monomers for molecular imprinting and enzyme entrapment in polysiloxane-coated porous silica , 1985 .

[14]  Molecularly imprinted polymeric membranes for optical resolution , 1995 .

[15]  B. Sellergren,et al.  Chiral ion-exchange chromatography. Correlation between solute retention and a theoretical ion-exchange model using imprinted polymers. , 1993, Journal of chromatography. A.

[16]  B. Sellergren.  Moleclar imprinting by noncovalent interactions: Tailor‐made chiral stationary phases of high selectivity and sample load capacity , 1989 .

[17]  Luis A. Berrueta,et al.  A review of solid phase extraction: Basic principles and new developments , 1995 .

[18]  B. Sellergren,et al.  Influence of polymer morphology on the ability of imprinted network polymers to resolve enantiomers , 1993 .

[19]  L. Andersson,et al.  Capillary Electrochromatography with Predetermined Selectivity Obtained through Molecular Imprinting , 1997 .

[20]  B. Sellergren,et al.  Imprinted polymers as antibody mimetics and new affinity gels for selective separations in capillary electrophoresis , 1994 .

[21]  B. Sellergren,et al.  Discrimination between amino acid amide conformers by imprinted polymers , 1989 .

[22]  John W. Dolan,et al.  Introduction to modern liquid chromatography , 1974 .

[23]  G. Wulff,et al.  Enzyme‐analogue built polymers, 23. Influence of the structure of the binding sites on the selectivity for racemic resolution , 1987 .

[24]  Olof Ramström,et al.  Insights into the role of the hydrogen bond and hydrophobic effect on recognition in molecularly imprinted polymer synthetic peptide receptor mimics , 1995 .

[25]  G. Subramanian.  A practical approach to chiral separations by liquid chromatography , 1994 .

[26]  M. Kempe.  Antibody-mimicking polymers as chiral stationary phases in HPLC. , 1996, Analytical chemistry.

[27]  K. Shea,et al.  Molecular recognition on synthetic amorphous surfaces. The influence of functional group positioning on the effectiveness of molecular recognition , 1986 .

[28]  Kenneth J. Shea,et al.  Polymer complements to nucleotide bases. Selective binding of adenine derivatives to imprinted polymers , 1993 .

[29]  J. Scott,et al.  Searching for peptide ligands with an epitope library. , 1990, Science.

[30]  G. Wulff,et al.  Enzyme‐analogue built polymers, 4. On the synthesis of polymers containing chiral cavities and their use for the resolution of racemates , 1977 .

[31]  M. Muldoon,et al.  Molecularly imprinted solid phase extraction of atrazine from beef liver extracts. , 1997, Analytical chemistry.

[32]  B. Sellergren,et al.  Direct Drug Determination by Selective Sample Enrichment on an Imprinted Polymer , 1994 .

[33]  D. Sasaki,et al.  On the control of microenvironment shape of functionalized network polymers prepared by template polymerization , 1989 .

[34]  Jean-Marie Lehn,et al.  Supramolecular Chemistry—Scope and Perspectives Molecules, Supermolecules, and Molecular Devices (Nobel Lecture) , 1988 .

[35]  Frances H. Arnold,et al.  Template-mediated synthesis of metal-complexing polymers for molecular recognition , 1991 .

[36]  K Mosbach,et al.  Separation of amino acids, peptides and proteins on molecularly imprinted stationary phases. , 1995, Journal of chromatography. A.

[37]  Toshifumi Takeuchi,et al.  Solid-phase Extraction of a Triazine Herbicide Using a Molecularly Imprinted Synthetic Receptor , 1997 .

[38]  J. Finn,et al.  A widely useful chiral stationary phase for the high-performance liquid chromatography separation of enantiomers , 1981 .

[39]  Michael J. Whitcombe,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 , 1995 .

[40]  Olof Ramström,et al.  Synthetic peptide receptor mimics: highly stereoselective recognition in non-covalent molecularly imprinted polymers , 1994 .

[41]  K. Uchiyama,et al.  Molecularly imprinted polymer as chiral selector for enantioseparation of amino acids by capillary gel electrophoresis , 1996 .

[42]  G. Wulff.  Molecular Imprinting in Cross‐Linked Materials with the Aid of Molecular Templates— A Way towards Artificial Antibodies , 1995 .

[43]  L. Andersson,et al.  Application of molecular imprinting to the development of aqueous buffer and organic solvent based radioligand binding assays for (s)-propranolol. , 1996, Analytical chemistry.

[44]  K. Shea,et al.  Imprinted Polymer Membranes for the Selective Transport of Targeted Neutral Molecules , 1996 .

[45]  L. Fischer,et al.  Direct enantioseparation of .beta.-adrenergic blockers using a chiral stationary phase prepared by molecular imprinting , 1991 .

[46]  Y. Baba,et al.  Gel-filled capillaries for nucleic acid separations in capillary electrophoresis , 1992 .

[47]  K Mosbach,et al.  Sugar binding polymers showing high anomeric and epimeric discrimination obtained by noncovalent molecular imprinting. , 1994, Analytical biochemistry.

[48]  L. Andersson,et al.  Molecular recognition in macroporous polymers prepared by a substrate analog imprinting strategy , 1990 .