Direct synthesis of biodegradable polysaccharide derivative hydrogels through aqueous Diels-Alder chemistry

Macromolecular Rapid Communications

Volumn 32, Issue 12, 2011, Pages 905-911

  Tan, Huaping ^a   Rubin, J Peter ^a   Marra, Kacey G ^a  

^a UNIVERSITY OF PITTSBURGH MEDICAL CENTER   (United States)

Author keywords

biodegradable hydrogel; drug delivery; hyaluronic acid; hydrogels; polysaccharide; soft tissue engineering

Indexed keywords

BIO-CONJUGATION; BIODEGRADABLE HYDROGELS; CLICK CHEMISTRY; COUPLING REAGENTS; DIELS-ALDER; DIRECT SYNTHESIS; FUNCTIONALIZED; HIGH EFFICIENCY; HYALURONIC ACIDS; SELECTIVE REACTIONS; SOFT TISSUE ENGINEERING; SYNTHETIC APPROACH; SYNTHETIC STRATEGIES;

BIOSYNTHESIS; DRUG DELIVERY; ORGANIC ACIDS; TISSUE; TISSUE ENGINEERING;

HYDROGELS;

BIOMATERIAL; INSULIN; MALEIMIDE; MALEIMIDE DERIVATIVE; POLYSACCHARIDE;

ADIPOCYTE; ARTICLE; CELL LINE; CELL PROLIFERATION; CHEMISTRY; CYTOLOGY; DRUG EFFECT; HUMAN; HYDROGEL; METHODOLOGY; ORGANIC CHEMISTRY; POLYMERIZATION; SYNTHESIS;

ADIPOCYTES; BIOCOMPATIBLE MATERIALS; CELL LINE; CELL PROLIFERATION; CHEMISTRY, ORGANIC; HUMANS; HYDROGELS; INSULIN; MALEIMIDES; POLYMERIZATION; POLYSACCHARIDES;

EID: 79959265875     PISSN: 10221336     EISSN: 15213927     Source Type: Journal    
DOI: 10.1002/marc.201100125     Document Type: Article

References (40)

