Synthetic strategies in molecular imprinting

Advances in Biochemical Engineering/Biotechnology

Volumn 150, Issue , 2015, Pages 1-24

  Ye, Lei ^a  

^a LUND UNIVERSITY   (Sweden)

Author keywords

Affinity separation; Free radical polymerization; Molecular imprinting; Molecular recognition; Template

Indexed keywords

NANOPARTICLE; POLYMER;

CHEMISTRY; MOLECULAR IMPRINTING; PROCEDURES; SYNTHESIS;

MOLECULAR IMPRINTING; NANOPARTICLES; POLYMERS;

EID: 84938085711     PISSN: 07246145     EISSN: None     Source Type: Book Series    
DOI: 10.1007/10_2015_313     Document Type: Article

References (75)

1. Dickey FH (1949) The preparation of specific adsorbents. Proc Natl Acad Sci USA 35: 227-229
2. Katada N, Niwa M (2006) The re-birth of molecular Imprinting on silica. In: Piletsky S, Turner A (eds) Molecular imprinting of polymers. Landes Bioscience, Georgetown, USA
3. Díaz-Gacía ME, Laíño RB (2005) Molecular imprinting in sol-gel materials: recent developments and applications. Microchim Acta 149:19-36
4. Wulff G, Sarhan A (1972) The use of polymers with enzyme-analogous structures for the resolution of racemates. Angew Chem Int Ed 11:341
5. Arshady R, Mosbach K (1981) Synthesis of substrate-selective polymers by host-guest polymerization. Macromol Chem Phys 182:687-692
6. Whitcombe MJ, Rodriguez ME, Villar P, Vulfson EN (1995) A new method for the introduction of recognition site functionality into polymers prepared by molecular imprinting-synthesis and characterization of polymeric receptors for chloresterol. J Am Chem Soc 117:7105-7111
7. Matsumoto A (1995) Free-radical crosslinking polymerization and copolymerization of multivinyl compounds. Adv Polym Sci 123:41-80
8. Wulff G, Knorr K (2002) Stoichiometric noncovalent interaction in molecular imprinting. Bioseparation 10:257-276
9. Sellergren B, Hall A (2013) Synthetic chemistry in molecular imprinting. In: Ye L (ed) Molecular imprinting: principles and applications of micro-and nanostructured polymers. Pan Stanford Publishing, Singapore
10. Lieberzeit PA, Glanznig G, Jenik M, Gazda-Miarecka S, Dickert FL, Leidl A (2005) Soft lithography in chemical sensing-analytes from molecules to cells. Sensors 5:509-518
11. Ye L, Ramström O, Mosbach K (1998) Molecularly imprinted polymeric adsorbents for byproduct removal. Anal Chem 70:2789-2795
12. Ye L (2005) Molecularly imprinted polymers for solid phase extraction and byproduct removal. In: Yan M, Ramström O (eds) Molecularly imprinted materials. Science and Technology, Marcel Dekker Inc., New York
13. Cragg PJ (2010) Supramolecular chemistry: from biological inspiration to biomedical applications. Springer, London
14. Takeuchi T, Hishiya T (2008) Molecular imprinting of proteins emerging as a tool for protein recognition. Org Biomol Chem 6:2459-2467
15. Sibrian-Vazquez M, Spivak DA (2004) Molecular imprinting made easy. J Am Chem Soc 126:7827-7833
16. Hishiya T, Asanuma H, Komiyama M (2002) Spectroscopic anatomy of molecular imprinting of cyclodextrin. Evidence for preferential formation of ordered cyclodextrin assemblies. J Am Chem Soc 124:570-575
17. Andersson HS, Ramström O (1998) Crown ethers as a tool for the preparation of molecularly imprinted polymers. J Mol Recogn 11:103-106
18. Viton F, White P S, GagnéMR (2003) Crown-ether functionalized second coordination sphere palladium catalysts by molecular imprinting. Chem Commun 39:3040-3041
