Synthetic strategies for the generation of molecularly imprinted organic polymers.

Molecular imprinting is a method of inducing molecular recognition properties in synthetic polymers in response to the presence of a template species during formation of the three-dimensional structure of the polymer. The molecularly imprinted polymers (MIPs) prepared in this way have been termed "plastic antibodies" and combine the robustness of the polymer scaffold with binding properties more readily associated with biological receptors. Smart polymers of this type may find applications in drug delivery, controlled release and monitoring of drug and metabolite concentrations. In this review the main synthetic strategies used in the preparation of imprinted organic polymers are described in terms of the chemical principles used in the templating step. These are illustrated with examples taken from the literature and are classified as covalent, semi-covalent, non-covalent, metal-mediated and non-polar. Finally strategies for the selection of monomers, optimisation and modification of the properties of imprinted polymers are reviewed.

[1]  Mizuo Maeda,et al.  Metal Ion-Imprinted Microspheres Prepared by Reorganization of the Coordinating Groups on the Surface , 1992 .

[2]  I. Karube,et al.  ENHANCING THE SELECTIVITY OF MOLECULARLY IMPRINTED POLYMERS , 1997 .

[3]  P. Schaare,et al.  Propofol-imprinted membranes with potential applications in biosensors , 2004 .

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

[5]  Amy L. Graham,et al.  Development and characterization of molecularly imprinted sol-gel materials for the selective detection of DDT. , 2002, Analytical chemistry.

[6]  S. Shinkai,et al.  Selective re-binding of saccharide-imprinted [60]fullerene-bisadducts based on a saccharide-boronic acid interaction: Development of a molecular imprinting technique useful in a homogeneous system , 1999 .

[7]  Nicholas A Peppas,et al.  Molecular imprinting within hydrogels. , 2002, Advanced drug delivery reviews.

[8]  A. Y. Grosberg,et al.  Effect of Reversible Cross-linker, N,N‘-Bis(acryloyl)cystamine, on Calcium Ion Adsorption by Imprinted Gels , 2001 .

[9]  G. Mohr New chromoreactands for the detection of aldehydes, amines and alcohols , 2003 .

[10]  O. Buchardt,et al.  Molecular imprinting approach for the recognition of adenine in aqueous medium and hydrolysis of adenosine 5'-triphosphate. , 1995, Bioconjugate chemistry.

[11]  F. H. Dickey,et al.  The Preparation of Specific Adsorbents. , 1949, Proceedings of the National Academy of Sciences of the United States of America.

[12]  Liqing Wu,et al.  Study properties of molecular imprinting polymer using a computational approach , 2003 .

[13]  Takaomi Kobayashi,et al.  Surface molecular imprinting on photosensitive dithiocarbamoyl polyacrylonitrile membranes using photograft polymerization , 1997 .

[14]  A. Turner,et al.  "Bite-and-Switch" approach using computationally designed molecularly imprinted polymers for sensing of creatinine. , 2001, Biosensors & bioelectronics.

[15]  S. Striegler,et al.  Investigation of Sugar‐Binding Sites in Ternary Ligand−Copper(II)−Carbohydrate Complexes , 2002 .

[16]  K. Sreenivasan Imparting Cholesterol Recognition Sites in Radiation Polymerised Poly(2‐hydroxyethyl methacrylate) by Molecular Imprinting , 1997 .

[17]  Börje Sellergren,et al.  Peptide recognition via hierarchical imprinting , 2004, Analytical and bioanalytical chemistry.

[18]  L. Andersson,et al.  Efficient sample pre-concentration of bupivacaine from human plasma by solid-phase extraction on molecularly imprinted polymers. , 2000, The Analyst.

[19]  M. Maeda,et al.  Template-Dependent Metal Adsorptivity of Dialkyl Phosphate-Type Resins Prepared by Surface Template Polymerization Technique , 1994 .

[20]  S. Striegler Designing selective sites in templated polymers utilizing coordinative bonds. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[21]  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 .

[22]  C. Alexander,et al.  Imprinted Polymers as Protecting Groups for Regioselective Modification of Polyfunctional Substrates , 1999 .

[23]  S. Zimmerman,et al.  A monomolecularly imprinted dendrimer (MID) capable of selective binding with a tris(2-aminoethyl)amine guest through multiple functional group interactions. , 2004, Chemical communications.

