Progress in Functionalized Biodegradable Polyesters

Natural and Synthetic Biomedical Polymers

Volumn , Issue , 2014, Pages 167-180

  Heiny, Markus ^a   Wurth, Jonathan Johannes ^a   Shastri, Venkatram Prasad ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Biocompatibility; Copolymerization; Endcapping; Functionalization; PCL; PGA; PLA; Polyesters; ROP; Surface Modification

Indexed keywords

EID: 84902936214     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-396983-5.00009-0     Document Type: Chapter

References (77)

1. Tschan M.J.-L., Brulé E., Haquette P., Thomas C.M. Synthesis of biodegradable polymers from renewable resources. Polym. Chem. 2012, 3:836. 10.1039/c2py00452f.
2. Mülhaupt R. Green polymer chemistry and bio-based plastics: dreams and reality. Macromol. Chem. Phys. 2013, 214:159-174. 10.1002/macp.201200439.
3. Amass W., Amass A., Tighe B. A review of biodegradable polymers: uses, current developments in the synthesis and characterization of biodegradable polyesters, blends of biodegradable polymers and recent advances in biodegradation studies. Polym. Int. 1998, 47:89-144. 10.1002/(sici)1097-0126(1998100)47:2<89::aid-pi86>3.0.co;2-f.
4. Anscombe A.R., Hira N., Hunt B. The use of a new absorbable suture material (polyglycolic acid) in general surgery. Br. J. Surg. 1970, 57:917-920. 10.1002/bjs.1800571212.
5. Athanasiou K.A., Agrawal C.M., Barber F.A., Burkhart S.S. Orthopaedic applications for PLA-PGA biodegradable polymers. Arthroscopy 1998, 14:726-737. 10.1016/s0749-8063(98)70099-4.
6. Kumari A., Yadav S.K., Yadav S.C. Biodegradable polymeric nanoparticles based drug delivery systems. Colloids Surf. B: Biointerfaces 2010, 75:1-18. 10.1016/j.colsurfb.2009.09.001.
7. Gunatillake P.A., Adhikari R. Biodegradable synthetic polymers for tissue engineering. Eur. Cells Mater. 2003, 5:1-16.
8. Armentano I., Dottori M., Fortunati E., Mattioli S., Kenny J.M. Biodegradable polymer matrix nanocomposites for tissue engineering: a review. Polym. Degrad. Stab. 2010, 95:2126-2146. 10.1016/j.polymdegradstab.2010.06.007.
9. Hiljanen-Vainio M., Varpomaa P., Seppälä J., Törmälä P. Modification of poly(L-lactides) by blending: mechanical and hydrolytic behavior. Macromol. Chem. Phys. 1996, 197:1503-1523. 10.1002/macp.1996.021970427.
10. Langer R., Anseth K.S., Shastri V.R. Photopolymerizable degradable polyanhydrides with osteocompatibility. Nat. Biotechnol. 1999, 17:156-159. 10.1038/6152.
11. Rosen H.B., Chang J., Wnek G.E., Linhardt R.J., Langer R. Bioerodible polyanhydrides for controlled drug delivery. Biomaterials 1983, 4:131-133. 10.1016/0142-9612(83)90054-6.
12. Sant S., Iyer D., Gaharwar A.K., Patel A., Khademhosseini A. Effect of biodegradation and de novo matrix synthesis on the mechanical properties of valvular interstitial cell-seeded polyglycerol sebacate-polycaprolactone scaffolds. Acta Biomater. 2013, 9:5963-5973. 10.1016/j.actbio.2012.11.014.
13. Punet X., et al. Enhanced cell-material interactions through the biofunctionalization of polymeric surfaces with engineered peptides. Biomacromolecules 2013, 14:2690-2702. 10.1021/bm4005436.
14. Patel N. Spatially controlled cell engineering on biodegradable polymer surfaces. J. Federation Am. Soc. Exp. Biol. 1998, 1(2):1447-1454.
15. Wang A.Z., Langer R., Farokhzad O.C. Nanoparticle delivery of cancer drugs. Annu. Rev. Med. 2012, 63:185-198. 10.1146/annurev-med-040210-16254.
16. Ravi S., Chaikof E.L. Biomaterials for vascular tissue engineering. Regen. Med. 2010, 5:107-120. 10.2217/rme.09.77.
17. Kolandaivelu K., et al. Stent thrombogenicity early in high-risk interventional settings is driven by stent design and deployment and protected by polymer-drug coatings. Circulation 2011, 123:1400-1409. 10.1161/circulationaha.110.003210.
18. Niklason L.E. Functional arteries grown in vitro. Science 1999, 284:489-493. 10.1126/science.284.5413.489.