19. Tsarevsky NV, Sumerlin BS (2013) Fundamentals of controlled/living radical polymerization. RSC Publishing, Cambridge
20. Wei X, Li X, Husson SM (2005) Surface molecular imprinting by atom transfer radical polymerization. Biomacromolecules 6:1113-1121
21. Boonpangrak S, Whitcombe MJ, Prachayasittikul V, Mosbach K, Ye L (2006) Preparation of molecularly imprinted polymers using nitroxide-mediated living radical polymerization. Biosens Bioelectron 22:349-354
22. Titirici M-M, Sellergren B (2006) Thin molecularly imprinted polymer films via reversible addition-fragmentation chain transfer polymerization. Chem Mater 18:1773-1779
23. Zhang H (2014) Water-compatible molecularly imprinted polymers: promising synthetic substitutes for biological receptors. Polymer 55:699-714
24. Zhou T, Jørgensen L, Mattebjerg MA, Chronakis IS, Ye L (2014) Molecularly imprinted polymer beads for nicotine recognition prepared by RAFT precipitation polymerization: a step forward towards multi-functionalities. RSC Adv 4:30292-30299
25. Corbett PT, Leclaire J, Vial L, West KR, Wietor J-L, Sanders JKM, Otto S (2006) Dynamic combinatorial chemistry. Chem Rev 106:3652-3711
26. Patel A, Fouace S, Steinke J H G (2003) Enantioselective molecularly imprinted polymers via ring-opening metathesis polymerization. Chem Commun 39:88-89
27. Zimmerman SC, Wendland MS, Rakow NA, Zharov I, Suslick KS (2002) Synthetic hosts by monomolecular imprinting inside dendrimers. Nature 418:399-403
28. Iacob B-C, Bodoki E, Oprean R (2014) Recent advances in capillary electrochromatography using molecularly imprinted polymers. Electrophoresis 35:2722-2732
29. Schweitz L, Andersson LI, Nilsson S (1997) Capillary electrochromatography with predetermined obtained through molecular imprinting. Anal Chem 69:1179-1183
30. Svec F, Fréchet JMJ (1999) Molded rigid monolithic porous polymers: an inexpensive, efficient, and versatile alternative to beads for the design of materials for numerous applications. Ind Eng Chem Res 38:34-48
31. Yan M, Kapua A (2001) Fabrication of molecularly imprinted microstructures. Anal Chim Acta 435:163-167
32. Lalo H, Ayela C, Dague E, Vieu C, Haupt K (2010) Nanopatterning molecularly imprinted polymers by soft lithography: a hierarchical approach. Lab Chip 10:1316-1318
33. Shimizu KD, Stephenson C (2010) Molecularly imprinted polymer sensor arrays. Curr Opinion Chem Biol 14:743-750
34. Forchheimer D, Luo G, Montelius L, Ye L (2010) Molecularly imprinted nanostructures by nanoimprint lithography. Analyst 135:1219-1223
35. Minko S (2008) Grafting on solid surfaces: "grafting to and "grafting from" methods. In: Stamm M (ed) Polymer surfaces and interfaces. Springer, Heidelberg
36. Sellergren B, Bückert B, Hall AJ (2002) Layer-by-layer grafting of molecularly imprinted polymers via iniferter modified supports. Adv Mater 14:1204-1208
37. Pérez-Moral N, Mayes AG (2007) Molecularly imprinted multi-layer core-shell nanoparticles-a surface grafting approach. Macromol Rapid Commun 28:2170-2175
38. Gonzato C, Courty M, Pasetto P, Haupt K (2011) Magnetic molecularly imprinted polymer nanocomposites via surface-initiated RAFT polymerization. Adv Funct Mater 21:3947-3953
39. Qu P, Lei J, Ouyang R, Ju H (2009) Enantioseparation and amperometric detection of chiral compounds by in situ molecular imprinting on the microchannel wall. Anal Chem 81:9651-9656