[24]  M. Quaglia,et al.  Target analogue imprinted polymers with affinity for folic acid and related compounds. , 2001, Journal of the American Chemical Society.

[25]  H. Tao,et al.  Molecular imprinting of bisphenol A and alkylphenols using amylose as a host matrix. , 2002, Chemical communications.

[26]  H. Nishide,et al.  Adsorption of metal ions on crosslinked poly(4‐vinylpyridine) resins prepared with a metal ion as template , 1977 .

[27]  C. Alvarez‐Lorenzo,et al.  Timolol uptake and release by imprinted soft contact lenses made of N,N-diethylacrylamide and methacrylic acid. , 2002, Journal of controlled release : official journal of the Controlled Release Society.

[28]  S. Shinkai,et al.  Novel nucleotide‐responsive hydrogels designed from copolymers of boronic acid and cationic units and their applications as a QCM resonator system to nucleotide sensing , 2000 .

[29]  T. Rao,et al.  Effect of Porogen Type on the Synthesis of Uranium Ion Imprinted Polymer Materials for the Preconcentration/Separation of Traces of Uranium , 2004 .

[30]  T. Takeuchi,et al.  Preparation of sterol-imprinted polymers with the use of 2-(methacryloyloxy)ethyl phosphate. , 2001, Journal of chromatography. A.

[31]  M. Goto,et al.  Metal Ion-Imprinted Resins with Novel Bifunctional Monomer by Surface Template Polymerization , 1996 .

[32]  Klaus Mosbach,et al.  Molecular imprinting of amino acid derivatives at low temperature (0°C) using photolytic homolysis of azobisnitriles , 1989 .

[33]  X. Dong,et al.  Separation of ephedrine stereoisomers by molecularly imprinted polymers--influence of synthetic conditions and mobile phase compositions on the chromatographic performance. , 2002, The Analyst.

[34]  Shin,et al.  Imprinted polymers as tools for the recovery of secondary metabolites produced by fermentation , 1999, Biotechnology and bioengineering.

[35]  Chul Oh,et al.  The use of a thermally reversible bond for molecular imprinting of silica spheres. , 2002, Journal of the American Chemical Society.

[36]  M. Kempe,et al.  Synthesis and screening of a molecularly imprinted polymer library targeted for penicillin G. , 2003, Journal of combinatorial chemistry.

[37]  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 .

[38]  V. Kabanov,et al.  Complex‐forming polymeric sorbents with macromolecular arrangement favorable for ion sorption , 1979 .

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

[40]  S. Bystroem,et al.  Selective reduction of steroid 3- and 17-ketones using lithium aluminum hydride activated template polymers , 1993 .

[41]  D. Neckers,et al.  Stereoselective syntheses via a photochemical template effect , 1980 .

[42]  H. Nishide,et al.  Selective adsorption of metal ions on poly(4‐vinylpyridine) resins in which the ligand chain is immobilized by crosslinking , 1976 .

[43]  R. Kala,et al.  Preconcentrative separation of erbium from Y, Dy, Ho, Tb and Tm by using ion imprinted polymer particles via solid phase extraction , 2004 .

[44]  S. Zimmerman,et al.  Synthesis of Cored Dendrimers with Internal Cross-Links This work was supported by the National Institute of Health (GM 39782). L.G.S. acknowledges the Department of Chemistry, University of Illinois, and Pharmacia & Upjohn for fellowship support. , 2001, Angewandte Chemie.

[45]  Klaus Mosbach,et al.  Molecular Imprinting Utilizing an Amide Functional Group for Hydrogen Bonding Leading to Highly Efficient Polymers , 1997 .

[46]  R. Mashelkar,et al.  Molecularly imprinted adsorbents for positional isomer separation. , 1999, Journal of chromatography. A.

[47]  F. Deschamps,et al.  Simple NMR experiments as a means to predict the performance of an anti-17α-ethynylestradiol molecularly imprinted polymer , 2001 .

[48]  B. Sellergren,et al.  Pressure-Induced Binding Sites in Molecularly Imprinted Network Polymers , 1997 .

[49]  I. Willner,et al.  Imprinting of nucleotide and monosaccharide recognition sites in acrylamidephenylboronic acid-acrylamide copolymer membranes associated with electronic transducers. , 2002, Analytical chemistry.

[50]  M. Whitcombe,et al.  Imprinted polymers prepared by aqueous suspension polymerization , 2000 .