19. Poh M., et al. Blood vessels engineered from human cells. Lancet 2005, 365:2122-2124. 10.1016/s0140-6736(05)66735-9.
20. Xu X.-J., Sy J.C., Shastri V.P. Towards developing surface eroding poly(α-hydroxy acids). Biomaterials 2006, 27:3021-3030. 10.1016/j.biomaterials.2005.12.006.
21. Sawhney A.S., Pathak C.P., Hubbell J.A. Bioerodible hydrogels based on photopolymerized poly(ethylene glycol)-co-poly(.alpha.-hydroxy acid) diacrylate macromers. Macromolecules 1993, 26:581-587. 10.1021/ma00056a005.
22. Gref R., et al. Biodegradable long-circulating polymeric nanospheres. Science 1994, 263:1600-1603. 10.1126/science.8128245.
23. Carothers W.H., Dorough G.L., Van Natta F.J. Studies of polymerization and ring formation. X. The reversible polymerization of six-membered cyclic esters. J. Am. Chem. Soc. 1932, 54:761-772.
24. Pillai C.K.S., Sharma C.P. Review paper: absorbable polymeric surgical sutures: chemistry, production, properties, biodegradability, and performance. J. Biomater. Appl. 2010, 25:291-366. 10.1177/0885328210384890.
25. Fredenberg S., Wahlgren M., Reslow M., Axelsson A. The mechanisms of drug release in poly(lactic-co-glycolic acid)-based drug delivery systems-a review. Int. J. Pharm. 2011, 415:34-52. 10.1016/j.ijpharm.2011.05.049.
26. Mahmoudifar N., Doran P.M. Chondrogenic differentiation of human adipose-derived stem cells in polyglycolic acid mesh scaffolds under dynamic culture conditions. Biomaterials 2010, 31:3858-3867. 10.1016/j.biomaterials.2010.01.090.
27. Vaidya A.N., et al. Production and recovery of lactic acid for polylactide-an overview. Crit. Rev. Environ. Sci. Technol. 2005, 35:429-467. 10.1080/10643380590966181.
28. Saha B.C., Woodward J. ACS Symposium Series 1997, American Chemical Society, Washington, DC.
29. Albertsson A.-C., Varma I.K. Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules 2003, 4:1466-1486. 10.1021/bm034247a.
30. Makiguchi K., Kikuchi S., Satoh T., Kakuchi T. Synthesis of block and end-functionalized polyesters by triflimide-catalyzed ring-opening polymerization of ε-caprolactone, 1,5-dioxepan-2-one, and rac -lactide. J. Polym. Sci. A Polym. Chem. 2012, 51:2455-2463. 10.1002/pola.26631.
31. Bernard K., Degée P., Dubois P. Regioselective end-functionalization of polylactide oligomers with D-glucose and D-galactose. Polym. Int. 2003, 52:406-411. 10.1002/pi.1050.
32. Vuorinen S., et al. Sugar end-capped poly-d, l-lactides as excipients in oral sustained release tablets. AAPS PharmSciTech 2009, 10:566-573. 10.1208/s12249-009-9247-9.
33. Cross A.J., Davidson M.G., García-Vivó D., James T.D. Well- controlled synthesis of boronic-acid functionalised poly(lactide)s: a versatile platform for biocompatible polymer conjugates and sensors. RSC Adv. 2012, 2:5954. 10.1039/c2ra20373a.
34. Yu D.-H., Lu Q., Xie J., Fang C., Chen H.-Z. Peptide-conjugated biodegradable nanoparticles as a carrier to target paclitaxel to tumor neovasculature. Biomaterials 2010, 31:2278-2292. 10.1016/j.biomaterials.2009.11.047.
35. Dorff G., Hahn M., Laschewsky A., Lieske A. Optimization of the property profile of poly-L-lactide by synthesis of PLLA- polystyrene-block copolymers. J. Appl. Polym. Sci. 2013, 127:120-126. 10.1002/app.37836.
36. Vert M. Biomedical polymers from chiral lactides and functional lactones: properties and applications. Makromol. Chem. Macromol. Symp. 1986, 6:109-122. 10.1002/masy.19860060113.
37. Kimura Y., Shirotani K., Yamane H., Kitao T. Ring-opening polymerization of 3(S)-[(benzyloxycarbonyl)methyl]-1,4-dioxane- 2,5-dione: a new route to a poly(alpha-hydroxy acid) with pendant carboxyl groups. Macromolecules 1988, 21:3338-3340. 10.1021/ma00189a037.
38. Gerhardt W.W., et al. Functional lactide monomers: methodology and polymerization. Biomacromolecules 2006, 7:1735-1742. 10.1021/bm060024j.
