Polymerization-induced self-assembly of galactose-functionalized biocompatible diblock copolymers for intracellular delivery

Journal of the American Chemical Society

Volumn 135, Issue 36, 2013, Pages 13574-13581

  Ladmiral, Vincent ^a,b   Semsarilar, Mona ^a,c   Canton, Irene ^a   Armes, Steven P ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b CNRS   (France)

^c UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CELL BIOLOGY; GALECTINS; INTRACELLULAR DELIVERY; NANO-OBJECTS; POLYMER SCIENCE; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; SMART DRUG DELIVERIES; WORM-LIKE MICELLES;

BIOCOMPATIBILITY; BLOCK COPOLYMERS; CYTOLOGY; DRUG DELIVERY; SELF ASSEMBLY;

POLYMERIZATION;

COPOLYMER; GALACTOSE; GALECTIN; METHACRYLIC ACID; NANOSPHERE; RHODAMINE B;

AQUEOUS SOLUTION; ARTICLE; ATOM TRANSFER RADICAL POLYMERIZATION; BIOCOMPATIBILITY; CELL ENCAPSULATION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MICELLE; NANOBIOTECHNOLOGY; NANOENCAPSULATION; POLYMERIZATION; TRANSMISSION ELECTRON MICROSCOPY; TURBIDITY;

BIOCOMPATIBLE MATERIALS; CELL SURVIVAL; CELLS, CULTURED; DRUG DELIVERY SYSTEMS; GALACTOSE; HUMANS; MICELLES; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; POLYMERIZATION; POLYMERS;

EID: 84884200177     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja407033x     Document Type: Article

References (74)

