Preparation of organosoluble silica-polypeptide particles by "Click" chemistry

Macromolecules

Volumn 43, Issue 1, 2010, Pages 62-70

  Balamurugan, Sreelatha S ^a   Soto Cantu, Erick ^a   Cueto, Rafael ^a   Russo, Paul S ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CLICK CHEMISTRY; CLICK REACTION; COLLOIDAL PARTICLE; COPPER BROMIDE; ENZYME ACTIVATION; FTIR; FUNCTIONALIZATIONS; FUNCTIONALIZED; FUNCTIONALIZED SILICA; HELICAL POLYPEPTIDES; HYBRID PARTICLES; HYDROPHOBIC PROTEIN; IN-CELL; L-GLUTAMATE; MODEL SYSTEM; N-CARBOXYANHYDRIDE; NUCLEOPHILIC SUBSTITUTIONS; ORGANOSOLUBLE; SILICA CORES; SILICA PARTICLES; SODIUM AZIDE; TETRA-HYDROFURAN; XPS;

ACETYLENE; CELL MEMBRANES; CYTOLOGY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE; ORGANIC SOLVENTS; RING OPENING POLYMERIZATION; SILICA; SODIUM; SYNTHESIS (CHEMICAL); TOLUENE; X RAY PHOTOELECTRON SPECTROSCOPY;

POLYPEPTIDES;

EID: 73649101700     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma901840n     Document Type: Article

References (90)

