Imprinting Using Smart Polymers

Smart Polymers: Applications in Biotechnology and Biomedicine

Volumn , Issue , 2007, Pages 211-245

  Alvarez Lorenzo, Carmen ^a   Concheiro, Angel ^a   Chuang, Jeffrey ^b   Grosberg, Alexander Yu ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b BOSTON COLLEGE   (United States)

^c University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85136396277     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420008623-12     Document Type: Chapter

References (79)

1. Dusek, K. and Patterson, D., Transition in swollen polymer networks induced by intramolecular condensation, J. Polym. Sci. A2, 6, 1209, 1968.
2. Tanaka, T., Collapse of gels and the critical endpoint, Phys. Rev. Lett., 40, 820, 1978.
3. Ilmain, F., Tanaka, T., and Kokufuta, E., Volume transition in a gel driven by hydrogen bonding, Nature, 349, 400, 1991.
4. Flory, P.J., Principles of Polymer Chemistry, Cornell, New York, 1953.
5. Shibayama, M. and Tanaka, T., Volume phase transition and related phenomena of polymer gels, in Advances in Polymer Science, Responsive Gels: Volume Transitions I, Dusek, K., Ed., Springer, Berlin, 1993, vol. 109, pp. 1-62.
6. Pande, V.S., Grosberg, A.Yu., and Tanaka, T., Statistical mechanics of simple models of protein folding and design, Biophys. J., 73, 3192, 1997.
7. Tanaka, T. and Annaka, M., Multiple phases of gels and biological implications, J. Intel. Mat. Syst. Struct., 4, 548, 1993.
8. Pande, V.S., Grosberg, A.Yu., and Tanaka, T., Folding thermodynamics and kinetics of imprinted renaturable heteropolymers, J. Chem. Phys., 101, 8246, 1994.
9. Pande, V.S., Grosberg, A.Yu., and Tanaka, T., Thermodynamic procedure to synthesize heteropolymers that can renature to recognize a given target molecule, Proc. Natl. Acad. Sci., 91, 12976, 1994.
10. Wulff, G., Molecular imprinting in cross-linked materials with the aid of molecular templates: a way towards artificial antibodies, Angew. Chem. Int. Ed. Engl., 34, 1812, 1995.
11. Grosberg, A.Yu. and Khokhlov, A.R., Giant Molecules, Academic Press, San Diego, 1997.
12. Wulff, G. and Biffis, A., Molecularly imprinting with covalent or stoichiometric non-covalent interactions, in Molecularly Imprinted Polymers, Sellergren, B., Ed., Elsevier, Amsterdam, 2001, pp. 71-111.
13. Arshady, R. and Mosbach, K., Synthesis of substrate-selective polymers by hostguest polymerization, Makromol. Chem., 182, 687, 1981.
14. Sellergren, B., The non-covalent approach to molecular imprinting, in Molecularly Imprinted Polymers, Sellergren, B., Ed., Elsevier, Amsterdam, 2001, pp. 113-184.
15. Ansell, R.J., Molecularly imprinted polymers in pseudoimmunoassay, J. Chromatogr. B, 804, 151, 2004.
16. Yan, M. and Ramström, O., Molecular imprinting: an introduction, in Molecularly Imprinted Materials, Yan, M. and Ramström, O., Eds., Marcel Dekker, New York, 2005, pp. 1-12.
17. Mayes, A.G. and Whitcombe, M.J., Synthetic strategies for the generation of molecularly imprinted organic polymers, Adv. Drug Del. Rev., 57, 1742, 2005.
18. Andersson, L.I., Molecular imprinting for drug bioanalysis: a review on the application of imprinted polymers to solid-phase extraction and binding assay, J. Chromatogr. B, 739, 163, 2000.
19. Kandimalla, V.B. and Ju, H.X., Molecular imprinting: a dynamic technique for diverse applications in analytical chemistry, Anal. Bioanal. Chem., 380, 587, 2004.