1. Braunecker, W. A.; Matyjaszewski, K. Prog. Polym. Sci. 2007, 32, 93
2. Ladmiral, V.; Melia, E.; Haddleton, D. M. Eur. Polym. J. 2004, 40, 431
3. Voit, B.; Appelhans, D. Macromol. Chem. Phys. 2010, 211, 727
4. Li, Z.-C.; Liang, Y.-Z.; Li, F.-M. Chem. Commun. 1999, 16, 1557
5. Ejaz, M.; Ohno, K.; Tsujii, Y.; Fukuda, T. Macromolecules 2000, 33, 2870
6. Semsarilar, M.; Ladmiral, V.; Perrier, S. Macromolecules 2010, 43, 1438
7. Xu, J.; Boyer, C.; Bulmus, V.; Davis, T. P. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 4302
8. Brown, C. D.; Rusek, M. S.; Kiessling, L. L. J. Am. Chem. Soc. 2012, 134, 6552
9. Becer, C. R.; Gibson, M. I.; Geng, Ilyas, R.; Wallis, R.; Mitchell, D. A.; Haddleton, D. M. J. Am. Chem. Soc. 2010, 132, 15130
10. Ting, S. R. S.; Chen, G.; Stenzel, M. H. Polym. Chem. 2010, 1, 1392
11. Belardi, B.; O'Donoghue, G. P.; Smith, A. W.; Groves, J. T; Bertozzi, C. R. J. Am. Chem. Soc. 2012, 134, 9549
12. Godula, K.; Bertozzi, C. R. J. Am. Chem. Soc. 2012, 134, 15732
13. Ahmed, M.; Deng, Z.; Liu, S.; Lafrenie, R.; Kumar, A.; Narain, R. Bioconjugate Chem. 2009, 20, 2169
14. Pfaff, A.; Schallon, A.; Ruhland, T. M.; Majewski, A. P.; Schmalz, H.; Freitag, R.; Müller, A. H. E. Biomacromolecules 2011, 12, 3805
15. Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357
16. Rogers, J. C.; Kornfeld, S. Biochem. Biophys. Res. Commun. 1971, 45, 622
17. Ambrosi, M.; Cameron, N. R.; Davis, B. G. Org Biomol Chem. 2005, 9, 1593
18. Yang, R. Y.; Rabinovich, G. A.; Liu, F. T. Expert Rev. Mol. Med. 2008, 10, 1
19. Cooper, D. N. Biochim. Biophys. Acta 2002, 1572, 231
20. Hughes, R. C. Biochimie 2001, 83, 667
21. Rabinovich, G. A.; Toscano, M. A.; Jackson, S. S.; Vasta, G. R. Curr. Opin. Struct. Biol. 2007, 17, 513
22. Liu, F.-T.; Rabinovich, G. A. Nature Reviews Cancer 2005, 5, 29
23. Delacour, D.; Koch, A.; Jacob, R. Traffic 2009, 10, 1405
24. Stechly, L.; Morelle, W.; Dessein, A.-F.; André, S.; Grard, G.; Trinel, D.; Dejonghe, M.-J.; Leteurtre, E.; Drobecq, H.; Trugnan, G.; Gabius, H. J.; Huet, G. Traffic 2009, 10, 438
25. Mai, Y.; Eisenberg, A. Chem. Soc. Rev. 2012, 41, 5969
26. Zhang, L. F.; Eisenberg, A. Science 1995, 268, 1728
27. Geng, Y.; Dalhaimer, P.; Cai, S. S.; Tsai, R.; Tewari, M.; Minko, T.; Discher, D. E. Nat. Nanotechnol. 2007, 2, 249
28. Won, Y. Y.; Davis, H. T.; Bates, F. S. Science 1999, 283, 960
29. Discher, B. M.; Won, Y. Y.; Ege, D. S.; Lee, J. C. M.; Bates, F. S.; Discher, D. E.; Hammer, D. A. Science 1999, 284, 1143
30. Discher, D. E.; Eisenberg, A. Science 2002, 297, 967
31. Rodriguez-Hernandez, J.; Lecommandoux, S. J. Am. Chem. Soc. 2005, 127, 2026
32. Riess, G. Prog. Polym. Sci. 2003, 28, 1107
33. Kim, H-C; Park, S-M; Hinsberg, W. D. Chem. Rev. 2010, 110, 146
34. Orilall, M. C.; Wiesner, U. Chem. Soc. Rev. 2011, 40, 520
35. Schatz, C.; Lecommandoux, S. Macromol. Rapid Commun. 2010, 31, 1664
36. Pasparakis, G.; Alexander, C. Angew. Chem., Int. Ed. 2008, 47, 4847
37. Parry, A. L.; Clemson, N. A.; Ellis, J.; Bernhard, S. S. R.; Davis, B. G.; Cameron, N. R. J. Am. Chem. Soc. 2013, 135, 9362
38. Du, J. Z.; Tang, Y. P.; Lewis, A. L.; Armes, S. P. J. Am. Chem. Soc. 2005, 127, 17982
39. Kita-Tokarczyk, K.; Grumelard, J.; Haefele, T.; Meier, W. Polymer 2005, 46, 3540
40. Narain, R.; Armes, S. P. Chem. Commun. 2002, 23, 2776
41. Narain, R.; Armes, S. P. Macromolecules 2003, 36, 4675
42. Narain, R.; Armes, S. P. Biomacromolecules 2003, 4, 1746
