About this Journal Submit a Manuscript Table of Contents
International Journal of Polymer Science
Volume 2010 (2010), Article ID 423460, 8 pages
http://dx.doi.org/10.1155/2010/423460
Review Article

Amphiphilic Poly(3-hydroxy alkanoate)s: Potential Candidates for Medical Applications

Department of Chemistry, Zonguldak Karaelmas University, 67100 Zonguldak, Turkey

Received 3 December 2009; Accepted 31 December 2009

Academic Editor: Shanfeng Wang

Copyright © 2010 Baki Hazer. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. R. Langer and D. A. Tirrell, “Designing materials for biology and medicine,” Nature, vol. 428, no. 6982, pp. 487–492, 2004. View at Publisher · View at Google Scholar · View at Scopus
  2. S. Mitragotri and J. Lahann, “Physical approaches to biomaterial design,” Nature Materials, vol. 8, no. 1, pp. 15–23, 2009. View at Publisher · View at Google Scholar · View at Scopus
  3. S. P. Valappil, S. K. Misra, A. Boccaccini, and I. Roy, “Biomedical applications of polyhydroxyalkanoates, an overview of animal testing and in vivo responses,” Expert Review of Medical Devices, vol. 3, no. 6, pp. 853–868, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. A. J. Anderson and E. A. Dawes, “Occurrence, metabolism, metabolic role, and industrial uses of bacterial polyhydroxyalkanoates,” Microbiological Reviews, vol. 54, no. 4, pp. 450–472, 1990.
  5. R. W. Lenz and R. H. Marchessault, “Bacterial polyesters: biosynthesis, biodegradable plastics and biotechnology,” Biomacromolecules, vol. 6, no. 1, pp. 1–8, 2005. View at Publisher · View at Google Scholar · View at Scopus
  6. B. Hazer and A. Steinbüchel, “Increased diversification of polyhydroxyalkanoates by modification reactions for industrial and medical applications,” Applied Microbiology and Biotechnology, vol. 74, no. 1, pp. 1–12, 2007. View at Publisher · View at Google Scholar · View at Scopus
  7. K. Sudesh, H. Abe, and Y. Doi, “Synthesis, structure and properties of polyhydroxy alkanoates: biological polyesters,” Progress in Polymer Science, vol. 25, pp. 1503–1555, 2000.
  8. A. Steinbüchel and B. Füchtenbusch, “Bacterial and other biological systems for polyester production,” Trends in Biotechnology, vol. 16, no. 10, pp. 419–427, 1998. View at Publisher · View at Google Scholar · View at Scopus
  9. D. Y. Kim, W. K. Kim, M. G. Chung, and Y. H. Rhee, “Biosynthesis, modification, and biodegradation of bacterial medium-chain-length polyhydroxyalkanoates,” Journal of Microbiology, vol. 45, no. 2, pp. 87–97, 2007. View at Scopus
  10. R. H. Marchessault, “Polyhydroxyalkanoate (PHA) History at Syracuse University and Beyond,” Cellulose, vol. 16, pp. 357–359, 2009.
