Cytocompatible in situ forming chitosan/hyaluronan hydrogels via a metal-free click chemistry for soft tissue engineering

Acta Biomaterialia

Volumn 20, Issue , 2015, Pages 60-68

  Fan, Ming ^a   Ma, Ye ^a   Mao, Jiahui ^a   Zhang, Ziwei ^a   Tan, Huaping ^a  

^a NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Adipose derived stem cells; Chitosan; Hyaluronan; Hydrogel; Tissue engineering

Indexed keywords

BIOCOMPATIBILITY; CATALYSTS; CELL CULTURE; CELL ENGINEERING; CHITOSAN; GELATION; HYALURONIC ACID; METALS; SCAFFOLDS (BIOLOGY); STEM CELLS; SYNTHESIS (CHEMICAL);

ADIPOSE DERIVED STEM CELLS; CLICK CHEMISTRY; HYALURONAN; HYALURONAN HYDROGELS; IN-SITU FORMING; IN-VITRO; INJECTABLE HYDROGELS; METAL FREE; SOFT TISSUE ENGINEERING; TISSUES ENGINEERINGS;

HYDROGELS;

CHITOSAN; HYALURONIC ACID; 7-OXANORBORNADIENE; BIOMATERIAL; DNA; HYDROGEL; NORBORNANE DERIVATIVE;

ADIPOSE DERIVED STEM CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BIOCOMPATIBILITY; CELL DIFFERENTIATION; CELL PROLIFERATION; CELL SURVIVAL; CLICK CHEMISTRY; CONTROLLED STUDY; CROSS LINKING; CYCLOADDITION; ENGINEERING; GELATION; HUMAN; HUMAN CELL; HYDROGEL; IN VITRO STUDY; IN VIVO STUDY; INFRARED SPECTROSCOPY; MALE; MOUSE; NONHUMAN; PHENOTYPE; PRIORITY JOURNAL; SOFT TISSUE; SYNTHESIS; TISSUE ENGINEERING; TISSUE SCAFFOLD; ADIPOSE TISSUE; ANIMAL; BAGG ALBINO MOUSE; CHEMISTRY; COMPRESSIVE STRENGTH; CYTOLOGY; DRUG EFFECTS; FLOW KINETICS; MATERIALS TESTING; METABOLISM; PHARMACOLOGY; PROCEDURES; SCANNING ELECTRON MICROSCOPY; STEM CELL; SUBCUTANEOUS TISSUE; TIME;

ADIPOSE TISSUE; ANIMALS; BIOCOMPATIBLE MATERIALS; CHITOSAN; CLICK CHEMISTRY; COMPRESSIVE STRENGTH; DNA; HUMANS; HYALURONIC ACID; HYDROGELS; MALE; MATERIALS TESTING; MICE, INBRED BALB C; MICROSCOPY, ELECTRON, SCANNING; NORBORNANES; RHEOLOGY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEM CELLS; SUBCUTANEOUS TISSUE; TIME FACTORS; TISSUE ENGINEERING;

EID: 84929505963     PISSN: 17427061     EISSN: 18787568     Source Type: Journal    
DOI: 10.1016/j.actbio.2015.03.033     Document Type: Article

References (44)

