Polynonanolactone synthesized from vegetable oil: Evaluation of physical properties, biodegradation, and drug release behavior

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 47, Issue 23, 2009, Pages 6373-6387

  Abraham, Sinoj ^a,b   Narine, Suresh ^a  

^a TRENT UNIVERSITY   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Biodegradable; Biodegradation; Drug delivery; Drug delivery systems; Enzymatic degradation; Enzymes; Polyesters; Polylactams; Polylactone; Polynonanolactone; Renewable resources

Indexed keywords

BIODEGRADABLE; DRUG DELIVERY SYSTEM; DRUG DELIVERY SYSTEMS; ENZYMATIC DEGRADATION; RENEWABLE RESOURCE;

BIOCHEMISTRY; BIODEGRADATION; CATALYSTS; CHROMATOGRAPHIC ANALYSIS; CRYSTALLINE MATERIALS; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DELIVERY; ENZYMES; ESTERS; LEAKAGE (FLUID); LUBRICATING OILS; MICROBIOLOGY; PHOTODEGRADATION; PHYSICAL PROPERTIES; POLYESTERS; POLYMER FILMS; SCANNING ELECTRON MICROSCOPY; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS; VEGETABLE OILS; X RAY DIFFRACTION;

DEGRADATION;

EID: 72449120370     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23678     Document Type: Article

References (56)

