Functionalization of methacrylate polymers with thiooximes: A robust postpolymerization modification reaction and a method for the preparation of H2S-releasing polymers

Macromolecules

Volumn 47, Issue 15, 2014, Pages 5089-5095

  Foster, Jeffrey C ^a   Matson, John B ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DEGRADATION;

DEGRADATION KINETICS; ENDOGENOUS SIGNALING; ETHYL METHACRYLATES; FUNCTIONALIZATIONS; METHACRYLATE POLYMERS; POSTPOLYMERIZATION MODIFICATIONS; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER; THERAPEUTIC POTENTIALS;

POLYMERS;

EID: 84905904860     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma501044b     Document Type: Article

References (53)

1. Boaen, N. K.; Hillmyer, M. A. Chem. Soc. Rev. 2005, 34, 267
2. Gauthier, M. A.; Gibson, M. I.; Klok, H.-A. Angew. Chem., Int. Ed. 2009, 48, 48
3. Guenay, K. A.; Theato, P.; Klok, H.-A. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 1
4. Lutz, J.-F.; Sumerlin, B. S. In Click Chemistry for Biotechnology and Materials Science; John Wiley & Sons, Ltd: 2009; p 69.
5. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004
6. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620
7. Xi, W.; Scott, T. F.; Kloxin, C. J.; Bowman, C. N. Adv. Funct. Mater. 2014, n/a
8. Maynard, H. D.; Broyer, R. M.; Kolodziej, C. M. In Click Chemistry for Biotechnology and Materials Science; John Wiley & Sons, Ltd: 2009; p 53.
9. van der Ende, A. E.; Harrell, J.; Sathiyakumar, V.; Meschievitz, M.; Katz, J.; Adcock, K.; Harth, E. Macromolecules 2010, 43, 5665
10. Sumerlin, B. S.; Vogt, A. P. Macromolecules 2009, 43, 1
11. Durmaz, H.; Dag, A.; Altintas, O.; Erdogan, T.; Hizal, G.; Tunca, U. Macromolecules 2007, 40, 191
12. Gao, H.; Matyjaszewski, K. J. Am. Chem. Soc. 2007, 129, 6633
13. Boyer, C.; Liu, J.; Bulmus, V.; Davis, T. P. Aust. J. Chem. 2009, 62, 830
14. O'Reilly, R. K.; Joralemon, M. J.; Wooley, K. L.; Hawker, C. J. Chem. Mater. 2005, 17, 5976
15. Bapat, A. P.; Roy, D.; Ray, J. G.; Savin, D. A.; Sumerlin, B. S. J. Am. Chem. Soc. 2011, 133, 19832
16. Li, S.; Han, J.; Gao, C. Polym. Chem. 2013, 4, 1774
17. Wu, P.; Malkoch, M.; Hunt, J. N.; Vestberg, R.; Kaltgrad, E.; Finn, M. G.; Fokin, V. V.; Sharpless, K. B.; Hawker, C. J. Chem. Commun. 2005, 5775
18. Raasch, M. S. J. Org. Chem. 1972, 37, 3820
19. Foster, J. C.; Powell, C. R.; Radzinski, S. C.; Matson, J. B. Org. Lett. 2014, 16, 1558
20. Olson, K. R. Am. J. Physiol. 2011, 301, R297
21. Wang, R. Physiol. Rev. 2012, 92, 791
22. Whiteman, M.; Winyard, P. G. Expert. Rev. Clin. Pharmacol. 2010, 4, 13
23. Kimura, Y. D. R.; Schubert, D.; Kimura, H. Antioxid. Redox Signaling 2006, 8, 661
24. Polhemus, D. J.; Lefer, D. J. Circ. Res. 2014, 114, 730
25. Qiu, X.; Villalta, J.; Lin, G.; Lue, T. F. J. Andrology 2012, 33, 529
26. Paul, B. D.; Snyder, S. H. Nat. Rev. Mol. Cell Biol. 2012, 13, 499
27. Kodela, R.; Chattopadhyay, M.; Kashfi, K. ACS Med. Chem. Lett. 2012, 3, 257
28. Wallace, J. L. Trends Pharmacol. Sci. 2007, 28, 501
29. Zhao, Y.; Wang, H.; Xian, M. J. Am. Chem. Soc. 2011, 133, 15
30. Ma, X.; Wang, X.; Song, C. J. Am. Chem. Soc. 2009, 131, 5777
31. Mitsukami, Y.; Donovan, M. S.; Lowe, A. B.; McCormick, C. L. Macromolecules 2001, 34, 2248
32. 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
33. Lowe, A. B.; McCormick, C. L. Prog. Polym. Sci. 2007, 32, 283
34. Moad, G.; Rizzardo, E.; Thang, S. H. Aust. J. Chem. 2012, 65, 985
35. Li, R. C.; Hwang, J.; Maynard, H. D. Chem. Commun. 2007, 3631
36. Rossi, N. A. A.; Zou, Y.; Scott, M. D.; Kizhakkedathu, J. N. Macromolecules 2008, 41, 5272
37. Stukel, J. M.; Li, R. C.; Maynard, H. D.; Caplan, M. R. Biomacromolecules 2010, 11, 160
38. Sun, G.; Cheng, C.; Wooley, K. L. Macromolecules 2007, 40, 793
39. Sun, G.; Fang, H.; Cheng, C.; Lu, P.; Zhang, K.; Walker, A. V.; Taylor, J.-S. A.; Wooley, K. L. ACS Nano 2009, 3, 673
40. Murray, B. S.; Jackson, A. W.; Mahon, C. S.; Fulton, D. A. Chem. Commun. 2010, 46, 8651
41. Whitaker, D. E.; Mahon, C. S.; Fulton, D. A. Angew. Chem., Int. Ed. 2013, 52, 956
42. Heinenberg, M.; Menges, B.; Mittler, S.; Ritter, H. Macromolecules 2002, 35, 3448
43. Monthéard, J.-P.; Chatzopoulos, F.; Amine, H. E.; Cachard, A.; Trouillet, A. Angew. Makromol. Chem. 1994, 220, 75
44. Keddie, D. J. Chem. Soc. Rev. 2014, 43, 496
45. Greszta, D.; Mardare, D.; Matyjaszewski, K. Macromolecules 1994, 27, 638
46. Chen, B.; van der Poll, D. G.; Jerger, K.; Floyd, W. C.; Frechet, J. M.; Szoka, F. C. Bioconjugate Chem. 2011, 22, 617
47. Hill, M. R.; Mukherjee, S.; Costanzo, P. J.; Sumerlin, B. S. Polym. Chem. 2012, 3, 1758
48. Alani, A. W. G.; Bae, Y.; Rao, D. A.; Kwon, G. S. Biomaterials 2010, 31, 1765
49. Matson, J. B.; Stupp, S. I. Chem. Commun. 2011, 47, 7962
50. Lin, F.; Yu, J.; Tang, W.; Zheng, J.; Defante, A.; Guo, K.; Wesdemiotis, C.; Becker, M. L. Biomacromolecules 2013, 14, 3749
51. Willcock, H.; O'Reilly, R. K. Polym. Chem. 2010, 1, 149
52. Perrier, S.; Takolpuckdee, P.; Mars, C. A. Macromolecules 2005, 38, 2033
53. Kalia, J.; Raines, R. T. Angew. Chem., Int. Ed. 2008, 47, 7523