Synthesis of thermoresponsive glycopolymers via ATRP of N-isopropylacrylamide and N-allylacrylamide and subsequent thiol-ene reaction

European Polymer Journal

Volumn 49, Issue 9, 2013, Pages 2660-2669

  Von Der Ehe, Christian ^a,b   Czaplewska, Justyna A ^a   Gottschaldt, Michael ^a   Schubert, Ulrich S ^a,b  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b DUTCH POLYMER INSTITUTE DPI   (Netherlands)

Author keywords

ATRP; Glycopolymer; LCST; Lectin binding; Thiol ene reaction

Indexed keywords

COIL-TO-GLOBULE TRANSITION; DEGREE OF FUNCTIONALIZATION; GLYCOPOLYMERS; LCST; LECTIN BINDING; N-ISOPROPYLACRYLAMIDE COPOLYMERS; N-ISOPROPYLACRYLAMIDES; THIOL-ENE REACTIONS;

ATOM TRANSFER RADICAL POLYMERIZATION; COMPLEXATION; COPOLYMERS; POLYMERS;

ACRYLIC MONOMERS;

EID: 84881367890     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2013.03.025     Document Type: Article

References (35)

1. V. Ladmiral, E. Melia, and D.M. Haddleton Synthetic glycopolymers: an overview Eur Polym J 40 3 2004 431 449
2. B. Voit, and D. Appelhans Glycopolymers of various architectures - more than mimicking nature Macromol Chem Phys 211 7 2010 727 735
3. S.R.S. Ting, G. Chen, and M.H. Stenzel Synthesis of glycopolymers and their multivalent recognitions with lectins Polym Chem 1 9 2010 1392 1412
4. C.R. Becer The glycopolymer code: synthesis of glycopolymers and multivalent carbohydrate-lectin interactions Macromol Rapid Commun 33 9 2012 742 752
5. E.S. Gil, and S.M. Hudson Stimuli-reponsive polymers and their bioconjugates Prog Polym Sci 29 12 2004 1173 1222
6. M.H. Stenzel, L. Zhang, and W.T.S. Huck Temperature-responsive glycopolymer brushes synthesized via RAFT polymerization using the Z-group approach Macromol Rapid Commun 27 14 2006 1121 1126
7. E.H. Min, S.R.S. Ting, L. Billon, and M.H. Stenzel Thermo-responsive glycopolymer chains grafted onto honeycomb structured porous films via RAFT polymerization as a thermo-dependent switcher for lectin Concanavalin a conjugation J Polym Sci, Part A: Polym Chem 48 15 2010 3440 3455
8. V.S. Shinde, and V.U. Pawar Synthesis of thermosensitive glycopolymers containing d-glucose residue: copolymers with N-isopropylacrylamide J Appl Polym Sci 111 2009 2607 2615
9. Z. Özyürek, H. Komber, S. Gramm, D. Schmaljohann, A.H.E. Mueller, and B. Voit Thermoresponsive glycopolymers via controlled radical polymerization Macromol Chem Phys 208 10 2007 1035 1049
10. G. Pasparakis, A. Cockayne, and C. Alexander Control of bacterial aggregation by thermoresponsive glycopolymers J Am Chem Soc 129 36 2007 11014 11015
11. Y. Luo, L. Liu, X. Wang, H. Shi, W. Lv, and J. Li Sugar-installed thermoresponsive micellar aggregates self-assembled from "coil-comb- coil" triblock glycopolymers: preparation and recognition with Concanavalin A Soft Matter 8 5 2012 1634 1642
12. J. Bernard, X. Hao, T.P. Davis, C. Barner-Kowollik, and M.H. Stenzel Synthesis of various glycopolymer architectures via RAFT polymerization: from block copolymers to stars Biomacromolecules 7 1 2006 232 238
13. H. Yamanaka, K. Yoshizako, Y. Akiyama, H. Sota, Y. Hasegawa, and Y. Shinohara Affinity chromatography with collapsibly tethered ligands Anal Chem 75 7 2003 1658 1663
14. J. Geng, G. Mantovani, L. Tao, J. Nicolas, G. Chen, and R. Wallis Site-directed conjugation of "clicked" glycopolymers to form glycoprotein mimics: binding to mammalian lectin and induction of immunological function J Am Chem Soc 129 49 2007 15156 15163