40. Wang H-J, Zhou W-H, Yin X-F, Zhuang Z-X, Yang H-H, Wang X-R (2006) Template synthesized molecularly imprinted polymer nanotube membranes for chemical separations. J Am Chem Soc 128:15954-15955
41. Lofgreen JE, Ozin GA (2014) Controlling morphology and porosity to improve performance of molecularly imprinted sol-gel silica. Chem Soc Rev 43:911-933
42. Ye L, Yilmaz E (2005) Molecularly imprinted polymer beads. In: Yan M, Ramström O (eds) Molecularly imprinted materials. Science and Technology, Marcel Dekker Inc., New York
43. Awino JK, Zhao Y (2013) Protein-mimetic, molecularly imprinted nanoparticles for selective binding of bile salt derivatives in water. J Am Chem Soc 135:12552-12555
44. Zeng Z, Hoshino Y, Rodriguez A, Yoo H, Shea KJ (2010) Synthetic polymer nanoparticles with antibody-like affinity for a hydrophilic peptide. ACS Nano 4:199-204
45. Gruber-Traub C, Weber A, Dettling M, Herz M, Herold M, Brunner H, Tovar GEM (2006) NANOCYTES-inverse miniemulsion polymerization technology for specific protein recognition. Polym Preprints 47:901-902
46. Downey JS, Mclsaac G, Frank RS, Stöver HDH (2001) Poly(divinylbenzene) microspheres as an intermediate morphology between microgel, macrogel, and coagulum in cross-linking precipitation polymerization. Macromolecules 34:4534-4541
47. Yoshimatsu K, Reimhult K, Krozer A, Mosbach K, Sode K, Ye L (2007) Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization: the control of particle size suitable for different analytical applications. Anal Chim Acta 584:112-121
48. Long Y, Philip JYN, Schillén K, Liu F, Ye L (2011) Insight into molecular imprinting in precipitation polymerization systems using solution NMR and dynamic light scattering. J Mol Recogn 24:619-630
49. Yang K, Berg MM, Zhao C, Ye L (2009) One-pot synthesis of hydrophilic molecularly imprinted nanoparticles. Macromolecules 42:8739-8746
50. Lai J-P, Lu X-Y, Lu C-Y, Ju H-F, He X-W (2001) Preparation and evaluation of molecularly imprinted polymeric microspheres by aqueous suspension polymerization for use as a highperformance liquid chromatography stationary phase. Anal Chim Acta 442:105-111
51. Zourob M, Mohr S, Mayes AG, Macaskill A, Pérez-Moral N, Fielden PR, Goddard NJ (2006) A micro-reactor for preparing uniform molecularly imprinted polymer beads. Lab Chip 6:296-301
52. Haginaka J, Takehira H, Hosoya K, Tanaka N (1999) Unifor-sized molecularly imprinted polymer for (S)-naproxen selectively modified with hydrophilic external layer. J Chromatogr A 849:331-339
53. Mayes A, Mosbach K (1996) Molecularly imprinted polymer beads: suspension polymerization using a liquid perfluorocarbon as the dispersing phase. Anal Chem 68:3769-3774
54. Pérez-Moral N, Mayes AG (2006) Direct rapid synthesis of MIP beads in SPE cartridges. Biosens Bioelectron 21:1798-1803
55. Shen X, Ye L (2011) Molecular imprinting in Pickering emulsions: new insight into molecular recognition in water. Chem Commun 47:10359-10361
56. Shen X, Zhou T, Ye L (2012) Molecular imprinting of protein in Pickering emulsion. Chem Commun 48:8198-8200
57. Zhou T, Shen X, Chaudhary S, Ye L (2014) Molecularly imprinted polymer beads prepared by Pickering emulsion polymerization for steroid recognition. J Appl Polym Sci 131:39606