[51]  J. Matsui,et al.  MOLECULARLY IMPRINTED POLYMER LIBRARY ON A MICROTITER PLATE. HIGH–THROUGHPUT SYNTHESIS AND ASSESSMENT OF CINCHONA ALKALOID–IMPRINTED POLYMERS , 2001 .

[52]  Stellan Hjertén,et al.  Some studies of the chromatographic properties of gels (‘Artificial antibodies/receptors’) for selective adsorption of proteins , 2001 .

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

[54]  Maria-Magdalena Titirici,et al.  Hierarchical Imprinting Using Crude Solid Phase Peptide Synthesis Products as Templates , 2003 .

[55]  M. Kulkarni,et al.  Enhanced capacities and selectivities for cholesterol in aqueous media by molecular imprinting: role of novel cross-linkers. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[56]  H. Asanuma,et al.  Molecularly imprinted polymer of β-cyclodextrin for the efficient recognition of cholesterol , 1997 .

[57]  I. Nicholls,et al.  Molecular recognition in cinchona alkaloid molecular imprinted polymer rods , 1998 .

[58]  Evgeny N Vulfson,et al.  Template-Mediated Synthesis of a Polymeric Receptor Specific to Amino Acid Sequences. , 1999, Angewandte Chemie.

[59]  M. Maeda,et al.  Metal-Ion Complexation Behavior of Resins Prepared by a Novel Template Polymerization Technique , 1992 .

[60]  H. Nishide,et al.  Complexation of metal ion with poly(1‐vinylimidazole) resin prepared by radiation‐induced polymerization with template metal ion , 1981 .

[61]  Neal A. Rakow,et al.  Synthetic hosts by monomolecular imprinting inside dendrimers , 2002, Nature.

[62]  P. Russo,et al.  A New Synthesis of Fluorescein Isothiocyanate Labeled Poly(styrenesulfonate sodium salt) , 2004 .

[63]  K Mosbach,et al.  Mimics of the binding sites of opioid receptors obtained by molecular imprinting of enkephalin and morphine. , 1995, Proceedings of the National Academy of Sciences of the United States of America.

[64]  Sui Wang,et al.  Solid-phase extraction and preconcentration of cadmium(II) in aqueous solution with Cd(II)-imprinted resin (poly-Cd(II)-DAAB-VP) packed columns , 2004 .

[65]  Sergey A. Piletsky,et al.  Rational design of a polymer specific for microcystin-LR using a computational approach. , 2002, Analytical chemistry.

[66]  Mark E. Davis,et al.  Molecular imprinting of bulk, microporous silica , 2000, Nature.

[67]  Martha Sibrian-Vazquez,et al.  Characterization of molecularly imprinted polymers employing crosslinkers with nonsymmetric polymerizable groups , 2004 .

[68]  A. Turner,et al.  A new reactive polymer suitable for covalent immobilisation and monitoring of primary amines , 2001 .

[69]  C. Alexander,et al.  Directed nucleation of calcite at a crystal-imprinted polymer surface , 1999, Nature.

[70]  Isao Karube,et al.  Testosterone Receptor Binding Mimic Constructed Using Molecular Imprinting , 1997 .

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

[72]  J. Matsui Molecularly imprinted receptor having metalloporphyrin-based signaling binding site , 1998 .

[73]  N. Minoura,et al.  Molecular imprinting: synthesis of polymer particles with antibody-like binding characteristics for glucose oxidase. , 1996, Biochemical and biophysical research communications.

[74]  Barbara Wandelt,et al.  Fluorescent Functional Recognition Sites through Molecular Imprinting. A Polymer-Based Fluorescent Chemosensor for Aqueous cAMP. , 1998 .

[75]  K. Landfester,et al.  Molecularly imprinted polymer nanospheres as synthetic affinity receptors obtained by miniemulsion polymerisation , 2002 .

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

[77]  S. Shinkai,et al.  Regioselective introduction of two boronic acid groups into [60]fullerene using saccharides as imprinting templates , 1998 .

[78]  K. Mosbach,et al.  Synthesis and catalysis by molecularly imprinted materials. , 1999, Current opinion in chemical biology.

[79]  J. Schram,et al.  Metal-Ion-Selective Exchange Resins by Matrix Imprint with Methacrylates , 1988 .

[80]  R. Suedee,et al.  Direct enantioseparation of adrenergic drugs via thin-layer chromatography using molecularly imprinted polymers. , 1999, Journal of pharmaceutical and biomedical analysis.

