Synthesis and characterization of enzymatically biodegradable peg and peptide-based hydrogels prepared by click chemistry

Biomacromolecules

Volumn 11, Issue 6, 2010, Pages 1608-1614

  Van Dijk, Maarten ^a,b   Van Nostrum, Cornelus F ^b   Hennink, Wim E ^b   Rijkers, Dirk T S ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b Division of Pharmaceutics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AMIDES; CYCLOADDITION; PEPTIDES; SODIUM; SYNTHESIS (CHEMICAL);

AQUEOUS SOLUTIONS; CLICK CHEMISTRY; DIPOLAR CYCLOADDITION REACTION; FUNCTIONALIZED; PEPTIDE SEQUENCES; RHEOLOGICAL CHARACTERIZATION; SODIUM ASCORBATE; SOLID CONTENTS; STORAGE MODULI; SWELLING RATIO; SYNTHESIS AND CHARACTERIZATION;

HYDROGELS;

ALKYNE; ASCORBIC ACID; COPPER; COPPER SULFATE; MACROGOL; MACROGOL DERIVATIVE; N ALPHA(AZIDO) DEXTRO ALANYLPHENYLALANYLLYSYL( 2 AZIDOETHYL)AMIDE; PEPTIDE; PEPTIDE DERIVATIVE; POLYMER; PROTEINASE; UNCLASSIFIED DRUG; BIOMATERIAL; CROSS LINKING REAGENT; HYDROGEL; PLASMIN; SOLUTION AND SOLUBILITY; TRYPSIN;

1,3 DIPOLAR CYCLOADDITION; AQUEOUS SOLUTION; ARTICLE; BIODEGRADABILITY; CATALYST; CLICK CHEMISTRY; CYCLOADDITION; ENZYME ACTIVITY; FLOW KINETICS; HYDROGEL; MOLECULAR WEIGHT; MOLECULE; PRIORITY JOURNAL; SOLID; STEREOCHEMISTRY; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ENZYME SPECIFICITY; HYDROLYSIS; MEDICINAL CHEMISTRY; PROCEDURES; SOLUBILITY; SOLUTION AND SOLUBILITY; SURFACE PROPERTY;

BIOCOMPATIBLE MATERIALS; CATALYSIS; CHEMISTRY, PHARMACEUTICAL; COPPER; CROSS-LINKING REAGENTS; CYCLIZATION; FIBRINOLYSIN; HYDROGELS; HYDROLYSIS; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PEPTIDES; POLYETHYLENE GLYCOLS; RHEOLOGY; SOLUBILITY; SOLUTIONS; SUBSTRATE SPECIFICITY; SURFACE PROPERTIES; TRYPSIN;

EID: 77954610157     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm1002637     Document Type: Article

References (43)

