Copolyesters from soybean oil for use as resorbable biomaterials

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 5, 2015, Pages 880-891

  Kolanthai, Elayaraja ^a   Sarkar, Kishor ^a   Meka, Sai Rama Krishna ^a   Madras, Giridhar ^a   Chatterjee, Kaushik ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Controlled release; Elastomer; Polyester; Renewable resources; Tissue scaffold

Indexed keywords

BIOCOMPATIBILITY; BIOLOGICAL MATERIALS; BIOMECHANICS; CELL ENGINEERING; COST ENGINEERING; CROSSLINKING; DEGRADATION; DIFFERENTIAL SCANNING CALORIMETRY; ELASTOMERS; MECHANICAL PROPERTIES; OIL SHALE; POLYESTERS; POLYMERS; SOYBEAN OIL; STEM CELLS; TISSUE; TISSUE ENGINEERING;

BONE TISSUE ENGINEERING; CONTROLLED RELEASE; DIFFUSION CONTROLLED MECHANISM; EPOXIDIZED SOYBEAN OIL; OSTEOGENIC DIFFERENTIATION; PHYSIOLOGICAL TEMPERATURE; RENEWABLE RESOURCE; TISSUE SCAFFOLDS;

SCAFFOLDS (BIOLOGY);

EID: 84929994950     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00001     Document Type: Article

References (54)

