Synthesis and orthogonal photopatterning of hyaluronic acid hydrogels with thiol-norbornene chemistry

Biomaterials

Volumn 34, Issue 38, 2013, Pages 9803-9811

  Gramlich, William M ^a   Kim, Iris L ^a   Burdick, Jason A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Biomaterials; Biomechanics; Hyaluronic acid; Hydrogel; Patterning

Indexed keywords

BIOMEDICAL APPLICATIONS; EXTENT OF CROSS-LINKING; HYALURONIC ACID HYDROGELS; MECHANICAL SIGNALS; MICROENVIRONMENTS; ORTHOGONAL CHEMISTRIES; PATTERNING; SECONDARY REACTIONS;

BIOLOGICAL MATERIALS; BIOMATERIALS; BIOMECHANICS; CROSSLINKING; HYALURONIC ACID; MECHANICAL PROPERTIES; MEDICAL APPLICATIONS; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

HYDROGELS;

FLUORESCENT DYE; HYALURONIC ACID; NORBORNENE DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CONFOCAL MICROSCOPY; CROSS LINKING; GELATION; HUMAN; HUMAN CELL; HYDROGEL; MECHANICS; PRIORITY JOURNAL; SYNTHESIS;

BIOMATERIALS; BIOMECHANICS; HYALURONIC ACID; HYDROGEL; PATTERNING;

BIOCOMPATIBLE MATERIALS; CROSS-LINKING REAGENTS; HYALURONIC ACID; HYDROGEL; SULFHYDRYL COMPOUNDS;

EID: 84885385889     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2013.08.089     Document Type: Article

References (38)