[81]  K. Shea,et al.  Combinatorial methods in molecular imprinting. , 2003, Current opinion in chemical biology.

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

[83]  T. Takeuchi,et al.  Novel strategy for molecular imprinting of phenolic compounds utilizing disulfide templates. , 2003, Journal of pharmaceutical and biomedical analysis.

[84]  S. Zimmerman,et al.  Kinetics and thermodynamics of amine and diamine signaling by a trifluoroacetyl azobenzene reporter group. , 2003, Organic letters.

[85]  P. Dean Affinity chromatography and related techniques : Analytical chemistry symposia series, volume 9 Edited by T. C. J. Gribnau, J. Visser and R. J. F. Nivard Elsevier Scientific; Amsterdam, New York, 1982 xviii + 584 pages. $83.00, Dfl 170.15 , 1982 .

[86]  A. Mayes,et al.  A direct comparison of the performance of ground, beaded and silica-grafted MIPs in HPLC and turbulent flow chromatography applications. , 2004, Biosensors & bioelectronics.

[87]  J. Matsui,et al.  2-(Trifluoromethyl)acrylic acid: a novel functional monomer in non-covalent molecular imprinting , 1997 .

[88]  Atsushi Ikeda,et al.  Saccharide Libraries as Potential Templates for Regio- and Chiroselective Introduction of Two Functional Groups into [60]Fullerene. , 1999, The Journal of organic chemistry.

[89]  Olof Ramström,et al.  Enantiomeric recognition by molecularly imprinted polymers using hydrophobic interactions , 1997 .

[90]  Sergey A. Piletsky,et al.  Selective recognition of atrazine by molecularly imprinted polymer membranes. Development of conductometric sensor for herbicides detection , 1999 .

[91]  Sergey A. Piletsky,et al.  Recognition of ephedrine enantiomers by molecularly imprinted polymers designed using a computational approach , 2001 .

[92]  D. Neckers,et al.  Template effects in chelating polymers , 1982 .

[93]  D. Sherrington,et al.  Non-covalent and semi-covalent molecularly imprinted polymers for selective on-line solid-phase extraction of 4-nitrophenol from water samples. , 2002, Journal of chromatography. A.

[94]  M. Whitcombe,et al.  Molecularly imprinted nanoparticles prepared by core‐shell emulsion polymerization , 2000 .

[95]  Sergey A. Piletsky,et al.  Polymer cookery: Influence of polymerization conditions on the performance of molecularly imprinted polymers , 2002 .

[96]  I. Nicholls,et al.  Combined Hydrophobic and Electrostatic Interaction-Based Recognition in Molecularly Imprinted Polymers , 1999 .

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

[98]  Isao Karube,et al.  Recognition of barbiturates in molecularly imprinted copolymers using multiple hydrogen bonding , 1995 .

[99]  F. Arnold,et al.  A glucose-sensing polymer , 1997, Nature Biotechnology.

[100]  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 .

[101]  K. Mosbach,et al.  Molecularly imprinted composite polymers based on trimethylolpropane trimethacrylate (TRIM) particles for efficient enantiomeric separations , 1995 .

[102]  A. Turner,et al.  Surface-grafted molecularly imprinted polymers for protein recognition. , 2001, Analytical chemistry.

[103]  G. Wulff,et al.  Functional mimicry of the active site of carboxypeptidase a by a molecular imprinting strategy: cooperativity of an amidinium and a copper ion in a transition-state imprinted cavity giving rise to high catalytic activity. , 2004, Journal of the American Chemical Society.

[104]  Martha Sibrian-Vazquez,et al.  Molecular imprinting made easy. , 2004, Journal of the American Chemical Society.

[105]  N. Sugimoto,et al.  Molecular imprinting in alcohols: utility of a pre-polymer based strategy for synthesizing stereoselective artificial receptor polymers in hydrophilic media , 2002 .

[106]  G. Horvai,et al.  Characterization of the selectivity of a phenytoin imprinted polymer. , 2004, Journal of chromatography. A.

[107]  R. N. Shah,et al.  Recognition Directed Site-Selective Chemical Modification of Molecularly Imprinted Polymers , 2001 .

[108]  S. Zimmerman,et al.  Cross-linked dendrimer hosts containing reporter groups for amine guests. , 2003, Journal of the American Chemical Society.