1. OBrien, F. J. Biomaterials & scaffolds for tissue engineering Mater. Today 2011, 14 (3) 88-95
2. Langer, R. Biomaterials in drug delivery and tissue engineering: One laboratorys experience Acc. Chem. Res. 2000, 33 (2) 94-101
3. Bose, S.; Vahabzadeh, S.; Bandyopadhyay, A. Bone tissue engineering using 3D printing Mater. Today 2013, 16 (12) 496-504
4. Gunatillake, P. A.; Adhikari, R. Biodegradable synthetic polymers for tissue engineering Eur. Cell. Mater. 2003, 5 (1) 1-16
5. Cheung, R. Y.; Ying, Y.; Rauth, A. M.; Marcon, N.; Yu Wu, X. Biodegradable dextran-based microspheres for delivery of anticancer drug mitomycin C Biomaterials 2005, 26 (26) 5375-5385
6. Ulery, B. D.; Nair, L. S.; Laurencin, C. T. Biomedical applications of biodegradable polymers J. Polym. Sci., Part B: Polym. Phys. 2011, 49 (12) 832-864
7. Natarajan, J.; Rattan, S.; Singh, U.; Madras, G.; Chatterjee, K. Polyanhydrides of castor oil-sebacic acid for controlled release applications Ind. Eng. Chem. Res. 2014, 53 (19) 7891-7901
8. Heller, J.; Barr, J.; Ng, S. Y.; Abdellauoi, K. S.; Gurny, R. Poly(ortho esters): Synthesis, characterization, properties and uses Adv. Drug Delivery. Rev. 2002, 54 (7) 1015-1039
9. Laurencin, C. T.; Norman, M. E.; Elgendy, H. M.; el-Amin, S. F.; Allcock, H. R.; Pucher, S. R.; Ambrosio, A. A. Use of polyphosphazenes for skeletal tissue regeneration J. Biomed. Mater. Res. 1993, 27 (7) 963-973
10. Chanprateep, S. Current trends in biodegradable polyhydroxyalkanoates J. Biosci. Bioeng. 2010, 110 (6) 621-632
11. Dunkelman, N. S.; Zimber, M. P.; LeBaron, R. G.; Pavelec, R.; Kwan, M.; Purchio, A. Cartilage production by rabbit articular chondrocytes on polyglycolic acid scaffolds in a closed bioreactor system Biotechnol. Bioeng. 1995, 46 (4) 299-305
12. Jonoobi, M.; Mathew, A. P.; Abdi, M. M.; Makinejad, M. D.; Oksman, K. A comparison of modified and unmodified cellulose nanofiber reinforced polylactic acid (PLA) prepared by twin screw extrusion J. Polym. Environ. 2012, 20 (4) 991-997
13. Lu, T.-L.; Sun, W.-g.; Zhao, W.; Chen, T. Preparation of amifostine polylactide-co-glycolide microspheres and its irradiation protective to mouse through oral administration Drug Dev. Ind. Pharm. 2011, 37 (12) 1473-1480
14. Daebritz, S. H.; Fausten, B.; Hermanns, B.; Schroeder, J.; Groetzner, J.; Autschbach, R.; Messmer, B. J.; Sachweh, J. S. Introduction of a flexible polymeric heart valve prosthesis with special design for aortic position Eur. J. Cardiothorac. Surg. 2004, 25 (6) 946-952
15. 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 (10) 4022-4050
16. Miao, S.; Wang, P.; Su, Z.; Zhang, S. Vegetable-oil-based polymers as future polymeric biomaterials Acta Biomater. 2014, 10 (4) 1692-1704
17. Tan, S.; Abraham, T.; Ference, D.; Macosko, C. W. Rigid polyurethane foams from a soybean oil-based polyol Polymer 2011, 52 (13) 2840-2846
18. Bahr, M.; Mulhaupt, R. Linseed and soybean oil-based polyurethanes prepared via the non-isocyanate route and catalytic carbon dioxide conversion Green Chem. 2012, 14 (2) 483-489
19. Howard, G. T. Biodegradation of polyurethane: A review Int. Biodeterior. Biodegrad. 2002, 49 (4) 245-252
20. Miao, S.; Sun, L.; Wang, P.; Liu, R.; Su, Z.; Zhang, S. Soybean oil-based polyurethane networks as candidate biomaterials: Synthesis and biocompatibility Eur. J. Lipid Sci. Technol. 2012, 114 (10) 1165-1174
21. Tokiwa, Y.; Calabia, B.; Ugwu, C.; Aiba, S. Biodegradability of Plastics Int. J. Mol. Sci. 2009, 10 (9) 3722-3742
22. Qin, Y.; Jia, J. R.; Zhao, L.; Huang, Z. X.; Zhao, S. W.; Zhang, G. W.; Dai, B. F. Synthesis and characterization of soybean oil based unsaturated polyester resin Adv. Mater. Res. 2012, 393, 349-353
23. Dai, J.; Ma, S.; Han, L.; Zhang, L. Polyesters derived from itaconic acid for the properties and bio-based content enhancement of soybean oil-based thermosets Green Chem. 2015, 10.1039/C4GC02057J
24. Miyagawa, H.; Mohanty, A. K.; Burgueño, R.; Drzal, L. T.; Misra, M. Novel biobased resins from blends of functionalized soybean oil and unsaturated polyester resin J. Polym. Sci., Part B: Polym. Phys. 2007, 45 (6) 698-704
25. List, G.; Neff, W.; Holliday, R.; King, J.; Holser, R. Hydrogenation of soybean oil triglycerides: Effect of pressure on selectivity J. Am. Oil Chem. Soc. 2000, 77 (3) 311-314
26. Zhang, C.; Xia, Y.; Chen, R.; Huh, S.; Johnston, P. A.; Kessler, M. R. Soy-castor oil based polyols prepared using a solvent-free and catalyst-free method and polyurethanes therefrom Green Chem. 2013, 15 (6) 1477-1484
27. 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 (8) 1059-1069
28. Vieira, C.; Evangelista, S.; Cirillo, R.; Lippi, A.; Maggi, C. A.; Manzini, S. Effect of ricinoleic acid in acute and subchronic experimental models of inflammation Mediators Inflamm. 2000, 9 (5) 223-228
29. Chandorkar, Y.; Madras, G.; Basu, B. Structure, tensile properties and cytotoxicity assessment of sebacic acid based biodegradable polyesters with ricinoleic acid J. Mater. Chem. 2013, 1 (6) 865-875
