Light-triggered intramolecular cyclization in poly(lactic- co -glycolic acid)-based polymers for controlled degradation

Macromolecules

Volumn 48, Issue 10, 2015, Pages 3166-3172

  Olejniczak, Jason ^a   Chan, Minnie ^a   Almutairi, Adah ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADABLE POLYMERS; BIODEGRADATION; COPOLYMERS; CYCLIZATION; DEGRADATION; RING OPENING POLYMERIZATION;

CONTROLLED DEGRADATION; DEGRADATION KINETICS; HYDROLYTIC DEGRADATION; INTRAMOLECULAR CYCLIZATIONS; MOLECULAR ENGINEERING; POLY LACTIC-CO-GLYCOLIC ACID; POLY(DL-LACTIDE-COGLYCOLIDE); POLYMERIC STRUCTURES;

POLYMERS;

EID: 84930620515     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/acs.macromol.5b00455     Document Type: Article

References (51)

1. Dong, H. D.; Esser-Kahn, A. P.; Thakre, P. R.; Patrick, J. F.; Sottos, N. R.; White, S. R.; Moore, J. S. ACS Appl. Mater. Interfaces 2012, 4, 503
2. Nie, Z. H.; Kumacheva, E. Nat. Mater. 2008, 7, 277
3. Vozzi, G.; Flaim, C.; Ahluwalia, A.; Bhatia, S. Biomaterials 2003, 24, 2533
4. Lu, Y.; Chen, S. C. Adv. Drug Delivery Rev. 2004, 56, 1621
5. Nair, L. S.; Laurencin, C. T. Prog. Polym. Sci. 2007, 32, 762
6. Vauthier, C.; Dubernet, C.; Fattal, E.; Pinto-Alphandary, H.; Couvreur, P. Adv. Drug Delivery Rev. 2003, 55, 519
7. Cheng, R.; Meng, F. H.; Deng, C.; Klok, H. A.; Zhong, Z. Y. Biomaterials 2013, 34, 3647
8. de Gracia Lux, C.; Olejniczak, J.; Fomina, N.; Viger, M. L.; Almutairi, A. J. Polym. Sci., Part A 2013, 51, 3783
9. Mejia, J. S.; Gillies, E. R. Polym. Chem. 2013, 4, 1969
10. Lux, C. D.; Almutairi, A. ACS Macro Lett. 2013, 2, 432
11. Lv, A.; Li, Z. L.; Du, F. S.; Li, Z. C. Macromolecules 2014, 47, 7707
12. Jain, R. A. Biomaterials 2000, 21, 2475
13. Athanasiou, K. A.; Niederauer, G. G.; Agrawal, C. M. Biomaterials 1996, 17, 93
14. Woodruff, M. A.; Hutmacher, D. W. Prog. Polym. Sci. 2010, 35, 1217
15. Park, T. G. Biomaterials 1995, 16, 1123
16. Panyam, J.; Labhasetwar, V. Adv. Drug Delivery Rev. 2003, 55, 329
17. Pitt, C. G.; G, M. M.; Kimmel, G. L.; Surles, J.; Schindler, A. Biomaterials 1981, 2, 215
18. Patchorn, A.; Amit, B.; Woodward, R. B. J. Am. Chem. Soc. 1970, 92, 6333
19. Blanc, A.; Bochet, C. G. J. Am. Chem. Soc. 2004, 126, 7174
20. Klinger, D.; Landfester, K. Macromolecules 2011, 44, 9758
21. Osornio, Y. M.; Uebelhart, P.; Bosshard, S.; Konrad, F.; Siegel, J. S.; Landau, E. M. J. Org. Chem. 2012, 77, 10583
22. Yin, L. C.; Tang, H. Y.; Kim, K. H.; Zheng, N.; Song, Z. Y.; Gabrielson, N. P.; Lu, H.; Cheng, J. J. Angew. Chem., Int. Ed. 2013, 52, 9182
23. Azagarsamy, M. A.; Anseth, K. S. Angew. Chem., Int. Ed. 2013, 52, 13803