1. Peppas, N. A.; Bures, P.; Leobandung, W.; Ichikawa, H. Eur. J. Pharm. Biopharm. 2000, 50, 27-46
2. Hoffman, A. S. Adv. Drug Delivery Rev. 2002, 54, 3-12.
3. Kopecek, J. Biomaterials 2007, 28, 5185-5192.
4. Hennink, W. E.; van Nostrum, C. F. Adv. Drug Delivery Rev. 2002, 54, 13-36.
5. van de Manakker, F. V.; van der Pot, M.; Vermonden, T.; van Nostrum, C. F.; Hennink, W. E. Macromolecules 2008, 41, 1766-1773.
6. Levesque, S. G.; Shoichet, M. S. Bioconjugate Chem. 2007, 18, 874-885.
7. Lutolf, M. P.; Hubbell, J. A. Nat. Biotechnol. 2005, 23, 47-55.
8. Pratt, A. B.; Weber, F. E.; Schmoekel, H. G.; Muller, R.; Hubbell, J. A. Biotechnol. Bioeng. 2004, 86, 27-36.
9. Halstenberg, S.; Panitch, A.; Rizzi, S.; Hall, H.; Hubbell, J. A. Biomacromolecules 2002, 3, 710-723.
10. Kim, S.; Healy, K. E. Biomacromolecules 2003, 4, 1214-1223.
11. Lutolf, M. P.; Lauer-Fields, J. L.; Schmoekel, H. G.; Metters, A. T.; Weber, F. E.; Fields, G. B.; Hubbell, J. A. Proc. Natl. Acad. Sci. USA 2003, 100, 5413-5418.
12. West, J. L.; Hubbell, J. A. Macromolecules 1999, 32, 241-244.
13. Polizzotti, B. D.; Fairbanks, B. D.; Anseth, K. S. Biomacromolecules 2008, 9, 1084-1087.
14. Lui, S. Q.; Ee, P. L. R.; Ke, C. Y.; Hendrick, J. L.; Yang, Y. Y. Biomaterials 2009, 30, 1453-1461.
15. van Dijk, M.; Rijkers, D. T. S.; Liskamp, R. M. J.; van Nostrum, C. F.; Hennink, W. E. Bioconjugate Chem. 2009, 20, 2001-2016.
16. Yang, J.; Jacobsen, M. T.; Pan, H.; Kopecek, J. Macromol. Biosci. 2010, 10, 445-454.
17. Tornøe, C. W.; Meldal, M. In Peptides: The WaVe of the Future, Proceedings of the 2nd International and the 17th American Peptide Symposium, San Diego, CA, June 9-14, 2001; Lebl, M., Houghten, R. A., Eds.; American Peptide Society and Kluwer Academic Publishers: San Diego, CA, 2001; p 263.
18. Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
19. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2599.
20. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
21. Meldal, M.; Tornøe, C. W. Chem. Rev. 2008, 108, 2952-3015.
22. Malkoch, M.; Vestberg, R.; Gupta, N.; Mespouille, L.; Dubois, P.; Mason, A. F.; Hedrick, J. L.; Liao, Q.; Frank, C. W.; Kingsbury, K.; Hawker, C. J. Chem. Commun. 2006, 2774-2776.
23. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620-5686.
24. van Dijk, M.; Mustafa, K.; Dechesne, A. C.; van Nostrum, C. F.; Hennink, W. E.; Rijkers, D. T. S.; Liskamp, R. M. J. Biomacromolecules 2007, 8, 327-330.
25. van Dijk, M.; Nollet, M. L.; Weijers, P.; Dechesne, A. C.; van Nostrum, C. F.; Hennink, W. E.; Rijkers, D. T. S.; Liskamp, R. M. J. Biomacromolecules 2008, 9, 2834-2843.
26. von Arx, E.; Faupel, M.; Brugger, M. J. Chromatogr. 1976, 120, 224.
27. Punna, S.; Finn, M. G. Synlett 2004, 99-100.
28. Lundquist, J. T., IV; Pelletier, J. C. Org. Lett. 2001, 3, 781-783.
29. Alper, P. B.; Hung, S. C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029-6032.
30. Nyffeler, P. T.; Liang, C.-H.; Koeller, K. M.; Wong, C.-H. J. Am. Chem. Soc. 2002, 124, 10773-10778.
31. de Groot, F. M. H.; Broxterman, H. J.; Adams, H. P. H. M.; van Vliet, A.; Tesser, G. I.; Elderkamp, Y. W.; Schraa, A. J.; Kok, R. J.; Molema, G.; Pinedo, H. M.; Scheeren, H. W. Mol. Cancer Ther. 2002, 1, 901-911.
32. Barrett, A. J.; Rawlings, N. D.; Woessner, J. F. Handbook of Proteolytic Enzymes, 2nd ed.; Academic Press: New York, 2004.
33. Bencherif, S. A.; Sheehan, J. A.; Hollinger, J. O.; Walker, L. M.; Matyjaszewski, K.; Washburn, N. R. J. Biomed. Mater. Res. A 2009, 90, 142-153.
34. Flory, P. J. Principles of Polymer Chemistry; Cornell University Press: Ithaca, NY, 1953.
35. Treloar, L. R. G. Physics of Rubber Elasticity; Clarendon Press: Oxford, 1975.
36. Goodwin, J. W.; Hughes, R. W. Rheology for Chemists, An Introduction; The Royal Society of Chemistry: Cambridge, U.K., 2000.
37. Ossipov, D. A.; Hilborn, J. Macromolecules 2006, 39, 1709-1718.
38. Testa, G.; Di Meo, C.; Nardecchia, S.; Capitani, D.; Mannina, L.; Lamanna, R.; Barbetta, A.; Dentini, M. Int. J. Pharm. 2009, 378, 86-92.
39. Schmitt, M.; Harbeck, N.; Thomssen, C.; Wilhelm, O.; Magdolen, V.; Reuning, U.; Ulm, K.; Hofler, H.; Janicke, F.; Graeff, H. Thromb. Haemostasis 1997, 78, 285-296.
40. Andreasen, P. A.; Egelund, R.; Petersen, H. H. Cell. Mol. Life Sci. 2000, 57, 25-40.
41. Hewitt, R.; Dano, K. Enzyme Protein 1996, 49, 163-173
42. de Groot, F. M. H.; van Berkom, L. W. A.; Scheeren, H. W. J. Med. Chem. 2000, 43, 3093-3102.
43. Lind, S. E.; Mcdonagh, J. R.; Smith, C. J. Blood 1993, 82, 1522-1531.