Microcapsules with three orthogonal reactive sites

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1479-1482

  Mason, Brian P ^a,b   Hira, Steven M ^a,b   Strouse, Geoffrey F ^a,b   McQuade, D Tyler ^a,b  

^a FLORIDA STATE UNIVERSITY   (United States)

^b Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIC ACID DERIVATIVE; NANOMATERIAL; POLYMER; POLYMETHYLENE POLYPHENYLISOCYANATE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFOCAL MICROSCOPY; FLUORESCENCE;

CYANATES; FLUORESCENCE; MICROSCOPY, CONFOCAL; MOLECULAR STRUCTURE; NANOSTRUCTURES; POLYMERS;

EID: 64349103826     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802843v     Document Type: Article

References (59)

1. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Molecular Biology of The Cell, 2nd ed.; Garland Publishing, Inc.: New York, 1989.
2. Israelachvili, J. N.; Mitchell, D. J.; Ninham, B. W. J. Chem. Soc, Faraday Trans. 1976, 72, 1525-1568.
3. Schwuger, M. J.; Stickdorn, K.; Schomacker, R. Chem. Rev. 1995, 95, 849-864.
4. (a) Discher, D. E.; Eisenberg, A. Science 2002, 297, 967-973.
5. (b) Szoka, F.; Papahadjopoulos, D. Annu. Rev. Biophys. Bioeng. 1980, 9, 467-508.
6. (a) Tschierske, C. J. Mater. Chem. 1998, 8, 1485-1508.
7. (b) Vroege, G. J.; Lekkerkerker, H. N. W. Pros. Phys. 1992, 55, 1241-1309.
8. (a) Ban, N.; Nissen, P.; Hansen, J.; Moore, P. B.; Steitz, T. A. Science 2000, 289, 905-920.
9. (b) Noji, H.; Yasuda, R.; Yoshida, M.; Kinosita, K. Nature 1997, 386, 299-302.
10. (c) Wimberly, B. T.; Brodersen, D. E.; Clemons, W. M.; Morgan-Warren, R. J.; Carter, A. P.; Vonrhein, C.; Hartsch, T.; Ramakrishnan, V. Nature 2000, 407, 327-339.
11. (a) Alexandridis, P.; Hatton, T. A. Col. Surf. A 1995, 96, 1-46.
12. (b) Forster, S.; Antonietti, M. AdV. Mater. 1998, 10, 195-197.
13. (c) Kataoka, K.; Harada, A.; Nagasaki, Y. Adv. Drug Del. Rev. 2001, 47, 113-131.
14. (d) Riess, G. Prog. Polym. Sci. 2003, 28, 1107-1170.
15. (e) Zhang, L. F.; Eisenberg, A. J. Am. Chem. Soc. 1996, 118, 3168-3181.
16. Kunitake, T. Angew. Chem. Int. Ed. 1992, 31, 709-726.
17. (a) Frechet, J. M. J. Science 1994, 263, 1710-1715.
18. (b) Grayson, S. M.; Frechet, J. M. J. Chem. Rev. 2001, 101, 3819-3867.
19. (c) Inoue, K. Prog. Polym. Sci. 2000, 25, 453-571.
20. (d) Zeng, F. W.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681-1712.
21. (a) Daoud, M.; Cotton, J. P. J. Phys. (Paris) 1982, 43, 531-538.
22. (b) Halperin, A.; Tirrell, M.; Lodge, T. P. Adv. Polym. Sci. 1992, 100, 31-71.
23. (c) Hawker, C. J.; Frechet, J. M. J. J. Am. Chem. Soc. 1990, 112, 7638-7647.
24. (d) Hawker, C. J.; Lee, R.; Frechet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583-4588.
25. (a) Thurmond, K. B.; Kowalewski, T.; Wooley, K. L. J. Am. Chem. Soc. 1997, 119, 6656-6665.
26. (b) Wooley, K. L. J. Polym. Sci. A 2000, 38, 1397-1407.
27. Kreft, O.; Javier, A. M.; Sukhorukov, G. B.; Parak, W. J. J. Mater. Chem. 2007, 17, 4471-4476.
28. Mason, B. P.; Steinbacher, J. L.; McQuade, D. T. Polymeric Capsules: Catalysis and Drug Delivery. In Molecular Recognition and Polymers: Control of Polymer Structure and Self-Assembly; Rotello, V., Thayumanavan, S., Eds.; Wiley: Hoboken, 2008; pp 179-206.
29. (a) Breitenkamp, K.; Junge, D.; Emrick, T. Polym. Drug Del. 2006, 923, p. 253-267.
