Synthesis of highly substituted amide hyaluronan derivatives with tailored degree of substitution and their crosslinking via click chemistry

Carbohydrate Polymers

Volumn 84, Issue 4, 2011, Pages 1293-1300

  Huerta Angeles, Gloria ^a   Šmejkalová, Daniela ^a   Chládková, Drahomíra ^a   Ehlová, Tereza ^a   Buffa, Radovan ^a   Velebný, Vladimír ^a  

^a R and D Department Contipro Group   (Czech Republic)

Author keywords

Chemical modification; Click chemistry; Hyaluronic acid; Hydrogels

Indexed keywords

ALKYNYL GROUPS; ALKYNYLS; CARBOXYL GROUPS; CARBOXYLIC GROUP; CHEMOSELECTIVE; CLICK CHEMISTRY; CROSSLINKING REACTION; DEGREE OF SUBSTITUTION; DRUG DELIVERY SYSTEM; ETHYL CHLOROFORMATE; FUNCTIONALIZATIONS; HIGH STABILITY; HYALURONAN; HYALURONIC ACIDS; MOLECULAR ARCHITECTURE; POROUS NETWORKS; PRIMARY AMINES; REACTION CONDITIONS; THERMAL DEGRADATIONS;

AMIDES; CHEMICAL MODIFICATION; CROSSLINKING; DRUG DELIVERY; HYDROGELS; ORGANIC ACIDS; SCAFFOLDS (BIOLOGY); SYNTHESIS (CHEMICAL);

DEGRADATION;

EID: 79952372933     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2011.01.021     Document Type: Article

References (29)

