Visible light cured thiol-vinyl hydrogels with tunable degradation for 3D cell culture

Acta Biomaterialia

Volumn 10, Issue 1, 2014, Pages 104-114

  Hao, Yiting ^a   Shih, Han ^a   Muňoz, Zachary ^a   Kemp, Arika ^a   Lin, Chien Chi ^a  

^a Indiana University Purdue University Indianapolis   (United States)

Author keywords

Hydrogels; Mesenchymal stem cells; Photopolymerization; Thiol ene; Visible light

Indexed keywords

CELL CULTURE; DEGRADATION; GELATION; GELS; KINETICS; LIGHT; PHOTOPOLYMERIZATION; PHOTOSENSITIZERS; POLYETHYLENE GLYCOLS; REACTION KINETICS; STIFFNESS;

CROSSLINKER; FUNCTIONALIZED; MACROMERS; MESENCHYMAL STEM CELL; MIXED MODE; N VINYLPYRROLIDONE; PHOTO POLYMERIZATION; THIOL/ENE; TUNABLES; VISIBLE LIGHT;

HYDROGELS;

1 VINYL 2 PYRROLIDINONE; ACRYLAMIDE; EOSIN; MACROGOL; THIOL; TRIETHANOLAMINE; VINYL DERIVATIVE;

ARTICLE; BIOCOMPATIBILITY; CELL CULTURE; CELL ENCAPSULATION; DEGRADATION KINETICS; GELATION; HUMAN; HUMAN CELL; HYDROGEL; HYDROLYSIS; LIGHT; MESENCHYMAL STEM CELL; PHOTOSENSITIZATION; POLYMERIZATION; PRIORITY JOURNAL;

HYDROGELS; MESENCHYMAL STEM CELLS; PHOTOPOLYMERIZATION; THIOL-ENE; VISIBLE LIGHT;

ACRYLATES; CELL CULTURE TECHNIQUES; CELL DIFFERENTIATION; CELL SURVIVAL; CELLS, IMMOBILIZED; HUMANS; HYDROGELS; HYDROLYSIS; LIGHT; MESENCHYMAL STROMAL CELLS; OSTEOGENESIS; POLYETHYLENE GLYCOLS; PYRROLIDINONES; RHEOLOGY; SULFHYDRYL COMPOUNDS;

EID: 84888645365     PISSN: 17427061     EISSN: 18787568     Source Type: Journal    
DOI: 10.1016/j.actbio.2013.08.044     Document Type: Article

References (60)

