Synthesis of Glycopolymer Architectures by Reversible-Deactivation Radical Polymerization

Polymers

Volumn 5, Issue 2, 2013, Pages 431-526

  Ghadban, Ali ^a   Albertin, Luca ^b  

^a UNIVERSITÉ DE LYON   (France)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL POLYMERIZATION;

DEGREE OF CONTROL; EXPERIMENTAL CONDITIONS; GLYCOPOLYMERS; NITROXIDE MEDIATED RADICAL POLYMERIZATION; POLYMERIZATION PROCESS; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; REVERSIBLEDEACTIVATION RADICAL POLYMERIZATION (RDRP); STATE OF THE ART;

ATOM TRANSFER RADICAL POLYMERIZATION;

EID: 84881072821     PISSN: None     EISSN: 20734360     Source Type: Journal    
DOI: 10.3390/polym5020431     Document Type: Article

References (251)

1. Horejsi, V.; Smolek, P.; Kocourek, J. Studies on lectins. XXXV. Water-soluble O-glycosyl polyacrylamide derivatives for specific precipitation of lectins. Biochim. Biophys. Acta Gen. Subj. 1978, 538, 293-298.
2. Choi, S.K.; Mammen, M.; Whitesides, G.M. Generation and in situ evaluation of libraries of poly(acrylic acid) presenting sialosides as side chains as polyvalent inhibitors of influenza-mediated hemagglutination. J. Am. Chem. Soc. 1997, 119, 4103-4111.
3. Gordon, E.J.; Strong, L.E.; Kiessling, L.L. Glycoprotein-inspired materials promote the proteolytic release of cell surface l-selectin. Bioorg. Med. Chem. 1998, 6, 1293-1299.
4. Kiessling, L.L.; Gestwicki, J.E.; Strong, L.E. Synthetic multivalent ligands in the exploration of cell-surface interactions. Curr. Opin. Chem. Biol. 2000, 4, 696-703.
5. David, A.; Kopeckova, P.; Kopecek, J.; Rubinstein, A. The role of galactose, lactose, and galactose valency in the biorecognition of N-(2-hydroxypropyl)methacrylamide copolymers by human colon adenocarcinoma cells. Pharm. Res. 2002, 19, 1114-1122.
6. Roy, R.; Baek, M.G. Glycodendrimers: Novel glycotope isosteres unmasking sugar coding. Case study with T-antigen markers from breast cancer MUC1 glycoprotein. Rev. Mol. Biotechnol. 2002, 90, 291-309.
7. Gambaryan, A.S.; Boravleva, E.Y.; Matrosovich, T.Y.; Matrosovich, M.N.; Klenk, H.D.; Moiseeva, E.V.; Tuzikov, A.B.; Chinarev, A.A.; Pazynina, G.V.; Bovin, N.V. Polymer-bound 6' sialyl-N-acetyllactosamine protects mice infected by influenza virus. Antivir. Res. 2005, 68, 116-123.
8. Fleming, C.; Maldjian, A.; Da Costa, D.; Rullay, A.K.; Haddleton, D.M.; John, J.St.; Penny, P.; Noble, R.C.; Cameron, N.R.; Davis, B.G. A carbohydrate-antioxidant hybrid polymer reduces oxidative damage in spermatozoa and enhances fertility. Nat. Chem. Biol. 2005, 1, 270-274.
9. Palomino, E. Carbohydrate handles as natural resources in drug delivery. Adv. Drug Deliv. Rev. 1994, 13, 311-323.
10. Wadhwa, M.S.; Rice, K.G. Receptor mediated glycotargeting. J. Drug Target. 1995, 3, 111-127.
11. Wang, Y.; Zhang, X.; Han, Y.; Cheng, C.; Li, C. pH- and glucose-sensitive glycopolymer nanoparticles based on phenylboronic acid for triggered release of insulin. Carbohydr. Polym. 2012, 89, 124-131.
12. Song, E.-H.; Manganiello, M.J.; Chow, Y.-H.; Ghosn, B.; Convertine, A.J.; Stayton, P.S.; Schnapp, L.M.; Ratner, D.M. In vivo targeting of alveolar macrophages via RAFT-based glycopolymers. Biomaterials 2012, 33, 6889-6897.
13. Karamuk, E.; Mayer, J.; Wintermantel, E.; Akaike, T. Partially degradable film/fabric composites: Textile scaffolds for liver cell culture. Artif. Organs 1999, 23, 881-884.
14. Chaikof, E.L.; Grande, D.; Baskaran, S. Glycopolymers and Free Radical Polymerization Methods. U.S. Patent 7,244,830 B2, 17 July 2007.
15. Liu, X.C.; Dordick, J.S. Sugar acrylate-based polymers as chiral molecularly imprintable hydrogels. J. Polym. Sci. A Polym. Chem. 1999, 37, 1665-1671.
16. Gruber, H.; Knaus, S. Synthetic polymers based on carbohydrates: Preparation, properties and applications. Macromol. Symp. 2000, 152, 95-105.
17. Baek, M.G.; Roy, R. Design and synthesis of water-soluble glycopolymers bearing breast tumor marker and enhanced lipophilicity for solid-phase assays. Biomacromolecules 2000, 1, 768-770.
18. Miyata, T.; Uragami, T.; Nakamae, K. Biomolecule-sensitive hydrogels. Adv. Drug Deliv. Rev. 2002, 54, 79-98.
19. Novick, S.J.; Dordick, J.S. Preparation of active and stable biocatalytic hydrogels for use in selective transformations. Chem. Mater. 1998, 10, 955-958.
20. Wulff, G.; Schmid, J.; Venhoff, T.P. The preparation of new types of polymerizable vinyl sugars with C-C bonds between sugar and double bond. Macromol. Chem. Phys. 1996, 197, 1285-1299.
21. Wulff, G.; Zhu, L.; Schmidt, H. Investigations on surface-modified bulk polymers. 1. copolymers of styrene with a styrene moiety containing a sugar monomer. Macromolecules 1997, 30, 4533-4539.
22. Miyata, T.; Nakamae, K. Polymers with pendent saccharides: "glycopolymers". Trends Polym. Sci. 1997, 5, 198-206.
23. Wulff, G.; Schmidt, H.; Zhu, L.M. Generating hydrophilic surfaces on standard polymers after copolymerization with low amounts of protected vinyl sugars. Macromol. Chem. Phys. 1999, 200, 774-782.
24. Varki, A.; Cummings, R.; Esko, J.; Freeze, H.; Hart, G.; Marth, J. Essentials of Glycobiology, 2nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, USA, 2009.
25. Whittaker, G.R. Intracellular trafficking of influenza virus: Clinical implications for molecular medicine. Expert Rev. Mol. Med. 2001, 3, 1-13.
26. Weis, W.; Brown, J.H.; Cusack, S.; Paulson, J.C.; Skehel, J.J.; Wiley, D.C. Structure of the influenza-virus haemagglutinin complexed with its receptor, sialic-acid. Nature 1988, 333, 426-431.
27. Bertozzi, C.R.; Kiessling, L.L. Chemical glycobiology. Science 2001, 291, 2357-2364.
28. Vandamme, E.J.; de Baets, S.; Steinbüchel, A. Polysaccharides I: Polysaccharides from Prokaryotes; Wiley-VCH: Weinheim, Germany, 2002.
29. Vandamme, E.J.; de Baets, S.; Steinbüchel, A. Polysaccharides II: Polysaccharides from Eukaryotes; Wiley-VCH: Weinheim, Germany, 2002.
30. Haddleton, D.M.; Ohno, K. Well-Defined oligosaccharide-terminated polymers from living radical polymerization. Biomacromolecules 2000, 1, 152-156.
31. Halila, S.; Manguian, M.; Fort, S.; Cottaz, S.; Hamaide, T.; Fleury, E.; Driguez, H. Syntheses of well-defined glyco-polyorganosiloxanes by "click" chemistry and their surfactant properties. Macromol. Chem. Phys. 2008, 209, 1282-1290.
