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Molecularly Imprinted Polymers

  • Karsten HauptEmail author
  • Ana V. Linares
  • Marc Bompart
  • Bernadette Tse Sum Bui
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 325)

Abstract

Molecular imprinting is a process that allows for the synthesis of artificial receptors for a given target molecule based on synthetic polymers. The target molecule acts as a template around which interacting and cross-linking monomers are arranged and co-polymerized to form a cast-like shell. In essence, a molecular memory is imprinted in the polymer, which is now capable of selectively binding the target. Molecularly imprinted polymers (MIPs) thus possess the most important feature of biological antibodies - specific molecular recognition. They can thus be used in applications where selective binding events are of importance, such as immunoassays, affinity separation, biosensors, and directed synthesis and catalysis. Since its beginnings in the 1970s, the technique of molecular imprinting has greatly diversified during the last decade both from a materials point of view and from an application point of view. Still, there is much room for further improvement. The key challenges, in particular the binding site homogeneity and water compatibility of MIPs, and the possibility of synthesizing MIPs specific for proteins, are actively addressed by research groups over the World. Other important points are the conception of composite materials based on MIPs, in order to include additional interesting properties into the material, and the synthesis of very small and quasi-soluble MIPs, close in size to proteins.

Keywords

Artificial receptors Molecularly imprinted polymers Plastic antibodies Protein imprinting Water compatible MIP Controlled/living radical polymerization 