1. J. D. Kretlow, L. Klouda, A. G. Mikos, Adv. Drug Delivery Rev. 2007, 59, 263.
2. J. L. Drury, D. J. Mooney, Biomaterials 2003, 24, 4337.
3. J. Kost, R. Langer, Adv. Drug Delivery Rev. 2001, 46, 125.
4. B. V. Slaughter, S. S. Khurshid, O. Z. Fisher, A. Khademhosseini, N. A. Peppas, Adv. Mater. 2009, 21, 1.
5. M. P. Lutolf, G. P. Raeber, A. H. Zisch, T. Nicola, J. A. Hubbell, Adv. Mater. 2003, 15, 888.
6. D. A. Wang, S. Varghese, B. Sharma, I. Strehin, S. Fermanian, J. Gorham, D. H. Fairbrother, B. Cascio, J. H. Elisseeff, Nat. Mater. 2007, 6, 385.
7. K. Kataoka, H. Miyazaki, M. Bunya, T. Okano, Y. Sakurai, J. Am. Chem. Soc. 1998, 120, 12694.
8. A. Guiseppi-Elie, S. I. Brahim, D. Narinesingh, Adv. Mater. 2002, 14, 743.
9. F. Khan, R. S. Tare, R. O. C. Oreffo, M. Bradley, Angew. Chem., Int. Ed. 2009, 48, 978.
10. M. Morishita, A. M. Lowman, K. Takayama, T. Nagai, N. A. Peppas, J. Controlled Release 2002, 81, 25.
11. K. Y. Lee, H. J. Kong, R. G. Larson, D. J. Mooney, Adv. Mater. 2003, 15, 1828.
12. J. B. Leach, C. E. Schmidt, Biomaterials 2005, 26, 125.
13. X. Z. Shu, Y. Liu, M. C. Roberts, G. D. Prestwich, Biomacromolecules 2002, 3, 1304.
14. J. A. Wieland, T. L. Houchin-Ray, L. D. Shea, J. Controlled Release 2007, 120, 233.
15. Q. Hou, P. A. De Bank, K. M. Shakesheff, J. Mater. Chem. 2004, 14, 1915.
16. C. A. DeForest, B. D. Polizzotti, K. S. Anseth, Nat. Mater. 2009, 8, 659.
17. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
18. J. E. Moses, A. D. Moorhouse, Chem. Soc. Rev. 2007, 36, 1249.
19. N. J. Agard, J. A. Prescher, C. R. Bertozzi, J. Am. Chem. Soc. 2004, 126, 15046.
20. M. Malkoch, R. Vestberg, N. Gupta, L. Mespouille, P. Dubois, A. F. Mason, J. L. Hedrick, Q. Liao, C. W. Frank, K. Kingsbury, C. J. Hawker, Chem. Commun. 2006, 26, 2774.
21. H. C. Kolb, K. B. Sharpless, Drug Discov. Today 2003, 8, 1128.
22. C. J. Hawker, K. L. Wooley, Science 2005, 309, 1200.
23. T. M. Tarasow, S. L. Tarasow, B. E. Eaton, Nature 1997, 389, 54.
24. D. C. Rideout, R. Breslow, J. Am. Chem. Soc. 1980, 102, 7816.
25. S. Tiwari, A. Kumar, Angew. Chem., Int. Ed. 2006, 45, 4824.
26. S. Otto, J. B. F. N. Engberts, J. C. T. Kwak, J. Am. Chem. Soc. 1998, 120, 9517.
27. J. B. F. N. Engberts, Pure Appl. Chem. 1995, 67, 823.
28. S. Otto, W. Blokzijl, J. B. F. N. Engberts, J. Org. Chem. 1994, 59, 5372.
29. X. L. Sun, C. L. Stabler, C. S. Cazalis, E. L. Chaikof, Bioconjugate Chem. 2006, 17, 52.
30. A. D. De Araújo, J. M. Palomo, J. Cramer, M. Köhn, H. Schröder, R. Wacker, C. Niemeyer, K. Alexandrov, H. Waldmann, Angew. Chem., Int. Ed. 2006, 45, 296.
31. M. N. Yousaf, M. Mrksich, J. Am. Chem. Soc. 1999, 121, 4286.
32. M. N. Yousaf, B. T. Houseman, M. Mrksich, Angew. Chem., Int. Ed. 2001, 40, 1093.
33. R. Tona, R. Häner, Bioconjugate Chem. 2005, 16, 837.
34. K. W. Hill, J. Taunton-Rigby, J. D. Carter, E. Kropp, K. Vagle, W. Pieken, D. P. C. Mcgee, G. M. Husar, M. Leuck, D. J. Anziano, D. P. Sebesta, J. Org. Chem. 2001, 66, 5352.
35. E. Y. L. Kim, C. Gronewold, A. Chatterjee, C. W. von der Lieth, C. Kliem, B. Schmauser, M. Wiessler, E. Frei, ChemBioChem 2005, 6, 422.
36. M. Shi, K. Ho, A. Keating, M. S. Shoichet, Adv. Funct. Mater. 2009, 19, 1689.
37. M. Shi, J. H. Wosnick, K. Ho, A. Keating, M. S. Shoichet, Angew. Chem., Int. Ed. 2007, 46, 6126.
38. H. Tan, C. R. Chu, K. A. Payne, K. G. Marra, Biomaterials 2009, 30, 2499.
39. H. Tan, C. M. Ramirez, N. Miljkovic, H. Li, J. P. Rubin, K. G. Marra, Biomaterials 2009, 30, 6844.
40. Y. L. Chiu, S. C. Chen, C. J. Su, C. W. Hsiao, Y. M. Chen, H. L. Chen, H. W. Sung, Biomaterials 2009, 30, 4877.