Preparation of biodegradable networks by photo-crosslinking lactide, ε-caprolactone and trimethylene carbonate-based oligomers functionalized with fumaric acid monoethyl ester

Biomaterials

Volumn 26, Issue 16, 2005, Pages 2795-2802

  Grijpma, Dirk W ^a   Hou, Qingpu ^a   Feijen, Jan ^a  

^a Faculty of Science and Technology   (Netherlands)

Author keywords

Biodegradable networks; Fumaric acid monoethyl ester; Oligomer functionalization; Photo crosslinking

Indexed keywords

BENIGN DEGRADATION; FUMARIC ACIDS; NON-TOXIC COMPOUNDS; PHOTO-CROSSLINKING LACTIDES;

BIODEGRADATION; BIOMEDICAL ENGINEERING; CROSSLINKING; OLIGOMERS; ORGANIC ACIDS; POLYMERIZATION; TISSUE;

ESTERS;

CARBONIC ACID; CYCLOPROPANE; FUMARIC ACID ETHYL ESTER; LACTONE DERIVATIVE; OLIGOMER;

ARTICLE; BIODEGRADABILITY; CHEMICAL REACTION; CROSS LINKING; DEGRADATION; OLIGOMERIZATION; PHYSICAL CHEMISTRY; POLYMER PRODUCTION; PRIORITY JOURNAL; ROOM TEMPERATURE; TEMPERATURE DEPENDENCE; TISSUE ENGINEERING; ULTRAVIOLET RADIATION;

4-AMINOPYRIDINE; BIOCOMPATIBLE MATERIALS; BIODEGRADATION, ENVIRONMENTAL; CROSS-LINKING REAGENTS; DICYCLOHEXYLCARBODIIMIDE; DIOXANES; FREE RADICALS; FUMARATES; GLASS; HEXANOIC ACIDS; LACTONES; LIGHT; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, SCANNING; MODELS, CHEMICAL; POLYESTERS; POLYMERS; TEMPERATURE; TENSILE STRENGTH; TISSUE ENGINEERING; ULTRAVIOLET RAYS;

EID: 10644237198     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2004.08.002     Document Type: Article

References (30)