References

  1. 1.
    Arshady R, Mosbach K (1981) Makromol Chem 182:687CrossRefGoogle Scholar
  2. 2.
    Wulff G, Sarhan A (1972) Angew Chem Int Ed 11:341Google Scholar
  3. 3.
    Haupt K (2003) Anal Chem 75:376ACrossRefGoogle Scholar
  4. 4.
    Dickert FL, Hayden O, Halikias KP (2001) Analyst 126:766CrossRefGoogle Scholar
  5. 5.
    Katz A, Davis ME (2000) Nature 403:286CrossRefGoogle Scholar
  6. 6.
    Lordel S, Chapuis-Hugon F, Eudes V, Pichon V (2010) J Chromatogr A 1217:6674CrossRefGoogle Scholar
  7. 7.
    Ansell RJ, Mosbach K (1998) Analyst 123:1611CrossRefGoogle Scholar
  8. 8.
    Pérez N, Whitcombe MJ, Vulfson EN (2000) J Appl Polym Sci 77:1851CrossRefGoogle Scholar
  9. 9.
    Bompart M, De Wilde Y, Haupt K (2009) Adv Mater 22:2343CrossRefGoogle Scholar
  10. 10.
    Lakshmi D, Bossi A, Whitcombe MJ, Chianella I, Fowler SA, Subrahmanyam S, Piletska EV, Piletsky SA (2009) Anal Chem 81:3576CrossRefGoogle Scholar
  11. 11.
    Umpleby RJ, Baxter SC, Chen Y, Shah RN, Shimizu KD (2001) Anal Chem 73:4584CrossRefGoogle Scholar
  12. 12.
    Zimmerman SC, Lemcoff NG (2004) Chem Commun 1:5Google Scholar
  13. 13.
    Möller K, Crescenzi C, Nilsson U (2004) Anal Bioanal Chem 378:197CrossRefGoogle Scholar
  14. 14.
    Wulff G, Knorr K (2002) Bioseparation 10:257CrossRefGoogle Scholar
  15. 15.
    Shea KJ, Thompson EA (1978) J Org Chem 43:4253Google Scholar
  16. 16.
    Whitcombe MJ, Rodriguez ME, Villar P, Vulfson EN (1995) J Am Chem Soc 117:7105CrossRefGoogle Scholar
  17. 17.
    Chianella I, Lotierzo M, Piletsky SA, Tothill IE, Chen B, Karim K, Turner APF (2002) Anal Chem 74:1288CrossRefGoogle Scholar
  18. 18.
    Wu L, Li Y (2004) J Mol Recognit 17:567CrossRefGoogle Scholar
  19. 19.
    Yañez F, Chianella I, Piletsky SA, Concheiro A, Alvarez-Lorenzo C (2010) Anal Chim Acta 659:178CrossRefGoogle Scholar
  20. 20.
    O'Mahony J, Molinelli A, Nolan K, Smyth MR, Mizaikoff B (2005) Biosens Bioelectron 20:1884CrossRefGoogle Scholar
  21. 21.
    Molinelli A, O'Mahony J, Nolan K, Smyth MR, Jakusch M, Mizaikoff B (2005) Anal Chem 77:5196CrossRefGoogle Scholar
  22. 22.
    Hall AJ, Manesiotis P, Emgenbroich M, Quaglia M, De Lorenzi E, Sellergren B (2005) J Org Chem 70:1732CrossRefGoogle Scholar
  23. 23.
    Ansell RJ, Wang DY, Kuah JKL (2008) Analyst 133:1673CrossRefGoogle Scholar
  24. 24.
    Lanza F, Sellergren B (1999) Anal Chem 71:2092CrossRefGoogle Scholar
  25. 25.
    Takeuchi T, Fukuma D, Matsui J (1999) Anal Chem 71:285CrossRefGoogle Scholar
  26. 26.
    Takeuchi T, Seko A, Matsui J, Mukawa T (2001) Instrum Sci Technol 29:1CrossRefGoogle Scholar
  27. 27.
    Dirion B, Cobb Z, Schillinger E, Andersson LI, Sellergren B (2003) J Am Chem Soc 125:15101CrossRefGoogle Scholar
  28. 28.
    Ceolin G, Navarro-Villoslada F, Moreno-Bondi MC, Horvai G, Horvath V (2009) J Comb Chem 11:645CrossRefGoogle Scholar
  29. 29.
    Navarro-Villoslada F, San Vicente B, Moreno-Bondi MC (2004) Anal Chim Acta 504:149CrossRefGoogle Scholar
  30. 30.
    Navarro-Villoslada F, Takeuchi T (2005) Bull Chem Soc Jpn 78:1354CrossRefGoogle Scholar
  31. 31.
    Rossi C, Haupt K (2007) Anal Bioanal Chem 389:455CrossRefGoogle Scholar
  32. 32.
    Patel A, Fouace S, Steinke JHG (2003) Chem Commun 1:88Google Scholar
  33. 33.
    Patel A, Fouace S, Steinke JHG (2004) Anal Chim Acta 504:53CrossRefGoogle Scholar
  34. 34.
    Bompart M, Haupt K (2009) Aust J Chem 62:751CrossRefGoogle Scholar
  35. 35.
    Chiefari J, Chong YK, Ercole F, Krstina J, Jeffery J, Le TPT, Mayadunne RTA, Meijs GF, Moad CL, Moad G, Rizzardo E, Thang SH (1998) Macromolecules 31:5559CrossRefGoogle Scholar
  36. 36.
    Moad G, Rizzardo E, Thang SH (2006) Aust J Chem 59:669CrossRefGoogle Scholar
  37. 37.
    Titirici MM, Sellergren B (2006) Chem Mater 18:1773CrossRefGoogle Scholar
  38. 38.
    Du Zhenxia I, Zhifeng F (2006) Chin Chem Lett 17:549Google Scholar
  39. 39.
    Southard GE, Van Houten KA, Ott EW, Murray GM (2007) Anal Chim Acta 581:202CrossRefGoogle Scholar
