Synthesis of chitosan-PEO hydrogels via mesylation and regioselective Cu(I)-catalyzed cycloaddition

Carbohydrate Polymers

Volumn 112, Issue , 2014, Pages 736-745

  Tirino, Pasquale ^a   Laurino, Rosaria ^b   Maglio, Giovanni ^b   Malinconico, Mario ^a   D'Ayala, Giovanna Gomez ^a   Laurienzo, Paola ^a  

^a CNR   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Chitosan; Click chemistry; Well defined hydrogels

Indexed keywords

CATALYSIS; CHITOSAN; DRIERS (MATERIALS); REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

CHITOSAN HYDROGEL; CLICK CHEMISTRY; CONTROLLED DRUG RELEASE; CROSS-LINKING DEGREE; HYDROXYL GROUPS; REGIO-SELECTIVE; SWELLING PROPERTIES; SYNTHETIC APPROACH;

HYDROGELS;

CHITOSAN; HYDROGEL; MACROGOL DERIVATIVE;

CHEMISTRY; CLICK CHEMISTRY; CYCLOADDITION; HYDROGEL; PROCEDURES; SYNTHESIS;

CHITOSAN; CLICK CHEMISTRY; CYCLOADDITION REACTION; HYDROGELS; POLYETHYLENE GLYCOLS;

EID: 84904296227     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2014.06.026     Document Type: Article

References (50)

