Degradable thiol-acrylate photopolymers: Polymerization and degradation behavior of an in situ forming biomaterial

Biomaterials

Volumn 26, Issue 22, 2005, Pages 4495-4506

  Rydholm, Amber E ^a   Bowman, Christopher N ^a,b   Anseth, Kristi S ^a,c  

^a UCB 450   (United States)

^b UNIVERSITY OF COLORADO   (United States)

^c UNIVERSITY OF COLORADO   (United States)

Author keywords

Hydrolytic degradation; In situ cross linking; Photopolymerization; Poly(ethylene glycol); Thiol acrylate polymerization

Indexed keywords

DEGRADATION; MOLECULAR STRUCTURE; MONOMERS; PHYSIOLOGY; POLYMERIZATION; REACTION KINETICS; ULTRAVIOLET RADIATION;

DEGRADATION PRODUCTS; PHOTOINITIATORS; PHOTOPOLYMERS; REACTION MIXTURES;

BIOMATERIALS;

ACRYLIC ACID; BIOMATERIAL; MONOMER; POLYMER; THIOL;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPRESSIVE STRENGTH; DEGRADATION; LIGHT EXPOSURE; MASS; MOLECULAR WEIGHT; PHOTOREACTIVITY; POLYMERIZATION; PRIORITY JOURNAL;

BIOCOMPATIBLE MATERIALS; MAGNETIC RESONANCE SPECTROSCOPY; MATERIALS TESTING; PHOTOCHEMISTRY; POLYMERS; SULFHYDRYL COMPOUNDS;

EID: 13944255099     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2004.11.046     Document Type: Article

References (48)

