Polyanhydrides of castor oil-sebacic acid for controlled release applications

Industrial and Engineering Chemistry Research

Volumn 53, Issue 19, 2014, Pages 7891-7901

  Natarajan, Janeni ^a   Rattan, Shruti ^a   Singh, Utkarsh ^a   Madras, Giridhar ^a   Chatterjee, Kaushik ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION REACTIONS; CYTOTOXICITY; DEGRADATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; HYDROPHOBICITY; THERMOANALYSIS; VEGETABLE OILS; X RAY DIFFRACTION;

BIODEGRADABLE POLYANHYDRIDES; CONTACT ANGLE GONIOMETRY; DEGRADATION KINETICS; DEGRADATION PRODUCTS; HIGH MOLECULAR WEIGHT; HYDROLYTIC DEGRADATION; HYDROPHOBIC AND HYDROPHILIC; STRUCTURE OF THE POLYMERS;

POLYMERS;

EID: 84900538730     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie500679u     Document Type: Article

References (63)

1. Guelcher, S. A. Biodegradable polyurethanes: Synthesis and applications in regenerative medicine Tissue Eng., Part B 2008, 14, 3-17
2. Gunatillake, P. A.; Adhikari, R. Biodegradable synthetic polymers for tissue engineering Eur. Cells Mater. 2003, 5, 1-16
3. Kumar, N.; Langer, R. S.; Domb, A. J. Polyanhydrides: An overview Adv. Drug Delivery Rev. 2002, 54, 889-910
4. Nair, L. S.; Laurencin, C. T. Biodegradable polymers as biomaterials Prog. Polym. Sci. 2007, 32, 762-798
5. Surrao, D. C.; Waldman, S. D.; Amsden, B. G. Biomimetic poly(lactide) based fibrous scaffolds for ligament tissue engineering Acta Biomater. 2012, 8, 3997-4006
6. Ulery, B. D.; Nair, L. S.; Laurencin, C. T. Biomedical applications of biodegradable polymers J. Polym. Sci., Part B: Polym. Phys. 2011, 49, 832-864
7. Göpferich, A. Polymer Bulk Erosion Macromolecules 1997, 30, 2598-2604
8. Zhou, Z.; Yi, Q.; Liu, L.; Liu, X.; Liu, Q. Influence of degradation of poly- l -lactide on mass loss, mechanical properties, and crystallinity in phosphate-buffered solution J. Macromol. Sci., Part B: Polym. Phys. 2009, 48, 309-317
9. Leong, K. W.; Brott, B. C.; Langer, R. Bioerodible polyanhydrides as drug-carrier matrices. I: Characterization, degradation, and release characteristics J. Biomed. Mater. Res. 1985, 19, 941-955
10. Leong, K. W.; DAmore, P.; Marletta, M.; Langer, R. Bioerodible polyanhydrides as drug-carrier matrices. II. Biocompatibility and chemical reactivity J. Biomed. Mater. Res. 1986, 20, 51-64
11. Mayberg, M. R.; Gross, A. S.; Mathiowitz, E.; Langer, R. Sustained release of acetylcholine in rat hippocampus using a polyanhydride drug-delivery system Polym. Adv. Technol. 1992, 3, 331-335
12. Li, L. C.; Deng, J.; Stephens, D. Polyanhydride implant for antibiotic delivery - From the bench to the clinic Adv. Drug Delivery Rev. 2002, 54, 963-986
13. Erdmann, L.; Uhrich, K. E. Synthesis and degradation characteristics of salicylic acid-derived poly(anhydride-esters) Biomaterials 2000, 21, 1941-1946
14. Shelke, N. B.; Aminabhavi, T. M. Synthesis and characterization of novel poly(sebacic anhydride- co -Pluronic F68/F127) biopolymeric microspheres for the controlled release of nifedipine Int. J. Pharm. 2007, 345, 51-58
15. Zhang, N.; Guo, S.-R. Synthesis and micellization of amphiphilic poly(sebacic anhydride)-poly(ethylene glycol)-poly(sebacic anhydride) block copolymers J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 1271-1278
16. Zhao, A.; Zhou, S.; Zhou, Q.; Chen, T. Thermosensitive micelles from PEG-based ether-anhydride triblock copolymers Pharm. Res. 2010, 27, 1627-1643
17. Tamada, J.; Langer, R. The development of polyanhydrides for drug delivery applications J. Biomater. Sci., Polym. Ed. 1992, 3, 315-353
18. Zhai, Y.; Guo, S.; Dong, A.; Jin, F.; Xie, C.; Zhang, J.; Deng, L. Influences of the content of POA on the properties of poly(sebacic acid-octadecanic diacid) copolyanhydrides React. Funct. Polym. 2008, 68, 1415-1421
19. Jain, J. P.; Sokolsky, M.; Kumar, N.; Domb, A. J. Fatty acid based biodegradable polymer Polym. Rev. (Philadelphia, PA, U.S.) 2008, 48, 156-191