  40. 40.
    Southard GE, Van Houten KA, Murray GM (2007) Macromolecules 40:1395CrossRefGoogle Scholar
  41. 41.
    Liu H, Zhuang X, Turson M, Zhang M, Dong X (2008) J Sep Sci 31:1694CrossRefGoogle Scholar
  42. 42.
    Gonzato C, Courty M, Pasetto P, Haupt K (2011) Adv Funct Mater 21:3947Google Scholar
  43. 43.
    Otsu T (2000) J Polym Sci Pol Chem 38:2121CrossRefGoogle Scholar
  44. 44.
    Otsu T, Yoshida M, Tazaki T (1982) Makromol Chem Rapid Commun 3:133CrossRefGoogle Scholar
  45. 45.
    Wang HY, Kobayashi T, Fujii N (1997) J Chem Technol Biotechnol 70:355CrossRefGoogle Scholar
  46. 46.
    Rückert B, Hall A, Sellergren B (2002) J Mater Chem 12:2275CrossRefGoogle Scholar
  47. 47.
    Sellergren B, Rückert B, Hall A (2002) Adv Mater 14:1204CrossRefGoogle Scholar
  48. 48.
    Rong F, Feng X, Li P, Yuan C, Fu D (2006) Chinese Sci Bull 51:2566CrossRefGoogle Scholar
  49. 49.
    Pérez-Moral N, Mayes AG (2007) Macromol Rapid Commun 28:2170CrossRefGoogle Scholar
  50. 50.
    Vaughan AD, Sizemore SP, Byrne ME (2007) Polymer 48:74CrossRefGoogle Scholar
  51. 51.
    Su S, Zhang M, Li B, Zhang H, Dong X (2008) Talanta 76:1141CrossRefGoogle Scholar
  52. 52.
    Kamigaito M, Ando T, Sawamoto M (2001) Chem Rev 101:3689CrossRefGoogle Scholar
  53. 53.
    Kato M, Kamigaito M, Sawamoto M, Higashimura T (1995) Macromolecules 28:1721CrossRefGoogle Scholar
  54. 54.
    Wang J-S, Matyjaszewski K (1995) J Am Chem Soc 117:5614CrossRefGoogle Scholar
  55. 55.
    Matyjaszewski K, Xia J (2001) Chem Rev 101:2921CrossRefGoogle Scholar
  56. 56.
    Salomon DH, Rizzardo E, Cacioli P (1985) US Patent US4581429Google Scholar
  57. 57.
    Hawker CJ, Bosman AW, Harth E (2001) Chem Rev 101:3661CrossRefGoogle Scholar
  58. 58.
    Boonpangrak S, Whitcombe MJ, Prachayasittikul V, Mosbach K, Ye L (2006) Biosens Bioelectron 22:349CrossRefGoogle Scholar
  59. 59.
    Teodorescu M, Matyjaszewski K (2000) Macromol Rapid Commun 21:190CrossRefGoogle Scholar
  60. 60.
    Xia J, Zhang X, Matyjaszewski K (1999) Macromolecules 32:3531CrossRefGoogle Scholar
  61. 61.
    Wei X, Li X, Husson SM (2005) Biomacromolecules 6:1113CrossRefGoogle Scholar
  62. 62.
    Li X, Husson SM (2006) Biosens Bioelectron 22:336CrossRefGoogle Scholar
  63. 63.
    Wei X, Husson SM (2007) Ind Eng Chem Res 46:2117CrossRefGoogle Scholar
  64. 64.
    Zu BY, Pan GQ, Guo XZ, Zhang Y, Zhang HQ (2009) J Polym Sci A Polym Chem 47:3257CrossRefGoogle Scholar
  65. 65.
    Sasaki S, Ooya T, Takeuchi T (2010) Polym Chem 1:1684CrossRefGoogle Scholar
  66. 66.
    Zu BY, Zhang Y, Guo XZ, Zhang HQ (2010) J Polym Sci A Polym Chem 48:532CrossRefGoogle Scholar
  67. 67.
    Sulitzky C, Ruckert B, Hall AJ, Lanza F, Unger K, Sellergren B (2002) Macromolecules 35:79CrossRefGoogle Scholar
  68. 68.
    Vaughan AD, Zhang JB, Byrne ME (2010) AIChE J 56:268Google Scholar
  69. 69.
    Lu C, Zhou W, Han B, Yang H, Chen X, Wang X (2007) Anal Chem 79:5457CrossRefGoogle Scholar
  70. 70.
    Pan GQ, Zu BY, Guo XZ, Zhang Y, Li CX, Zhang HQ (2009) Polymer 50:2819CrossRefGoogle Scholar
  71. 71.
    Pan G, Ma Y, Zhang Y, Guo X, Li C, Zhang H (2011) Soft Matter 7:8428CrossRefGoogle Scholar
  72. 72.
    Pichon V, Haupt K (2006) J Liq Chromatogr Relat Technol 29:989CrossRefGoogle Scholar
  73. 73.
    Andersson LI (1996) Anal Chem 68:111CrossRefGoogle Scholar
  74. 74.
    Bengtsson H, Roos U, Andersson LI (1997) Anal Comm 34:233CrossRefGoogle Scholar
  75. 75.
    Haupt K, Dzgoev A, Mosbach K (1998) Anal Chem 70:628CrossRefGoogle Scholar
  76. 76.
    Caro E, Marcé RM, Cormack PAG, Sherrington DC, Borrull F (2004) J Chromatogr A 1047:175Google Scholar
  77. 77.
    Haupt K, Mayes AG, Mosbach K (1998) Anal Chem 70:3936CrossRefGoogle Scholar
  78. 78.
    Legido-Quigley C, Oxelbark J, De Lorenzi E, Zurutuza-Elorza A, Cormack PAG (2007) Anal Chim Acta 591:22CrossRefGoogle Scholar
  79. 79.
    Díaz-Alvarez M, Turiel E, Martín-Esteban A (2009) Anal Bioanal Chem 393:899CrossRefGoogle Scholar
  80. 80.