32. Chiron, S.; Labeau, M.-P.; Fleury, E.; Viet, D.; Cottaz, S.; Driguez, H.; Halila, S. Novel Glycopolymers, Uses Thereof, and Monomers Useful for Preparation Thereof. WO Patent 2006016063 A1, 13 November 2008.
33. Narumi, A.; Miura, Y.; Otsuka, I.; Yamane, S.; Kitajyo, Y.; Satoh, T.; Hirao, A.; Kaneko, N.; Kaga, H.; Kakuchi, T. End-functionalization of polystyrene by malto-oligosaccharide generating aggregation-tunable polymeric reverse micelle. J. Polym. Sci. A Polym. Chem. 2006, 44, 4864-4879.
34. Houga, C.; Le Meins, J.-F.; Borsali, R.; Taton, D.; Gnanou, Y. Synthesis of ATRP-induced dextran-b-polystyrene diblock copolymers and preliminary investigation of their self-assembly in water. Chem. Commun. 2007, 3063-3065.
35. Aissou, K.; Otsuka, I.; Rochas, C.; Fort, S.; Halila, S.; Borsali, R. Nano-Organization of Amylose-b-polystyrene block copolymer films doped with bipyridine. Langmuir 2011, 27, 4098-4103.
36. Bernard, J.; Save, M.; Arathoon, B.; Charleux, B. Preparation of a xanthate-terminated dextran by click chemistry: Application to the synthesis of polysaccharide-coated nanoparticles via surfactant-free ab initio emulsion polymerization of vinyl acetate. J. Polym. Sci. A Polym. Chem. 2008, 46, 2845-2857.
37. Ghadban, A.; Albertin, L.; Rinaudo, M.; Heyraud, A. Biohybrid glycopolymer capable of ionotropic gelation. Biomacromolecules 2012, 13, 3108-3119.
38. Sigal, G.B.; Mammen, M.; Dahmann, G.; Whitesides, G.M. Polyacrylamides bearing pendant alpha-sialoside groups strongly inhibit agglutination of erythrocytes by influenza virus-The strong inhibition reflects enhanced binding through cooperative polyvalent interactions. J. Am. Chem. Soc. 1996, 118, 3789-3800.
39. Kanai, M.; Mortell, K.H.; Kiessling, L.L. Varying the size of multivalent ligands-The dependence of concanavalin A binding on neoglycopolymer length. J. Am. Chem. Soc. 1997, 119, 9931-9932.
40. Georges, M.K.; Veregin, R.P.N.; Kazmaier, P.M.; Hamer, G.K. Narrow molecular weight resins by a free-radical polymerization process. Macromolecules 1993, 26, 2987-2988.
41. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashimura, T. Polymerization of methyl methacrylate with the carbon tetrachloride/dichlorotris- (triphenylphosphine)ruthenium(II)/Methylaluminum Bis(2,6-di-tert-butylphenoxide) initiating System: Possibility of living radical polymerization. Macromolecules 1995, 28, 1721-1723.
42. Chiefari, J.; Chong, Y.K.; Ercole, F.; Krstina, J.; Jeffery, J.; Le, T.P.T.; Mayadunne, R.T.A.; Meijs, G.F.; Moad, C.L.; Moad, G.; et al. Living free-radical polymerization by reversible addition-fragmentation chain transfer-The RAFT process. Macromolecules 1998, 31, 5559-5562.
43. Matyjaszewski, K.; Davis, T.P. Handbook of radical polymerization; John Wiley and Sons, Inc.: Hoboken, NJ, USA, 2002.
44. Lowe, A.B.; McCormick, C.L. Homogeneous controlled free radical polymerization in aqueous media. Aust. J. Chem. 2002, 55, 367-379.
45. Xia, J.H.; Gaynor, S.G.; Matyjaszewski, K. Controlled/"living" radical polymerization. Atom transfer radical polymerization of acrylates at ambient temperature. Macromolecules 1998, 31, 5958-5959.
46. Robinson, K.L.; Khan, M.A.; Banez, M.V.D.; Wang, X.S.; Armes, S.P. Controlled polymerization of 2-hydroxyethyl methacrylate by ATRP at ambient temperature. Macromolecules 2001, 34, 3155-3158.
47. Quinn, J.F.; Rizzardo, E.; Davis, T.P. Ambient temperature reversible addition-fragmentation chain transfer polymerisation. Chem. Commun. 2001, 1044-1045.
48. Moad, G.; Rizzardo, E.; Thang, S.H. Living radical polymerization by the RAFT process. Aust. J. Chem. 2005, 58, 379-410.
49. Moad, G.; Rizzardo, E.; Thang, S.H. Living radical polymerization by the RAFT process-A first update. Aust. J. Chem. 2006, 59, 669-692.
50. Moad, G.; Rizzardo, E.; Thang, S.H. Living radical polymerization by the RAFT process-A second update. Aust. J. Chem. 2009, 62, 1402-1472.
51. Matyjaszewski, K. Atom Transfer Radical Polymerization (ATRP): Current status and future perspectives. Macromolecules 2012, 45, 4015-4039.
52. Grubbs, R.B. Nitroxide-Mediated radical polymerization: Limitations and versatility. Polym. Rev. 2011, 51, 104-137.
53. Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Nitroxide-mediated polymerization. Prog. Polym. Sci. 2013, 63-235.
54. Jenkins, A.D.; Jones, R.G.; Moad, G. Terminology for reversible-deactivation radical polymerization previously called "controlled" radical or "living" radical polymerization (IUPAC Recommendations 2010). Pure Appl. Chem. 2010, 82, 483-491.
55. Fukuda, T.; Goto, A.; Tsujii, Y. Kinetics of Living Radical Polymerisation. In Handbook of Radical Polymerization; Matyjaszewski, K., Davis, T.P., Eds.; John Wiley and Sons, Inc.: Hoboken, NJ, USA, 2002; pp. 407-462.
56. Matyjaszewski, K. General Concepts and History of Living Radical Polymerisation. In Handbook of Radical Polymerization; Matyjaszewski, K., Davis, T.P., Eds.; John Wiley and Sons, Inc.: Hoboken, NJ, USA, 2002; pp. 361-406.
57. Miura, Y. Design and synthesis of well-defined glycopolymers for the control of biological functionalities. Polym. J. 2012, 44, 679-689.
58. Becer, C.R. The glycopolymer code: Synthesis of glycopolymers and multivalent carbohydrate-lectin interactions. Macromol. Rapid Commun. 2012, 33, 742-752.
59. Spain, S.G.; Cameron, N.R. A spoonful of sugar: The application of glycopolymers in therapeutics. Polym. Chem. 2011, 2, 60-68.
60. Pearson, S.; Chen, G.; Stenzel, M.H. Synthesis of Glycopolymers. In Engineered Carbohydrate-Based Materials for Biomedical Applications; John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2011; pp. 1-118.
61. Voit, B.; Appelhans, D. Glycopolymers of various architectures-more than mimicking nature. Macromol. Chem. Phys. 2010, 211, 727-735.
62. Ting, S.R.S.; Chen, G.; Stenzel, M.H. Synthesis of glycopolymers and their multivalent recognitions with lectins. Polym. Chem. 2010, 1, 1392-1412.
63. Zhang, Y.; Wang, J.; Xia, C.; Wang, P.G. Glycopolymers: The Future Antiadhesion Drugs. In Polymer Biocatalysis and Biomaterials II; American Chemical Society: Washington, DC, USA, 2008; Volume 999, pp. 342-361.
64. Spain, S.G.; Gibson, M.I.; Cameron, N.R. Recent advances in the synthesis of well-defined glycopolymers. J. Polym. Sci. A Polym. Chem. 2007, 45, 2059-2072.
65. Rice, K.G.; Kim, J.-S.; Liu, D. Glycopolymer Tools for Studying Targeted Nonviral Gene Delivery. In Polymeric Gene Delivery Principles and Applications; Amiji, M.M., Ed.; CRC Press: Punta Gorda, FL, USA, 2005; pp. 509-521.
