Degradable and comb-like PEG-Based copolymers by nitroxide-mediated radical ring-opening polymerization

Biomacromolecules

Volumn 14, Issue 10, 2013, Pages 3769-3779

  Delplace, Vianney ^a   Tardy, Antoine ^b   Harrisson, Simon ^a   Mura, Simona ^a   Gigmes, Didier ^b   Guillaneuf, Yohann ^b   Nicolas, Julien ^a  

^a UNIV PARIS SUD   (France)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BIO-CONJUGATION; BIOMEDICAL APPLICATIONS; CYCLIC KETENE ACETALS; ESTER GROUPS; HYDROLYTIC DEGRADATION; MONOMER CONVERSIONS; OLIGO(ETHYLENE GLYCOL) METHYL ETHER METHACRYLATE; RADICAL RING OPENING POLYMERIZATION;

CELL CULTURE; COPOLYMERS; ENDOTHELIAL CELLS; ETHYLENE GLYCOL; MEDICAL APPLICATIONS; POLYETHYLENE OXIDES; POLYMERIZATION; STYRENE;

POLYETHYLENE GLYCOLS;

2 METHYLENE 1,3 DIOXEPANE; 2 METHYLENE 4 PHENYL 1,3 DIOXOLANE; 5,6 BENZO 2 METHYLENE 1,3 DIOXEPANE; ACETAL; ACRYLONITRILE; COPOLYMER; MACROGOL; UNCLASSIFIED DRUG; ACETAL DERIVATIVE; ETHYLENE DERIVATIVE; FREE RADICAL; KETENE; KETONE; MACROGOL DERIVATIVE; NITROGEN OXIDE;

ANIMAL CELL; AQUEOUS SOLUTION; ARTICLE; CELL VIABILITY; CYTOTOXICITY; ENVIRONMENTAL TEMPERATURE; HUMAN; HUMAN CELL; HYDROLYSIS; MOUSE; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING METATHESIS POLYMERIZATION; SYNTHESIS; 3T3 CELL LINE; ANIMAL; CELL CULTURE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; FIBROBLAST; MACROPHAGE; UMBILICAL VEIN ENDOTHELIAL CELL;

ACETALS; ANIMALS; CELL SURVIVAL; CELLS, CULTURED; ETHYLENES; FIBROBLASTS; FREE RADICALS; HUMAN UMBILICAL VEIN ENDOTHELIAL CELLS; HUMANS; KETONES; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NIH 3T3 CELLS; NITROGEN OXIDES; POLYETHYLENE GLYCOLS; POLYMERIZATION;

EID: 84885640131     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm401157g     Document Type: Article

References (74)