1. D. Bruneel, and E. Schacht Chemical modification of pullulan: 2 chloroformate activation Polymer 34 12 1993 2633 2637
2. P. Bulpitt, and D. Aeschlimann New strategy for chemical modification of hyaluronic acid: Preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels Journal of Biomedical Materials Research 47 2 1999 152 169 (Pubitemid 29409734)
3. J.A. Burdick, C. Chung, X. Jia, M.A. Randolph, and R. Langer Controlled degradation and mechanical behavior of photopolymerized hyaluronic acid networks Biomacromolecules 6 1 2004 386 391 (Pubitemid 40277037)
4. V. Crescenzi, L. Cornelio, C. Di Meo, S. Nardecchia, and R. Lamanna Novel hydrogels via click chemistry: Synthesis and potential biomedical applications Biomacromolecules 8 6 2007 1844 1850 (Pubitemid 47009962)
5. R.C. Domszy, R. Alamo, C.O. Edwards, and L. Mandelkern Thermoreversible gelation and crystallization of homopolymers and copolymers Macromolecules 19 2 1986 310 325
6. V. Dulong, S. Lack, D. Le Cerf, L. Picton, J.P. Vannier, and G. Muller Hyaluronan-based hydrogels particles prepared by crosslinking with trisodium trimetaphosphate. Synthesis and characterization Carbohydrate Polymers 57 1 2004 1 6
7. J.R.E. Fraser, T.C. Laurent, and U.B.G. Laurent Hyaluronan: Its nature, distribution, functions and turnover Journal of Internal Medicine 242 1997 27 33 (Pubitemid 27323862)
8. Y. Gao, Z. Zhang, L. Chen, W. Gu, and Y. Li Synthesis of 6-N,N,N-trimethyltriazole chitosan via "click chemistry" and evaluation for gene delivery Biomacromolecules 10 8 2009 2175 2182
9. T. Hasegawa, M. Umeda, M. Numata, C. Li, A.-H. Bae, and T. Fujisawa Click chemistry on polysaccharides: a convenient, general, and monitorable approach to develop (1 → 3)-β-d-glucans with various functional appendages Carbohydrate Research 341 1 2006 35 40 (Pubitemid 41796974)
10. A. Chanda, and V.V. Fokin Organic synthesis on water Chemical Reviews 109 2 2009 725 748
11. C. Chung, M. Beecham, R.L. Mauck, and J.A. Burdick The influence of degradation characteristics of hyaluronic acid hydrogels on in vitro neocartilage formation by mesenchymal stem cells Biomaterials 30 26 2009 4287 4296
12. P. Ilgin, G. Avci, C. Silan, S. Ekici, N. Aktas, and R.S. Ayyala Colloidal drug carries from (sub) micron hyaluronic acid hydrogel particles with tunable properties for biomedical applications Carbohydrate Polymers 82 3 2010 997 1003
13. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angewandte Chemie International Edition 40 11 2001 2004 2021
14. J.W. Kuo, D.A. Swann, and G.D. Prestwich Chemical modification of hyaluronic acid by carbodiimides Bioconjugate Chemistry 2 4 1991 232 241
15. L. Lapčik, S. De Smedt, J. Demeester, and P. Chabreček Hyaluronan: Preparation, structure, properties, and applications Chemical Reviews 98 8 1998 2663 2684
16. T. Liebert, C. Hänsch, and T. Heinze Click chemistry with polysaccharides Macromolecular Rapid Communications 27 3 2006 208 213 (Pubitemid 43220960)
17. E.J. Oh, S.W. Kang, B.S. Kim, G. Jiang, I.H. Cho, and S.K. Hahn Control of the molecular degradation of hyaluronic acid hydrogels for tissue augmentation Journal of Biomedical Materials Research Part A 86A 3 2008 685 693
18. D.A. Ossipov, and J.N. Hilborn Poly(vinyl alcohol)-based hydrogels formed by click chemistry Macromolecules 39 5 2006 1709 1718
19. M.H.M. Oudshoorn, R. Rissmann, J.A. Bouwstra, and W.E. Hennink Synthesis of methacrylated hyaluronic acid with tailored degree of substitution Polymer 48 7 2007 1915 1920 (Pubitemid 46400740)
20. N. Pahimanolis, A.-H. Vesterinen, J. Rich, and J. Seppala Modification of dextran using click-chemistry approach in aqueous media Carbohydrate Polymers 82 1 2010 78 82
21. A. Prusová, D. Smejkalová, M. Chytil, V. Velebný, and J. Kucerík An alternative DSC approach to study hydration of hyaluronan Carbohydrate Polymers 82 2 2010 498 503
22. V.O. Rodionov, S.I. Presolski, S. Gardinier, Y.-H. Lim, and M.G. Finn Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition Journal of the American Chemical Society 129 42 2007 12696 12704 (Pubitemid 350004481)
23. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angewandte Chemie International Edition 41 14 2002 2596 2599 (Pubitemid 34803480)
24. S. Sahoo, C. Chung, S. Khetan, and J.A. Burdick Hydrolytically degradable hyaluronic acid hydrogels with controlled temporal structures Biomacromolecules 9 4 2008 1088 1092 (Pubitemid 351639559)
25. B.V. Slaughter, S.S. Khurshid, O.Z. Fisher, A. Khademhosseini, and N.A. Peppas Hydrogels in regenerative medicine Advanced Materials 21 32-33 2009 3307 3329
26. G. Testa, C. Di Meo, S. Nardecchia, D. Capitani, L. Mannina, and R. Lamanna Influence of dialkyne structure on the properties of new click-gels based on hyaluronic acid International Journal of Pharmaceutics 378 1-2 2009 86 92
27. C.W. Tornøe, C. Christensen, and M. Meldal Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides The Journal of Organic Chemistry 67 9 2002 3057 3064 (Pubitemid 34457265)
28. F. Vandoorne, R. Vercauteren, D. Permentier, and E. Schacht Re-investigation of the 4-nitrophenyl chloroformate activation of dextran. Evidence for the formation of different types of carbonate moieties Die Makromolekulare Chemie 186 12 1985 2455 2460
29. X. Zheng Shu, Y. Liu, F.S. Palumbo, Y. Luo, and G.D. Prestwich In situ crosslinkable hyaluronan hydrogels for tissue engineering Biomaterials 25 2004 1339 1348 (Pubitemid 37476210)