1. R.F. Storey, S.C. Warren, C.J. Allison, J.S. Wiggins, and A.D. Puckett Synthesis of bioabsorbable networks from methacrylate-endcapped polyesters Polymer 34 1993 4365 4372
2. A.S. Sawhney, C.P. Pathak, and J.A. Hubbell Bioerodible hydrogels based on photopolymerized poly(ethylene glycol)-co-poly(alpha-hydroxy acid) diacrylate macromers Macromolecules 26 1993 581 587
3. M.P.K. Turunen, H. Korhonen, J. Tuominen, and J.V. Seppälä Synthesis, characterization and crosslinking of functional star-shaped poly(-caprolactone) Polym Int 51 2001 92 100
4. J.A. Hubbell In situ material transformations in tissue engineering MRS Bull. 21 1996 33 35
5. K.S. Anseth, and J.A. Burdick New directions in photopolymerizable biomaterials MRS Bull. 27 2002 130 136
6. J.A. Burdick, L.M. Philpott, and K.S. Anseth Synthesis and chracterization of tetrafunctional lactic acid oligomers a potential in situ forming degradable orthopaedic biomaterial J Polym Sci A Polym Chem 39 2001 683 692
7. K.T. Nguyen, and J.L. West Photopolymerizable hydrogels for tissue engineering applications Biomaterials 23 2002 4307 4314
8. J. Elisseeff, K. Anseth, D. Sims, W. McIntosh, M. Randolph, and R. Langer Transdermal photopolymerization for minimally invasive implantation Proc Natl Acad Sci 96 1999 3104 3107
9. M.N. Cooke, J.P. Fisher, D. Dean, C. Rimnac, and A.G. Mikos Use of stereolithography to manufacture critical-sized 3D biodegradable scaffolds for bone ingrowth J Biomed Mater Res B Appl Biomater 64B 2002 65 69
10. K. Itoga, M. Yamamoto, J. Kobayashi, A. Kikuchi, and T. Okano Cell micropatterning using photopolymerization with a liquid crystal device commercial projector Biomaterials 25 2004 2047 2053
11. E. Leclerc, K.S. Furukawa, F. Miyata, Y. Sakai, T. Ushida, and T. Fujii Fabrication of microstructures in photosensitive biodegradable polymers for tissue engineering applications Biomaterials 25 2004 4683 4690
12. T. Matsuda, M. Mizutani, and S.C. Arnold Molecular design of photocurable liquid biodegradable copolymers. 1. Synthesis and photocuring characteristics Macromolecules 33 2000 795 800
13. T. Matsuda, and T. Magoshi Preparation of vinylated polysaccharides and photofabrication of tubular scaffolds as potential use in tissue engineering Biomacromolecules 3 2002 942 950
14. M. Mizutani, S.C. Arnold, and T. Matsuda Liquid, phenylazide-end-capped copolymers of epsilon-caprolactone and trimethylene carbonate Preparation, photocuring characteristics, and surface layering Biomacromolecules 3 2002 668 675
15. H. Shin, J.S. Temenoff, and A.G. Mikos In vitro cytotoxicity of unsaturated oligo[poly(ethylene glycol) fumarate] macromers and their crosslinked hydrogels Biomacromolecules 4 2003 552 560
16. A.J. Domb, E. Mathiowitz, E. Ron, S. Giannos, and R. Langer Polyanhydrides IV. Unsaturated and crosslinked polyanhydrides J Polym Sci A Polym Chem Edn 29 1991 571 579
17. R.F. Storey, S.C. Warren, C.J. Allison, and A.D. Puckett Methacrylate-endcapped poly(d,l-lactide-co-trimethylene carbonate) oligomers. Network formation by thermal free-radical curing Polymer 38 1997 6295 6301
18. S. He, M.D. Timmer, M.J. Yaszemski, A.W. Yasko, P.S. Engel, and A.G. Mikos Synthesis of biodegradable poly(propylene fumarate) networks with poly(propylene fumarate)-diacrylate macromers as crosslinking agents and characterization of their degradation products Polymer 42 2001 1251 1260
19. J.P. Fisher, M.D. Timmer, T.A. Holland, D. Dean, P.S. Engel, and A.G. Mikos Photoinitiated cross-linking of the biodegradable polyester poly(propylene fumarate). Part 1. Determination of network structure Biomacromolecules 4 2003 1327 1334
20. Y.K. Han, P.G. Edelman, and S.J. Huang Synthesis and characterization of crosslinked polymers for biomedical composites J Macromol Sci Chem A25 1988 847 869
21. A.K. Shung, M.D. Timmer, S. Jo, P.S. Engel, and A.G. Mikos Kinetics of poly(propylene fumarate synthesis by step polymerization of diethyl fumarate and propylene glycol using zinc chloride as a catalyst J Biomater Sci Polym Edn 13 2002 95 108
22. M. Lang, and C.C. Chu Functionalized multiarm poly(-caprolactone)s synthesis, structure analysis, and network formation J Appl Polym Sci 86 2002 2296 2306
23. S.J. Peter, M.J. Yaszemski, L.J. Suggs, R.G. Payne, R. Langer, W.C. Hayes, M.R. Unroe, L.B. Alemany, P.S. Engel, and A.G. Mikos Characterization of partially saturated poly(propylene fumarate) for orthopaedic application J Biomater Sci Polym Edn 8 1997 893 904
24. S.J. Peter, L.J. Suggs, M.J. Yaszemski, P.S. Engel, and A.G. Mikos Synthesis of poly(propylene fumarate) by acylation of propylene glycol in the presence of a proton scavenger J Biomater Sci Polym Edn 10 1999 363 373
25. A. Hassner, and V. Alexanian Direct room temperature esterification of carboxylic acids Tetrahedron Lett 46 1978 4475 4478
26. S.J. Bryant, C.R. Nuttelman, and K.S. Anseth Cytocompatibility of UV and visible light photoinitiating systems on cultured NIH/3T3 fibroblasts in vitro J Biomater Sci Polym Edn 11 2000 439 457
27. A.P. Pêgo, A.A. Poot, D.W. Grijpma, and J. Feijen Copolymers of trimethylene carbonate and -caprolactone for porous nerve guides synthesis and properties J Biomater Sci Polym Edn 12 2001 35 53
28. A.P. Pêgo, A.A. Poot, D.W. Grijpma, and J. Feijen Physical properties of high molecular weight 1,3-trimethylene carbonate and d,l-lactide copolymers J Mater Sci Mater Med 14 2003 767 773
29. J.P. Fisher, T.A. Holland, D. Dean, P.S. Engel, and A.G.J. Mikos Synthesis and properties of photocross-linked poly(propylene fumarate) scaffolds J Biomater Sci Polym Edn 12 2001 673 687
30. J.A. Burdick, D. Frankel, W.S. Dernell, and K.S. Anseth An initial investigation of photocurable three-dimensional lactic acid based scaffolds in a critical-sized cranial defect Biomaterials 24 2003 1613 1620