15. V. Ladmiral, G. Mantovani, G.J. Clarkson, S. Cauet, J.L. Irwin, and D.M. Haddleton Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization J Am Chem Soc 128 14 2006 4823 4830
16. A. Dondoni, and A. Marra Recent applications of thiol-ene coupling as a click process for glycoconjugation Chem Soc Rev 41 2 2012 573 586
17. Burns JA, Gibson MI, Becer CR. Glycopolymers via post-polymerization modification techniques. In: Theato P, KlokFunctional H-A, editors. Polymers by post-polymerization modification: concepts, guidelines, and applications. Weinheim, Germany; 2012. p. 237-66.
18. J.C. Wilson, M.J. Kiefel, D.I. Angus, and M. Von Itzstein Investigation of the stability of thiosialosides toward hydrolysis by sialidases using NMR spectroscopy Org Lett 1 3 1999 443 446
19. H. Shen, and L.D. Byers Thioglycoside hydrolysis catalyzed by beta-glucosidase Biomed Biophys Res Commun 362 3 2007 717 720
20. G. Chen, S. Amajjahe, and M.H. Stenzel Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier Chem Commun 10 2009 1198 1200
21. A. Gress, A. Voelkel, and H. Schlaad Thio-click modification of poly[2-(3-butenyl)-2-oxazoline] Macromolecules 40 2007 7928 7933
22. K. Kempe, T. Neuwirth, J. Czaplewska, M. Gottschaldt, R. Hoogenboom, and U.S. Schubert Poly(2-oxazoline) glycopolymers with tunable LCST behavior Polym Chem 2 8 2011 1737 1743
23. C. Diehl, and H. Schlaad Thermo-responsive polyoxazolines with widely tuneable LCST Macromol Biosci 9 2 2009 157 161
24. L. Trossarelli, M. Guaita, and A. Priola Free radical polymerization of unconjugated dienes Macromol Chem 100 2277 1967 147 155
25. W. Kawai Polymerizations of some diene monomers. Preparations and polymerizations of vinyl methacrylate, allyl methacrylate, N-allylacrylamide, and N-allylmethacrylamide J Polym Sci, Part A: Polym Chem 4 5 1966 1191 1201
26. L. Trossarelli, M. Guaita, and A. Priola Some remarks on the free-radical polymerization of diene monomers N-allylmethacrylamide Polym Lett 5 1967 129 130
27. T. Kodaira, and S. Sakaki Cyclopolymerization 14: influence of temperature on free-radical cyclopolymerization of N-allylmethacrylamide and N-allylacrylamide Makromol Chem 189 1988 1835 1844
28. R. Paris, and J.L. de la Fuente Synthesis and characterization of functional gradient copolymers of allyl methacrylate and butyl acrylate J Polym Sci, Part A: Polym Chem 44 2006 5304 5315
29. M. Mennicken, R. Nagelsdiek, H. Keul, and H. Hoecker ATRP of allyl methacrylate with alkyl methacrylates - crosslinking of poly(methacrylate)s with allyl ester side groups Macromol Chem Phys 205 18 2004 2429 2437
30. R.N. Keller, and H.D. Wycoff Purification of copper(I) bromide Inorg Synth 1946 1 4
31. M. Ciampolini, and N. Nardi Five-coordinated high-spin complexes of bivalent cobalt, nickel, and copper with tris(2-dimethylaminoethyl)amine Inorg Chem 5 1 1966 41 44
32. D.A. Fulton, and J.F. Stoddart Synthesis of cyclodextrin-based carbohydrate clusters by photoaddition reactions J Org Chem 66 25 2001 8309 8319
33. C.R. Becer, K. Babiuch, D. Pilz, S. Hornig, T. Heinze, and M. Gottschaldt Clicking pentafluorostyrene copolymers: synthesis, nanoprecipitation, and glycosylation Macromolecules 42 7 2009 2387 2394
34. Y. Chen, G. Chen, and M.H. Stenzel Synthesis and lectin recognition of glyco star polymers prepared by "clicking" thiocarbohydrates onto a reactive scaffold Macromolecules 43 19 2010 8109 8114
35. K. Kempe, C. Weber, K. Babiuch, M. Gottschaldt, R. Hoogenboom, and U.S. Schubert Responsive glyco-poly(2-oxazoline)s: synthesis, cloud point tuning, and lectin binding Biomacromolecules 12 7 2011 2591 2600