1. Nicolas, J.; Mura, S.; Brambilla, D.; Mackiewicz, N.; Couvreur, P. Chem. Soc. Rev. 2013, 42, 1147
2. Elsabahy, M.; Wooley, K. L. Chem. Soc. Rev. 2012, 41, 2545
3. Nicolas, J.; Guillaneuf, Y.; Lefay, C.; Bertin, D.; Gigmes, D.; Charleux, B. Prog. Polym. Sci. 2013, 38, 63
4. Chauvin, F.; Dufils, P.-E.; Gigmes, D.; Guillaneuf, Y.; Marque, S. R. A.; Tordo, P.; Bertin, D. Macromolecules 2006, 39, 5238
5. Benoit, D.; Chaplinski, V.; Braslau, R.; Hawker, C. J. J. Am. Chem. Soc. 1999, 121, 3904
6. Benoit, D.; Grimaldi, S.; Robin, S.; Finet, J.-P.; Tordo, P.; Gnanou, Y. J. Am. Chem. Soc. 2000, 122, 5929
7. Couvreur, L.; Lefay, C.; Belleney, J.; Charleux, B.; Guerret, O.; Magnet, S. Macromolecules 2003, 36, 8260
8. Charleux, B.; Nicolas, J.; Guerret, O. Macromolecules 2005, 38, 5485
9. Guillaneuf, Y.; Gigmes, D.; Marque, S. R. A.; Astolfi, P.; Greci, L.; Tordo, P.; Bertin, D. Macromolecules 2007, 40, 3108
10. Nicolas, J.; Brusseau, S.; Charleux, B. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 34
11. Nicolas, J.; Dire, C.; Mueller, L.; Belleney, J.; Charleux, B.; Marque, S. R. A.; Bertin, D.; Magnet, S.; Couvreur, L. Macromolecules 2006, 39, 8274
12. Harrisson, S.; Couvreur, P.; Nicolas, J. Macromolecules 2011, 44, 9230
13. Harrisson, S.; Couvreur, P.; Nicolas, J. Macromol. Rapid Commun. 2012, 33, 805
14. Harrisson, S.; Nicolas, J.; Maksimenko, A.; Bui, D. T.; Mougin, J.; Couvreur, P. Angew. Chem., Int. Ed. 2013, 52, 1678
15. Becker, M. L.; Liu, J.; Wooley, K. L. Chem. Commun. 2003, 180
16. Chenal, M.; Boursier, C.; Guillaneuf, Y.; Taverna, M.; Couvreur, P.; Nicolas, J. Polym. Chem. 2011, 2, 1523
17. Trimaille, T.; Mabrouk, K.; Monnier, V.; Charles, L.; Bertin, D.; Gigmes, D. Macromolecules 2010, 43, 4864
18. Dingels, C.; Müller, S. S.; Steinbach, T.; Tonhauser, C.; Frey, H. Biomacromolecules 2012, 14, 448
19. Tomlinson, R.; Klee, M.; Garrett, S.; Heller, J.; Duncan, R.; Brocchini, S. Macromolecules 2001, 35, 473
20. Lundberg, P.; Lee, B. F.; van den Berg, S. A.; Pressly, E. D.; Lee, A.; Hawker, C. J.; Lynd, N. A. ACS Macro Lett. 2012, 1, 1240
21. Agarwal, S.; Ren, L. Macromolecules 2009, 42, 1574
22. Huang, J.; Gil, R.; Matyjaszewski, K. Polymer 2005, 46, 11698
23. Lutz, J.-F.; Andrieu, J.; Üzgün, S.; Rudolph, C.; Agarwal, S. Macromolecules 2007, 40, 8540
24. Ren, L.; Speyerer, C.; Agarwal, S. Macromolecules 2007, 40, 7834
25. Riachi, C.; Schüwer, N.; Klok, H.-A. Macromolecules 2009, 42, 8076
26. Siegwart, D. J.; Bencherif, S. A.; Srinivasan, A.; Hollinger, J. O.; Matyjaszewski, K. J. Biomed. Mater. Res., Part A 2008, 87A, 345
27. Undin, J.; Finne-Wistrand, A.; Albertsson, A.-C. Biomacromolecules 2013, 14, 2095
28. Undin, J.; Illanes, T.; Finne-Wistrand, A.; Albertsson, A.-C. Polym. Chem. 2012, 3, 1260
29. Undin, J.; Plikk, P.; Finne-Wistrand, A.; Albertsson, A.-C. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 4965
30. Wickel, H.; Agarwal, S. Macromolecules 2003, 36, 6152
31. Wickel, H.; Agarwal, S.; Greiner, A. Macromolecules 2003, 36, 2397
32. Yuan, J.-Y.; Pan, C.-Y. Eur. Polym. J. 2002, 38, 2069
33. Zhang, Y.; Chu, D.; Zheng, M.; Kissel, T.; Agarwal, S. Polym. Chem. 2012, 3, 2752
34. Nicolaÿ, R.; Marx, L.; Hémery, P.; Matyjaszewski, K. Macromolecules 2007, 40, 9217
35. Paulusse, J. M. J.; Amir, R. J.; Evans, R. A.; Hawker, C. J. J. Am. Chem. Soc. 2009, 131, 9805
36. Endo, T. Radical Ring-Opening Polymerization. In Polymer Science: A Comprehensive Reference; Matyjaszewski, K.; Möller, M., Eds.; Elsevier: Amsterdam, 2012; p 507.
37. Sanda, F.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 265
38. Agarwal, S. Polym. Chem. 2010, 1, 953