1. M.C. Cushing, and K.S. Anseth Hydrogel cell cultures Science 316 2007 1133 1134
2. C.C. Lin, and K.S. Anseth PEG hydrogels for the controlled release of biomolecules in regenerative medicine Pharm Res 26 2009 631 643
3. M.B. Mellott, K. Searcy, and M.V. Pishko Release of protein from highly cross-linked hydrogels of poly(ethylene glycol) diacrylate fabricated by UV polymerization Biomaterials 22 2001 929 941
4. B.V. Slaughter, S.S. Khurshid, O.Z. Fisher, A. Khademhosseini, and N.A. Peppas Hydrogels in regenerative medicine Adv Mater 21 2009 3307 3329
5. J. Li, and W.J. Kao Synthesis of polyethylene glycol (PEG) derivatives and PEGylated-peptide blopolymer conjugates Biomacromolecules 4 2003 1055 1067
6. A.S. Sawhney, C.P. Pathak, and J.A. Hubbell Interfacial photopolymerization of poly(ethylene glycol)-based hydrogels upon alginate poly(l-lysine) microcapsules for enhanced biocompatiblity Biomaterials 14 1993 1008 1016
7. L.M. Weber, J. He, B. Bradley, K. Haskins, and K.S. Anseth PEG-based hydrogels as an in vitro encapsulation platform for testing controlled beta-cell microenvironments Acta Biomater 2 2006 1 8
8. S. Lin-Gibson, R.L. Jones, N.R. Washburn, and F. Horkay Structure-property relationships of photopolymerizable poly(ethylene glycol) dimethacrylate hydrogels Macromolecules 38 2005 2897 2902
9. M.B. Browning, T. Wilems, M. Hahn, and E. Cosgriff-Hernandez Compositional control of poly(ethylene glycol) hydrogel modulus independent of mesh size J Biomed Mater Res A 98A 2011 268 273
10. 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 2001 430 441
11. M.B. Browning, and E. Cosgriff-Hernandez Development of a biostable replacement for PEGDA hydrogels Biomacromolecules 13 2012 779 786
12. 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 2003 5413 5418
13. M.P. Lutolf, and J.A. Hubbell Synthetic biomaterials as instructive extracellular microenvironments for morphogenesis in tissue engineering Nat Biotechnol 23 2005 47 55
14. E.A. Phelps, N.O. Enemchukwu, V.F. Fiore, J.C. Sy, N. Murthy, and T.A. Sulchek Maleimide cross-linked bioactive PEG hydrogel exhibits improved reaction kinetics and cross-linking for cell encapsulation and in situ delivery Adv Mater 24 2012 64 70
15. B.D. Fairbanks, M.P. Schwartz, A.E. Halevi, C.R. Nuttelman, C.N. Bowman, and K.S. Anseth A versatile synthetic extracellular matrix mimic via thiol-norbornene photopolymerization Adv Mater 21 2009 5005 5010
16. C.C. Lin, A. Raza, and H. Shih PEG hydrogels formed by thiol-ene photo-click chemistry and their effect on the formation and recovery of insulin-secreting cell spheroids Biomaterials 32 2011 9685 9695
17. J.H. Ward, and N.A. Peppas Preparation of controlled release systems by free-radical UV polymerizations in the presence of a drug J Control Release 71 2001 183 192
18. 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
19. D.L. Hern, and J.A. Hubbell Incorporation of adhesion peptides into nonadhesive hydrogels useful for tissue resurfacing J Biomed Mater Res 39 1998 266 276
20. A. Metters, and J. Hubbell Network formation and degradation behavior of hydrogels formed by Michael-type addition reactions Biomacromolecules 6 2005 290 301
21. C.A. DeForest, B.D. Polizzotti, and K.S. Anseth Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments Nat Mater 8 2009 659 664
22. G.N. Grover, J. Lam, T.H. Nguyen, T. Segura, and H.D. Maynard Biocompatible hydrogels by oxime click chemistry Biomacromolecules 13 2012 3013 3017
23. D.L. Alge, M.A. Azagarsamy, D.F. Donohue, and K.S. Anseth Synthetically tractable click hydrogels for three-dimensional cell culture formed using tetrazine-norbornene chemistry Biomacromolecules 14 2013 949 953
24. J.A. Burdick, and K.S. Anseth Photoencapsulation of osteoblasts in injectable RGD-modified PEG hydrogels for bone tissue engineering Biomaterials 23 2002 4315 4323
25. C.N. Salinas, and K.S. Anseth Mixed mode thiol-acrylate photopolymerizations for the synthesis of PEG-peptide hydrogels Macromolecules 41 2008 6019 6026
26. C.C. Lin, and K.S. Anseth Glucagon-like peptide-1 functionalized PEG hydrogels promote survival and function of encapsulated pancreatic beta-cells Biomacromolecules 10 2009 2460 2467
27. J.L. West, and J.A. Hubbell Polymeric biomaterials with degradation sites for proteases involved in cell migration Macromolecules 32 1999 241 244
28. B.K. Mann, A.S. Gobin, A.T. Tsai, R.H. Schmedlen, and J.L. West Smooth muscle cell growth in photopolymerized hydrogels with cell adhesive and proteolytically degradable domains: synthetic ECM analogs for tissue engineering Biomaterials 22 2001 3045 3051
29. S. Sokic, and G. Papavasiliou Controlled proteolytic cleavage site presentation in biomimetic PEGDA hydrogels enhances neovascularization in vitro Tissue Eng A 18 2012 2477 2486
30. M.V. Turturro, M.C. Christenson, J.C. Larson, D.A. Young, E.M. Brey, and G. Papavasiliou MMP-sensitive PEG diacrylate hydrogels with spatial variations in matrix properties stimulate directional vascular sprout formation PLoS One 8 2013