66. Ladmiral, V.; Melia, E.; Haddleton, D.M. Synthetic glycopolymers: An overview. Eur. Polym. J. 2004, 40, 431-449.
67. Okada, M. Molecular design and syntheses of glycopolymers. Prog. Polym. Sci. 2001, 26, 67-104.
68. Roy, R. Blue-prints, synthesis and applications of glycopolymers. Trends Glycosci. Glycotechnol. 1996, 8, 79-99.
69. Druliner, J.D. Living radical polymerization involving oxygen-centered species attached to propagating chain ends. Macromolecules 1991, 24, 6079-6082.
70. Gnanou, Y.; Grande, D.; Guerrero, R. (Meth)Acrylate-based graft copolymers via cyanoxyl-mediated free-radical polymerization. Polym. Prepr. 1999, 40, 99-100.
71. Grande, D.; Guerrero, R.; Gnanou, Y. Cyanoxyl-mediated free-radical polymerization of acrylic acid: Its scope and limitations. J. Polym. Sci. A Polym. Chem. 2005, 43, 519-533.
72. David, G.; Boyer, C.; Tonnar, J.; Ameduri, B.; Lacroix-Desmazes, P.; Boutevin, B. Use of iodocompounds in radical polymerization. Chem. Rev. 2006, 106, 3936-3962.
73. Yamago, S. Development of organotellurium-mediated and organostibine-mediated living radical polymerization reactions. J. Polym. Sci. A Polym. Chem. 2006, 44, 1-12.
74. Goto, A.; Hirai, N.; Nagasawa, K.; Tsujii, Y.; Fukuda, T.; Kaji, H. Phenols and carbon compounds as efficient organic catalysts for reversible chain transfer catalyzed living radical polymerization (RTCP). Macromolecules 2010, 43, 7971-7978.
75. Kickelbick, G.; Pintauer, T.; Matyjaszewski, K. Structural comparison of Cu-II complexes in atom transfer radical polymerization. New J. Chem. 2002, 26, 462-468.
76. Baskaran, S.; Grande, D.; Sun, X.L.; Yayon, A.; Chaikof, E.L. Glycosaminoglycan-Mimetic biomaterials. 3. Glycopolymers prepared from alkene-derivatized mono- and disaccharide-based glycomonomers. Bioconjug. Chem. 2002, 13, 1309-1313.
77. Grande, D.; Baskaran, S.; Baskaran, C.; Gnanou, Y.; Chaikof, E.L. Glycosaminoglycan-mimetic biomaterials 1 Nonsulfated and sulfated glycopolymers by cyanoxyl-mediated free-radical polymerization. Macromolecules 2000, 33, 1123-1125.
78. Grande, D.; Baskaran, S.; Chaikof, E.L. Glycosaminoglycan mimetic biomaterials. 2. Alkene- and acrylate-derivatized glycopolymers via cyanoxyl-mediated free-radical polymerization. Macromolecules 2001, 34, 1640-1646.
79. Sun, X.L.; Grande, D.; Baskaran, S.; Hanson, S.R.; Chaikof, E.L. Glycosaminoglycan mimetic biomaterials. 4. Synthesis of sulfated lactose-based glycopolymers that exhibit anticoagulant activity. Biomacromolecules 2002, 3, 1065-1070.
80. Guan, R.; Sun, X.L.; Hou, S.; Wu, P.; Chaikof, E.L. A glycopolymer chaperone for fibroblast growth factor-2. Bioconjug. Chem. 2004, 15, 145-151.
81. Narla, S.N.; Sun, X.-L. Orientated glyco-macroligand formation based on site-specific immobilization of O-cyanate chain-end functionalized glycopolymer. Org. Biomol. Chem. 2011, 9, 845-850.
82. Sun, X.-L.; Cui, W.; Haller, C.; Chaikof, E.L. Site-Specific multivalent carbohydrate labeling of quantum dots and magnetic beads. ChemBioChem 2004, 5, 1593-1596.
83. Hou, S.; Sun, X.-L.; Dong, C.-M.; Chaikof, E.L. Facile synthesis of chain-end functionalized glycopolymers for site-specific bioconjugation. Bioconjug. Chem. 2004, 15, 954-959.
84. Faucher, K.M.; Sun, X.L.; Chaikof, E.L. Fabrication and characterization of glycocalyx-mimetic surfaces. Langmuir 2003, 19, 1664-1670.
85. Sun, X.L.; Faucher, K.M.; Houston, M.; Grande, D.; Chaikof, E.L. Design and synthesis of biotin chain-terminated glycopolymers for surface glycoengineering. J. Am. Chem. Soc. 2002, 124, 7258-7259.
86. Ting, S.R.S.; Min, E.-H.; Escale, P.; Save, M.; Billon, L.; Stenzel, M.H. Lectin recognizable biomaterials synthesized via nitroxide-mediated polymerization of a methacryloyl galactose monomer. Macromolecules 2009, 42, 9422-9434.
87. Gotz, H.; Harth, E.; Schiller, S.M.; Frank, C.W.; Knoll, W.; Hawker, C.J. Synthesis of lipo-glycopolymer amphiphiles by nitroxide-mediated living free-radical polymerization. J. Polym. Sci. A Polym. Chem. 2002, 40, 3379-3391.
88. Chen, Y.M.; Wulff, G. Synthesis of poly(styryl sugar)s by TEMPO mediated free radical polymerization. Macromol. Chem. Phys. 2001, 202, 3426-3431.
89. Chen, Y.M.; Wulff, G. Amphiphilic block copolymers with pendent sugar as hydrophilic segments and their surface properties. Macromol. Chem. Phys. 2001, 202, 3273-3278.
90. Narumi, A.; Matsuda, T.; Kaga, H.; Satoh, T.; Kakuchi, T. Glycoconjugated polymer II. Synthesis of polystyrene-block-poly(4-vinylbenzyl glucoside) and polystyrene-block-poly (4-vinylbenzyl maltohexaoside) via 2,2,6,6-tetramethylpiperidine-1-oxyl-mediated living radical polymerization. Polym. J. 2001, 33, 939-945.
91. Narumi, A.; Matsuda, T.; Kaga, H.; Satoh, T.; Kakuchi, T. Synthesis of amphiphilic triblock copolymer of polystyrene and poly(4-vinylbenzyl glucoside) via TEMPO-mediated living radical polymerization. Polymer 2002, 43, 4835-4840.
92. Narumi, A.; Otsuka, I.; Matsuda, T.; Miura, Y.; Satoh, T.; Kaneko, N.; Kaga, H.; Kakuchi, T. Glycoconjugated polymer: synthesis and characterization of poly(vinyl saccharide)-block-polystyrene-block-poly(vinyl saccharide) as an amphiphilic ABA triblock copolymer. J. Polym. Sci. A Polym. Chem. 2006, 44, 3978-3985.
93. Ohno, K.; Tsujii, Y.; Miyamoto, T.; Fukuda, T.; Goto, M.; Kobayashi, K.; Akaike, T. Synthesis of a well-defined glycopolymer by nitroxide-controlled free radical polymerization. Macromolecules 1998, 31, 1064-1069.
94. Ohno, K.; Fukuda, T.; Kitano, H. Free radical polymerization of a sugar residue-carrying styryl monomer with a lipophilic alkoxyamine initiator: Synthesis of a well-defined novel glycolipid. Macromol. Chem. Phys. 1998, 199, 2193-2197.
95. Miura, Y.; Koketsu, D.; Kobayashi, K. Synthesis and properties of a well-defined glycopolymer via living radical polymerization. Polym. Adv. Technol. 2007, 18, 647-651.
96. Babiuch, K.; Wyrwa, R.; Wagner, K.; Seemann, T.; Hoeppener, S.; Becer, C.R.; Linke, R.; Gottschaldt, M.; Weisser, J.; Schnabelrauch, M.; et al. Functionalized, biocompatible coating for superparamagnetic nanoparticles by controlled polymerization of a thioglycosidic monomer. Biomacromolecules 2011, 12, 681-691.
97. Babiuch, K.; Becer, C.R.; Gottschaldt, M.; Delaney, J.T.; Weisser, J.; Beer, B.; Wyrwa, R.; Schnabelrauch, M.; Schubert, U.S. Adhesion of Preosteoblasts and fibroblasts onto Poly(pentafluorostyrene)-based glycopolymeric films and their biocompatibility. Macromol. Biosci. 2011, 11, 535-548.