1. C.K. Kuo, and P.X. Ma Ionically crosslinked alginate hydrogels as scaffolds for tissue engineering Part 1. Structure, gelation rate and mechanical properties Biomaterials 22 6 2001 511 521
2. Y.L. Cao, C. Ibarra, and C. Vacanti Preparation and use of thermosensitive polymers J.R. Morgan M.L. Yarmush Tissue Engineering Methods and Protocols 1999 Humana Press Totowa, NJ
3. S. Kim, and K.E. Healy Synthesis and characterization of injectable poly(N-isopropylacrylamide-co-acrylic acid) hydrogels with proteolytically degradable cross-links Biomacromolecules 4 5 2003 1214 1223
4. T.H. Chen, H.D. Embree, E.M. Brown, M.M. Taylor, and G.F. Payne Enzyme-catalyzed gel formation of gelatin and chitosan potential for in situ applications Biomaterials 24 17 2003 2831 2841
5. A. Gutowska, B. Jeong, and M. Jasionowski Injectable gels for tissue engineering Anat Rec 263 4 2001 342 349
6. P.J. Martens, S.J. Bryant, and K.S. Anseth Tailoring the degradation of hydrogels formed from multivinyl poly(ethylene glycol) and poly(vinyl alcohol) macromers for cartilage tissue engineering Biomacromolecules 4 2 2003 283 292
7. J.S. Temenoff, H. Park, E. Jabbari, D.E. Conway, T.L. Sheffield, and C.G. Ambrose Thermally cross-linked oligo(poly(ethylene glycol) fumarate) hydrogels support osteogenic differentiation of encapsulated marrow stromal cells in vitro Biomacromolecules 5 1 2004 5 10
8. E. Behravesh, S. Jo, K. Zygourakis, and A.G. Mikos Synthesis of in situ cross-linkable macroporous biodegradable poly(propylene fumarate-co-ethylene glycol) hydrogels Biomacromolecules 3 2 2002 374 381
9. K.T. Nguyen, and J.L. West Photopolymerizable hydrogels for tissue engineering applications Biomaterials 23 22 2002 4307 4314
10. A.K. Burkoth, and K.S. Anseth A review of photocrosslinked polyanhydrides in situ forming degradable networks Biomaterials 21 23 2000 2395 2404
11. K.A. Davis, J.A. Burdick, and K.S. Anseth Photoinitiated crosslinked degradable copolymer networks for tissue engineering applications Biomaterials 24 14 2003 2485 2495
12. 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 4 1993 581 587
13. J. Heller, B.K. Fritzinger, S.Y. Ng, and D.W.H. Penhale In vitro and in vivo release of levonorgestrel from poly(ortho esters) II. Crosslinked polymers J Controlled Rel 1 1985 233 238
14. J.L. West, and J.A. Hubbell Polymeric biomaterials with degradation sites for proteases involved in cell migration Macromolecules 32 1 1999 241 244
15. M.P. Lutolf, G.P. Raeber, A.H. Zisch, N. Tirelli, and J.A. Hubbell Cell-responsive synthetic hydrogels Adv Mater 15 11 2003 888 892
16. M. Kurisawa, M. Terano, and N. Yui Doublestimuli-responsive degradable hydrogels for drug-delivery - interpenetrating polymer networks composed of oligopeptide-terminated poly(ethylene glycol) and dextran Macromol Rapid Commun 16 9 1995 663 666
17. W.N.E. Vandijkwolthuis, O. Franssen, H. Talsma, M.J. Vansteenbergen, J.J.K. Vandenbosch, and W.E. Hennink Synthesis, characterization, and polymerization of glycidyl methacrylate derivatized dextran Macromolecules 28 18 1995 6317 6322
18. M.N. Mason, A.T. Metters, C.N. Bowman, and K.S. Anseth Predicting controlled-release behavior of degradable PLA-b-PEG-b-PLA hydrogels Macromolecules 34 13 2001 4630 4635
19. A.T. Metters, K.S. Anseth, and C.N. Bowman Fundamental studies of a novel, biodegradable PEG-b-PLA hydrogel Polymer 41 11 2000 3993 4004
20. J.S. Temenoff, and A.G. Mikos Injectable biodegradable materials for orthopedic tissue engineering Biomaterials 21 23 2000 2405 2412
21. K.S. Anseth, and D.J. Quick Polymerizations of multifunctional anhydride monomers to form highly crosslinked degradable networks Macromol Rapid Commun 22 8 2001 564 572
22. A.T. Metters, K.S. Anseth, and C.N. Bowman A statistical kinetic model for the bulk degradation of PLA-b-PEG-b-PLA hydrogel networks J Phys Chem B 104 30 2000 7043 7049
23. A. Gopferich Mechanisms of polymer degradation and erosion Biomaterials 17 2 1996 103 114
24. J.S. Temenoff, K.A. Athanasiou, R.G. LeBaron, and A.G. Mikos Effect of poly(ethylene glycol) molecular weight on tensile and swelling properties of oligo(poly(ethylene glycol) fumarate) hydrogels for cartilage tissue engineering J Biomed Mater Res 59 3 2002 429 437