  11. W. J. Orts, G. A. R. Nobes, J. Kawada, S. Nguyen, G.-E. Yu, and F. Ravenelle, “Poly(hydroxyalkanoates): biorefinery polymers with a whole range of applications. The work of Robert H. Marchessault,” Canadian Journal of Chemistry, vol. 86, no. 6, pp. 628–640, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. M. Zinn, B. Witholt, and T. Egli, “Occurrence, synthesis and medical application of bacterial polyhydroxyalkanoate,” Advanced Drug Delivery Reviews, vol. 53, no. 1, pp. 5–21, 2001. View at Publisher · View at Google Scholar · View at Scopus
  13. Q. Wu, Y. Wang, and G.-Q. Chen, “Medical application of microbial biopolyesters polyhydroxyalkanoates,” Artificial Cells, Blood Substitutes, and Biotechnology, vol. 37, no. 1, pp. 1–12, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. K. Ruth, G. de Roo, T. Egli, and Q. Ren, “Identification of two acyl-CoA synthetases from Pseudomonas putida GPo1: one is located at the surface of polyhydroxyalkanoates granules,” Biomacromolecules, vol. 9, no. 6, pp. 1652–1659, 2008. View at Publisher · View at Google Scholar · View at Scopus
  15. A. Steinbuchel and H. E. Valentin, “Diversity of bacterial polyhydroxyalkanoic acids,” FEMS Microbiology Letters, vol. 128, no. 3, pp. 219–228, 1995. View at Publisher · View at Google Scholar · View at Scopus
  16. S. Förster and M. Antonietti, “Amphiphilic block copolymers in structure-controlled nanomaterial hybrids,” Advanced Materials, vol. 10, no. 3, pp. 195–217, 1998. View at Scopus
  17. N. Hadjichristidis, M. Pitsikalis, S. Pispas, and H. Iatrou, “Polymers with complex architecture by living anionic polymerization,” Chemical Reviews, vol. 101, no. 12, pp. 3747–3792, 2001. View at Publisher · View at Google Scholar · View at Scopus
  18. K. J. Townsend, K. Busse, J. Kressler, and C. Scholz, “Contact angle, WAXS, and SAXS analysis of poly(β-hydroxybutyrate) and poly(ethylene glycol) block copolymers obtained via Azotobacter vinelandii UWD,” Biotechnology Progress, vol. 21, no. 3, pp. 959–964, 2005. View at Publisher · View at Google Scholar · View at Scopus
  19. L. J. R. Foster, “Biosynthesis, properties and potential of natural-synthetic hybrids of polyhydroxyalkanoates and polyethylene glycols,” Applied Microbiology and Biotechnology, vol. 75, no. 6, pp. 1241–1247, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. B. Hazer, “Chemical modification of synthetic and biosynthetic polyesters,” in Biopolymers, A. Steinbuchel, Ed., vol. 10, chapter 6, pp. 181–208, John Wiley & Sons, Weinheim, Germany, 2003.
  21. S. Ilter, B. Hazer, M. Borcakli, and O. Atici, “Graft copolymerisation of methyl methacrylate onto a bacterial polyester containing unsaturated side chains,” Macromolecular Chemistry and Physics, vol. 202, no. 11, pp. 2281–2286, 2001. View at Publisher · View at Google Scholar · View at Scopus
  22. B. Hazer, “Chemical modification of bacterial polyester,” Current Trends in Polymer Science, vol. 7, pp. 131–138, 2002.
  23. B. Cakmakli, B. Hazer, and M. Borcakli, “Poly(styrene peroxide) and poly(methyl methacrylate peroxide) for grafting on unsaturated bacterial polyesters,” Macromolecular Bioscience, vol. 1, no. 8, pp. 348–354, 2001.
  24. B. Hazer, “Poly(β-hydroxynonanoate) and polystyrene or poly(methyl methacrylate) graft copolymers: microstructure characteristics and mechanical and thermal behavior,” Macromolecular Chemistry and Physics, vol. 197, no. 2, pp. 431–441, 1996. View at Scopus
  25. F. Ravenelle and R. H. Marchessault, “One-step synthesis of amphiphilic diblock copolymers from bacterial poly([R]-3-hydroxybutyric acid),” Biomacromolecules, vol. 3, no. 5, pp. 1057–1064, 2002. View at Publisher · View at Google Scholar · View at Scopus
  26. T. D. Hirt, P. Neuenschwander, and U. W. Suter, “Telechelic diols from poly[(R)-3-hydroxybutyric acid] and poly{[(R)-3-hydroxy butyric acid]-co-[(R)-3-hydroxyvaleric acid]},” Macromolecular Chemistry and Physics, vol. 197, no. 5, pp. 1609–1614, 1996. View at Scopus
  27. G. R. Saad, “Calorimetric and dielectric study of the segmented biodegradable poly(ester-urethane)s based on bacterial poly[(R)-3-hydroxybutyrate],” Macromolecular Bioscience, vol. 1, no. 9, pp. 387–396, 2001. View at Scopus
  28. G. R. Saad, Y. J. Lee, and H. Seliger, “Synthesis and characterization of biodegradable poly(ester-urethanes) based on bacterial poly(R-3-hydroxybutyrate),” Journal of Applied Polymer Science, vol. 83, no. 4, pp. 703–718, 2001. View at Publisher · View at Google Scholar · View at Scopus
  29. H. Erduranlı, B. Hazer, and M. Borcakli, “Post polymerization of saturated and unsaturated poly(3-hydroxy alkanoate)s,” Macromolecular Symposia, vol. 269, no. 1, pp. 161–169, 2008. View at Publisher · View at Google Scholar · View at Scopus
  30. B. Hazer, O. Torul, M. Borcakli, R. W. Lenz, R. C. Fuller, and S. D. Goodwin, “Bacterial production of polyesters from free fatty acids obtained from natural oils by Pseudomonas oleovorans,” Journal of Environmental Polymer Degradation, vol. 6, no. 2, pp. 109–113, 1998. View at Scopus
  31. R. D. Ashby and T. A. Foglia, “Poly(hydroxyalkanoate) biosynthesis from triglyceride substrates,” Applied Microbiology and Biotechnology, vol. 49, no. 4, pp. 431–437, 1998. View at Publisher · View at Google Scholar · View at Scopus
  32. K. Fritzsche and R. W. Lenz, “Production of unsaturated polyesters by Pseudomonas oleovorans,” International Journal of Biological Macromolecules, vol. 12, no. 2, pp. 85–91, 1990. View at Publisher · View at Google Scholar · View at Scopus
  33. Y. B. Kim, R. W. Lenz, and R. C. Fuller, “Poly-3-hydroxyalkanoates containing unsaturated repeating units produced by Pseudomonas oleovorans,” Journal of Polymer Science Part A, vol. 33, pp. 1367–1374, 1995.