1. E. Bellas, T.J. Lo, E.P. Fournier, J.E. Brown, R.D. Abbott, and E.S. Gil Injectable silk foams for soft tissue regeneration Adv Healthc Mater 4 2015 452 459
2. S. Kennedy, S. Bencherif, D. Norton, L. Weinstock, M. Mehta, and D. Mooney Rapid and extensive collapse from electrically responsive macroporous hydrogels Adv Healthc Mater 3 2014 500 507
3. S. Van Vlierberghe, P. Dubruel, and E. Schacht Biopolymer-based hydrogels as scaffolds for tissue engineering applications: a review Biomacromolecules 12 2011 1387 1408
4. J.J. Rice, M.M. Martino, L. De Laporte, F. Tortelli, P.S. Briquez, and J.A. Hubbell Engineering the regenerative microenvironment with biomaterials Adv Healthc Mater 2 2013 57 71
5. H. Tan, M. Fan, Y. Ma, J. Qiu, X. Li, and J. Yan Injectable gel scaffold based on biopolymer microspheres via enzymatic reaction Adv Healthc Mater 3 2014 1769 1775
6. A. Khademhosseini, and N.A. Peppas Micro- and nanoengineering of biomaterials for healthcare applications Adv Healthc Mater 2 2013 10 12
7. J. Elisseeff, W. McIntosh, K. Anseth, S. Riley, P. Ragan, and R. Langer Photoencapsulation of chondrocytes in poly(ethylene oxide)-based semi-interpenetrating networks J Biomed Mater Res 51 2000 164 171
8. H. Tan, C.R. Chu, K.A. Payne, and K.G. Marra Injectable in situ forming biodegradable chitosan-hyaluronic acid based hydrogels for cartilage tissue engineering Biomaterials 30 2009 2499 2506
9. C.M. Kirschner, D.L. Alge, S.T. Gould, and K.S. Anseth Clickable, photodegradable hydrogels to dynamically modulate valvular interstitial cell phenotype Adv Healthc Mater 3 2014 649 657
10. J.B. Leach, K.A. Bivens, C.N. Collins, and C.E. Schmidt Development of photocrosslinkable hyaluronic acid polyethylene glycol-peptide composite hydrogels for soft tissue engineering J Biomed Mater Res 70A 2004 74 82
11. H. Tan, C. Xiao, J. Sun, D. Xiong, and X. Hu Biological self-assembly of injectable hydrogel as cell scaffold via specific nucleobase pairing Chem Commun 48 2012 10289 10291
12. T.A. Holland, J.K. Tessmar, Y. Tabata, and A.G. Mikos Transforming growth factor-beta1 release from oligo(poly(ethylene glycol) fumarate) hydrogels in conditions that model the cartilage wound healing environment J Control Release 94 2004 101 114
13. J.A. Wieland, T.L. Houchin-Ray, and L.D. Shea Non-viral vector delivery from PEG-hyaluronic acid hydrogels J Control Release 120 2007 233 241
14. K.L. Moffat, and K.G. Marra Biodegradable poly(ethylene glycol) hydrogels crosslinked with genipin for tissue engineering applications J Biomed Mater Res Part B: Appl Biomater 71B 2004 181 187
15. H. Tan, Q. Shen, X. Jia, Z. Yuan, and D. Xiong Injectable nano-hybrid scaffold for biopharmaceuticals delivery and soft tissue engineering Macromol Rapid Commun 33 2012 2015 2022
16. H.C. Kolb, and K.B. Sharpless The growing impact of click chemistry on drug discovery Drug Discovery Today 8 2003 1128 1137
17. M. van Dijk, D.T.S. Rijkers, R.M.J. Liskamp, C.F. van Nostrum, and W.E. Hennink Synthesis and applications of biomedical and pharmaceutical polymers via click chemistry methodologies Bioconjugate Chem 20 2009 2001 2016
18. A.O. Dmitri, and H. Jons Poly(vinyl alcohol)-based hydrogels formed by ''click chemistry'' Macromolecules 39 2006 1709 1718
19. M. Malkoch, R. Vestberg, N. Gupta, L. Mespouille, P. Dubois, and A.F. Mason Synthesis of well-defined hydrogel networks using click chemistry Chem Commun 14 2006 2774 2776
20. V. Crescenzi, L. Cornelio, C. Di Meo, S. Nardecchia, and R. Lamanna Novel hydrogels via click chemistry: synthesis and potential biomedical applications Biomacromolecules 8 2007 1844 1850
21. B.D. Polizzotti, B.D. Fairbanks, and K.S. Anseth Three-dimensional biochemical patterning of click-based composite hydrogels via thiolene photopolymerization Biomacromolecules 9 2008 1084 1087
22. X.D. Xu, C.S. Chen, B. Lu, Z.C. Wang, S.X. Cheng, and X.Z. Zhang Modular synthesis of thermosensitive p(NIPAAm-co-HEMA)/bb-CD based hydrogels via click chemistry Macromol Rapid Commun 30 2009 157 164