1. Zou, H.; Wu, S.; Shen, J. Chem. Rev. 2008,108 (9), 3893-3957.
2. Radhakrishnan, B.; Ranjan, R.; Brittain, W. J. Soft Matter 2006, 2 (5), 386-396.
3. Chen, X.; Huang, Y.-F.; Tan, W. J. Biomed. Nanotechnol 2008, 4 (4), 400-409.
4. Tallury, P.; Payton, K.; Santra, S. Nanomedicine 2008, 3 (4), 579592.
5. Kickelbick, G. Prog. Polym. Sci 2002, 28 (1), 83-114.
6. Balazs, A. C; Emrick, T.; Russell, T. P. Science 2006, 314 (5802), 1107-1110.
7. Piao, Y.; Burns, A.; Kim, J.; Wiesner, U.; Hyeon, T. Adv. Funct. Mater. 2008,18 (23), 3745-3758.
8. Daly, W. H.; Poche, D.; Negulescu, I. I. Prog. Polym. Sci. 1994, 19(1), 79-135.
9. Block, H. Poly(γ-benzyl-L-glutamate) and Other Glutamic Acid Containing Polymers; Gordon and Breach:Langhome, PA, 1983.
10. Kricheldorf, H. R. Angew. Chem., Int. Ed. 2006, 45(35), 5752-5784.
11. Deming, T.J. Adv. Polym. Sci 2006,202 (Peptide Hybrid Polymers), 1-18.
12. Wang, Y.; Chang, Y.-C. Langmuir 2002,18 (25), 9859-9866.
13. Wang, Y.; Chang, Y. C. Macromolecules 2003, 36 (17), 65036510.
14. Wang, Y.;ChangYing,C.J. Am. Chem. Soc. 2003,125 (21), 63766377.
15. Wieringa, R. H.; Siesling, E. A.; Geurts, P. F. M.; Werkman, P. J.; Vorenkamp, E. J.; Erb, V.; Stamm, M.; Schouten, A. J. Langmuir 2001,17 (21), 6477-6484.
16. Wieringa, R. H.; Siesling, E. A.; Werkman, P. J.; Angerman, H. J.; Vorenkamp, E. J.; Schouten, A. J. Langmuir 2001,17 (21), 64856490.
17. Wieringa, R. H.; Siesling, E. A.; Werkman, P. J.; Vorenkamp, E. J.; Schouten, A. J. Langmuir 2001,17 (21), 6491-6495.
18. Higashi, N.; Kawahara, J.; Niwa, M. J. Colloid Interface Sci. 2005, 288 (1), 83-87.
19. Higashi, N.; Koga, T.; Niwa, M. Langmuir2000,16(7), 3482-3486.
20. Niwa, M.; Morikawa, M.-A.; Higashi, N. Angew. Chem. 2000, 39 (5), 960-963.
21. Jaworek, T.; Neher, D.; Wegner, G.; Wieringa, R. H.; Schouten, A. J. Science 1998, 279 (5347), 57-60.
22. Chang, Y.-C; Frank, C. W. Langmuir 1998,14 (2), 326-334.
23. Chang, Y.-C; Frank, C. W. Langmuir 1996,12 (24), 5824-5829.
24. Oosterling, M. L. C. M.;Willems, E.; Schouten, A. J. Polymer 1995, 36 (23), 4485-4490.
25. Oosterling, M. L. C. M.;Willems, E.; Schouten, A. J. Polymer 1995, 36 (23), 4463-4470.
26. Hollman, A. M.; Bhattacharyya, D. Langmuir 2002,18 (15), 59465952.
27. Lee, N. H.; Frank, C. W. Polym. Mater. Sci. Eng. 2001,84,27-28.
28. Poche, D. S.; Daly, W. H.; Russo, P. S. Macromolecules 1995, 28, 6745-53.
29. Poche, D. S. Synthesis and characterization of linear and starbranched poly(γ-stearyl L-glutamate). Dissertation, Louisiana State University, 1990.
30. Jamil, T.; Russo, P. S.; Negulescu, L; DaIy,W. H.; Schaefer, D. W.; Beaucage, G. Macromolecules 1994, 27(1), 171-178.
31. Schmidtke, S.; Russo, P.; Nakamatsu, J.; Buyuktanir, E.; Turfan, B.; Temyanko, E.; Negulescu, I. Macromolecules 2000, 33 (12), 4427-4432.
32. Watanabe, J.; Sakajiri, K.; Okoshi, K.; Kawauchi, S.; Magoshi, J. Macromol. Chem. Phys. 2001, 202 (7), 1004-1009.
33. Watanabe, J.; Takashina, Y. Macromolecules 1991, 24(11),3423-6.
34. Deng, H.-T.; Xu, Z.-K.; Liu, Z.-M.; Wu, J.; Ye, P. Enzyme Microb. Technol 2004, 35 (5), 437-443.
35. Deng, H.-T.; Xu, Z.-K.; Wu, J.; Ye, P.; Liu, Z.-M.; Seta, P. J. Mol Catal B: Enzym. 2004, 28 (2-3), 95-100.
36. Sackmann, E. Science 1996, 271 (5245), 43-8.
37. Sohn, D.; Kitaev, V.; Kumacheva, E. Langmuir 1999,15 (5), 16981702.
38. Fong, B.; Turksen, S.; Russo, P. S.; Stryjewski, W. Langmuir 2004, 20 (1), 266-269.
39. Fong, B.; Russo, P. S. Langmuir 1999,15 (13), 4421-4426.
40. Prucker, O.; Ruehe, J. Macromolecules 1998, 31 (3), 602-613.
41. Zhang, Y.; Ye, Z. Macromolecules 2008, 41 (17), 6331-6338.
42. von Werne, T.; Patten, T. E. J. Am. Chem. Soc. 2001, 123 (31), 7497-7505.
43. Li, D.; Sheng, X.; Zhao, B. J. Am. Chem. Soc. 2005,127(17), 62486256.
44. Sakakibara, S.; Shimonishi, Y. Bull. Chem. Soc. Jpn. 1965, 38 (8), 1412-1413.
45. Matsuura, S.; Niu, C.-h.; Cohen, J. S. J. Chem. Soc, Chem. Commun. 1976,72,451-452.
46. Huisgen, R. 1,3-Dipolar Cycloaddition Chemistry; Wiley: New York, 1984.
47. Ruehe, J. Polym. Brushes 2004, 1-31.
48. Huang, H.; Penn, L. S. Macromolecules 2005, 38 (11), 4837-4843.