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

[110]  C. Shin,et al.  Binding properties of an aminostyrene-based polymer imprinted with glutamylated monascus pigments , 1999 .

[111]  C. Chassaing,et al.  Selective solid phase extraction of a drug lead compound using molecularly imprinted polymers prepared by the target analogue approach , 2002 .

[112]  Klaus Mosbach,et al.  Direct resolution of naproxen on a non-covalently molecularly imprinted chiral stationary phase , 1994 .

[113]  G. Wulff,et al.  Molecularly imprinted polymers with strong carboxypeptidase a-like activity: combination of an amidinium function with a zinc-ion binding site in transition-state imprinted cavities. , 2004, Angewandte Chemie.

[114]  C. Percival,et al.  Molecular imprinted polymer coated QCM for the detection of nandrolone. , 2002, The Analyst.

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

[116]  S. D. Pandey,et al.  Template synthesis of macromolecules. Synthesis and chemistry of functionalized macroporous poly(divinylbenzene) , 1980 .

[117]  F. Navarro-Villoslada,et al.  APPLICATION OF MULTIVARIATE ANALYSIS TO THE SCREENING OF MOLECULARLY IMPRINTED POLYMERS FOR BISPHENOL A , 2004 .

[118]  Andrew G. Mayes,et al.  Novel MIP formats , 2001, Bioseparation.

[119]  P. Schaare,et al.  Molecular imprinting of a small substituted phenol of biological importance , 2001 .

[120]  B. Sellergren,et al.  Studies on the Process of Formation, Nature and Stability of Binding Sites in Molecularly Imprinted Polymers , 2002 .

[121]  N. Hilal,et al.  Characterization of molecularly imprinted composite membranes using an atomic force microscope , 2002 .

[122]  B. Sellergren,et al.  Influence of Thermal Annealing on the Thermodynamic and Mass-Transfer Kinetic Properties of d- and l-Phenylalanine Anilide on Imprinted Polymeric Stationary Phases. , 1999, Analytical chemistry.

[123]  K. Shea,et al.  Molecular Imprinting of Carboxylic Acids Employing Novel Functional Macroporous Polymers. , 1999, The Journal of organic chemistry.

[124]  G. Wulff,et al.  Preparation of chromatographic sorbents with chiral cavities for racemic resolution , 1978 .

[125]  C. Alexander,et al.  Control of crystal morphology via molecular imprinting , 2001 .

[126]  Wen‐Chien Lee,et al.  Chromatographic characteristics of cholesterol-imprinted polymers prepared by covalent and non-covalent imprinting methods. , 2002, Journal of chromatography. A.

[127]  M. Quaglia,et al.  A substructure approach toward polymeric receptors targeting dihydrofolate reductase inhibitors. 2. Molecularly imprinted polymers against Z-l-glutamic acid showing affinity for larger molecules. , 2003, The Journal of organic chemistry.

[128]  K. Shea,et al.  Template synthesis of macromolecules. Selective functionalization of an organic polymer , 1978 .

[129]  G. Wulff,et al.  Enzyme-analogue built polymers, 22. Influence of the nature of the crosslinking agent on the performance of imprinted polymers in racemic resolution† , 1987 .

[130]  J. Matsui,et al.  A Molecularly Imprinted Polymer Rod as Nicotine Selective AffinityMedia Prepared With 2-(Trifluoromethyl)acrylic Acid , 1997 .

[131]  K. Mosbach,et al.  Acrylic polymer preparations containing recognition sites obtained by imprinting with substrates , 1984 .

[132]  I. Nicholls,et al.  Spectroscopic Evaluation of Molecular Imprinting Polymerization Systems , 1997 .

[133]  Thomas Gross,et al.  Enzyme Models Based on Molecularly Imprinted Polymers with Strong Esterase Activity , 1997 .

[134]  K. Mosbach,et al.  The Use of Immobilized Templates-A New Approach in Molecular Imprinting. , 2000, Angewandte Chemie.

[135]  M. Davies,et al.  Approaches to the rational design of molecularly imprinted polymers , 2004 .

[136]  T. Takeuchi,et al.  Bisphenol A-recognition polymers prepared by covalent molecular imprinting , 2003 .

[137]  D. Sherrington,et al.  Evaluation of methods aimed at complete removal of template from molecularly imprinted polymers. , 2001, The Analyst.

[138]  G. Wulff,et al.  Template Imprinted Polymers for HPLC Separation of Racemates , 1990 .