1. S.A. Agnihotri, and T.M. Aminabhavi Novel interpenetrating network chitosan-poly(ethylene oxide-g-acrylamide) hydrogel microspheres for the controlled release of Capecitabine International Journal of Pharmaceutics 324 2006 103 115 (Pubitemid 44528908)
2. N.M. Alves, and J.F. Mano Chitosan derivatives obtained by chemical modifications for biomedical and environmental applications International Journal of Biological Macromolecules 43 2008 401 414
3. R.O. Beauchamp, M.B. St Clair, T.R. Fennell, D.O. Clarke, and K.T. Morgan A critical review of the toxicology of glutaraldehyde Critical Reviews in Toxicology 22 1992 143 174
4. J. Berger, M. Reist, J.M. Mayer, O. Felt, N.A. Peppas, and R. Gurny Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications European Journal of Pharmaceutics and Biopharmaceutics 57 2004 19 34 (Pubitemid 38058801)
5. J. Bernard, M. Save, B. Arathoon, and B. Charleux Preparation of a xanthate-terminated dextran by click chemistry: Application to the synthesis of polysaccharide-coated nanoparticles via surfactant-free ab initio emulsion polymerization of vinyl acetate Journal of Polymer Science - Polymer Chemistry 46 2008 2845 2857 (Pubitemid 351489786)
6. H.P. Brack, S.A. Tirmizi, and W.M. Risen A spectroscopic and viscometric study of the metal ion-induced gelation of the biopolymer chitosan Polymer 38 1997 2351 2362 (Pubitemid 127422212)
7. M.S. Chiou, and H.Y. Li Adsorption behavior of reactive dye in aqueous solution on chemical cross-linked chitosan beads Chemosphere 50 2003 1095 1105 (Pubitemid 36134367)
8. M.S. Chiou, P.Y. Ho, and H.Y. Li Adsorption of anionic dyes in acid solutions using chemically cross-linked chitosan beads Dyes and Pigments 60 2004 69 84
9. 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 (Pubitemid 47009962)
10. V. Crescenzi, G. Paradossi, P. Desideri, M. Dentini, F. Cavalieri, E. Amici, and R. Lisi New hydrogels based on carbohydrate and on carbohydrate-synthetic polymer networks Polymer Gels and Networks 5 1997 225 239 (Pubitemid 127451755)
11. 13C CP-MAS NMR characterization of a new chitosan-based polymeric network Macromolecules 31 1998 1595 1601
12. B.G. De Geest, W. Van Camp, F.E. Du Prez, S.C. De Smedt, J. Demeester, and W.E. Hennink Biodegradable microcapsules designed via 'click' chemistry Chemical Communications 2008 190 192 (Pubitemid 350294107)
13. K.I. Draget, K.M. Varum, E. Moen, H. Gynnild, and O. Smidsrod Chitosan cross-linked with Mo(VI) polyoxyanions: A new gelling system Biomaterials 13 1992 635 638
14. S. Dumitriu, P.F. Vidal, and E. Chornet Polysaccharides in medicinal applications 1999 Marcel Dekker New York, NY
15. G.W.J. Fleet, S.J. Nicholas, P.W. Smith, S.V. Evans, L.E. Fellows, and R.J. Nash Potent competitive inhibition of a-galactosidase and a-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: Syntheses of 1,4-dideoxy-1,4-imino- d-lyxitol and of both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol Tetrahedron Letters 26 1985 3127 3130
16. M.H. Franz, S. Roper, R. Wartchow, and H.M.R. Hoffmann The first and second Cinchona rearrangement. Two fundamental transformations of alkaloid chemistry Journal of Organic Chemistry 69 2004 2983 2991 (Pubitemid 38542550)
17. G. Gomez d'Ayala, M. Malinconico, and P. Laurienzo Marine derived polysaccharides for biomedical applications: Chemical modification approaches Molecules 13 2008 2069 2106
18. R. Gruškienė, G. Čiuta, and R. Makuška Grafting of poly(ethylene glycol) to chitosan at c(6) position of glucosamine units via click chemistry reactions Chemija 20 2009 241 249
19. J. Hafrén, W. Zou, and A. Córdova Macromolecular Rapid Communications 27 2006 1362 1366
20. C.D. Hein, X.M. Liu, and D. Wang Click chemistry, a powerful tool for pharmaceutical sciences Pharmaceutical Research 25 2008 2216 2230
21. M.N. Khalid, L. Ho, F. Agnely, J.L. Grossiord, and G. Couarraze Swelling properties and mechanical characterization of a semi-interpenetrating chitosan/polyethylene oxide network: Comparison with a chitosan reference gel STP Pharma Sciences 9 1999 359 364 (Pubitemid 29480170)
22. M.S. Kim, Y.J. Choi, I. Noh, and G. Tae Synthesis and characterization of in situ chitosan-based hydrogel via grafting of carboxyethyl acrylate Journal of Biomedical Materials Research Part A 83 2007 674 682 (Pubitemid 350086293)
23. S.S. Kim, Y.M. Lee, and C.S. Cho Synthesis and properties of semiinterpenetrating polymer networks composed of b-chitin and poly(ethylene glycol) macromer Polymer 36 1995 4497 4501
24. K. Kurita Controlled functionalization of the polysaccharide chitin Progress in Polymer Science 26 2001 1921 1971 (Pubitemid 33089088)
25. Y. Lei, H. Li, H. Pan, and S. Han Structures and hydrogen bonding analysis of N,N-dimethylformamide and N,N-dimethylformamide-water mixtures by molecular dynamics simulations Journal of Physical Chemistry A 107 2003 1574 1583