98. Wild, A.; Babiuch, K.; Konig, M.; Winter, A.; Hager, M.D.; Gottschaldt, M.; Prokop, A.; Schubert, U.S. Synthesis of a glycopolymeric PtII carrier and its induction of apoptosis in resistant cancer cells. Chem. Commun. 2012, 48, 6357-6359.
99. Becer, C.R.; Babiuch, K.; Pilz, D.; Hornig, S.; Heinze, T.; Gottschaldt, M.; Schubert, U.S. Clicking pentafluorostyrene copolymers: Synthesis, nanoprecipitation, and glycosylation. Macromolecules 2009, 42, 2387-2394.
100. Narla, S.N.; Sun, X.-L. Immobilized sialyloligo-macroligand and its protein binding specificity. Biomacromolecules 2012, 13, 1675-1682.
101. Mammen, M.; Choi, S.K.; Whitesides, G.M. Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors. Angew. Chem. Int. Ed. 1998, 37, 2755-2794.
102. Chaikof, E.L.; Sun, X.L. Multivalent Polymers with Chain-Terminating Binding Groups. WO Patent 2003099835 A1, 4 December 2003.
103. Grande, D.; Baskaran, S.; Chaikof, E.L. Mono- and disaccharide-based glycopolymers by free-radical polymerization processes. Polym. Mater. Sci. Eng. 2001, 84, 141-142.
104. Yu, K.; Kizhakkedathu, J.N. Synthesis of functional polymer brushes containing carbohydrate residues in the pyranose form and their specific and nonspecific interactions with proteins. Biomacromolecules 2010, 11, 3073-3085.
105. Chen, Y.M.; Wulff, G. ABA and star amphiphilic block copolymers composed of polymethacrylate bearing a galactose fragment and poly(ε-caprolactone). Macromol. Rapid Commun. 2002, 23, 59-63.
106. Ke, B.-B.; Wan, L.-S.; Zhang, W.-X.; Xu, Z.-K. Controlled synthesis of linear and comb-like glycopolymers for preparation of honeycomb-patterned films. Polymer 2010, 51, 2168-2176.
107. Ladmiral, V.; Monaghan, L.; Mantovani, G.; Haddleton, D.M. α-Functional glycopolymers: New materials for (poly)peptide conjugation. Polymer 2005, 46, 8536-8545.
108. Bes, L.; Angot, S.; Limer, A.; Haddleton, D.M. Sugar-coated amphiphilic block copolymer micelles from living radical polymerization: Recognition by immobilized lectins. Macromolecules 2003, 36, 2493-2499.
109. Ohno, K.; Tsujii, Y.; Fukuda, T. Synthesis of a well-defined glycopolymer by atom transfer radical polymerization. J. Polym. Sci. A Polym. Chem. 1998, 36, 2473-2481.
110. Ejaz, M.; Ohno, K.; Tsujii, Y.; Fukuda, T. Controlled grafting of a well-defined glycopolymer on a solid surface by surface-initiated atom transfer radical polymerization. Macromolecules 2000, 33, 2870-2874.
111. Muthukrishnan, S.; Plamper, F.; Mori, H.; Muller, A.H.E. Synthesis and characterization of glycomethacrylate hybrid stars from silsesquioxane nanoparticles. Macromolecules 2005, 38, 10631-10642.
112. Muthukrishnan, S.; Jutz, G.; Andre, X.; Mori, H.; Muller, A.H.E. Synthesis of hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization of a sugar-carrying acrylate. Macromolecules 2005, 38, 9-18.
113. Muthukrishnan, S.; Mori, H.; Muller, A.H.E. Synthesis and characterization of methacrylate-type hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization. Macromolecules 2005, 38, 3108-3119.
114. Muthukrishnan, S.; Zhang, M.; Burkhardt, M.; Drechsler, M.; Mori, H.; Muller, A.H.E. Molecular sugar sticks: Cylindrical glycopolymer brushes. Macromolecules 2005, 38, 7926-7934.
115. Gao, C.; Muthukrishnan, S.; Li, W.W.; Yuan, J.Y.; Xu, Y.Y.; Muller, A.H.E. Linear and hyperbranched glycopolymer-functionalized carbon nanotubes: Synthesis, kinetics, and characterization. Macromolecules 2007, 40, 1803-1815.
116. Wang, J.; Qian, Y.; Zhang, F.; Zhu, B.; Xu, Y. Synthesis and self-assembly of amphiphilic ABA type triblock copolymer with well-defined glycopolymer segments. Chin. Sci. Bull. 2008, 53, 1343-1351.
117. Liang, Y.-Z.; Li, Z.-C.; Chen, G.-Q.; Li, F.-M. Synthesis of well-defined poly[(2-β-D-glucopyranosyloxy)ethyl acrylate] by atom transfer radical polymerization. Polym. Int. 1999, 48, 739-742.
118. You, L.-C.; Lu, F.-Z.; Li, Z.-C.; Zhang, W.; Li, F.-M. Glucose-Sensitive aggregates formed by Poly(ethylene oxide)-block-poly(2-glucosyloxyethyl acrylate) with concanavalin A in dilute aqueous medium. Macromolecules 2003, 36, 1-4.
119. Dong, C.-M.; Sun, X.-L.; Faucher, K.M.; Apkarian, R.P.; Chaikof, E.L. Synthesis and characterization of glycopolymer-polypeptide triblock copolymers. Biomacromolecules 2004, 5, 224-231.
120. Dong, C.-M.; Faucher, K.M.; Chaikof, E.L. Synthesis and properties of biomimetic poIy(L-glutamate)-b-poly(2-acryloyloxyethyllactoside)-b-poly(L-glutamate) triblock copolymers. J. Polym. Sci. A Polym. Chem. 2004, 42, 5754-5765.
121. Pfaff, A.; Muller, A.H.E. Hyperbranched glycopolymer grafted microspheres. Macromolecules 2011, 44, 1266-1272.
122. Pfaff, A.; Shinde, V.S.; Lu, Y.; Wittemann, A.; Ballauff, M.; Muller, A.H.E. Glycopolymer-grafted polystyrene nanospheres. Macromol. Biosci. 2011, 11, 199-210.
123. Narain, R.; Armes, S.P. Direct synthesis and aqueous solution properties of well-defined cyclic sugar methacrylate polymers. Macromolecules 2003, 36, 4675-4678.
124. Narain, R.; Armes, S.P. Synthesis of low polydispersity, controlled-structure sugar methacrylate polymers under mild conditions without protecting group chemistry. Chem. Commun. 2002, 2776-2777.
125. Qiu, S.; Huang, H.; Dai, X.-H.; Zhou, W.; Dong, C.-M. Star-shaped polypeptide/glycopolymer biohybrids: Synthesis, self-assembly, biomolecular recognition, and controlled drug release behavior. J. Polym. Sci. A Polym. Chem. 2009, 47, 2009-2023.
126. Narain, R.; Armes, S.P. Synthesis and aqueous solution properties of novel sugar methacrylate-based homopolymers and block copolymers. Biomacromolecules 2003, 4, 1746-1758.
127. Mateescu, A.; Ye, J.; Narain, R.; Vamvakaki, M. Synthesis and characterization of novel glycosurfaces by ATRP. Soft Matter 2009, 5, 1621-1629.
128. Kitano, H.; Saito, D.; Kamada, T.; Gemmei-Ide, M. Binding of β-amyloid to sulfated sugar residues in a polymer brush. Colloids Surf. B 2012, 93, 219-225.
129. Fleet, R.; van den Dungen, E.T.A.; Klumperman, B. Novel glycopolymer brushes via ATRP: 1. synthesis and characterization. Macromol. Chem. Phys. 2011, 212, 2191-2208.
130. Narain, R. Tailor-made protein-glycopolymer bioconjugates. React. Funct. Polym. 2006, 66, 1589-1595.
131. Yang, Q.; Ulbricht, M. Cylindrical membrane pores with well-defined grafted linear and comblike glycopolymer layers for lectin binding. Macromolecules 2011, 44, 1303-1310.