  34. M. Y. Lee, W. H. Park, and R. W. Lenz, “Hydrophilic bacterial polyesters modified with pendant hydroxyl groups,” Polymer, vol. 41, no. 5, pp. 1703–1709, 2000. View at Publisher · View at Google Scholar · View at Scopus
  35. M. Y. Lee and W. H. Park, “Preparation of bacterial copolyesters with improved hydrophilicity by carboxylation,” Macromolecular Chemistry and Physics, vol. 201, no. 18, pp. 2771–2774, 2000. View at Scopus
  36. D. J. Stigers and G. N. Tew, “Poly(3-hydroxyalkanoate)s functionalized with carboxylic acid groups in the side chain,” Biomacromolecules, vol. 4, no. 2, pp. 193–195, 2003. View at Publisher · View at Google Scholar · View at Scopus
  37. M. S. Eroglu, B. Hazer, T. Ozturk, and T. Caykara, “Hydroxylation of pendant vinyl groups of poly(3-hydroxy undec-10-enoate) in high yield,” Journal of Applied Polymer Science, vol. 97, no. 5, pp. 2132–2139, 2005. View at Publisher · View at Google Scholar · View at Scopus
  38. E. Renard, A. Poux, L. Timbart, V. Langlois, and P. Guérin, “Preparation of a novel artificial bacterial polyester modified with pendant hydroxyl groups,” Biomacromolecules, vol. 6, no. 2, pp. 891–896, 2005. View at Publisher · View at Google Scholar · View at Scopus
  39. D. M. Zhang, F. Z. Cui, Z. S. Luo, Y. B. Lin, K. Zhao, and G. Q. Chen, “Wettability improvement of bacterial polyhydroxyalkanoates via ion implantation,” Surface and Coatings Technology, vol. 131, pp. 350–354, 2000.