30. Yang, J.; Webb, A. R.; Ameer, G. A. Novel citric acid-based biodegradable elastomers for tissue engineering Adv. Mater. 2004, 16 (6) 511-516
31. Katti, D.; Lakshmi, S.; Langer, R.; Laurencin, C. Toxicity, biodegradation and elimination of polyanhydrides Adv. Drug Delivery. Rev. 2002, 54 (7) 933-961
32. Saithai, P.; Lecomte, J.; Dubreucq, E.; Tanrattanakul, V. Effects of different epoxidation methods of soybean oil on the characteristics of acrylated epoxidized soybean oil-co-poly(methyl methacrylate) copolymer eXPRESS Polym. Lett. 2013, 7 (11) 910-924
33. Sarkar, K.; Krishna Meka, S. R.; Bagchi, A.; Krishna, N. S.; Ramachandra, S. G.; Madras, G.; Chatterjee, K. Polyester derived from recycled poly(ethylene terephthalate) waste for regenerative medicine RSC Adv. 2014, 4 (102) 58805-58815
34. Kumar, S.; Raj, S.; Kolanthai, E.; Sood, A. K.; Sampath, S.; Chatterjee, K. Chemical functionalization of graphene to augment stem cell osteogenesis and inhibit biofilm formation on polymer composites for orthopedic applications ACS Appl. Mater. Interfaces 2015, 7 (5) 3237-3252
35. Lu, Y.; Larock, R. C. New hybrid latexes from a soybean oil-based waterborne polyurethane and acrylics via emulsion polymerization Biomacromolecules 2007, 8 (10) 3108-3114
36. Xia, Y.; Larock, R. C. Castor oil-based thermosets with varied crosslink densities prepared by ring-opening metathesis polymerization (ROMP) Polymer 2010, 51 (12) 2508-2514
37. Tan, S.; Chow, W. Thermal properties, curing characteristics and water absorption of soybean oil-based thermoset eXPRESS Polym. Lett. 2011, 5 (6) 480-492
38. Lu, Y.; Larock, R. C. Soybean-oil-based waterborne polyurethane dispersions: Effects of polyol functionality and hard segment content on properties Biomacromolecules 2008, 9 (11) 3332-3340
39. Zhang, P.; Zhang, J. One-step acrylation of soybean oil (SO) for the preparation of SO-based macromonomers Green Chem. 2013, 15 (3) 641-645
40. Biswas, A.; Sharma, B. K.; Willett, J.; Advaryu, A.; Erhan, S.; Cheng, H. Azide derivatives of soybean oil and fatty esters J. Agric. Food Chem. 2008, 56 (14) 5611-5616
41. Sathiskumar, P.; Madras, G. Synthesis, characterization, degradation of biodegradable castor oil based polyesters Polym. Degrad. Stab. 2011, 96 (9) 1695-1704
42. Lei, L.; Ding, T.; Shi, R.; Liu, Q.; Zhang, L.; Chen, D.; Tian, W. Synthesis, characterization and in vitro degradation of a novel degradable poly((1,2-propanediol-sebacate)-citrate) bioelastomer Polym. Degrad. Stab. 2007, 92 (3) 389-396
43. Sharma, V. K.; Kalonia, D. S. Effect of vacuum drying on protein-mannitol interactions: The physical state of mannitol and protein structure in the dried state AAPS PharmSciTech 2004, 5 (1) 58-69
44. Ha, S. K. Finite element modeling of multi-level cervical spinal segments (C3-C6) and biomechanical analysis of an elastomer-type prosthetic disc Med. Eng. Phys. 2006, 28 (6) 534-541
45. Gosline, J.; Lillie, M.; Carrington, E.; Guerette, P.; Ortlepp, C.; Savage, K. Elastic proteins: biological roles and mechanical properties Philos. Trans. R. Soc., B 2002, 357 (1418) 121-132
46. Pan, X.; Sengupta, P.; Webster, D. C. High biobased content epoxy-anhydride thermosets from epoxidized sucrose esters of fatty acids Biomacromolecules 2011, 12 (6) 2416-2428
47. Caillol, S.; Desroches, M.; Boutevin, G.; Loubat, C.; Auvergne, R.; Boutevin, B. Synthesis of new polyester polyols from epoxidized vegetable oils and biobased acids Eur. J. Lipid Sci. Technol. 2012, 114 (12) 1447-1459
48. Liu, Z.; Xu, Y.; Cao, L.; Bao, C.; Sun, H.; Wang, L.; Dai, K.; Zhu, L. Phosphoester cross-linked vegetable oil to construct a biodegradable and biocompatible elastomer Soft Matter 2012, 8 (21) 5888-5895
49. Dasgupta, Q.; Chatterjee, K.; Madras, G. Combinatorial approach to develop tailored biodegradable poly(xylitol dicarboxylate) polyesters Biomacromolecules 2014, 15 (11) 4302-4313
50. Costa, P.; Sousa Lobo, J. M. Modeling and comparison of dissolution profiles Eur. J. Pharm. Sci. 2001, 13 (2) 123-133
51. Soppirnath, K. S.; Aminabhavi, T. M. Water transport and drug release study from cross-linked polyacrylamide grafted guar gum hydrogel microspheres for the controlled release application Eur. J. Pharm. Biopharm. 2002, 53 (1) 87-98
52. Murphy, C. M.; Haugh, M. G.; OBrien, F. J. The effect of mean pore size on cell attachment, proliferation and migration in collagen-glycosaminoglycan scaffolds for bone tissue engineering Biomaterials 2010, 31 (3) 461-466
53. Hartles, R. Citrate in mineralized tissues Adv. Oral Biol. 1964, 1, 225-253
54. Tran, R. T.; Wang, L.; Zhang, C.; Huang, M.; Tang, W.; Zhang, C.; Zhang, Z.; Jin, D.; Banik, B.; Brown, J. L.; Xie, Z.; Bai, X.; Yang, J. Synthesis and characterization of biomimetic citrate-based biodegradable composites J. Biomed. Mater. Res., Part A 2014, 102 (8) 2521-2532