132. O'Connell, M.A.; de Cuendias, A.; Gayet, F.; Shirley, I.M.; Mackenzie, S.R.; Haddleton, D.M.; Unwin, P.R. Evanescent Wave Cavity Ring-Down Spectroscopy (EW-CRDS) as a probe of macromolecule adsorption kinetics at functionalized interfaces. Langmuir 2012, 28, 6902-6910.
133. Xu, L.Q.; Huang, C.; Wang, R.; Neoh, K.-G.; Kang, E.-T.; Fu, G.D. Synthesis and characterization of fluorescent perylene bisimide-containing glycopolymers for Escherichia coli conjugation and cell imaging. Polymer 2011, 52, 5764-5771.
134. Kitano, H.; Takahashi, Y.; Mizukami, K.; Matsuura, K. Kinetic study on the binding of lectin to mannose residues in a polymer brush. Colloids Surf. B 2009, 70, 91-97.
135. Geng, J.; Mantovani, G.; Tao, L.; Nicolas, J.; Chen, G.; Wallis, R.; Mitchell, D.A.; Johnson, B.R.G.; Evans, S.D.; Haddleton, D.M. Site-Directed conjugation of "clicked" glycopolymers to form glycoprotein mimics: Binding to mammalian lectin and induction of immunological function. J. Am. Chem. Soc. 2007, 129, 15156-15163.
136. Vazquez-Dorbatt, V.; Maynard, H.D. Biotinylated glycopolymers synthesized by atom transfer radical polymerization. Biomacromolecules 2006, 7, 2297-2302.
137. Vazquez-Dorbatt, V.; Tolstyka, Z.P.; Chang, C.-W.; Maynard, H.D. Synthesis of a pyridyl disulfide end-functionalized glycopolymer for conjugation to biomolecules and patterning on gold surfaces. Biomacromolecules 2009, 10, 2207-2212.
138. Leon, O.; Bordege, V.; Munoz-Bonilla, A.; Sanchez-Chaves, M.; Fernandez-Garcia, M. Well-controlled amphiphilic block glycopolymers and their molecular recognition with lectins. J. Polym. Sci. A Polym. Chem. 2010, 48, 3623-3631.
139. Leon, O.; Munoz-Bonilla, A.; Bordege, V.; Sanchez-Chaves, M.; Fernandez-Garcia, M. Amphiphilic block glycopolymers via atom transfer radical polymerization: Synthesis, self-assembly and biomolecular recognition. J. Polym. Sci. A Polym. Chem. 2011, 49, 2627-2635.
140. Munoz-Bonilla, A.; Heuts, J.P.A.; Fernandez-Garcia, M. Glycoparticles and bioactive films prepared by emulsion polymerization using a well-defined block glycopolymer stabilizer. Soft Matter 2011, 7, 2493-2499.
141. De, L.A.S.; Munoz-Bonilla, A.; Fernandez-Garcia, M.; Rodriguez-Hernandez, J. Breath figures method to control the topography and the functionality of polymeric surfaces in porous films and microspheres. J. Polym. Sci. A Polym. Chem. 2012, 50, 851-859.
142. Menon, S.; Das, S. A photoresponsive fluorescent glycopolymer. Polym. Chem. 2012, 3, 2619-2624.
143. Ladmiral, V.; Mantovani, G.; Clarkson, G.J.; Cauet, S.; Irwin, J.L.; Haddleton, D.M. Synthesis of neoglycopolymers by a combination of "click chemistry" and living radical polymerization. J. Am. Chem. Soc. 2006, 128, 4823-4830.
144. Richards, S.-J.; Jones, M.W.; Hunaban, M.; Haddleton, D.M.; Gibson, M.I. Probing bacterial-toxin inhibition with synthetic glycopolymers prepared by tandem post-polymerization modification: Role of linker length and carbohydrate density. Angew. Chem. Int. Ed. 2012, 51, 7812-7816.
145. Gou, Y.; Slavin, S.; Geng, J.; Voorhaar, L.; Haddleton, D.M.; Becer, C.R. Controlled alternate layer-by-layer assembly of lectins and glycopolymers using QCM-D. ACS Macro Lett. 2011, 1, 180-183.
146. Houga, C.; Giermanska, J.; Lecommandoux, S.; Borsali, R.; Taton, D.; Gnanou, Y.; Le, M.J.-F. Micelles and polymersomes obtained by self-assembly of dextran and polystyrene based block copolymers. Biomacromolecules 2009, 10, 32-40.
147. Yu, K.; Lai, B.F.L.; Kizhakkedathu, J.N. Carbohydrate structure dependent hemocompatibility of biomimetic functional polymer brushes on surfaces. Adv. Healthc. Mater. 2012, 1, 199-213.
148. Fleet, R.; van den Dungen, E.T.A.; Klumperman, B. Novel glycopolymer brushes via ATRP: 2. thermal and mechanical properties. Macromol. Chem. Phys. 2011, 212, 2209-2216.
149. Fleet, R.; van den Dungen, E.T.A.; Klumperman, B. Synthesis of novel glycopolymer brushes via a combination of RAFT-mediated polymerization and ATRP. S. Afr. J. Sci. 2011, 107, 101-111.
150. Yuan, J.; Meng, J.-Q.; Kang, Y.-L.; Du, Q.-Y.; Zhang, Y.-F. Facile surface glycosylation of PVDF microporous membrane via direct surface-initiated AGET ATRP and improvement of antifouling property and biocompatibility. Appl. Surf. Sci. 2012, 258, 2856-2863.
151. Meng, J.; Yuan, J.; Kang, Y.; Zhang, Y.; Du, Q. Surface glycosylation of polysulfone membrane towards a novel complexing membrane for boron removal. J. Colloid Interface Sci. 2012, 368, 197-207.
152. Hardy, J.; Selkoe, D.J. The amyloid hypothesis of Alzheimer's disease: Progress and problems on the Road to therapeutics. Science 2002, 297, 353-356.
153. Kohri, M.; Sato, M.; Abo, F.; Inada, T.; Kasuya, M.; Taniguchi, T.; Nakahira, T. Preparation and lectin binding specificity of polystyrene particles grafted with glycopolymers bearing S-linked carbohydrates. Eur. Polym. J. 2011, 47, 2351-2360.
154. Becer, C.R.; Gibson, M.I.; Geng, J.; Ilyas, R.; Wallis, R.; Mitchell, D.A.; Haddleton, D.M. High-Affinity glycopolymer binding to human DC-SIGN and disruption of DC-SIGN interactions with HIV envelope glycoprotein. J. Am. Chem. Soc. 2010, 132, 15130-15132.
155. Gou, Y.; Richards, S.-J.; Haddleton, D.M.; Gibson, M.I. Investigation of glycopolymer-lectin interactions using QCM-d: Comparison of surface binding with inhibitory activity. Polym. Chem. 2012, 3, 1634-1640.
156. Geng, J.; Biedermann, F.; Zayed, J.M.; Tian, F.; Scherman, O.A. Supramolecular glycopolymers in water: A reversible route toward multivalent carbohydrate-lectin conjugates using Cucurbit[8]uril. Macromolecules 2011, 44, 4276-4281.
157. Muñoz-Bonilla, A.; León, O.; Cerrada, M.L.; Rodríguez-Hernández, J.; Sánchez-Chaves, M.; Fernández-García, M. Glycopolymers obtained by chemical modification of well-defined block copolymers. J. Polym. Sci. A Polym. Chem. 2012, 50, 2565-2577.
158. Gody, G.; Boullanger, P.; Ladaviere, C.; Charreyre, M.T.; Delair, T. Biotin alpha-end-functionalized gradient glycopolymers synthesized by RAFT copolymerization. Macromol. Rapid Commun. 2008, 29, 511-519.
159. Su, L.; Zhao, Y.; Chen, G.; Jiang, M. Polymeric vesicles mimicking glycocalyx (PV-Gx) for studying carbohydrate-protein interactions in solution. Polym. Chem. 2012, 3, 1560-1566.