    Sun H-W, Qiao F-X (2008) J Chromatogr A 1212:1CrossRefGoogle Scholar
  81. 81.
    Wulff G, Biffis A (2001) In: Sellergren B (ed) Molecularly imprinted polymers: man-made mimics of antibodies and their applications in analytical chemistry. Elsevier, Amsterdam, pp 71–111Google Scholar
  82. 82.
    Wulff G, Schönfeld R (1998) Adv Mater 10:957CrossRefGoogle Scholar
  83. 83.
    Sellergren B (1994) Anal Chem 66:1578CrossRefGoogle Scholar
  84. 84.
    Lübke C, Lübke M, Whitcombe MJ, Vulfson EN (2000) Macromolecules 33:5098CrossRefGoogle Scholar
  85. 85.
    Urraca JL, Moreno-Bondi MC, Hall AJ, Sellergren B (2007) Anal Chem 79:695CrossRefGoogle Scholar
  86. 86.
    Sadlej-Sosnowska N (1997) J Incl Phenom Mol Rec Chem 27:31CrossRefGoogle Scholar
  87. 87.
    Piletsky SA, Andersson HS, Nicholls IA (1998) J Mol Recogn 11:94CrossRefGoogle Scholar
  88. 88.
    Song SH, Shirasaka K, Hirokawa Y, Asanuma H, Wada T, Sumaoka J, Komiyama M (2010) Supramol Chem 22:149CrossRefGoogle Scholar
  89. 89.
    Hishiya T, Shibata M, Kakazu M, Asanuma H, Komiyama M (1999) Macromolecules 32:2265CrossRefGoogle Scholar
  90. 90.
    Hochuli E, Döbeli H, Schacher A (1987) J Chromatogr A 411:177CrossRefGoogle Scholar
  91. 91.
    Hart BR, Shea KJ (2002) Macromolecules 35:6192CrossRefGoogle Scholar
  92. 92.
    Hart BR, Shea KJ (2001) J Am Chem Soc 123:2072CrossRefGoogle Scholar
  93. 93.
    Striegler S (2001) Tetrahedron 57:2349CrossRefGoogle Scholar
  94. 94.
    Striegler S (2004) J Chromatogr B 804:183CrossRefGoogle Scholar
  95. 95.
    Tse Sum Bui B, Haupt K (2010) Anal Bioanal Chem 398:2481CrossRefGoogle Scholar
  96. 96.
    Andersson LI, Müller R, Mosbach K (1996) Macromol Res Comm 17:65CrossRefGoogle Scholar
  97. 97.
    Fu GQ, Zhu J, Jiang YZ (2008) Anal Chem 80:2634CrossRefGoogle Scholar
  98. 98.
    Verheyen E, Schillemans JP, van Wijk M, Demeniex MA, Hennink WE, van Nostrum CF (2011) Biomaterials 32:3008CrossRefGoogle Scholar
  99. 99.
    Hjertén S, Liao JL, Nakazato K, Wang Y, Zamaratskaia G, Zhang HX (1997) Chromatographia 44:227CrossRefGoogle Scholar
  100. 100.
    Janiak DS, Kofinas P (2007) Anal Bioanal Chem 389:399CrossRefGoogle Scholar
  101. 101.
    Hansen DE (2007) Biomaterials 28:4178CrossRefGoogle Scholar
  102. 102.
    Bossi A, Bonini F, Turner APF, Piletsky SA (2007) Biosens Bioelectron 22:1131CrossRefGoogle Scholar
  103. 103.
    Shi HQ, Tsai WB, Garrison MD, Ferrari S, Ratner BD (1999) Nature 398:593CrossRefGoogle Scholar
  104. 104.
    El Kirat K, Bartkowski M, Haupt K (2009) Biosens Bioelectron 24:2618CrossRefGoogle Scholar
  105. 105.
    Linares AV, Vandevelde F, Pantigny J, Falcimaigne-Cordin A, Haupt K (2009) Adv Funct Mater 19:1CrossRefGoogle Scholar
  106. 106.
    Uysal A, Demirel G, Turan E, Çaykara T (2008) Anal Chim Acta 625:110CrossRefGoogle Scholar
  107. 107.
    Casey BJ, Kofinas P (2008) J Biomed Mater Res A 87A:359CrossRefGoogle Scholar
  108. 108.
    Cutivet A, Schembri C, Kovensky J, Haupt K (2009) J Am Chem Soc 131:14699Google Scholar
  109. 109.
    Hoshino Y, Kodama T, Okahata Y, Shea KJ (2008) J Am Chem Soc 130:15242CrossRefGoogle Scholar
  110. 110.
    Hoshino Y, Urakami T, Kodama T, Koide H, Oku N, Okahata Y, Shea KJ (2009) Small 5:1562Google Scholar
  111. 111.
    Hoshino Y, Koide H, Urakami T, Kanazawa H, Kodama T, Oku N, Shea KJ (2010) J Am Chem Soc 132:6644CrossRefGoogle Scholar
  112. 112.
    Rachkov A, Minoura N (2000) J Chromatogr A 889:111CrossRefGoogle Scholar
  113. 113.
    Rachkov A, Minoura N (2001) Biochim Biophys Acta 1544:255CrossRefGoogle Scholar
  114. 114.
    Nishino H, Huang C-S, Shea KJ (2006) Angew Chem Int Ed 45:2392CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2011

Authors and Affiliations

  • Karsten Haupt
    • 1
    Email author
  • Ana V. Linares
    • 1
  • Marc Bompart
    • 1
  • Bernadette Tse Sum Bui
    • 1
  1. 1.Compiègne University of Technology, UMR CNRS 6022CompiègneFrance

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