1. Seliktar D. Designing cell-compatible hydrogels for biomedical applications. Science 2012, 336:1124-1128.
2. Van Vlierberghe S., Dubruel P., Schacht E. Biopolymer-based hydrogels as scaffolds for tissue engineering applications: a review. Biomacromolecules 2011, 12:1387-1408.
3. Khetan S., Burdick J.A. Patterning hydrogels in three dimensions towards controlling cellular interactions. Soft Matter 2011, 7:830-838.
4. Burdick J.A., Murphy W.L. Moving from static to dynamic complexity in hydrogel design. Nat Commun 2012, 3:1269.
5. Zhu J. Bioactive modification of poly(ethylene glycol) hydrogels for tissue engineering. Biomaterials 2010, 31:4639-4656.
6. Kloxin A.M., Kasko A.M., Salinas C.N., Anseth K.S. Photodegradable hydrogels for dynamic tuning of physical and chemical properties. Science 2009, 324:59-63.
7. Guvendiren M., Burdick J.A. The control of stem cell morphology and differentiation by hydrogel surface wrinkles. Biomaterials 2010, 31:6511-6518.
8. Xia Y., Whitesides G.M. Soft lithography. Annu Rev Mater Sci 1998, 28:153-184.
9. Lee S.-H., Moon J.J., West J.L. Three-dimensional micropatterning of bioactive hydrogels via two-photon laser scanning photolithography for guided 3D cell migration. Biomaterials 2008, 29:2962-2968.
10. Polizzotti B.D., Fairbanks B.D., Anseth K.S. Three-dimensional biochemical patterning of click-based composite hydrogels via thiolene photopolymerization. Biomacromolecules 2008, 9:1084-1087.
11. DeForest C.A., Polizzotti B.D., Anseth K.S. Sequential click reactions for synthesizing and patterning three-dimensional cell microenvironments. Nat Mater 2009, 8:659-664.
12. DeForest C.A., Anseth K.S. Cytocompatible click-based hydrogels with dynamically tunable properties through orthogonal photoconjugation and photocleavage reactions. Nat Chem 2011, 3:925-931.
13. DeForest C.A., Anseth K.S. Photoreversible patterning of biomolecules with click-based hydrogels. Angew Chem Int Ed 2012, 51:1816-1819.
14. Nimmo C.M., Owen S.C., Shoichet M.S. Diels-Alder click cross-linked hyaluronic acid hydrogels for tissue engineering. Biomacromolecules 2011, 12:824-830.
15. Owen S.C., Fisher S.A., Tam R.Y., Nimmo C.M., Shoichet M.S. Hyaluronic acid click hydrogels emulate the extracellular matrix. Langmuir 2013, 29:7393-7400.
16. Alge D.L., Azagarsamy M.A., Donohue D.F., Anseth K.S. Synthetically tractable click hydrogels for three-dimensional cell culture formed using tetrazine-norbornene chemistry. Biomacromolecules 2013, 14:949-953.
17. Khetan S., Katz J.S., Burdick J.A. Sequential crosslinking to control cellular spreading in 3-dimensional hydrogels. Soft Matter 2009, 5:1601-1606.
18. Marklein R.A., Burdick J.A. Spatially controlled hydrogel mechanics to modulate stem cell interactions. Soft Matter 2010, 6:136-143.
19. Khetan S., Burdick J.A. Patterning network structure to spatially control cellular remodeling and stem cell fate within 3-dimensional hydrogels. Biomaterials 2010, 31:8228-8234.
20. Khetan S., Guvendiren M., Legant W.R., Cohen D.M., Chen C.S., Burdick J.A. Degradation-mediated cellular traction directs stem cell fate in covalently crosslinked three-dimensional hydrogels. Nat Mater 2013, 12:458-465.
21. Labòria N., Wieneke R., Tampé R. Control of nanomolar interaction and in situ assembly of proteins in four dinmensions by light. Angew Chem Int Ed 2013, 52:848-853.
22. Guvendiren M., Burdick J.A. Stiffening hydrogels to probe short- and long-term cellular responses to dynamic mechanics. Nat Commun 2012, 3:729.
23. Marklein R.A., Soranno D.E., Burdick J.A. Magnitude and presentation of mechanical signals influence adult stem cell behavior in 3-dimensional macroporous hydrogels. Soft Matter 2012, 8:8113-8120.
24. Wylie R.G., Ahsan S., Aizawa Y., Maxwell K.L., Morshead C.M., Shoichet M.S. Spatially controlled simultaneous patterning of multiple growth factors in three-dimensional hydrogels. Nat Mater 2011, 10:799-806.
25. Zawko S.A., Suri S., Truong Q., Schmidt C.E. Photopatterned anisotropic swelling of dual-crosslinked hyaluronic acid hydrogels. Acta Biomater 2009, 5:14-22.
26. Tibbitt M.W., Kloxin A.M., Dyamenahalli K.U., Anseth K.S. Controlled two-photon photodegradation of PEG hydrogels to study and manipulate subcellular interactions on soft materials. Soft Matter 2010, 6:5100-5108.
27. Reddy S.K., Cramer N.B., Bowman C.N. Thiol-vinyl mechanisms. 2. Kinetic modeling of ternary thiol-vinyl photopolymerizations. Macromolecules 2006, 39:3681-3687.
28. Hoyle C.E., Bowman C.N. Thiol-ene click chemistry. Angew Chem Int Ed 2010, 49:1540-1573.
29. Anderson S.B., Lin C.-C., Kuntzler D.V., Anseth K.S. The performance of human mesenchymal stem cells encapsulated in cell-degradable polymer-peptide hydrogels. Biomaterials 2011, 32:3564-3574.
30. Aimetti A.A., Machen A.J., Anseth K.S. Poly(ethylene glycol) hydrogels formed by thiol-ene photopolymerization for enzyme-responsive protein delivery. Biomaterials 2009, 30:6048-6054.
31. McCall J.D., Anseth K.S. Thiol-ene photopolymerizations provide a facile method to encapsulate proteins and maintain their bioactivity. Biomacromolecules 2012, 13:2410-2417.
32. Cui J., Lackey M.A., Madkour A.E., Saffer E.M., Griffin D.M., Bhatia S.R., et al. Synthetically simple, highly resilient hydrogels. Biomacromolecules 2012, 13:584-588.
33. Cui J., Lackey M.A., Tew G.N., Crosby A.J. Mechanical properties of end-linked PEG/PDMS hydrogels. Macromolecules 2012, 45:6104-6110.
34. Gould S.T., Darling N.J., Anseth K.S. Small peptide functionalized thiol-ene hydrogels as culture substrates for understanding valvular interstitial cell activation and de novo tissue deposition. Acta Biomater 2012, 8:3201-3209.
35. Lin C.-C., Raza A., Shih H. PEG hydrogels formed by thiol-ene photo-click chemistry and their effect on the formation and recovery of insulin-secreting cell spheroids. Biomaterials 2011, 32:9685-9695.
36. Fairbanks B.D., Schwartz M.P., Halevi A.E., Nuttelman C.R., Bowman C.N., Anseth K.S. Aversatile synthetic extracellular matrix mimic via thiol-norbornene photopolymerization. Adv Mater 2009, 21:5005-5010.
37. Shih H., Lin C.-C. Cross-linking and degradation of step-growth hydrogels formed by thiol-ene photoclick chemistry. Biomacromolecules 2012, 13:2003-2012.
38. Lin D.C., Horkay F. Nanomechanics of polymer gels and biological tissues: a critical review of analytical approaches in the Hertzian regime and beyond. Soft Matter 2008, 4:669-682.