24. Huu, V. A.; Luo, J.; Zhu, J.; Patel, S.; Boone, A.; Mahmoud, E.; McFearin, C.; Olejniczak, J.; de Gracia Lux, C.; Lux, J.; Fomina, N.; Huynh, M.; Zhang, K.; Almutairi, A. J. Controlled Release 2015, 200, 71
25. Griffin, D. R.; Schlosser, J. L.; Lam, S. F.; Nguyen, T. H.; Maynard, H. D.; Kasko, A. M. Biomacromolecules 2013, 14, 1199
26. Stanton-Humphreys, M. N.; Taylor, R. D. T.; McDougall, C.; Hart, M. L.; Brown, C. T. A.; Emptage, N. J.; Conway, S. J. Chem. Commun. 2012, 48, 657
27. Gu, Z.; Biswas, A.; Joo, K. I.; Hu, B. L.; Wang, P.; Tang, Y. Chem. Commun. 2010, 46, 6467
28. Kostiainen, M. A.; Smith, D. K.; Ikkala, O. Angew. Chem., Int. Ed. 2007, 46, 7600
29. Griffin, D. R.; Kasko, A. M. J. Am. Chem. Soc. 2012, 134, 17833
30. DeForest, C. A.; Anseth, K. S. Nat. Chem. 2011, 3, 925
31. Fomina, N.; McFearin, C.; Sermsakdi, M.; Edigin, O.; Almutairi, A. J. Am. Chem. Soc. 2010, 132, 9540
32. Olejniczak, J.; Sankaranarayanan, J.; Viger, M. L.; Almutairi, A. ACS Macro Lett. 2013, 2, 683
33. Carling, C. J.; Viger, M. L.; Huu, V. A. N.; Garcia, A. V.; Almutairi, A. Chem. Sci. 2015, 6, 335
34. Nazemi, A.; Schon, T. B.; Gillies, E. R. Org. Lett. 2013, 15, 1830
35. Soleimani, A.; Borecki, A.; Gillies, E. R. Polym. Chem. 2014, 5, 7062
36. McIntosh, J. T.; Nazemi, A.; Bonduelle, C. V.; Lecommandoux, S.; Gillies, E. R. Can. J. Chem. 2015, 93, 126
37. Zhang, Y. F.; Ma, L.; Deng, X. J.; Cheng, J. J. Polym. Chem. 2013, 4, 224
38. Zhang, Y. F.; Yin, Q.; Yin, L. C.; Ma, L.; Tang, L.; Cheng, J. J. Angew. Chem., Int. Ed. 2013, 52, 6435
39. Deng, X. J.; Zheng, N.; Song, Z. Y.; Yin, L. C.; Cheng, J. J. Biomaterials 2014, 35, 5006
40. Ma, L.; Baumgartner, R.; Zhang, Y.; Song, Z.; Cai, K.; Cheng, J. J. Polym. Sci., Part A 2015, 53, 1161
41. Yu, Y.; Zou, J.; Cheng, C. Polym. Chem. 2014, 5, 5854
42. Pounder, R. J.; Dove, A. P. Polym. Chem. 2010, 1, 260
43. Pounder, R. J.; Dove, A. P. Biomacromolecules 2010, 11, 1930
44. Levy, D. E.; Lapierre, F.; Liang, W. S.; Ye, W. Q.; Lange, C. W.; Li, X. Y.; Grobelny, D.; Casabonne, M.; Tyrrell, D.; Holme, K.; Nadzan, A.; Galardy, R. E. J. Med. Chem. 1998, 41, 199
45. Dove, A. P. ACS Macro Lett. 2012, 1, 1409
46. Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813
47. Kiesewetter, M. K.; Shin, E. J.; Hedrick, J. L.; Waymouth, R. M. Macromolecules 2010, 43, 2093
48. Pratt, R. C.; Lohmeijer, B. G. G.; Long, D. A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2006, 128, 4556
49. Aujard, I.; Benbrahim, C.; Gouget, M.; Ruel, O.; Baudin, J. B.; Neveu, P.; Jullien, L. Chem.-Eur. J. 2006, 12, 6865
50. Pathak, T.; Thomas, N. F.; Akhtar, M.; Gani, D. Tetrahedron 1990, 46, 1733
51. Denmark, S. E.; Yang, S. M. J. Am. Chem. Soc. 2004, 126, 12432