43. Suriano, F.; Pratt, R.; Tan, J. P.K.; Wiradharma, N.; Nelson, A.; Yang, Y.-Y.; Dubois, P.; Hedrick, J. L. Biomaterials 2010, 31, 2637
44. You, L.; Schlaad, H. J. Am. Chem. Soc. 2006, 128, 13336
45. Schlaad, H.; You, L.; Sigel, R.; Smarsly, B.; Heydenreich, M.; Mantione, A.; Mašic, A. Chem. Commun. 2009, 12, 1478
46. Huang, J.; Bonduelle, C.; Thévenot, J.; Lecommandoux, S.; Heise, A. J. Am. Chem. Soc. 2012, 134, 119
47. Kim, B.-S.; Hong, D.-J.; Bae, J.; Lee, M. J. Am. Chem. Soc. 2005, 127, 16333
48. Dal Bó, A. G.; Soldi, V.; Giacomelli, F. C.; Travelet, C.; Jean, B.; Pignot-Paintrand, I.; Borsali, R.; Fort, S. Langmuir 2012, 28, 1418
49. 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.; Rizzardo, E.; Thang, S. H. Macromolecules 1998, 31, 5559
50. Li, Y.; Armes, S. P. Angew. Chem., Int. Ed. 2010, 49, 4042
51. Blanazs, A.; Madsen, J.; Battaglia, G.; Ryan, A. J.; Armes, S. P. J. Am. Chem. Soc. 2011, 133, 16581
52. Semsarilar, M.; Ladmiral, V.; Blanazs, A.; Armes, S. P. Langmuir 2012, 28, 914
53. Semsarilar, M.; Ladmiral, V.; Blanazs, A.; Armes, S. P. Langmuir 2013, 29, 7416
54. Jones, E. R.; Semsarilar, M.; Blanazs, A.; Armes, S. P. Macromolecules 2012, 45, 5091
55. Boissé, S.; Rieger, J.; Belal, K.; Di-Cicco, A.; Beaunier, P.; Li, M.-H.; Charleux, B. Chem. Commun. 2010, 46, 1950
56. Zhang, X.; Boissé, S.; Zhang, W.; Beaunier, P.; D'Agosto, F.; Rieger, J.; Charleux, B. Macromolecules 2011, 44, 4149
57. Cai, W.; Wan, W.; Hong, C.; Huang, C.; Pan, C.-Y. Soft Matter 2010, 6, 5554
58. He, W.-D.; Sun, X.-L.; Wan, W.-M.; Pan, C.-Y. Macromolecules 2011, 44, 3358
59. Floyd, N.; Vijayakrishnan, B.; Koeppe, J. R.; Davis, B. G. Angew. Chem., Int. Ed. 2009, 48, 7798
60. Mossman, T. J. Immunol. Methods 1983, 65, 55
61. McKee, J. R.; Ladmiral, V.; Niskanen, J.; Tenhu, H.; Armes, S. P. Macromolecules 2011, 44, 7692
62. Mazzolini, J.; Boyron, O.; Monteil, V.; D'Agosto, F.; Boisson, C.; Sanders, G. C.; Heuts, J. P. A.; Duchateau, R.; Gigmes, D.; Bertin, D. Polym. Chem. 2012, 3, 2383
63. Davis, B. G.; Robinson, M. A. Curr. Opin. Drug Discovery Dev. 2002, 5, 279
64. Gabor, F.; Bogner, E.; Weissenboeck, A.; Wirth, M. Adv. Drug Delivery Rev. 2004, 56, 459
65. Dreiss, C. A. Soft Matter 2007, 3, 956
66. Blanazs, A.; Verber, R.; Mykhaylyk, O. O.; Ryan, A. J.; Heath, J. Z.; Douglas, C. W. I.; Armes, S. P. J. Am. Chem. Soc. 2012, 134, 9741
67. Madsen, J.; Armes, S. P.; Lewis, A. L. Macromolecules 2006, 39, 7455
68. Chang, J. S.; Chang, K. L.; Hwang, D. F.; Kong, Z. L. Environ. Sci. Technol. 2007, 41, 2064
69. Akimoto, Y.; Hirabayashi, J.; Kasai, K.-I.; Hirano, H. Cell Tissue Res. 1995, 280, 1
70. Massignani, M.; Canton, I.; Sun, T.; Hearnden, V.; MacNeil, S.; Blanazs, A.; Armes, S. P.; Lewis, A.; Battaglia, G. PLoS One 2010, 5, e10459
71. Antonenko, Y. N.; Avetisyan, A. V.; Cherepanov, D. A.; Knorre, D. A.; Korshunova, G. A.; Markova, O. V.; Ojovan, S. M.; Perevoshchikova, I. V.; Pustovidko, A. V.; Rokitskaya, T. I.; Severina, I. I.; Simonyan, R. A.; Smirnova, E. A.; Sobko, A. A.; Sumbatyan, N. V.; Severin, F. F.; Skulachev, V. P. J. Biol. Chem. 2011, 286, 17831
72. Madsen, J.; Armes, S. P.; Bertal, K.; MacNeil, S.; Lewis, A. L. Biomacromolecules 2009, 10, 1875
73. Canton, I.; Massignani, M.; Patikarnmonthon, N.; Chierico, L.; Robertson, J.; Renshaw, S. A.; Warren, N. J.; Madsen, J. P.; Armes, S P.; Lewis, A. L.; Battaglia, G. FASEB J. 2013, 1, 98
74. Lomas, H.; Canton, I.; MacNeil, S.; Du, J.; Armes, S. P.; Ryan, A. J.; Lewis, A. L.; Battaglia, G. Adv. Mater. 2007, 19, 4238