30. (b) Croll, L. M.; Stover, H. D. H.; Hitchcock, A. P. Macromolecules 2005, 38, 2903-2910.
31. (c) Glogowski, E.; Tangirala, R.; He, J. B.; Russell, T. P.; Emrick, T. Nano Lett. 2007, 7, 389-393.
32. (d) Jiang, Y. B.; Wang, D. J.; Zhao, T. J. Appl. Polym. Sci. 2007, 104, 2799-2806.
33. (e) Kim, C. A.; Joung, M. J.; Ahn, S. D.; Kim, G. H.; Kang, S. Y.; You, I. K.; Oh, J.; Myoung, H. J.; Baek, K. H.; Suh, K. S. Synth. Met. 2005, 151, 181-185.
34. (f) Li, G.; Feng, Y. Q.; Li, X. G.; Gao, P.; Wang, J.; Xie, J. Y. J. Mater. Sci. 2007, 42, 4838-4844.
35. (g) Long, M. S.; Cans, A. S.; Keating, C. D. J. Am. Chem. Soc. 2008, 130, 756-762.
36. (h) Scott, C.; Wu, D.; Ho, C. C.; Co, C. C. J. Am. Chem. Soc. 2005, 127, 4160-4161.
37. (h) Skaff, H.; Lin, Y.; Tangirala, R.; Breitenkamp, K; Boker, A.; Russell, T. P.; Emrick, T. Adv. Mater. 2005, 17, 2082-2084.
38. (i) Sukhorukov, G. B.; Rogach, A. L.; Garstka, M.; Springer, S.; Parak, W. J.; Munoz-Javier, A.; Kreft, O.; Skirtach, A. G.; Susha, A. S.; Ramaye, Y.; Palankar, R.; Winterhalter, M. Small 2007, 3, 944-955.
39. (j) Wang, J. P.; Zhao, X. P.; Guo, H. L.; Zheng, Q. Langmuir 2004, 20, 10845-10850.
40. (k) Wu, D.; Scott, C.; Ho, C. C.; Co, C. C. Macromolecules 2006, 39, 5848-5853.
41. (l) Breitenkamp, K.; Emrick, T. J. Am. Chem. Soc. 2003, 125, 12070-12071.
42. (a) Kobaslija, M.; Bogdan, A. R.; Poe, S. L.; Escobedo, F.; McQuade, D. T. J. Polym. Sci. A 2008, 46, 2309-2315.
43. (b) Kobaslija, M.; McQuade, D. T. Macromolecules 2006, 39, 6371-6375.
44. (c) Poe, S. L.; Kobaslija, M.; McQuade, D. T. J. Am. Chem. Soc. 2006, 128 (49), 15586-15587.
45. (d) Poe, S. L.; Kobaslija, M.; McQuade, D. T. J. Am. Chem. Soc. 2007, 129, 9216-9221.
46. (e) Price, K. E.; Broadwater, S. J.; Bogdan, A. R.; Keresztes, I.; Steinbacher, J. L.; McQuade, D. T. Macromolecules 2006, 39, 7681-7685.
47. (f) Price, K. E.; Mason, B. P.; Bogdan, A. R.; Broadwater, S. J.; Steinbacher, J. L.; McQuade, D. T. J. Am. Chem. Soc. 2006, 128, 10376-10377.
48. (g) Mason, B. P.; Bogdan, A. R.; Goswami, A.; McQuade, D. T. Org. Lett. 2007, 9, 3449-3451.
49. (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int Ed. 2001, 40, 2004-2021.
50. (b) Tornøe, C. W.; Meldal, M. Peptidotriazoles: Copper(I)-catalyzed 1,3-dipolar cycloadditions on solid-phase; Lebl, M., Houghten, R. A., Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, 2001; pp 263-264.
51. (c) Tornoe, C. W.; Christensen, C; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
52. (d) Ikeda, M.; Minari, J.; Shimada, N.; Numata, M.; Sakurai, K.; Shinkai, S. Org. Biomol. Chem. 2007, 5, 2219-2224.
53. (a) Tong, W. J.; Gao, C. Y.; Mohwald, H. Chem. Mater. 2005, 17, 4610-4616.
54. (b) Koo, H. Y.; Chang, S. T.; Choi, W. S.; Park, J. H.; Kim, D. Y.; Velev, O. D. Chem. Mater. 2006, 18, 3308-3313.
55. (c) Lebedeva, O. V.; Kim, B. S.; Vinogradova, O. I. Langmuir 2004, 20, 10685-10690.
56. (d) Khopade, A. J.; Caruso, F. Chem. Mater. 2004, 16, 2107-2112.
57. (e) Dai, Z. F.; Mohwald, H.; Tiersch, B.; Dahne, L. Langmuir 2002, 18, 9533-9538.
58. (f) Lavergne, F. M.; Cot, D.; Ganachaud, F. Langmuir 2007, 23, 6744-6753.
59. (g) Rochefort, D.; Kouisni, L.; Gendron, K. J. Electroanal. Chem. 2008, 617, 53-63.