160. Wei, Z.; Hao, X.; Gan, Z.; Hughes, T.C. One-pot synthesis of hyperbranched glycopolymers by RAFT polymerization. J. Polym. Sci. A Polym. Chem. 2012, 50, 2378-2388.
161. Ozyurek, Z.; Komber, H.; Gramm, S.; Schmaljohann, D.; Muller, A.H.E.; Voit, B. Thermoresponsive glycopolymers via controlled radical polymerization. Macromol. Chem. Phys. 2007, 208, 1035-1049.
162. Jiang, X.; Housni, A.; Gody, G.; Boullanger, P.; Charreyre, M.-T.; Delair, T.; Narain, R. Synthesis of Biotinylated α-d-Mannoside or N-Acetyl β-D-Glucosaminoside decorated gold nanoparticles: Study of their biomolecular recognition with ConA and WGA lectins. Bioconjug. Chem. 2010, 21, 521-530.
163. Belardi, B.; O'Donoghue Geoff, P.; Smith Adam, W.; Groves Jay, T.; Bertozzi Carolyn, R. Investigating cell surface galectin-mediated cross-linking on glycoengineered cells. J. Am. Chem. Soc. 2012, 134, 9594-9552.
164. Toyoshima, M.; Oura, T.; Fukuda, T.; Matsumoto, E.; Miura, Y. Biological specific recognition of glycopolymer- modified interfaces by RAFT living radical polymerization. Polym. J. 2009, 42, 172-178.
165. Deng, Z.; Ahmed, M.; Narain, R. Novel well-defined glycopolymers synthesized via the reversible addition fragmentation chain transfer process in aqueous media. J. Polym. Sci. A Polym. Chem. 2009, 47, 614-627.
166. Ahmed, M.; Narain, R. The effect of polymer architecture, composition, and molecular weight on the properties of glycopolymer-based non-viral gene delivery systems. Biomaterials 2011, 32, 5279-5290.
167. Ahmed, M.; Lai, B.F.L.; Kizhakkedathu, J.N.; Narain, R. Hyperbranched glycopolymers for blood biocompatibility. Bioconjug. Chem. 2012, 23, 1050-1058.
168. Ahmed, M.; Narain, R. The effect of molecular weight, compositions and lectin type on the properties of hyperbranched glycopolymers as non-viral gene delivery systems. Biomaterials 2012, 33, 3990-4001.
169. Bernard, J.; Hao, X.J.; Davis, T.P.; Barner-Kowollik, C.; Stenzel, M.H. Synthesis of various glycopolymer architectures via RAFT polymerization: From block copolymers to stars. Biomacromolecules 2006, 7, 232-238.
170. Ting, S.R.S.; Min, E.H.; Zetterlund, P.B.; Stenzel, M.H. Controlled/Living ab initio emulsion polymerization via a glucose RAFTstab: degradable cross-linked glyco-particles for concanavalin A/FimH conjugations to cluster E. coli bacteria. Macromolecules 2010, 43, 5211-5221.
171. Smith, A.E.; Sizovs, A.; Grandinetti, G.; Xue, L.; Reineke, T.M. Diblock glycopolymers promote colloidal stability of polyplexes and effective pDNA and siRNA delivery under physiological salt and serum conditions. Biomacromolecules 2011, 12, 3015-3022.
172. Abdelkader, O.; Moebs-Sanchez, S.; Queneau, Y.; Bernard, J.; Fleury, E. Generation of well-defined clickable glycopolymers from aqueous RAFT polymerization of isomaltulose-derived acrylamides. J. Polym. Sci. A Polym. Chem. 2011, 49, 1309-1318.
173. Albertin, L.; Wolnik, A.; Ghadban, A.; Dubreuil, F. Aqueous RAFT Polymerization of N-Acryloylmorpholine, synthesis of an ABA triblock glycopolymer and study of its self-association behavior. Macromol. Chem. Phys. 2012, 213, 1768-1782.
174. Miura, Y.; Mizuno, H. Interaction analyses of amyloid β peptide (1-40) with glycosaminoglycan model polymers. Bull. Chem. Soc. Jpn. 2010, 83, 1004-1009.
175. Toyoshima, M.; Miura, Y. Preparation of glycopolymer-substituted gold nanoparticles and their molecular recognition. J. Polym. Sci. A Polym. Chem. 2009, 47, 1412-1421.
176. Ishii, J.; Toyoshima, M.; Chikae, M.; Takamura, Y.; Miura, Y. Preparation of glycopolymer-modified gold nanoparticles and a new approach for a lateral flow assay. Bull. Chem. Soc. Jpn. 2011, 84, 466-470.
177. Al-Bagoury, M.; Buchholz, K.; Yaacoub, E.J. Synthesis of well-designed polymers carrying saccharide moieties via RAFT miniemulsion polymerization. Polym. Adv. Technol. 2007, 18, 313-322.
178. Lowe, A.B.; Wang, R. Synthesis of controlled-structure AB diblock copolymers of 3-O-methacryloyl-1,2:3,4-di-O-isopropylidene-D-galactopyranose and 2-(dimethylamino)ethyl methacrylate. Polymer 2007, 48, 2221-2230.
179. Ting, S.R.S.; Gregory, A.M.; Stenzel, M.H. Polygalactose containing nanocages: The RAFT process for the synthesis of hollow sugar balls. Biomacromolecules 2009, 10, 342-352.
180. Liu, L.; Zhang, J.; Lv, W.; Luo, Y.; Wang, X. Well-defined pH-sensitive block glycopolymers via reversible addition-fragmentation chain transfer radical polymerization: Synthesis, characterization, and recognition with lectin. J. Polym. Sci. A Polym. Chem. 2010, 48, 3350-3361.
181. Pfaff, A.; Schallon, A.; Ruhland, T.M.; Majewski, A.P.; Schmalz, H.; Freitag, R.; Muller, A.H.E. Magnetic and fluorescent glycopolymer hybrid nanoparticles for intranuclear optical imaging. Biomacromolecules 2011, 12, 3805-3811.
182. Shi, H.; Liu, L.; Wang, X.; Li, J. Glycopolymer-peptide bioconjugates with antioxidant activity via RAFT polymerization. Polym. Chem. 2012, 3, 1182-1188.
183. Luo, Y.; Liu, L.; Wang, X.; Shi, H.; Lv, W.; Li, J. Sugar-installed thermoresponsive micellar aggregates self-assembled from "coil-comb-coil" triblock glycopolymers: Preparation and recognition with Concanavalin A. Soft Matter 2012, 8, 1634-1642.
184. Glassner, M.; Delaittre, G.; Kaupp, M.; Blinco, J.P.; Barner-Kowollik, C. (Ultra)Fast catalyst-free macromolecular conjugation in aqueous environment at ambient temperature. J. Am. Chem. Soc. 2012, 134, 7274-7277.
185. Kaupp, M.; Vogt, A.P.; Natterodt, J.C.; Trouillet, V.; Gruendling, T.; Hofe, T.; Barner, L.; Barner-Kowollik, C. Modular design of glyco-microspheres via mild pericyclic reactions and their quantitative analysis. Polym. Chem. 2012, 3, 2605-2614.
186. Dan, K.; Ghosh, S. pH-Responsive Aggregation of amphiphilic glyco-homopolymer. Macromol. Rapid Commun. 2012, 33, 127-132.
187. Guo, T.Y.; Liu, P.; Zhu, J.W.; Song, M.D.; Zhang, B.H. Well-Defined lactose-containing polymer grafted onto silica particles. Biomacromolecules 2006, 7, 1196-1202.
188. Zhou, D.; Li, C.; Hu, Y.; Zhou, H.; Chen, J.; Zhang, Z.; Guo, T. Glycopolymer modification on physicochemical and biological properties of poly(l-lysine) for gene delivery. Int. J. Biol. Macromol. 2012, 50, 965-973.
189. Spain, S.G.; Albertin, L.; Cameron, N.R. Facile in situ preparation of biologically active multivalent glyconanoparticles. Chem. Commun. 2006, 4198-4200.