1. Uhrich, K. E.; Cannixarro, S. M.; Langer, R. S.; Shakesheff, K. M. Chem Rev 1999, 99, 3181-3198.
2. Kemnitzer, J. E.; Mccarty, S. P.; Grop, R. A. Macromolecules 1993, 26, 1221-1229.
3. Vanionpaa, S.; Rokkamen, P.; Tormala, P. Prog Polym Sci 1989, 14, 679-716.
4. Leenslag, J. W.; Pennings, A. J.; Bos, R. R. M.; Rozema, F. R.; Boering, G. Biomaterials 1987, 8, 311-314.
5. Gopferich, A. Biomaterials 1996, 17, 103-114.
6. Darwis, D.; Mitomo, H.; Enjoji, T.; Yoshi, F.; Makuuchi, K. Polym Degrad Stab 1998, 62, 259-265.
7. Wang, S.; Cai, Q.; Bei, J. Macromol Symp 2003, 195, 263-268.
8. Liu, G.; Kong, X.; Wan, H.; Narine, S. S. Biomacromolecules 2008, 9, 949-953.
9. Kong, X.; Narine, S. S. Biomacromolecules 2007, 8, 2203-2209.
10. Kong, X.; Yue, J.; Narine, S. S. Biomacromolecules 2007, 8, 3584-3589.
11. Batista, E.; Monnerat, S.; Kato, K.; Stragevitch, L.; Meirelles, A. J. A. J Chem Eng DATA 1999, 44, 1360-1364.
12. Teonim, D.; Domb, A. J. Biomacromolecules 2001, 2, 37-44.
13. Domb, A. J.; Nudelman, R. J Polym Sci Part A: Polym Chem 1995, 33, 717-725.
14. Kula, J.; Smigielski, K.; Quang, T. B.; Grzelak, I.; Sikora, M. J Am Oil Chem Soc 1999, 76, 811-817.
15. Mitz, M. A.; Heinriks, R. L. Biochem Biophys Acta 1961, 46, 45-50.
16. Corey, E. J.; Nicolaou, K. C. J Am Chem Soc 1974, 96, 5614-5616.
17. Shiina, I.; Kubota, M.; Oshiumi, H.; Hashizume, M. J Org Chem 2004, 69, 1822-1830.
18. Shiina, I. Tetrahedron 2004, 60, 1587-1599.
19. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J Org Chem 1996, 61, 4560-4567.
20. Dvorak, C. A.; Schmitz, W. D.; Poon, D. J.; Pryde, D. C.; Lawson, J. P.; Amos, R. A.; Meyers, A. I. Angew Chem Int Ed 2000, 39, 1664-1666.
21. Oohashi, Y.; Fukumoto, K.; Mukaiyama, T. Chem Lett 2005, 34, 72-73.
22. Rawe, A. Principles of Polymer Chemistry, 2nd ed.; Kluwer Academic/Plenum Publishers, New York, 2000; pp 355-358.
23. Perkins, R. B.; Roden, J. J.; Pryde, E. H. J Am Oil Chem Soc 1975, 52, 473-477.
24. Nieschlag,H. J.; Rothfus, J. A.; Sohns, V. E.; Perkins, R. B. Ind Eng Chem Prod Res Dev 1977, 16, 101-107.
25. Dale, J. J Chem Soc 1965, 72-78.
26. Abe, M.; Hayashikoshi, T.; Kurata, T. Chem Lett 1994, 23, 1789-1792.
27. (a) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 9, 839-841;
28. (b) Oohashi, Y.; Fukumoto, K.; Mukaiyama, T. Chem Lett 2005, 34, 710-711.
29. Mukaiyama, T.; Izumi, J.; Miyashita, M.; Shiina, I. Chem Lett 1997, 28, 187-188.
30. (a) Ha, C. S.; Gardella, J. A. Chem Rev 2005, 105, 4205-4232;
31. (b)Ryou, J. H.; Ha, C. S.; Kim, J.W.; Lee, J. K. Macromol Biosci 2003, 3, 44-50;
32. (c) Lee, W. K.; Ryou, J. H.; Ha, C. S. Surf Sci 2003, 542, 235-243;
33. (d)Jung, B. O.; Roseman. S.; Park, J. K. Macromol Res 2008, 16, 1-5;
34. (e) Lee,C.W.; Kimura.Y.; Chung, J. D. Macromol Res 2008, 16, 651-658.
35. Williams, D. F. Eng Med 1981, 10, 5-7.
36. Kikkawa, Y.; Takayuki, S.; Tsuge, T.; Kanesato, M.; Doi, Y.; Abe, H. Biomacromolecules 2006, 7, 1921-1928.
37. Zou, T.; Cheng, S. X.; Zhuo, R. X. Colloid Polym Sci 2005, 283, 1091-1099.
38. Liu, L.; Li, S.; Garreau, H.; Vert, M. Biomacromolecules 2000, 1, 350-359.
39. Miao, Z. M.; Cheng, S. X.; Wang, Q. R.; Zhuo, R. X. J Biomed Mater Res Part B: Appl Biomater 2007, 81, 40-49.
40. Gan, Z.; Liang, O.; Zhang, J.; Jing, X. Polym Degrad Stab 1997, 56, 209-213.
41. Gan, Z.; Yu, D.; Zhong, Z.; Liang, O.; Jing, X. Polymer 1999, 40, 2859-2862.
42. Ramalinga, K.; Vijayalakshmi, P.; Kaimal, T. N. B. Tetrahedron Lett 2002, 43, 879-882.
43. Pryde, E. H.; Anders, D. E.; Teeter, H. M.; Cowan, J. C. J Org Chem 1960, 25, 618-621.
44. Diaper, D. G. M.; Mitchell, D. L. Can J Chem 1960, 38, 1976-1982.
45. Galli, C.; Mandolini, L. Acc Chem Res 1981, 15, 95-102.
46. Lebedev, B.; Evstropov, A. Makromol Chem 1984, 185, 1235-1253.
47. Dell'erba, R.; Groeninckx, G.; Maglio, G.; Malinconico, M.; Migliozzi, A. Polymer 2001, 42, 7831-7840.
48. Su, T.-T.; Jiang, H.; Gong, H. Polym Plast Tech Eng 2008, 47, 398-403.
49. Persenaire, O.; Alexandre, M.; Degée, P.; Dubois, P. Biomacromolecules 2001, 2, 288-294.
50. Sivalingam, G.; Madras, G. Polym Degrad Stab 2004, 84, 393-398.
51. Crescenzi, V.; Manzini, G.; Calzolari, G.; Borri, C. Eur Polym J 1972, 8, 449-463.
52. Timms, R. E. Prog Lipid Res 1984, 23, 1-8.
53. Himavan, C.; Starov, V. M.; Stapley, A. G. F. Adv Colloid Interface Sci 2006, 122, 3-33.
54. Li, R.; Nie, K.; Pang, W.; Zhu, Q. J Biomed Mater Res Part A 2007, 83, 114-122.
55. Zhang, Y.; Leblanc-Boily, V.; Zhao, Y.; Prud'homme, R. E. Polymer 2005, 46, 8141-8150.
56. Hirotsu, T.; Ketelaars, A. A. J.; Nakayama, K. Polym Degrad Stab 2000, 68, 311-316