39. in't Veld P.J.A., Dijkstra P.J., Feijen J. Synthesis of biodegradable polyesteramides with pendant functional groups. Makromol. Chem. 1992, 193:2713-2730. 10.1002/macp.1992.021931101.
40. Barrera D.A., Zylstra E., Lansbury P.T., Langer R. Synthesis and RGD peptide modification of a new biodegradable copolymer: poly(lactic acid-co-lysine). J. Am. Chem. Soc. 1993, 115:11010-11011. 10.1021/ja00076a077.
41. Pang Z., et al. Controllable ring-opening copolymerization of L-lactide and (3S)-benzyloxymethyl-(6S)-methyl-morpholine-2,5-dione initiated by a biogenic compound creatinine acetate. J. Polym. Sci. A Polym. Chem. 2012, 50:4004-4009. 10.1002/pola.26196.
42. Chen W., et al. Versatile synthesis of functional biodegradable polymers by combining ring-opening polymerization and postpolymerization modification via Michael-type addition reaction. Macromolecules 2010, 43:201-207. 10.1021/ma901897y.
43. Chiu F.-C., Wang S.-W., Peng K.-Y., Lee R.-S. Synthesis and characterization of amphiphilic PLA-(PαN3CL-g-PBA) copolymers by ring-opening polymerization and click reaction. Polymer 2012, 53:3476-3484. 10.1016/j.polymer.2012.06.004.
44. V.P. Shastri, Biodegradable Polymers from Derivatized Ring-Opened Epoxides. US 6730772, 2004.
45. R.M. Rasal, B.G. Bohannon, D.E. Hirt, Effect of the photoreaction solvent on surface and bulk properties of poly(lactic acid) and poly(hydroxyalkanoate) films, 2008. http://onlinelibrary.wiley.com/store/10.1002/jbm.b.30980/asset/30980_ftp.pdf?v=1&t=hiypzu7h&s=c97c4765807e96c50836e74d93bfa1a4fc25c8bf.
46. Guo B., Finne-Wistrand A., Albertsson A.-C. Electroactive hydrophilic polylactide surface by covalent modification with tetraaniline. Macromolecules 2012, 45:652-659. 10.1021/ma202508h.
47. Yang J., et al. Enhancing the cell affinity of macroporous poly(L-lactide) cell scaffold by a convenient surface modification method. Polym. Int. 2003, 52:1892-1899. 10.1002/pi.1272.
48. T.G. Kim, T.G. Park, Biodegradable polymer nanocylinders fabricated by transverse fragmentation of electrospun nanofibers through aminolysis, 2008. http://onlinelibrary.wiley.com/store/10.1002/marc.200800094/asset/1231_ftp.pdf?v=1&t=hizo7uah&s=72268303b8d3d5c4574c6f44b82c42b7889f7c2a.
49. Zhu Y., Gao C., Liu X., He T., Shen J. Immobilization of biomacromolecules onto aminolyzed poly(L-lactic acid) toward acceleration of endothelium regeneration. Tissue Eng. 2004, 10:53-61. 10.1089/107632704322791691.
50. Xu F.J., Yang X.C., Li C.Y., Yang W.T. Functionalized polylactide film surfaces via surface-initiated ATRP. Macromolecules 2011, 44:2371-2377. 10.1021/ma200160h.
51. Saulnier B., Ponsart S., Coudane J., Garreau H., Vert M. Lactic acid-based functionalized polymers via copolymerization and chemical modification. Macromol. Biosci. 2004, 4:232-237. 10.1002/mabi.200300087.
52. Barakat I., Dubois P., Grandfils C., Jérôme R. Poly(e-caprolactone-b-glycolide) and poly(D, L-lactide-b-glycolide) diblock copolyesters: controlled synthesis, characterization, and colloidal dispersions. J. Polym. Sci. A Polym. Chem. 2001, 39:294-306. 10.1002/1099-0518(20010115)39:2<294::aid-pola50>3.0.co;2-a.
53. Jiang X., Vogel E.B., Smith M.R., Baker G.L. "Clickable" polyglycolides: tunable synthons for thermoresponsive, degradable polymers. Macromolecules 2008, 41:1937-1944. 10.1021/ma7027962.
54. Lee K.-B., Yoon K.R., Woo S.I., Choi I.S. Surface modification of poly(glycolic acid) (PGA) for biomedical applications. J. Pharm. Sci. 2003, 92:933-937. 10.1002/jps.10556.
55. Wei Y., et al. A novel sustained-release formulation of recombinant human growth hormone and its pharmacokinetic. Pharmacodyn. Safety Profiles Mol. Pharm. 2012, 9:2039-2048. 10.1021/mp300126t.
56. Farokhzad O.C., et al. Targeted nanoparticle-aptamer bioconjugates for cancer chemotherapy in vivo. Proc. Natl. Acad. Sci. U.S.A. 2006, 103:6315-6320. 10.1073/pnas.0601755103.