39. Bailey, W. J.; Wu, S. R.; Ni, Z. Makromol. Chem. 1982, 183, 1913
40. Bailey, W. J.; Ni, Z.; Wu, S. R. J. Polym. Sci., Polym. Chem. Ed. 1982, 20, 3021
41. Bailey, W. J.; Chou, J. L.; Feng, P.-Z.; Issari, B.; Kuruganti, V.; Zhou, L. L. J. Macromol. Sci., Chem. 1988, 25, 781
42. Bailey, W. J.; Kuruganti, V. K.; Angle, J. S. ACS Symp. Ser. 1990, 433, 149
43. Evans, R. A.; Rizzardo, E. Macromolecules 1996, 29, 6983
44. Harrisson, S.; Davis, T. P.; Evans, R. A.; Rizzardo, E. Macromolecules 2001, 34, 3869
45. Tardy, A.; Delplace, V.; Siri, D.; Lefay, C.; Harrisson, S.; de Fatima Albergaria Pereira, B.; Charles, L.; Gigmes, D.; Nicolas, J.; Guillaneuf, Y. Polym. Chem. 2013, 4, 4776
46. Wei, Y.; Connors, E. J.; Jia, X.; Wang, B. Chem. Mater. 1996, 8, 604
47. Wei, Y.; Connors, E. J.; Jia, X.; Wang, C. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 761
48. Jia, X.; Wang, J.; Liu, Y.; Jin, Z.; Li, M.; Wei, Y. Polym. Int. 2000, 49, 1496
49. Chenal, M.; Mura, S.; Marchal, C.; Gigmes, D.; Charleux, B.; Fattal, E.; Couvreur, P.; Nicolas, J. Macromolecules 2010, 43, 9291
50. Lecolley, F.; Tao, L.; Mantovani, G.; Durkin, I.; Lautru, S.; Haddleton, D. M. Chem. Commun. 2004, 2026
51. Lutz, J.-F.; Akdemir, O.; Hoth, A. J. Am. Chem. Soc. 2006, 128, 13046
52. Heredia, K. L.; Tolstyka, Z. P.; Maynard, H. D. Macromolecules 2007, 40, 4772
53. Zhang, L.; Nguyen, T. L. U.; Bernard, J.; Davis, T. P.; Barner-Kowollik, C.; Stenzel, M. H. Biomacromolecules 2007, 8, 2890
54. Nicolas, J.; Khoshdel, E.; Haddleton, D. M. Chem. Commun. 2007, 1722
55. Nicolas, J.; Couvreur, P.; Charleux, B. Macromolecules 2008, 41, 3758
56. Lessard, B.; Maric, M. Macromolecules 2008, 41, 7870
57. Veronese, F. M.; Caliceti, P.; Schiavon, O. J. Bioact. Comp. Polym. 1997, 12, 196
58. Veronese, F. M.; Monfardini, C.; Caliceti, P.; Schiavon, O.; Scrawen, M. D.; Beer, D. J. Controlled Release 1996, 40, 199
59. Webster, R.; Elliott, V.; Park, B. K.; Walker, D.; Hankin, M.; Taupin, P. PEG and PEG conjugates toxicity: towards an understanding of the toxicity of PEG and its relevance to PEGylated biologicals. In PEGylated Protein Drugs: Basic Science and Clinical Applications; Veronese, F., Ed.; Birkhäuser: Basel, 2009; p 127.
60. Knop, K.; Hoogenboom, R.; Fischer, D.; Schubert, U. S. Angew. Chem., Int. Ed. 2010, 49, 6288
61. Moghimi, S. M.; Andersen, A. J.; Hashemi, S. H.; Lettiero, B.; Ahmadvand, D.; Hunter, A. C.; Andresen, T. L.; Hamad, I.; Szebeni, J. J. Controlled Release 2010, 146, 175
62. Schellekens, H.; Hennink, W.; Brinks, V. Pharm. Res. 2013, 30, 1729
63. Bailey, W. J.; Ni, Z.; Wu, S. R. Macromolecules 1982, 15, 711
64. Ananchenko, G. S.; Souaille, M.; Fischer, H.; Le Mercier, C.; Tordo, P. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 3264
65. Nicolas, J.; Mueller, L.; Dire, C.; Matyjaszewski, K.; Charleux, B. Macromolecules 2009, 42, 4470
66. Storm, G.; Belliot, S. O.; Daemen, T.; Lasic, D. D. Adv. Drug Delivery Rev. 1995, 17, 31
67. Veronese, F. M.; Harris, J. M. Adv. Drug Delivery Rev. 2002, 54, 453
68. Nicolas, J.; Mantovani, G.; Haddleton, D. M. Macromol. Rapid Commun. 2007, 28, 1083
69. Le Droumaguet, B.; Nicolas, J. Polym. Chem. 2010, 1, 563
70. Heredia, K. L.; Maynard, H. D. Org. Biomol. Chem. 2007, 5, 45
71. Klok, H.-A. Macromolecules 2009, 42, 7990
72. Sumerlin, B. S. ACS Macro Lett. 2011, 1, 141
73. VanKooten, T. G.; Klein, C. L.; Kohler, H.; Kirkpatrick, C. J.; Williams, D. F.; Eloy, R. J. Mater. Sci.: Mater. Med. 1997, 8, 835
74. Kirkpatrick, C. J.; Otto, M.; Kooten, T. V.; Krump, V.; Kriegsmann, J.; Bittinger, F. J. Mater. Sci.: Mater. Med. 1999, 10, 589