20. Teomim, D.; Nyska, A.; Domb, A. J. Ricinoleic acid-based biopolymers J. Biomed. Mater. Res. 1999, 45, 258-267
21. Teomim, D.; Domb, A. J. Fatty acid terminated polyanhydrides J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3337-3344
22. Teomim, D.; Domb, A. J. Nonlinear fatty acid terminated polyanhydrides Biomacromolecules 2000, 2, 37-44
23. Sathiskumar, P. S.; Madras, G. Synthesis, characterization, degradation of biodegradable castor oil based polyesters Polym. Degrad. Stab. 2011, 96, 1695-1704
24. Shelke, N. B.; Sairam, M.; Halligudi, S. B.; Aminabhavi, T. M. Development of transdermal drug-delivery films with castor-oil-based polyurethanes J. Appl. Polym. Sci. 2007, 103, 779-788
25. Ristić, I. S.; Marinović-Cincović, M.; Cakić, S. M.; Tanasić, L. M.; Budinski-Simendić, J. K. Synthesis and properties of novel star-shaped polyesters based on l -lactide and castor oil Polym. Bull. (Berlin, Ger.) 2013, 1-16
26. Vaisman, B.; Ickowicz, D. E.; Abtew, E.; Haim-Zada, M.; Shikanov, A.; Domb, A. J. In vivo degradation and elimination of injectable ricinoleic acid-based poly(ester-anhydride) Biomacromolecules 2013, 14, 1465-1473
27. Chandorkar, Y.; Madras, G.; Basu, B. Structure, tensile properties and cytotoxicity assessment of sebacic acid based biodegradable polyesters with ricinoleic acid J. Mater. Chem. B 2013, 1, 865-875
28. Jain, J.; Sokolsky, M.; Kumar, N.; Domb, A. Fatty acid based biodegradable polymer Polym. Rev. (Philadelphia, PA, U.S.) 2008, 4, 156-191
29. Hiremath, J. G.; Rudani, C. G.; Domb, A. J.; Suthar, R. V.; Khamar, N. S. Preparation and in vitro characterization of poly(sebacic acid- co -ricinoleic acid)-based tamoxifen citrate-loaded microparticles for breast cancer J. Appl. Polym. Sci. 2012, 124, 4747-4754
30. Barrett, D. G.; Yousaf, M. N. Design and applications of biodegradable polyester tissue scaffolds based on endogenous monomers found in human metabolism Molecules 2009, 14, 4022-4050
31. Conix, A. Synthesis of poly(bis-1,3- p -carboxyphenoxy propane). Die Makromolekulare Chemie 1957, 24, 76-78.
32. Sudo, H.; Kodama, H.-A.; Amagai, Y.; Yamamoto, S.; Kasai, S. In vitro differentiation and calcification in a new clonal osteogenic cell line derived from newborn mouse calvaria J. Cell Biol. 1983, 96, 191-198
33. Attawia, M. A.; Uhrich, K. E.; Botchwey, E.; Fan, M.; Langer, R.; Laurencin, C. T. Cytotoxicity testing of poly (anhydride- co -imides) for orthopedic applications J. Biomed. Mater. Res. 1995, 29, 1233-1240
34. Ogunniyi, D. S. Castor oil: A vital industrial raw material Bioresour. Technol. 2006, 97, 1086-1091
35. Jain, J. P.; Modi, S.; Kumar, N. Hydroxy fatty acid based polyanhydride as drug delivery system: Synthesis, characterization, in vitro degradation, drug release, and biocompatibility J. Biomed. Mater. Res., Part A 2008, 84, 740-752
36. Schmeltzer, R. C.; Schmalenberg, K. E.; Uhrich, K. E. Synthesis and cytotoxicity of salicylate-based poly(anhydride esters) Biomacromolecules 2005, 6, 359-367
37. Wang, H. J.; Rong, M. Z.; Zhang, M. Q.; Hu, J.; Chen, H. W.; Czigány, T. Biodegradable foam plastics based on castor oil Biomacromolecules 2008, 9, 615-623
38. Mathiowitz, E.; Kreitz, M.; Pekarek, K. Morphological characterization of bioerodible polymers. 2. Characterization of polyanhydrides by Fourier-transform infrared spectroscopy Macromolecules 1993, 26, 6749-6755
39. Mathiowitz, E.; Ron, E.; Mathiowitz, G.; Amato, C.; Langer, R. Morphological characterization of bioerodible polymers. 1. Crystallinity of polyanhydride copolymers Macromolecules 1990, 23, 3212-3218
40. Vogler, E. A. Structure and reactivity of water at biomaterial surfaces Adv. Colloid Interface Sci. 1998, 74, 69-117
41. Park, E.-S.; Maniar, M.; Shah, J. Water uptake in to polyanhydride devices: kinetics of uptake and effects of model compounds incorporated, and device geometry on water uptake J. Controlled Release 1996, 40, 55-65