  40. M.-M. Bear, M.-A. Leboucher-Durand, V. Langlois, R. W. Lenz, S. Goodwin, and P. Guerin, “Bacterial poly-3-hydroxyalkenoates with epoxy groups in the side chains,” Reactive and Functional Polymers, vol. 34, no. 1, pp. 65–77, 1997. View at Scopus
  41. M. Y. Lee, S. Y. Cha, and W. H. Park, “Crosslinking of microbial copolyesters with pendant epoxide groups by diamine,” Polymer, vol. 40, no. 13, pp. 3787–3793, 1999. View at Publisher · View at Google Scholar · View at Scopus
  42. J. Sparks and C. Scholz, “Synthesis and characterization of a cationic Poly(β-hydroxyalkanoate),” Biomacromolecules, vol. 9, no. 8, pp. 2091–2096, 2008. View at Publisher · View at Google Scholar · View at Scopus
  43. A. H. Arkin, B. Hazer, and M. Borcakli, “Chlorination of poly(3-hydroxy alkanoates) containing unsaturated side chains,” Macromolecules, vol. 33, no. 9, pp. 3219–3223, 2000. View at Publisher · View at Google Scholar · View at Scopus
  44. A. H. Arkin and B. Hazer, “Chemical modification of chlorinated microbial polyesters,” Biomacromolecules, vol. 3, no. 6, pp. 1327–1335, 2002. View at Publisher · View at Google Scholar · View at Scopus
  45. G. Yu, F. G. Morin, G. A. R. Nobes, and R. H. Marchessault, “Degree of acetylation of chitin and extent of grafting PHB on chitosan determined by solid state 15N NMR,” Macromolecules, vol. 32, no. 2, pp. 518–520, 1999. View at Publisher · View at Google Scholar · View at Scopus
  46. H. Arslan, B. Hazer, and S. C. Yoon, “Grafting of poly(3-hydroxyalkanoate) and linoleic acid onto chitosan,” Journal of Applied Polymer Science, vol. 103, no. 1, pp. 81–89, 2007. View at Publisher · View at Google Scholar · View at Scopus
  47. S. Muthukrishnan, G. Jutz, X. André, H. Mori, and A. H. E. Müller, “Synthesis of hyperbranched glycopolymers via self-condensing atom transfer radical copolymerization of a sugar-carrying acrylate,” Macromolecules, vol. 38, no. 1, pp. 9–18, 2005. View at Publisher · View at Google Scholar · View at Scopus
  48. M. Constantin, C. I. Simionescu, A. Carpov, E. Samain, and H. Driguez, “Chemical modification of poly(hydroxyalkanoates). Copolymers bearing pendant sugars,” Macromolecular Rapid Communications, vol. 20, no. 2, pp. 91–94, 1999. View at Scopus
  49. Y. B. Kim, R. W. Lenz, and R. C. Fuller, “Poly(β-hydroxyalkanoate) copolymers containing brominated repeating units produced by Pseudomonas oleovorans,” Macromolecules, vol. 25, no. 7, pp. 1852–1857, 1992. View at Scopus
  50. B. Hazer, R. W. Lenz, B. Çakmaklı, M. Borcaklı, and H. Koçer, “Preparation of poly(ethylene glycol) grafted poly(3-hydroxyalkanoate) networks,” Macromolecular Chemistry and Physics, vol. 200, no. 8, pp. 1903–1907, 1999. View at Scopus
  51. B. Hazer, “Poly(β-hydroxynonanoate) and polystyrene or poly(methyl methacrylate) graft copolymers: microstructure characteristics and mechanical and thermal behavior,” Macromolecular Chemistry and Physics, vol. 197, no. 2, pp. 431–441, 1996. View at Scopus
  52. S. Ilter, B. Hazer, M. Borcakli, and O. Atici, “Graft copolymerisation of methyl methacrylate onto a bacterial polyester containing unsaturated side chains,” Macromolecular Chemistry and Physics, vol. 202, no. 11, pp. 2281–2286, 2001. View at Publisher · View at Google Scholar · View at Scopus
  53. H. W. Kim, C. W. Chung, and Y. H. Rhee, “UV-induced graft copolymerization of monoacrylate-poly(ethylene glycol) onto poly(3-hydroxyoctanoate) to reduce protein adsorption and platelet adhesion,” International Journal of Biological Macromolecules, vol. 35, no. 1-2, pp. 47–53, 2005. View at Publisher · View at Google Scholar · View at Scopus
  54. C. W. Chung, H. W. Kim, Y. B. Kim, and Y. H. Rhee, “Poly(ethylene glycol)-grafted poly(3-hydroxyundecenoate) networks for enhanced blood compatibility,” International Journal of Biological Macromolecules, vol. 32, no. 1-2, pp. 17–22, 2003. View at Publisher · View at Google Scholar · View at Scopus
  55. H. W. Kim, M. G. Chung, Y. B. Kim, and Y. H. Rhee, “Graft copolymerization of glycerol 1,3-diglycerolate diacrylate onto poly(3-hydroxyoctanoate) to improve physical properties and biocompatibility,” International Journal of Biological Macromolecules, vol. 43, no. 3, pp. 307–313, 2008. View at Publisher · View at Google Scholar · View at Scopus
  56. S. Domenek, V. Langlois, and E. Renard, “Bacterial polyesters grafted with poly(ethylene glycol): behaviour in aqueous media,” Polymer Degradation and Stability, vol. 92, no. 7, pp. 1384–1392, 2007. View at Publisher · View at Google Scholar · View at Scopus