57. Labet M., Thielemans W. Synthesis of polycaprolactone: a review. Chem. Soc. Rev. 2009, 38:3484-3504. 10.1039/b820162p.
58. Woodruff M.A., Hutmacher D.W. The return of a forgotten polymer-polycaprolactone in the 21st century. Prog. Polym. Sci. 2010, 35:1217-1256. 10.1016/j.progpolymsci.2010.04.002.
59. Mark J.E. Polymer Data Handbook 1999, Oxford University Press, New York.
60. Kammerer M., et al. Valproate release from polycaprolactone implants prepared by 3D-bioplotting. Pharmazie 2011, 66:511-516. 10.1691/ph.2011.0882.
61. Carrot G., Hilborn J.G., Trollsås M., Hedrick J.L. Two general methods for the synthesis of thiol-functional polycaprolactones. Macromolecules 1999, 32:5264-5269. 10.1021/ma990198b.
62. Wurth J.J., Shasti V.P. Synthesis and characterization of functionalized poly(ε-caprolactone). J. Polym. Sci. 2013, 51:3375-3382. 10.1002/pola.26734.
63. Cho K.Y., Park J.-K. Synthesis and characterization of poly(ethylene glycol) grafted poly(ε-caprolactone). Polym. Bull. 2006, 57:549-856. 10.1007/s00289-006-0658-4.
64. Habnouni S.E., Blanquer S., Darcos V., Coudane J., El Habnouni S. Aminated PCL-based copolymers by chemical modification of poly(α-iodo-ε-caprolactone- co -ε-caprolactone). Polymer 2009, 47:6104-6115. 10.1002/pola.23652.
65. Parrish B., Breitenkamp R.B., Emrick T. PEG- and peptide- grafted aliphatic polyesters by click chemistry. J. Am. Chem. Soc. 2005, 127:7404-7410. 10.1021/ja050310n.
66. Xu L., et al. Synthesis, characterization, and self-assembly of linear poly(ethylene oxide)-block-poly(propylene oxide)-block-poly(ε-caprolactone) (PEO-PPO-PCL) copolymers. J. Colloid Interface Sci. 2013, 393:174-181. 10.1016/j.jcis.2012.10.051.
67. Liu L., Chen L., Fang Y.E. Self-catalysis of phthaloylchitosan for graft copolymerization of ε-caprolactone with chitosan. Macromol. Rapid Commun. 2006, 27:1988-1994. 10.1002/marc.200600508.
68. Cai Q., Bei J., Wang S. Synthesis and properties of ABA-type triblock copolymers of poly(glycolide-co-caprolactone) (A) and poly(ethylene glycol) (B). Polymer 2002, 43:3585-3591. 10.1016/S0032-3861(02)00197-0.
69. Huang M.-H., Li S., Coudane J., Vert M. Synthesis and characterization of block copolymers of ε-caprolactone and DL-lactide initiated by ethylene glycol or poly(ethylene glycol). Macromol. Chem. Phys. 2003, 204:1994-2001. 10.1002/macp.200350054.
70. Srisa-ard M., Molloy R., Molloy N., Siripitayananon J., Sriyai M. Synthesis and characterization of a random terpolymer of l-lactide, ε-caprolactone and glycolide. Polym. Int. 2001, 50:891-896. 10.1002/pi.713.
71. Lou X., Detrembleur C., Jérôme R. Novel aliphatic polyesters based on functional cyclic (di)esters. Macromol. Rapid Commun. 2003, 24:161-172. 10.1002/marc.200390029.
72. Lecomte P., et al. New prospects for the grafting of functional groups onto aliphatic polyesters. Ring-opening polymerization of α- or γ-substituted ε-caprolactone followed by chemical derivatization of the substituents. Macromol. Symp. 2006, 240:157-165. 10.1002/masy.200650820.
73. Rieger J., et al. Versatile functionalization and grafting of poly(ε-caprolactone) by Michael-type addition. Chemical Commun. 2005, 41:274-276. 10.1039/b411565a.
74. Vert M. Aliphatic polyesters: great degradable polymers that cannot do everything. Biomacromolecules 2005, 6:538-546. 10.1021/bm0494702.
75. Lenz R.W., Marchessault R.H. Bacterial polyesters: biosynthesis. Biodegradable Plastics Biotechnol. Biomacromol. 2005, 6:1-8. 10.1021/bm049700c.
76. Poirier Y., Nawrath C., Somerville C. Production of polyhydroxyalkanoates, a family of biodegradable plastics and elastomers, in bacteria and plants. Bio/Technology 1995, 13:142-150. 10.1038/nbt0295-142.
77. Kim Y.B., Lenz R.W., Fuller R.C. Poly(β-hydroxyalkanoate) copolymers containing brominated repeating units produced by Pseudomonas oleovorans. Macromolecules 1992, 25:1852-1857. 10.1021/ma00033a002.