190. Housni, A.; Cai, H.J.; Liu, S.Y.; Pun, S.H.; Narain, R. Facile preparation of glyconanoparticles and their bioconjugation to streptavidin. Langmuir 2007, 23, 5056-5061.
191. Lowe, A.B.; Sumerlin, B.S.; McCormick, C.L. The direct polymerization of 2-methacryloxyethyl glucoside via aqueous reversible addition-fragmentation chain transfer (RAFT) polymerization. Polymer 2003, 44, 6761-6765.
192. Pearson, S.; Scarano, W.; Stenzel, M.H. Micelles based on gold-glycopolymer complexes as new chemotherapy drug delivery agents. Chem. Commun. 2012, 48, 4695-4697.
193. Albertin, L.; Stenzel, M.H.; Barner-Kowollik, C.; Foster, L.J.R.; Davis, T.P. Well-defined diblock glycopolymers from RAFT polymerization in homogeneous aqueous medium. Macromolecules 2005, 38, 9075-9084.
194. Albertin, L.; Stenzel, M.H.; Barner-Kowollik, C.; Davis, T.P. Effect of an added base on (4-cyanopentanoic acid)-4-dithiobenzoate mediated RAFT polymerization in water. Polymer 2006, 47, 1011-1019.
195. Albertin, L.; Stenzel, M.; Barner-Kowollik, C.; Foster, L.J.R.; Davis, T.P. Well-defined glycopolymers from RAFT polymerization: Poly(methyl 6-O-methacryloyl-a-D-glucoside) and its block copolymer with 2-hydroxyethyl methacrylate. Macromolecules 2004, 37, 7530-7537.
196. Pfaff, A.; Barner, L.; Muller, A.H.E.; Granville, A.M. Surface modification of polymeric microspheres using glycopolymers for biorecognition. Eur. Polym. J. 2011, 47, 805-815.
197. Granville, A.M.; Quemener, D.; Davis, T.P.; Barner-Kowollik, C.; Stenzel, M.H. Chemo-enzymatic synthesis and RAFT polymerization of 6-O-methacryloyl mannose: a suitable glycopolymer for binding to the tetrameric lectin concanavalin A? Macromol. Symp. 2007, 255, 81-89.
198. Albertin, L.; Kohlert, C.; Stenzel, M.; Foster, L.J.R.; Davis, T.P. Chemoenzymatic synthesis of narrow-polydispersity glycopolymers: Poly(6-O-vinyladipoyl-D-glucopyranose). Biomacromolecules 2004, 5, 255-260.
199. Bernard, J.; Favier, A.; Zhang, L.; Nilasaroya, A.; Davis, T.P.; Barner-Kowollik, C.; Stenzel, M.H. Poly(vinyl ester) star polymers via xanthate-mediated living radical polymerization: From poly(vinyl alcohol) to glycopolymer stars. Macromolecules 2005, 38, 5475-5484.
200. Hetzer, M.; Chen, G.; Barner-Kowollik, C.; Stenzel, M.H. Neoglycopolymers based on 4-vinyl-1,2,3-triazole monomers prepared by click chemistry. Macromol. Biosci. 2010, 10, 119-126.
201. Xiao, N.-Y.; Li, A.-L.; Liang, H.; Lu, J. A Well-defined novel aldehyde-functionalized glycopolymer: synthesis, micelle formation, and its protein immobilization. Macromolecules 2008, 41, 2374-2380.
202. Xiao, N.; Liang, H.; Lu, J. Degradable and biocompatible aldehyde-functionalized glycopolymer conjugated with doxorubicin via acid-labile Schiff base linkage for pH-triggered drug release. Soft Matter 2011, 7, 10834-10840.
203. Wang, J.; Zhu, X.; Cheng, Z.; Zhang, Z.; Zhu, J. Preparation, characterization, and chiral recognition of optically active polymers containing pendent chiral units via reversible addition-fragmentation chain transfer polymerization. J. Polym. Sci. A Polym. Chem. 2007, 45, 3788-3797.
204. Mancini, R.J.; Lee, J.; Maynard, H.D. Trehalose glycopolymers for stabilization of protein conjugates to environmental stressors. J. Am. Chem. Soc. 2012, 134, 8474-8479.
205. Boyer, C.; Bousquet, A.; Rondolo, J.; Whittaker, M.R.; Stenzel, M.H.; Davis, T.P. Glycopolymer decoration of gold nanoparticles using a lbl approach. Macromolecules 2010, 43, 3775-3784.
206. Boyer, C.; Davis, T.P. One-pot synthesis and biofunctionalization of glycopolymers via RAFT polymerization and thiol-ene reactions. Chem. Commun. 2009, 6029-6031.
207. Boyer, C.; Whittaker, M.; Davis, T.P. Synthesis and postfunctionalization of well-defined star polymers via "double" click chemistry. J. Polym. Sci. A Polym. Chem. 2011, 49, 5245-5256.
208. Semsarilar, M.; Ladmiral, V.; Perrier, S. Highly branched and hyperbranched glycopolymers via reversible addition-fragmentation chain transfer polymerization and click chemistry. Macromolecules 2010, 43, 1438-1443.
209. Chen, Y.; Chen, G.; Stenzel, M.H. Synthesis and lectin recognition of glyco star polymers prepared by "Clicking" thiocarbohydrates onto a reactive scaffold. Macromolecules 2010, 43, 8109-8114.
210. Kumar, J.; Bousquet, A.; Stenzel, M.H. Thiol-alkyne chemistry for the preparation of micelles with glycopolymer corona: Dendritic surfaces versus linear glycopolymer in their ability to bind to lectins. Macromol. Rapid Commun. 2011, 32, 1620-1626.
211. Alidedeoglu, A.H.; York, A.W.; Rosado, D.A.; McCormick, C.L.; Morgan, S.E. Bioconjugation of -glucuronic acid sodium salt to well-defined primary amine-containing homopolymers and block copolymers. J. Polym. Sci. A Polym. Chem. 2010, 48, 3052-3061.
212. Godula, K.; Bertozzi, C.R. Density variant glycan microarray for evaluating cross-linking of mucin-like glycoconjugates by lectins. J. Am. Chem. Soc. 2012, 134, 15732-15742.
213. Narain, R.; Housni, A.; Gody, G.; Boullanger, P.; Charreyre, M.-T.; Delair, T. Preparation of biotinylated glyconanoparticles via a photochemical process and study of their bioconjugation to streptavidin. Langmuir 2007, 23, 12835-12841.
214. Saricilar, S.; Knott, R.; Barner-Kowollik, C.; Davis, T.P.; Heuts, J.P.A. Reversible addition fragmentation chain transfer polymerization of 3-[tris(trimethylsilyloxy) silyl] propyl methacrylate. Polymer 2003, 44, 5169-5176.
215. Barner-Kowollik, C.; Buback, M.; Charleux, B.; Coote, M.L.; Drache, M.; Fukuda, T.; Goto, A.; Klumperman, B.; Lowe, A.B.; McLeary, J.B.; et al. Mechanism and kinetics of dithiobenzoate-mediated RAFT polymerization. I. The current situation. J. Polym. Sci. A Polym. Chem. 2006, 44, 5809-5831.
216. Konkolewicz, D.; Hawkett, B.S.; Gray-Weale, A.; Perrier, S. RAFT polymerization kinetics: Combination of Apparently conflicting models. Macromolecules 2008, 41, 6400-6412.
217. Konkolewicz, D.; Hawkett, B.S.; Gray-Weale, A.; Perrier, S. RAFT polymerization kinetics: How long are the cross-terminating oligomers? J. Polym. Sci. A Polym. Chem. 2009, 47, 3455-3466.
218. Ting, S.R.S.; Davis, T.P.; Zetterlund, P.B. Retardation in RAFT polymerization: Does cross-termination occur with short radicals only? Macromolecules 2011, 44, 4187-4193.
219. Yang, H.; Guo, T.-Y.; Zhou, D. Surface hydrophilic modification with well-defined glycopolymer for protein imprinting matrix. Int. J. Biol. Macromol. 2011, 48, 432-438.