25. A.K. Shung, E. Behravesh, S. Jo, and A.G. Mikos Crosslinking characteristics of and cell adhesion to an injectable poly(propylene fumarate-co-ethylene glycol) hydrogel using a water-soluble crosslinking system Tissue Eng 9 2 2003 243 254
26. B.D. Porter, J.B. Oldham, S.L. He, M.E. Zobitz, R.G. Payne, and K.N. An Mechanical properties of a biodegradable bone regeneration scaffold J Biomech Eng - Trans ASME 122 3 2000 286 288
27. A.T. Metters Investigation of degradable crosslinked hydrogels prediction of degradation behavior (Ph.D.) 2000 University of Colorado Boulder, CO
28. 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 Ed 11 5 2000 439 457
29. D.J. Quick, and K.S. Anseth Gene delivery in tissue engineering a photopolymer platform to coencapsulate cells and plasmid DNA Pharm Res 20 11 2003 1730 1737
30. D.L. Elbert, and J.A. Hubbell Conjugate addition reactions combined with free-radical cross-linking for the design of materials for tissue engineering Biomacromolecules 2 2 2001 430 441
31. D.L. Elbert, A.B. Pratt, M.P. Lutolf, S. Halstenberg, and J.A. Hubbell Protein delivery from materials formed by self-selective conjugate addition reactions J Controlled Rel 76 1-2 2001 11 25
32. M.P. Lutolf, and J.A. Hubbell Synthesis and physicochemical characterization of end-linked poly(ethylene glycol)-co-peptide hydrogels formed by Michael-type addition Biomacromolecules 4 3 2003 713 722
33. M.P. Lutolf, J.L. Lauer-Fields, H.G. Schmoekel, A.T. Metters, F.E. Weber, and G.B. Fields Synthetic matrix metalloproteinase-sensitive hydrogels for the conduction of tissue regeneration engineering cell-invasion characteristics Proc Natl Acad Sci USA 100 9 2003 5413 5418
34. M.P. Lutolf, N. Tirelli, S. Cerritelli, L. Cavalli, and J.A. Hubbell Systematic modulation of Michael-type reactivity of thiols through the use of charged amino acids Bioconjugate Chem 12 6 2001 1051 1056
35. M.P. Lutolf, F.E. Weber, H.G. Schmoekel, J.C. Schense, T. Kohler, and R. Muller Repair of bone defects using synthetic mimetics of collagenous extracellular matrices Nat Biotechnol 21 5 2003 513 518
36. B. Vernon, N. Tirelli, T. Bachi, D. Haldimann, and J.A. Hubbell Water-borne, in situ crosslinked biomaterials from phase-segregated precursors J Biomed Mater Res Part A 64A 3 2003 447 456
37. N.B. Cramer, and C.N. Bowman Kinetics of thiol-ene and thiol-acrylate photopolymerizations with real-time Fourier transform infrared J Polym Sci Part A - Polym Chem 39 19 2001 3311 3319
38. T. Posner Unsaturated compounds II. Addition of mercaptans to unsaturated hydrocarbons. Ber Deut Chem Ges 38 1905 646 657
39. A.F. Jacobine J.D. Fouassier J.F. Rabek Radiation curing in polymer science and technology III, polymerisation mechanisms 1993 Elsevier Applied Science London 219
40. J.G. Woods Radiation curable adhesives S.P. Peppas Radiation curing science and technology 1992 Plenum New York 333 398
41. A.T. Metters, K.S. Anseth, and C.N. Bowman A statistical kinetic model for the bulk degradation of PLA-b-PEG-b-PLA hydrogel networks incorporating network non-idealities J Phys Chem B 105 34 2001 8069 8076
42. Berchtold KA, Bowman CN. In: RadTech Europe 99 conference proceedings, Berlin, Germany, 1999. p. 767.
43. K.A. Berchtold, J. Nie, J.W. Stansbury, B. Hacioglu, E.R. Beckel, and C.N. Bowman Novel monovinyl methacrylic monomers containing secondary functionality for ultrarapid polymerization steady-state evaluation Macromolecules 37 9 2004 3165 3179
44. N.B. Cramer, S.K. Reddy, A.K. O'Brien, and C.N. Bowman Thiol-ene photopolymerization mechanism and rate limiting step changes for various vinyl functional group chemistries Macromolecules 36 21 2003 7964 7969
45. N.B. Cramer, J.P. Scott, and C.N. Bowman Photopolymerizations of thiol-ene polymers without photoinitiators Macromolecules 35 14 2002 5361 5365
46. Hoyle CE, Cole M, Bachemin M, Yoder B, Nguyen C, Kuang W, et al. In: RadTech Japan 2000 technical proceedings, 2000 December, Tokyo, Japan, 2001. p. 211.
47. N.B. Cramer, S.K. Reddy, M. Cole, C.E. Hoyle, and C.N. Bowman Initiation and kinetics of thiol-ene photopolymerizations without photoinitiators J Polym Sci Part A - Polym Chem 2004 in press
48. C.E. Hoyle, R.D. Hensel, and M.B. Grubb Temperature-dependence of the laser-initiated polymerization of a thiol-ene system J Polym Sci Part A - Polym Chem 22 8 1984 1865 1873