26. F.L. Mi, S.S. Shyu, C.T. Chen, and J.Y. Lai Adsorption of indomethacin onto chemically modified beads Polymer 43 2002 757 765
27. N. Murata-Kamiya, H. Kamiya, H. Kaji, and H. Kasai Mutational specificity of glyoxal, a product of DNA oxidation, in the lacI gene of wild-type Escherichia coli W3110 Mutation Research 377 1997 255 262 (Pubitemid 27290612)
28. R.A.A. Muzzarelli, F. Greco, A. Busilacchi, V. Sollazzo, and A. Gigante Chitosan, hyaluronan and chondroitin sulfate in tissue engineering for cartilage regeneration: A review Carbohydrate Polymers 89 2012 723 739
29. R.A.A. Muzzarelli Genipin-chitosan hydrogels as biomedical and pharmaceutical aids Carbohydrate Polymers 77 2009 1 9
30. R.A.A. Muzzarelli, and C. Muzzarelli Chitosan chemistry: Relevance to the biomedical science Advanced Polymer Science 186 2005 151 209
31. S.I. Nishimura, O. Kohgo, and K. Kurita Chemospecific manipulations of a rigid polysaccharide: Syntheses of novel chitosan derivatives with excellent solubility in common organic solvents by regioselective chemical modifications Macromolecules 24 1991 4745 4748 (Pubitemid 21698678)
32. V.R. Patel, and M.M. Amiji Preparation and characterization of freeze-dried chitosan-poly(ethylene oxide) hydrogels for site specific antibiotic delivery in the stomach Pharmaceutical Research 13 1996 588 593 (Pubitemid 26119684)
33. N.A. Peppas, K.B. Keys, M. Torres-Lugo, and A.M. Lowma Poly(ethylene glycol)-containing hydrogels in drug delivery Journal of Controlled Release 62 1999 81 87 (Pubitemid 29486486)
34. M. Pohl, J. Schaller, F. Meister, and T. Heinze Selectively dendronized cellulose: Synthesis and characterization Macromolecular Rapid Communications 29 2008 142 148 (Pubitemid 351169760)
35. A. Pourjavadi, H. Ghasemzadeh, and R. Soleyman Synthesis, characterization, and swelling behavior of alginate-g-poly(sodium acrylate)/kaolin superabsorbent hydrogel composites Journal of Applied Polymer Science 105 2007 2631 2639 (Pubitemid 47168947)
36. C. Qin, H. Li, Q. Xiao, Y. Liu, J. Zhu, and Y. Du Water-solubility of chitosan and its antimicrobial activity Carbohydrate Polymers 63 2006 367 374 (Pubitemid 43277626)
37. M.N.V. Ravi Kumar, R.A.A. Muzzarelli, C. Muzzarelli, H. Sashiwa, and A.J. Domb Chitosan chemistry and pharmaceutical perspectives Chemical Reviews 104 2004 6017 6084 (Pubitemid 40025733)
38. D. Rohindra, A.V. Nand, and J.R. Khurma Swelling properties of chitosan hydrogels The South Pacific Journal of Natural Science 22 2004 32 35
39. S. Roper, M.H. Franz, R. Wartchow, and H.M.R. Hoffmann Fused triazoles via tandem reactions of activated Cinchona alkaloids with azide ion. Second Cinchona rearrangement exemplified Organic Letters 5 2003 2773 2776 (Pubitemid 37140767)
40. 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 114 2002 2708 2711
41. C. Schatz, S. Louguet, J.-F. Le Meins, and S. Lecommandoux Polysaccharide-block-polypeptide copolymer vesicles: Towards synthetic viral capsids Angewandte Chemie International Edition 48 2009 2572 2575
42. E.F.V. Scriven, and K. Turnbull Azides: Their preparation and synthetic uses Chemical Reviews 88 1988 298 368
43. X. Shu, and K.J. Zhu A novel approach to prepare tripolyphosphate/ chitosan complex beads for controlled release drug delivery International Journal of Pharmaceutics 201 2000 51 58 (Pubitemid 30364969)
44. M.F. Shukur, R. Ithnin, H.A. Illias, and M.F.Z. Kadir Proton conducting polymer electrolyte based on plasticized chitosan-PEO blend and application in electrochemical devices Optical Materials 35 2013 1834 1841
45. P.F. Tankam, R. Müller, P. Mischnick, and H. Hopf Alkynyl polysaccharides: Synthesis of propargyl potato starch followed by subsequent derivatizations Carbohydrate Research 342 2007 2049 2060 (Pubitemid 47135602)
46. W.S. Wan Ngah, C.S. Endud, and R. Mayanar Removal of copper(II) ions from aqueous solution onto chitosan and cross-linked chitosan beads Reactive & Functional Polymers 50 2002 181 190 (Pubitemid 34086322)
47. Z.W. Xie, C.B. Paras, H. Weng, P. Punnakitikashem, L.C. Su, K. Vu, L.P. Tang, J. Yang, and K.T. Nguyen Dual growth factor releasing multi-functional nanofibers for wound healing Acta Biomaterialia 9 2013 9351 9359
48. K. Yamada, T. Chen, G. Kumar, O. Vesnovsky, L.D.T. Topoleski, and G.F. Payne Chitosan based water-resistant adhesive. Analogy to mussel glue Biomacromolecules 1 2000 252 258
49. G. Zampano, M. Bertoldo, and F. Ciardelli Defined chitosan-based networks by C-6-azide-alkyne "click" reaction Reactive & Functional Polymers 70 2010 272 281
50. X. Zhang, D. Yang, and J. Nie Chitosan/polyethylene glycol diacrylate films as potential wound dressing material International Journal of Biological Macromolecules 43 2008 456 462