[139]  Börje Sellergren,et al.  Development of a semiautomated procedure for the synthesis and evaluation of molecularly imprinted polymers applied to the search for functional monomers for phenytoin and nifedipine , 2001 .

[140]  G. Wulff,et al.  Enzyme-analogue built polymers, 17 Investigations on the racemic resolution of amino acids , 1984 .

[141]  K. Shea,et al.  Molecular Imprinting for the Recognition of N-Terminal Histidine Peptides in Aqueous Solution , 2002 .

[142]  G. Wulff,et al.  Enzyme‐analogue built polymers, 26. Enantioselective synthesis of amino acids using polymers possessing chiral cavities obtained by an imprinting procedure with template molecules , 1989 .

[143]  K. Mosbach,et al.  Preparation of Ca2+ selective sorbents by molecular imprinting using polymerisable ionophores , 1991 .

[144]  I. Karube,et al.  Recognition of Sialic Acid Using Molecularly Imprinted Polymer , 1995 .

[145]  I. Karube,et al.  Molecularly imprinted polymers which mimic multiple hydrogen bonds between nucleotide bases , 1998 .

[146]  R. Mashelkar,et al.  Novel separation strategies based on molecularly imprinted adsorbents , 1998 .

[147]  Jong-Man Kim,et al.  Cholesterol esterase activity of a molecularly imprinted polymer , 2001 .

[148]  R. Niessner,et al.  Molecularly imprinted polymer for metsulfuron-methyl and its binding characteristics for sulfonylurea herbicides , 2002 .

[149]  Börje Sellergren,et al.  Water-compatible molecularly imprinted polymers obtained via high-throughput synthesis and experimental design. , 2003, Journal of the American Chemical Society.

[150]  G. Wulff,et al.  Selective binding to polymers via covalent bonds. The construction of chiral cavities as specific receptor sites , 1982 .

[151]  L. Ye,et al.  Molecularly imprinted monodisperse microspheres for competitive radioassay , 1999 .

[152]  G. Wulff,et al.  A new enzyme model for enantioselective esterases based on molecularly imprinted polymers. , 2003, Chemistry.

[153]  B. Wang,et al.  Building Fluorescent Sensors by Template Polymerization: The Preparation of a Fluorescent Sensor for l-Tryptophan☆ , 1999 .

[154]  B. Sellergren,et al.  Imprinting of amino acid derivatives in macroporous polymers , 1984 .

[155]  G. Wulff,et al.  Stoichiometric noncovalent interaction in molecular imprinting , 2001, Bioseparation.

[156]  E. Vulfson,et al.  Surface imprinting of cholesterol on Submicrometer core-shell emulsion particles , 2001 .

[157]  Klaus Mosbach,et al.  Recognition sites incorporating both pyridinyl and carboxy functionalities prepared by molecular imprinting , 1993 .

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

[159]  C. Pinel,et al.  Separation of Lanthanides by Ion Chromatography with Imprinted Polymers , 2003 .

[160]  Layer‐by‐Layer Grafting of Molecularly Imprinted Polymers via Iniferter Modified Supports , 2002 .

[161]  S. Piletsky,et al.  Surface Functionalization of Porous Polypropylene Membranes with Molecularly Imprinted Polymers by Photograft Copolymerization in Water , 2000 .

[162]  Mingdi Yan,et al.  Fabrication of molecularly imprinted polymer microstructures , 2001 .

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

[164]  K. Mosbach,et al.  Synthesis of substrate‐selective polymers by host‐guest polymerization , 1981 .

[165]  Sacrificial spacer and non-covalent routes toward the molecular imprinting of “poorly-functionalized” N-heterocycles , 2004 .

[166]  G. Wulff,et al.  Zur Chemie von Haftgruppen, VI über die Eignung verschiedener Aldehyde und Ketone als Haftgruppen für Monoalkohole , 1986 .

[167]  E. V. Piletskaya,et al.  A biomimetic receptor system for sialic acid based on molecular imprinting , 1996 .

[168]  Maria-Magdalena Titirici,et al.  Hierarchically Imprinted Stationary Phases: Mesoporous Polymer Beads Containing Surface-Confined Binding Sites for Adenine , 2002 .

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

[170]  Franz L. Dickert,et al.  Molecularly Imprinted Sensor Layers for the Detection of Polycyclic Aromatic Hydrocarbons in Water , 1999 .