23. S.Q. Liu, P.L. Ee, C.Y. Ke, J.L. Hedrick, and Y.Y. Yang Biodegradable poly(ethylene glycol)-peptide hydrogels with well-defined structure and properties for cell delivery Biomaterials 30 2009 1453 1461
24. A. Huseyin, K. Irem, and S. Rana Fabrication of ''clickable'' hydrogels via dendron-polymer conjugates Macromolecules 43 2010 3801 3808
25. G. Yilmaz, M.U. Kahveci, and Y. Yagci A one pot, one step method for the preparation of clickable hydrogels by photoinitiated polymerization Macromol Rapid Commun 32 2011 1906 1909
26. M. van Dijk, C.F. van Nostrum, W.E. Hennink, D.T.S. Rijkers, and R.M.J. Liskamp Synthesis and characterization of enzymatically biodegradable PEG and peptide-based hydrogels prepared by click chemistry Biomacromolecules 11 2010 1608 1614
27. X. Hu, D. Li, F. Zhou, and C. Gao Biological hydrogel synthesized from hyaluronic acid, gelatin and chondroitin sulfate by click chemistry Acta Biomater 7 2011 1618 1626
28. R.T. Chen, S. Marchesan, R.A. Evans, K.E. Styan, G.K. Such, and A. Postma Photoinitiated alkyne-azide click and radical cross-linking reactions for the patterning of PEG hydrogels Biomacromolecules 13 2012 889 895
29. N. Pahimanolis, A. Sorvari, N.D. Luong, and J. Seppälä Thermoresponsive xylan hydrogels via copper-catalyzed azide-alkyne cycloaddition Carbohydr Polym 102 2014 637 644
30. N.J. Agard, J.A. Prescher, and C.R. Bertozzi A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems J Am Chem Soc 126 2004 15046 15047
31. D. Steinhilber, T. Rossow, S. Wedepohl, F. Paulus, S. Seiffert, and R. Haag A microgel construction kit for bioorthogonal encapsulation and pH-controlled release of living cells Angew Chem Int Ed 52 2013 13538 13543
32. S. Jung, and H. Yi Fabrication of chitosan-poly(ethylene glycol) hybrid hydrogel microparticles via replica molding and its application toward facile conjugation of biomolecules Langmuir 28 2012 17061 17070
33. C.A. DeForest, and K.S. Anseth Cytocompatible click-based hydrogels with dynamically-tunable properties through orthogonal photoconjugation and photocleavage reactions Nat Chem 3 2012 925 931
34. 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
35. A. Takahashi, Y. Suzuki, T. Suhara, K. Omichi, A. Shimizu, and K. Hasegawa In situ cross-linkable hydrogel of hyaluronan produced via copper-free click chemistry Biomacromolecules 14 2013 3581 3588
36. S.S. van Berkel, A.J. Dirks, M.F. Debets, F.L. van Delft, J.J.L.M. Cornelissen, and R.J.M. Nolte Metal-free triazole formation as a tool for bioconjugation Chem BioChem 8 2007 1504 1508
37. S.S. van Berkel, A.J. Dirks, S.A. Meeuwissen, D.L.L. Pingen, O.C. Boerman, and P. Laverman Application of metal-free triazole formation in the synthesis of cyclic RGD-DTPA conjugates Chem BioChem 9 2008 1805 1815
38. A. Krause, A. Kirschning, and G. Dräger Bioorthogonal metal-free click-ligation of cRGD-pentapeptide to alginate Org Biomol Chem 10 2012 5547 5553
39. J. Jirawutthiwongchai, A. Krause, G. Draeger, and S. Chirachanchai Chitosan-oxanorbornadiene: a convenient chitosan derivative for click chemistry without metal catalyst problem ACS Macro Lett 2 2013 177 180
40. H. Tan, L. Lao, J. Wu, Y. Gong, and C. Gao Biomimetic modification of chitosan with covalently grafted lactose and blended heparin for improvement of in vitro cellular interaction Polym Adv Technol 19 2008 15 23
41. H. Tan, X. Gao, J. Sun, C. Xiao, and X. Hu Doubly stimulus-induced stem cell aggregation during differentiation on biopolymer hydrogel substrate Chem Commun 49 2013 11554 11556
42. H. Tan, J. Wu, L. Lao, and C. Gao Gelatin/chitosan/hyaluronan scaffold integrated with PLGA microspheres for cartilage tissue engineering Acta Biomater 5 2009 328 337
43. H. Tan, C.M. Ramirez, N. Miljkovic, H. Li, J.P. Rubin, and K.G. Marra Thermosensitive injectable hyaluronic acid hydrogel for adipose tissue engineering Biomaterials 30 2009 6844 6853
44. H. Tan, J.P. Rubin, and K.G. Marra Direct synthesis of biodegradable polysaccharide derivative hydrogels through aqueous Diels-Alder chemistry Macromol Rapid Commun 32 2011 905 911