20. Xu, X., Zhu, L., and Chen, L., Separation and screening of compounds of biological origin using molecularly imprinted polymers, J. Chromatogr. B, 804, 61, 2004.
21. Piletsky, S.A. and Turner, A.P.F., Electrochemical sensors based on molecularly imprinted polymers, Electroanalysis, 14, 317, 2002.
22. Hillberg, A.L., Brain, K.R., and Allender, C.J., Molecular imprinted polymer sensors: implications for therapeutics, Adv. Drug Del. Rev., 57, 1875, 2005.
23. Sibrian-Vazquez, M. and Spivak, D.A., Improving the strategy and performance of molecularly imprinted polymers using cross-linking functional monomers, J. Org. Chem., 68, 9604, 2003.
24. Enoki, T., Tanaka, K., Watanabe, T. et al., Frustrations in polymer conformation in gels and their minimization through molecular imprinting, Phys. Rev. Lett., 85, 5000, 2000.
25. Byrne, M.E., Park, K., and Peppas, N.A., Molecular imprinting within hydrogels, Adv. Drug Del. Rev., 54, 149, 2002.
26. Miyata, T., Uragami, T., and Nakamae, K., Biomolecule-sensitive hydrogels, Adv. Drug Del. Rev., 54, 79, 2002.
27. Alvarez-Lorenzo, C. and Concheiro, A., Molecularly imprinted polymers for drug delivery, J. Chromatogr. B, 804, 231, 2004.
28. Cunliffe, D., Kirby, A., and Alexander, C., Molecularly imprinted drug delivery systems, Adv. Drug Del. Rev., 57, 1836, 2005.
29. Alvarez-Lorenzo, C. and Concheiro, A., Molecularly imprinted materials as advanced excipients for drug delivery systems, in Biotechnology Annual Review, vol. 12, El-Gewely, M.R., Ed., Elsevier, Amsterdam, 225, 2006.
30. Alvarez-Lorenzo, C. and Concheiro, A., Molecularly imprinted gels and nano- and microparticles: manufacture and applications, in Smart Assemblies and Particulates, vol. 7, Arshady, R. and Kono, K., Eds., Kentus Books, London, 2006, pp. 275-336.
31. Alvarez-Lorenzo, C. et al., Polymer gels that memorize elements of molecular conformation, Macromolecules, 33, 8693, 2000.
32. Alvarez-Lorenzo, C. et al., Reversible adsorption of calcium ions by imprinted temperature sensitive gels, J. Chem. Phys., 114, 2812, 2001.
33. D’Oleo, R., Alvarez-Lorenzo, C., and Sun, G., A new approach to design imprinted polymer gels without using a template, Macromolecules, 34, 4965, 2001.
34. Moritani, T. and Alvarez-Lorenzo, C., Conformational imprinting effect on stimuli-sensitive gels made with an imprinter monomer, Macromolecules, 34, 7796, 2001.
35. Stancil, K.A., Feld, M.S., and Kardar, M., Correlation and cross-linking effects in imprinting sites for divalent adsorption in gels, J. Phys. Chem. B, 109, 6636, 2005.
36. Oya, T. et al., Reversible molecular adsorption based on multiple point interaction by shrinkable gels, Science, 286, 1543, 1999.
37. Watanabe, T. et al., Affinity control through salt concentration on multiple contact adsorption into heteropolymer gel, J. Chem. Phys., 115, 1596, 2001.
38. Ito, K. et al., Multiple contact adsorption of target molecules, Macromol. Symp., 207, 1, 2004.
39. Ito, K. et al., Multiple point adsorption in a heteropolymer gel and the Tanaka approach to imprinting: experiment and theory, Prog. Polym. Sci., 28, 1489, 2003.