[171]  D. Billington,et al.  Molecular recognition by fluorescent imprinted polymers , 2000 .

[172]  Michael S. Wendland,et al.  SYNTHESIS OF CORED DENDRIMERS , 1999 .

[173]  A. Rachkov,et al.  Molecularly Imprinted Polymer Membranes with Photoregulated Template Binding , 2003 .

[174]  D. Spivak,et al.  Performance analysis of molecularly imprinted polymers for carboxylate and aminophosphate templates using commercially available basic functional monomers. , 2004, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[175]  Crown ethers as a tool for the preparation of molecularly imprinted polymers , 1998, Journal of molecular recognition : JMR.

[176]  Toshifumi Takeuchi,et al.  A molecularly imprinted synthetic polymer receptor selective for atrazine , 1995 .

[177]  Y. Kurauchi,et al.  Adsorption of Cu2+ or Hg2+ ion on resins prepared by crosslinking metal-complexed chitosans , 1987 .

[178]  Y. Ge,et al.  Selectivity of response in fluorescent polymers imprinted with N1-benzylidene pyridine-2-carboxamidrazones , 2001 .

[179]  I. Karube,et al.  Recognition in Novel Molecularly Imprinted Polymer Sialic Acid Receptors in Aqueous Media , 1996 .

[180]  Toshifumi Takeuchi,et al.  Combinatorial Molecular Imprinting: An Approach to Synthetic Polymer Receptors , 1999 .

[181]  A. Mayes,et al.  Noncovalent imprinting in the shell of core-shell nanoparticles. , 2004, Langmuir : the ACS journal of surfaces and colloids.

[182]  R. Mashelkar,et al.  Effect of Solvents on Selectivity in Separation Using Molecularly Imprinted Adsorbents: Separation of Phenol and Bisphenol A , 1999 .

[183]  T. Rao,et al.  Ion imprinted polymer particles: synthesis, characterization and dysprosium ion uptake properties suitable for analytical applications , 2003 .

[184]  T. Takeuchi,et al.  Chiral recognition of octadentate Na+ complex with tetra-armed cyclen by molecularly imprinted polymers , 2004 .

[185]  T. Sagawa,et al.  Influence of cross-linking monomer and hydrophobic styrene comonomer on stereoselective esterase activities of polymer catalyst imprinted with a transition-state analogue for hydrolysis of amino acid esters , 2001 .

[186]  B. Sellergren,et al.  Method for synthesis and screening of large groups of molecularly imprinted polymers. , 1999, Analytical chemistry.

[187]  T. Akiyama,et al.  Molecular imprinting of cyclodextrin in water for the recognition of nanometer-scaled guests , 2001 .

[188]  B. Sellergren,et al.  Selective trace enrichment of chlorotriazine pesticides from natural waters and sediment samples using terbuthylazine molecularly imprinted polymers , 2000, Analytical chemistry.

[189]  D. Sherrington,et al.  Syntheses and Separations Using Functional Polymers , 1988 .

[190]  K. Mosbach,et al.  Synthesis of a new amino acid based cross-linker for preparation of substrate selective acrylic polymers , 1985 .

[191]  J. Haginaka,et al.  An Unexpected Molecular Imprinting Effect for a Polyaromatic Hydrocarbon, Anthracene, Using Uniform Size Ethylene Dimethacrylate Particles , 1999 .

[192]  B. Sellergren,et al.  Molecularly Imprinted Polymers via High‐Throughput and Combinatorial Techniques , 2004 .

[193]  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.

[194]  J. Matsui,et al.  Synthesis of castasterone selective polymers prepared by molecular imprinting , 1998 .

[195]  B. Wandelt,et al.  Steady-state and time-resolved fluorescence studies of fluorescent imprinted polymers , 2003 .

[196]  Ö. Pekcan,et al.  Metal ion templated chemosensor for metal ions based on fluorescence quenching , 2002 .

[197]  I. Nicholls,et al.  Probing the molecular basis for ligand-selective recognition in molecularly imprinted polymers selective for the local anaesthetic bupivacaine , 2001 .

[198]  M. Whitcombe,et al.  Predicting the selectivity of imprinted polymers , 1998 .

[199]  Henrik Kempe,et al.  Novel Method for the Synthesis of Molecularly Imprinted Polymer Bead Libraries , 2004 .

[200]  Chenxi Li,et al.  Study on the mechanism of chiral recognition with molecularly imprinted polymers , 2003 .