49. Tornoe, C. W.; Christensen, C; Meldal, M. J. Org. Chem. 2002, 67 (9), 3057-3064.
50. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41 (14), 2596-2599.
51. Golas, P. L.; Matyjaszewski, K. QSAR Comb. Sci 2007,25(11-12), 1116-1134.
52. KoIb, H. C; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40 (11), 2004-2021.
53. Le Droumaguet, B.; Velonia, K. Macromol. Rapid Commun. 2008, 29(12-13), 1073-1089.
54. McCormick, C. L.; Sumerlin, B. S.; Lokitz, B. S.; Stempka, J. E. Soft Matter 2008, 4 (9), 1760-1773.
55. Binder, W. H.; Sachsenhofer, R. Macromol. Chem. Phys. 2008, 29 (12-13), 952-981.
56. Sanda, F.; Gao, G.; Masuda, T. Macromol. Biosci. 2004,4 (6), 570-574.
57. Agut, W.; Agnaou, R.; Lecommandoux, S.; Taton, D. Macromol. Rapid Commun. 2008, 29 (12-13), 1147-1155.
58. Rao, J.; Zhang, Y.; Zhang, J.; Liu, S. Biomacromoleeules 2008, 9 (10), 2586-2593
59. Agut, W.; Taton, D.; Lecommandoux, S. Macromolecules 2007, 40(16), 5653-5661.
60. Deng, L.; Shi, K.; Zhang, Y.; Wang, H.; Zeng, J.; Guo, X.; Du, Z.; Zhang, B. J. Colloid Interface Sci. 2008, 323 (1), 169-175.
61. Peng, S.-M.; Chen, Y.; Hua, C; Dong, C-M. Macromolecules 2009,42(1), 104-113.
62. Schatz, C; Louguet, S.; Le Meins, J.-F.; Lecommandoux, S. Angew. Chem., Int. Ed. 2009, 48 (14), 2572-2575.
63. Ranjan, R.; Brittain, W. J. Macromol. Rapid Commun. 2008, 29 (12-13), 1104-1110.
64. Ranjan, R.; Brittain, W. J. Macromol. Rapid Commun. 2007, 28 (21), 2084-2089.
65. Ranjan, R.; Brittain, W. J. Macromolecules 2007, 40 (17), 62176223.
66. Li, Y.; Benicewicz, B. C. Macromolecules 2008,41 (21), 7986-7992.
67. Wang, Y.; Chen, J.; Xiang, J.; Li, H.; Shen, Y.; Gao, X.; Liang, Y. React. Fund. Polym. 2009,69 (6), 393-399.
68. Lin, P.-C; Ueng, S.-H.; Yu, S.-C; Jan, M.-D.; Adak, A. K.; Yu, C-C; Lin, C-C Org. Lett. 2007, 9 (11), 2131-2134.
69. Ortega-Munoz, M.; Lopez-Jaramillo, J.; Hernandez-Mateo, F.; Santoyo-Gonzalez, F. Adv. Synth. Catal 2006,348 (16 +17), 24102420.
70. Wasserman, D. G., J. D.; Meigs, F. M. Esters of glutamic and aspartic acids and their derivatives. 6500089,1965.
71. Daly, W. H.; Poche, D. Tetrahedron Lett. 1988,29 (46), 5859-5862.
72. Stoeber,W.;Fink, A.;Bohn,E.y. Colloid Interface Sei. 1968,25(1), 62-69.
73. Wollman, E. W.; Kang, D.; Frisbie, C. D.; Lorkovic, I. M.; Wrighton, M. S. J. Am. Chem. Soc. 1994,116 (10), 4395-4404.
74. Coliman, J. P.; Devaraj, N. K.; Eberspacher, T. P. A.; Chidsey, C. E. D. Langmuir 2006, 22 (6), 2457-2464.
75. Schulze, R. K.; Boyd, D. C; Evans, J. F.; Gladfelter, W. L. J. Vac Sei. Technol 1990, 8 (3), 2338-2343.
76. Prakash, S.; Long, T. M.; Selby, J. C; Moore, J. S.; Shannon, M. A. Anal. Chem. 2007, 79 (4), 1661-1667.
77. Van Dijk-Wolthuis, W. N. E.; Van de Water, L.; Van de Wetering, P.; Van Steenbergen, M.; Kettenes-Van den Bosch, J. J.; Schuyl, W.; Hennink, W. E. Macromol. Chem. Phys. 1997,198 (12), 3893-3906.
78. Kricheldorf, H. R.; Von Lossow, C; Schwarz, G. Macromol. Chem. Phys. 2004, 205 (7), 918-924.
79. Sohn, D.; Yu, H.; Nakamatsu, J.; Russo, P. S.; Daly, W. H. J. Polym. Sci, Part B: Polym. Phys. 1996, 34 (17), 3025-3034.
80. Mitchell, J. C; Woodward, A. E.; Doty, P. J. Am. Chem. Soc. 1957, 79, 3955-3960.
81. Wu, X.; Yang, S.; Njus, J. M.; Nagarajan, R.; Cholli, A. L.; Samuelson, L. A.; Kumar, J. Biomacromoleeules 2004, 5 (4), 1214-1218.
82. Ferretti, J. A.; Ninham, B. W. Macromolecules 1970, 5 (1), 30-3.
83. Ferretti, J. A.; Paolillo, L. Biopolymers 1969, 7(2), 155-71.
84. Smith, J. C; Woody, R. W. Biopolymers 1973,12 (12), 2657-65.
85. Golas, P. L.; Tsarevsky, N. V.; Sumerlin, B. S.; Matyjaszewski, K. Macromolecules 2006,39 (19), 6451-6457.
86. Eroglu, M. S.; Guven, O. J. Appl. Polym. Sci. 1996, 61 (2), 201-206.
87. Blomberg, S.; Ostberg, S.; Harth, E.; Bosman, A. W.; Van Horn, B.; Hawker, C J. J. Polym. Sci, Part A: Polym. Chem. 2002,40 (9), 1309-1320.
88. Bartholome, C; Beyou, E.; Bourgeat-Lami, E.; Chaumont, P.; Zydowicz, N. Macromolecules 2003, 36 (21), 7946-7952.
89. Heise, A.; Menzel, H.; Yim, H.; Foster, M. D.; Wieringa, R. H.; Schouten, A. J.; Erb, V.; Stamm, M. Langmuir 1997,13 (4), 723728.
90. Whitesell, J. K.; Chang, H. K. Science 1993, 261 (5117), 73-6.