40. Rampey, A.M. et al., Characterization of the imprinting effect and the influence of imprinting conditions on affinity, capacity, and heterogeneity in molecularly imprinted polymers using the Freundlich isotherm-affinity distribution analysis, Anal. Chem., 76, 1123, 2004.
41. Pap, T. and Horvai, G., Binding assays with molecularly imprinted polymers:why do they work? J. Chromatogr. B, 804, 167, 2004.
42. Umpleby II, R.J. et al., Characterization of the heterogeneous binding site affinity distributions in molecularly imprinted polymers, J. Chromatogr. B, 804, 141, 2004.
43. Alvarez-Lorenzo, C. and Concheiro, A., Reversible adsorption by a pH- and temperature-sensitive acrylic hydrogel, J. Control. Rel., 80, 247, 2002.
44. Hsein, T.Y. and Rorrer, G.L., Heterogeneous cross-linking of chitosan gel beads:kinetics, modeling, and influence on cadmium ion adsorption capacity, Ind. Eng. Chem. Res., 36, 3631, 1997.
45. Eichenbaum, G.M. et al., Alkali earth metal binding properties of ionic microgels, Macromolecules, 33, 4087, 2000.
46. Takeoka, Y. et al., First order phase transition and evidence for frustration in polyampholytic gels, Phys. Rev. Lett., 82, 4863, 1999.
47. Alvarez-Lorenzo, C. et al., Simultaneous multiple-point adsorption of aluminum ions and charged molecules in a polyampholyte thermosensitive gel: controlling frustrations in a heteropolymer gel, Langmuir, 17, 3616, 2001.
48. Grosberg, A.Yu. and Khokhlov, A.R., Statistical Physics of Macromolecules, AIP, New York, 1994.
49. Pande, V.S., Grosberg, A.Yu., and Tanaka, T., Heteropolymer freezing and design: towards physical models of protein folding, Rev. Mod. Phys., 72, 259, 2000.
50. Bryngelson, J.D. and Wolynes, P.G., Spin glasses and the statistical mechanics of protein folding, Proc. Natl. Acad. Sci. USA, 2, 7524, 1987.
51. Tanaka, T. et al., Reversible molecular adsorption as a tool to observe freezing and to perform design of heteropolymer gels, Ber. Bunsenges. Phys. Chem., 102, 1529, 1998.
52. Hiratani, H. et al. Effect of reversible cross-linker, N, N′-bis(acryloyl)cystamine, on calcium ion adsorption by imprinted gels, Langmuir, 17, 4431, 2001.
53. Güney, O., Yilmaz, Y., and Pekcan, O., Metal ion templated chemosensor for metal ions based on fluorescence quenching, Sensors Actuators B, 85, 86, 2002.
54. Güney, O., Multiple-point adsorption of terbium ions by lead ion templated thermosensitive gel: elucidating recognition of conformation in gel by terbium probe, J. Molecular Recogn., 16, 67, 2003.
55. Kanazawa, R., Yoshida, T., Gotoh, T., and Sakohara, S., Preparation of molecular imprinted thermosensitive gel adsorbents and adsorption/desorption properties of heavy metal ions by temperature swing, J. Chem. Eng. Japan, 37, 59, 2004.
56. Kanazawa, R., Mori, K., Tokuyama, H., and Sakohara, S., Preparation of thermosensitive microgel adsorbent for quick adsorption of heavy metal ions by a temperature change, J. Chem. Eng. Japan, 37, 804, 2004.
57. Grinberg, N.V. et al., Studies of the thermal volume transition of poly(Nisopropylacrylamide) hydrogels by high-sensitivity differential scanning microcalorimetry, 1: dynamic effects, Macromolecules, 32, 1471, 1999.
58. Grinberg, V.Ya. et al., Studies of the thermal volume transition of poly(Nisopropylacrylamide) hydrogels by high-sensitivity microcalorimetry, 2: thermodynamic functions, Macromolecules, 33, 8685, 2000.