[201]  C. Alexander,et al.  Enhancement of selectivity of imprinted polymers via post-imprinting modification of recognition sites , 2000 .

[202]  I. Nicholls,et al.  The rational use of hydrophobic effect‐based recognition in molecularly imprinted polymers , 1998, Journal of molecular recognition : JMR.

[203]  K. Hosoya,et al.  Porogen Imprinting Effects , 1998 .

[204]  E. Vulfson,et al.  A Novel Approach to the Molecular Imprinting of Polychlorinated Aromatic Compounds , 1998 .

[205]  I. Nicholls,et al.  The roles of template complexation and ligand binding conditions on recognition in bupivacaine molecularly imprinted polymers. , 2004, The Analyst.

[206]  Sergey A. Piletsky,et al.  “Bite‐and‐Switch” Approach to Creatine Recognition by Use of Molecularly Imprinted Polymers , 2000 .

[207]  S. Striegler,et al.  Evaluation of new strategies to prepare templated polymers with sufficient oligosaccharide recognition capacity , 2003 .

[208]  D. Sherrington,et al.  A simple polymerisable carboxylic acid receptor: 2-acrylamido pyridine , 1999 .

[209]  W. Wang,et al.  Building fluorescent sensors for carbohydrates using template-directed polymerizations. , 2001, Bioorganic chemistry.

[210]  J. Steinke,et al.  Novel stereoselective molecularly imprinted polymers via ring-opening metathesis polymerisation , 2004 .

[211]  Isao Karube,et al.  Atrazine sensing by molecularly imprinted membranes , 1995 .

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

[213]  Enantioselective molecularly imprinted polymers via ring-opening metathesis polymerisation. , 2003, Chemical communications.

[214]  B. Sellergren,et al.  Molecular imprinting of amino acid derivatives in macroporous polymers , 1985 .

[215]  L. Ye,et al.  Synthesis and Characterization of Molecularly Imprinted Microspheres , 2000 .

[216]  D. Spivak,et al.  Improving the strategy and performance of molecularly imprinted polymers using cross-linking functional monomers. , 2003, Journal of Organic Chemistry.

[217]  F. Arnold,et al.  Molecularly imprinted polymers on silica: selective supports for high-performance ligand-exchange chromatography. , 1995, Journal of chromatography. A.

[218]  Andrew G. Mayes,et al.  Chapter 12 - Polymerisation techniques for the formation of imprinted beads , 2001 .

[219]  G. Wulff,et al.  Enzyme-analog-built polymers. 27. Racemic resolution of free sugars with macroporous polymers prepared by molecular imprinting. Selectivity dependence on the arrangement of functional groups versus spatial requirements , 1991 .

[220]  G. Wulff,et al.  POLYMERIZABLE AMIDINES-ADHESION MEDIATORS AND BINDING SITES FOR MOLECULAR IMPRINTING , 1998 .

[221]  Burkhard König,et al.  Synthetic creatinine receptor: imprinting of a Lewis acidic zinc(II)cyclen binding site to shape its molecular recognition selectivity. , 2004, Journal of the American Chemical Society.

[222]  Cong Yu,et al.  Insights into the origins of binding and the recognition properties of molecularly imprinted polymers prepared using an amide as the hydrogen‐bonding functional group , 1998, Journal of molecular recognition : JMR.

[223]  J. Matsui,et al.  Combinatorial Molecular Imprinting for Formation of Atrazine Decomposing Polymers , 2001 .

[224]  V. Remcho,et al.  Affinity screening by packed capillary high performance liquid chromatography using molecular imprinted sorbents. II. Covalent imprinted polymers. , 2001, Journal of chromatography. A.

[225]  M. Komiyama,et al.  Molecular Imprinting of Cyclodextrin in Water for the Recognition of Peptides , 1999 .

[226]  W. Wang,et al.  Building fluorescent sensors by template polymerization: the preparation of a fluorescent sensor for D-fructose. , 1999, Organic letters.

[227]  Takeo Araki,et al.  Molecularly imprinted uniform-size polymer-based stationary phase for high-performance liquid chromatography structural contribution of cross-linked polymer network on specific molecular recognition , 1996 .

[228]  T. Egan,et al.  Nucleation of calcium oxalate crystals on an imprinted polymer surface from pure aqueous solution and urine , 2004, JBIC Journal of Biological Inorganic Chemistry.