220. Stenzel, M.H.; Zhang, L.; Huck, W.T.S. Temperature-responsive glycopolymer brushes synthesized via RAFT polymerization using the Z-group approach. Macromol. Rapid Commun. 2006, 27, 1121-1126.
221. Jiang, X.; Ahmed, M.; Deng, Z.; Narain, R. Biotinylated glyco-functionalized quantum dots: Synthesis, characterization, and cytotoxicity studies. Bioconjug. Chem. 2009, 20, 994-1001.
222. Ishii, J.; Chikae, M.; Toyoshima, M.; Ukita, Y.; Miura, Y.; Takamura, Y. Electrochemical assay for saccharide-protein interactions using glycopolymer-modified gold nanoparticles. Electrochem. Commun. 2011, 13, 830-833.
223. Miura, Y.; Yasuda, K.; Yamamoto, K.; Koike, M.; Nishida, Y.; Kobayashi, K. Inhibition of alzheimer amyloid aggregation with sulfated glycopolymers. Biomacromolecules 2007, 8, 2129-2134.
224. Min, E.H.; Ting, S.R.S.; Billon, L.; Stenzel, M.H. 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. A Polym. Chem. 2010, 48, 3440-3455.
225. Buckwalter, D.J.; Sizovs, A.; Ingle, N.P.; Reineke, T.M. MAG versus PEG: Incorporating a Poly(MAG) layer to promote colloidal stability of nucleic acid/"click cluster" complexes. ACS Macro Lett. 2012, 1, 609-613.
226. Albertin, L.; Cameron, N.R. RAFT Polymerization of Methyl 6-O-Methacryloyl-a-D-glucoside in homogeneous aqueous medium. A detailed kinetic study at the low molecular weight limit of the process. Macromolecules 2007, 40, 6082-6093.
227. Cheng, C.; Zhang, X.; Wang, Y.; Li, C. Synthesis of glucose-sensitive block glycopolymers based on phenylboronic acid via raft polymerization. J. Control. Release 2011, 152, e267-e269.
228. Chiellini, E.; Corti, A.; D'Antone, S.; Solaro, R. Biodegradation of poly (vinyl alcohol) based materials. Prog. Polym. Sci. 2003, 28, 963-1014.
229. DeMerlis, C.C.; Schoneker, D.R. Review of the oral toxicity of polyvinyl alcohol (PVA). Food Chem. Toxicol. 2003, 41, 319-326.
230. Nikolaev, A.F.; Mosyagina, L.P. Poly(vinyl alcohol) and vinyl alcohol copolymers in medicine. Int. Polym. Sci. Technol. 2000, 27, T/47-T/58.
231. Yamaoka, T.; Tabata, Y.; Ikada, Y. Comparison of body distribution of poly(vinyl alcohol) with other water-soluble polymers after intravenous administration. J. Pharm. Pharmacol. 1995, 47, 479-486.
232. Frush, H.L.; Isbell, H.S. Mutorotation, hydrolysis, and structure of D-galactosamine. J. Res. Natl. Bur. Stand. 1951, 47, 239-247.
233. Brusseau, S.; D'Agosto, F.; Magnet, S.; Couvreur, L.; Chamignon, C.; Charleux, B. Nitroxide-Mediated copolymerization of methacrylic acid and sodium 4-styrenesulfonate in water solution and one-pot synthesis of amphiphilic block copolymer nanoparticles. Macromolecules 2011, 44, 5590-5598.
234. Phan, T.N.T.; Bertin, D. Synthesis of water-soluble homopolymers and block copolymers in homogeneous aqueous solution via nitroxide-mediated polymerization. Macromolecules 2008, 41, 1886-1895.
235. Rigolini, J.; Grassl, B.; Billon, L.; Reynaud, S.; Donard, O.F.X. Microwave-assisted nitroxide-mediated radical polymerization of acrylamide in aqueous solution. J. Polym. Sci. A Polym. Chem. 2009, 47, 6919-6931.
236. Rigolini, J.; Grassl, B.; Reynaud, S.; Billon, L. Microwave-assisted nitroxide-mediated polymerization for water-soluble homopolymers and block copolymers synthesis in homogeneous aqueous solution. J. Polym. Sci. A Polym. Chem. 2010, 48, 5775-5782.
237. Chenal, M.; Mura, S.; Marchal, C.; Gigmes, D.; Charleux, B.; Fattal, E.; Couvreur, P.; Nicolas, J. Facile synthesis of innocuous comb-shaped polymethacrylates with PEG side chains by nitroxide-mediated radical polymerization in hydroalcoholic solutions. Macromolecules 2010, 43, 9291-9303.
238. Ashford, E.J.; Naldi, V.; O'Dell, R.; Billingham, N.C.; Armes, S.P. First example of the atom transfer radical polymerisation of an acidic monomer: Direct synthesis of methacrylic acid copolymers in aqueous media. Chem. Commun. 1999, 14, 1285-1286.
239. Tsarevsky, N.V.; Matyjaszewski, K. "Green" atom transfer radical polymerization: From process design to preparation of well-defined environmentally friendly polymeric materials. Chem. Rev. 2007, 107, 2270-2299.
240. Jakubowski, W.; Matyjaszewski, K. Activators regenerated by electron transfer for atom-transfer radical polymerization of (meth)acrylates and related block copolymers. Angew. Chem. Int. Ed. 2006, 45, 4482-4486.
241. Matyjaszewski, K.; Jakubowski, W.; Min, K.; Tang, W.; Huang, J.; Braunecker, W.A.; Tsarevsky, N.V. Diminishing catalyst concentration in atom transfer radical polymerization with reducing agents. Proc. Natl. Acad. Sci. USA 2006, 103, 15309-15314.
242. Rosen, B.M.; Percec, V. Single-Electron transfer and single-electron transfer degenerative chain transfer living radical polymerization. Chem. Rev. 2009, 109, 5069-5119.
243. Percec, V.; Guliashvili, T.; Ladislaw, J.S.; Wistrand, A.; Stjerndahl, A.; Sienkowska, M.J.; Monteiro, M.J.; Sahoo, S. Ultrafast synthesis of ultrahigh molar mass polymers by metal-catalyzed living radical polymerization of acrylates, methacrylates, and vinyl chloride mediated by SET at 25 °C. J. Am. Chem. Soc. 2006, 128, 14156-14165.
244. Nicol, E.; Derouineau, T.; Puaud, F.; Zaitsev, A. Synthesis of double hydrophilic poly(ethylene oxide)-b-poly(2-hydroxyethyl acrylate) by single-electron transfer-living radical polymerization. J. Polym. Sci. A Polym. Chem. 2012, 50, 3885-3894.
245. Voepel, J.; Edlund, U.; Albertsson, A.C. A versatile single-electron-transfer mediated living radical polymerization route to galactoglucomannan graft-copolymers with tunable hydrophilicity. J. Polym. Sci. A Polym. Chem. 2011, 49, 2366-2372.
246. Zetterlund, P.B.; Kagawa, Y.; Okubo, M. Controlled/Living radical polymerization in dispersed systems. Chem. Rev. 2008, 108, 3747-3794.
247. Vyas, S.P.; Singh, A.; Sihorkar, V. Ligand-receptor-mediated drug delivery: An emerging paradigm in cellular drug targeting. Crit. Rev. Ther. Drug Carrier Syst. 2001, 18, 1-76.
248. Jones, M.N. Carbohydrate-mediated liposomal targeting and drug delivery. Adv. Drug Deliv. Rev. 1994, 13, 215-249.
249. Muñoz-Bonilla, A.; Marcelo, G.; Casado, C.; Teran, F.J.; Fernández-García, M. Preparation of glycopolymer-coated magnetite nanoparticles for hyperthermia treatment. J. Polym. Sci. A Polym. Chem. 2012, 50, 5087-5096.
250. Duncan, R. Development of HPMA copolymer-anticancer conjugates: Clinical experience and lessons learnt. Adv. Drug Deliv. Rev. 2009, 61, 1131-1148.
251. Duncan, R. The dawning era of polymer therapeutics. Nat. Rev. Drug Discov. 2003, 2, 347-360