58. Shen X, Ye L (2011) Interfacial molecular imprinting in nanoparticle-stabilized emulsions. Macromolecules 44:5631-5637
59. Shen X, Bonde JS, Bülow L, Leo JC, Linke D, Ye L (2014) Bacterial imprinting at Pickering emulsion interfaces. Angew Chem Int Ed 53:10687-10690
60. Bompart M, De Wilde Y, Haupt K (2010) Chemical nanosensors based on composite molecularly imprinted polymer particles and surface-enhanced Raman scattering. Adv Mater 22:2343-2348
61. Zhao M, Zhang C, Zhang Y, Guo X, Yan H, Zhang H (2014) Efficient synthesis of narrowly dispersed hydrophilic and magnetic molecularly imprinted polymer microspheres with excellent molecular recognition ability in a real biological sample. Chem Commun 50:2208-2210
62. Ma Y, Li H, He S, Zhang H, Zhang H (2014) Efficient one-pot synthesis of water-compatible and photoresponsive molecularly imprinted polymer nanoparticles by facile RAFT precipitation polymerization. J Polym Sci A Polym Chem 52:1941-1952
63. Piacham T, Josell Å, Arwin H, Prachayasittikul V, Ye L (2005) Molecularly imprinted polymer thin films on quartz crystal microbalance using a surface bound photo-radical initiator. Anal Chim Acta 536:191-196
64. Poma A, Guerreiro A, Caygill S, Moczko E, Piletsky S (2014) Automatic reactor for solidphase synthesis of molecularly imprinted nanoparticles (MIP NPs) in water. RSC Advances 4:4203-4206
65. Chronakis IS, Jakob A, Hagström B, Ye L (2006) Encapsulation and selective recognition of molecularly imprinted theophylline and 17β-estradiol nanoparticles within electrospun polymer nanofibers. Langmuir 22:8960-8965
66. Yoshimatsu K, Ye L, Linberg J, Chronakis IS (2008) Selective molecular adsorption using electrospun nanofiber affinity membranes. Biosens Bioelectron 23:1208-1215
67. Yoshimatsu K, Ye L, Stenlund P, Chronakis IS (2008) A simple method for preparation of molecularly imprinted nanofiber materials with signal transduction ability. Chem Commun 44:2022-2024
68. Reimhult K, Yoshimatsu K, Risveden K, Chen S, Ye L, Krozer A (2008) Characterization of QCM sensor surfaces coated with molecularly imprinted nanoparticles. Biosens Bioelectron 23:1908-1914
69. Hajizadeh S, Xu C, Kirsebom H, Ye L, Mattiasson B (2013) Cryogelation of molecularly imprinted nanoparticles: a macroporous structure as affinity chromatography column for removal of β-blockers from complex samples. J Chromatogr A 1274:6-12
70. Xu C, Ye L (2011) Clickable molecularly imprinted nanoparticles. Chem Commun 47: 6096-6098
71. Xu C, Shen X, Ye L (2012) Molecularly imprinted magnetic materials prepared from modular and clickable nanoparticles. J Mater Chem 22:7427-7433
72. Shen X, Xu C, Uddin KMA, Larsson P-O, Ye L (2013) Molecular recognition with colloidosomes enabled by imprinted polymer nanoparticles and fluorogenic boronic acid. J Mater Chem B 1:4612-4618
73. Chaudhary S, Kamra T, Uddin KMA, Snezhkova O, Jayawardena HSN, Yan M, Montelius L, Schnadt J, Ye L (2014) Controlled short-linkage assembly of functional nano-objects. Appl Sur Sci 300:22-28
74. Liu L-H, Yan M (2010) Perfluorophenyl azides: new applications in surface functionalization and nanomaterial synthesis. Acc Chem Res 43:1434-1443
75. Xu C, Uddin KMA, Shen X, Jayawardena HSN, Yan M, Ye L (2013) Photoconjugation of molecularly imprinted polymer with magnetic nanoparticles. ACS Appl Mater Interfaces 5:5208-5213