59. Burova, T. et al., Effects of ligand binding on relative stability of subchain conformations of weakly charged N-isopropylacrylamide gels in swollen and shrunken states, Macromolecules, 36, 9115, 2003.
60. Alvarez-Lorenzo, C. et al., Temperature-sensitive chitosan-poly(N-isopropylacrylamide) interpenetrated networks with enhanced loading capacity and controlled release properties, J. Control. Rel., 102, 629, 2005.
61. Yamashita, K., Nishimura, T., and Nango, M., Preparation of IPN-type stimuli responsive heavy-metal-ion adsorbent gel, Polym. Adv. Technol., 14, 189, 2003.
62. Yamashita, K. et al., Two-step imprinting procedure of inter-penetrating polymer network-type stimuli-responsive hydrogel adsorbents, Polym. J., 35, 545, 2003.
63. Watanabe, M., Akahoshi, T., Tabata, Y., and Nakayama, D., Molecular specific swelling change of hydrogels in accordance with the concentration of guest molecules, J. Am. Chem. Soc., 120, 5577, 1998.
64. Liu, X.Y. et al., Fabrication of temperature-sensitive imprinted polymer hydrogel, Macromol. Biosci., 4, 412, 2004.
65. Liu, X.Y. et al., Design of temperature sensitive imprinted polymer hydrogels based on multiple-point hydrogen bonding, Macromol. Biosci., 4, 680, 2004.
66. Aburto, J. and Le Borgne, S., Selective adsorption of dibenzothiophene sulfone by an imprinted and stimuli-sensitive chitosan hydrogel, Macromolecules, 37, 2938, 2004.
67. Berger, J. et al., Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications, Eur. J. Pharm. Biopharm., 57, 19, 2004.
68. Qiu, Y. and Park, K., Environment-sensitive hydrogels for drug delivery, Adv. Drug Del. Rev., 53, 321, 2001.
69. Kikuchi, A. and Okano, T., Pulsatile drug release control using hydrogels, Adv. Drug Del. Rev., 54, 53, 2002.
70. Puoci, F. et al., Spherical molecularly imprinted polymers (SMIPs) via a novel precipitation polymerization in the controlled delivery of salazine, Macromol. Biosci., 4, 22, 2004.
71. Chen, Y.B. et al., Influence of the pH on the behavior of an imprinted polymeric stationary phase: supporting evidence for a binding site model, J. Chromatog. A, 927, 1, 2001.
72. Kanekiyo, Y., Naganawa, R., and Tao, H., Molecular imprinting of bisphenol-A and alkylphenols using amylose as a host matrix, Chem. Commun., 22, 2698, 2002.
73. Kanekiyo, Y., Naganawa, R., and Tao, H., pH-responsive molecularly imprinted polymers, Angew. Chem., 42, 3014, 2003.
74. Oral, E. and Peppas, N.A., Responsive and recognitive hydrogels using star polymers, J. Biomed. Mater. Res., 68A, 439, 2004.
75. Guo, T.Y. et al., Chitosan beads as molecularly imprinted polymer matrix for selective separation of proteins, Biomaterials, 26, 5737, 2005.
76. Hawkins, D.M., Stevenson, D., and Reddy, S.M., Investigation of protein imprinting in hydrogel-based molecularly imprinted polymers (HydroMIPs), Anal. Chim. Acta, 542, 61, 2005.
77. Shnek, D.R. et al., Specific protein attachment to artificial membranes via coordination to lipid-bound copper(II), Langmuir, 10, 2382, 1994.
78. Rachkov, A. and Minoura, N., Towards molecularly imprinted polymers selective to peptides and proteins: the epitope approach, Biochim. Biophys. Acta, 1544, 255, 2001.
79. Demirel, G. et al., pH/temperature-sensitive imprinted ionic poly (N-tert-butylacrylamide-co-acrylamide/maleic acid) hydrogels for bovine serum albumin, Macromol. Biosci., 5, 1032, 2005.