31. J. Elisseeff, K. Anseth, D. Sims, W. McIntosh, M. Randolph, and R. Langer Transdermal photopolymerization for minimally invasive implantation Proc Natl Acad Sci USA 96 1999 3104 3107
32. 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 2000 439 457
33. C.C. Lin, and K.S. Anseth Controlling affinity binding with peptide-functionalized poly(ethylene glycol) hydrogels Adv Funct Mater 19 2009 2325 2331
34. S. Kizilel, V.H. Perez-Luna, and F. Teymour Photopolymerization of poly(ethylene glycol) diacrylate on eosin-functionalized surfaces Langmuir 20 2004 8652 8658
35. S. Kizilel, E. Sawardecker, F. Teymour, and V.H. Perez-Luna Sequential formation of covalently bonded hydrogel multilayers through surface initiated photopolymerization Biomaterials 27 2006 1209 1215
36. J.P. Fouassier, X. Allonas, and D. Burget Photopolymerization reactions under visible lights: principle, mechanisms and examples of applications Prog Org Coating 47 2003 16 36
37. S. Kizilel, V.H. Perez-Luna, and F. Teymour Mathematical model for surface-initiated photopolymerization of poly(ethylene glycol) diacrylate Macromol Theory Simulat 15 2006 686 700
38. M.V. Turturro, and G. Papavasiliou Generation of mechanical and biofunctional gradients in PEG diacrylate hydrogels by perfusion-based frontal photopolymerization J Biomater Sci Polym Ed 23 2012 917 939
39. S.H. Kim, and C.C. Chu Visible light induced dextran-methacrylate hydrogel formation using (-)-riboflavin vitamin B2 as a photoinitiator and L-arginine as a co-initiator Fibers Polym 10 2009 14 20
40. H. Shih, and C.C. Lin Visible-light-mediated thiol-ene hydrogelation using eosin-Y as the only photoinitiator Macromol Rapid Comm 34 2013 269 273
41. H. Shih, A.K. Fraser, and C.C. Lin Interfacial thiol-ene photoclick reactions for forming multilayer hydrogels ACS Appl Mater Interfaces 5 2013 1673 1680
42. G.M. Cruise, O.D. Hegre, D.S. Scharp, and J.A. Hubbell A sensitivity study of the key parameters in the interfacial photopolymerization of poly(ethylene glycol) diacrylate upon porcine islets Biotechnol Bioeng 57 1998 655 665
43. M.V. Turturro, S. Sokic, J.C. Larson, and G. Papavasiliou Effective tuning of ligand incorporation and mechanical properties in visible light photopolymerized poly(ethylene glycol) diacrylate hydrogels dictates cell adhesion and proliferation Biomed Mater 8 2013
44. S. Lin-Gibson, S. Bencherif, J.A. Cooper, S.J. Wetzel, J.M. Antonucci, and B.M. Vogel Synthesis and characterization of PEG dimethacrylates and their hydrogels Biomacromolecules 5 2004 1280 1287
45. A.E. Rydholm, S.K. Reddy, K.S. Anseth, and C.N. Bowman Development and characterization of degradable thiol-allyl ether photopolymers Polymer 48 2007 4589 4600
46. H. Shih, and C.C. Lin Cross-linking and degradation of step-growth hydrogels formed by thiol-ene photoclick chemistry Biomacromolecules 13 2012 2003 2012
47. S.B. Anderson, C.C. Lin, D.V. Kuntzler, and K.S. Anseth The performance of human mesenchymal stem cells encapsulated in cell-degradable polymer-peptide hydrogels Biomaterials 32 2011 3564 3574
48. C.S. Bahney, T.J. Lujan, C.W. Hsu, M. Bottlang, J.L. West, and B. Johnstone Visible light photoinitiation of mesenchymal stem cell-laden bioresponsive hydrogels Eu Cells Mater 22 2011 43 55
49. S. Kizilel Mathematical model for microencapsulation of pancreatic islets within a biofunctional PEG hydrogel Macromol Theory Simulat 19 2010 514 531
50. R. Kizilel, and S. Kizilel Application of the numerical fractionation approach to the design of biofunctional PEG hydrogel membranes Macromol React Eng 6 2012 160 179
51. S. Colak, and G.N. Tew Synthesis and solution properties of norbornene based polybetaines Macromolecules 41 2008 8436 8440
52. C.A. DeForest, and K.S. Anseth Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions Nat Chem 3 2011 925 931
53. 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 Bioconjug Chem 12 2001 1051 1056
54. 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 2003 713 722
55. S.G. Levesque, and M.S. Shoichet Synthesis of enzyme-degradable, peptide-cross-linked dextran hydrogels Bioconjug Chem 18 2007 874 885
56. M. Risbud, A. Hardikar, and R. Bhonde Growth modulation of fibroblasts by chitosan-polyvinyl pyrrolidone hydrogel: implications for wound management? J Biosci 25 2000 25 31
57. C.M.A. Lopes, and M.I. Felisberti Mechanical behaviour and biocompatibility of poly(1-vinyl-2-pyrrolidinone)-gelatin IPN hydrogels Biomaterials 24 2003 1279 1284
58. L.E. Smith, S. Rimmer, and S. MacNeil Examination of the effects of poly(N-vinylpyrrolidinone) hydrogels in direct and indirect contact with cells Biomaterials 27 2006 2806 2812
59. A. Raza, and C. Lin The Influence of matrix degradation and functionality on cell survival and morphogenesis in PEG-based hydrogels Macromol Biosci 13, 2013, 1048-1058.
60. S. Khetan, M. Guvendiren, W.R. Legant, D.M. Cohen, C.S. Chen, and J.A. Burdick Degradation-mediated cellular traction directs stem cell fate in covalently crosslinked three-dimensional hydrogels Nat Mater 12 2013 458 465