42. Wei, J.; Igarashi, T.; Okumori, N.; Igarashi, T.; Maetani, T.; Liu, B.; Yoshinari, M. Influence of surface wettability on competitive protein adsorption and initial attachment of osteoblasts Biomed. Mater. 2009, 10.1088/1748-6041/4/ 4/045002
43. Tamada, Y.; Ikada, Y. Fibroblast growth on polymer surfaces and biosynthesis of collagen J. Biomed. Mater. Res. 1994, 28, 783-789
44. Rutherglen, B. G.; McBath, R. A.; Huang, Y. L.; Shipp, D. A. Polyanhydride networks from thiol-ene polymerizations Macromolecules 2010, 43, 10297-10303
45. Alexis, F. Factors affecting the degradation and drug-release mechanism of poly(lactic acid) and poly[(lactic acid)- co -(glycolic acid)] Polym. Int. 2005, 54, 36-46
46. Whitaker-Brothers, K.; Uhrich, K. Poly(anhydride-ester) fibers: Role of copolymer composition on hydrolytic degradation and mechanical properties J. Biomed. Mater. Res., Part A 2004, 70A, 309-318
47. Domb, A. J.; Langer, R.; Polyanhydrides, I. Preparation of high molecular weight polyanhydrides J. Polym. Sci., Part A: Polym. Chem. 1987, 25, 3373-3386
48. Göpferich, A.; Tessmar, J. Polyanhydride degradation and erosion Adv. Drug Delivery Rev. 2002, 54, 911-931
49. Domb, A. J.; Nudelman, R. In vivo and in vitro elimination of aliphatic polyanhydrides Biomaterials 1995, 16, 319-323
50. Göpferich, A. Mechanisms of polymer degradation and erosion Biomaterials 1996, 17, 103-114
51. Vert, M.; Li, S.; Garreau, H. More about the degradation of LA/GA-derived matrices in aqueous media J. Controlled Release 1991, 16, 15-26
52. Anseth, K. S.; Shastri, V. R.; Langer, R. Photopolymerizable degradable polyanhydrides with osteocompatibility Nat. Biotechnol. 1999, 17, 156-159
53. Gopferich, A.; Langer, R. Influence of microstructure and monomer properties on the erosion mechanism of a class of polyanhydrides J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2445-2458
54. Krasko, M. Y.; Shikanov, A.; Ezra, A.; Domb, A. J. Poly(ester anhydride)s prepared by the insertion of ricinoleic acid into poly(sebacic acid) J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 1059-1069
55. Santos, C. A.; Freedman, B. D.; Leach, K. J.; Press, D. L.; Scarpulla, M.; Mathiowitz, E. Poly(fumaric- co -sebacic anhydride): A degradation study as evaluated by FTIR, DSC, GPC and X-ray diffraction J. Controlled Release 1999, 60, 11-22
56. Berrada, M.; Yang, Z.; Lehnert, S. Tumor treatment by sustained intratumoral release of 5-fluorouracil: Effects of drug alone and in combined treatments Int. J. Radiat. Oncol., Biol., Phys. 2002, 54, 1550-1557
57. Katti, D. S.; Lakshmi, S.; Langer, R.; Laurencin, C. T. Toxicity, biodegradation and elimination of polyanhydrides Adv. Drug Delivery Rev. 2002, 54, 933-961
58. Li, X.; Deng, X.; Yuan, M.; Xiong, C.; Huang, Z.; Zhang, Y.; Jia, W. In vitro degradation and release profiles of poly- dl -lactide-poly(ethylene glycol) microspheres with entrapped proteins J. Appl. Polym. Sci. 2000, 78, 140-148
59. Freiberg, S.; Zhu, X. X. Polymer microspheres for controlled drug release Int. J. Pharm. 2004, 282, 1-18
60. Shieh, L.; Tamada, J.; Tabata, Y.; Domb, A.; Langer, R. Drug release from a new family of biodegradable polyanhydrides J. Controlled Release 1994, 29, 73-82
61. Leong, K. W.; Kost, J.; Mathiowitz, E.; Langer, R. Polyanhydrides for controlled release of bioactive agents Biomaterials 1986, 7, 364-371
62. Wang, D.; Christensen, K.; Chawla, K.; Xiao, G.; Krebsbach, P. H.; Franceschi, R. T. Isolation and characterization of MC3T3-E1 preosteoblast subclones with distinct in vitro and in vivo differentiation/mineralization potential J. Bone Miner. Res. 1999, 14, 893-903
63. Jin, Q.; Mitschang, F.; Agarwal, S. Biocompatible drug delivery system for photo-triggered controlled release of 5-Fluorouracil Biomacromolecules 2011, 12, 3684-3691