Chitosan derivatives bearing cyclodextrin cavitiesas novel adsorbent matrices

Carbohydrate Polymers

Volumn 63, Issue 2, 2006, Pages 153-166

  Prabaharan, M ^a   Mano, J F ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

Adsorbent matrices; Chitosan; Cyclodextrins; Grafting; Inclusion complexes

Indexed keywords

ADSORBENTS; COMPLEXATION; DERIVATIVES; GRAFTING (CHEMICAL); HYDROPHOBICITY; OLIGOMERS;

ADSORBENT MATRICES; CHITOSAN; CYCLODEXTRINS (CD); INCLUSION COMPLEXES (IC);

POLYSACCHARIDES;

EID: 31344433232     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2005.08.051     Document Type: Review

References (74)

1. K. Akamatsu, S. Takei, M. Mizuhata, A. Kajinami, S. Deki, and S. Takeoka Preparation and characterization of polymer thin films containing silver and silver sulfide nanoparticles Thin Solid Films 359 2000 55 60
2. N. Aoki, M. Nishikawa, and K. Hattori Synthesis of chitosan derivatives bearing cyclodextrin and adsorption of p-nonylphenol and bisphenol A Carbohydrate Polymers 52 2003 219 223
3. H. Asanuma, T. Akiyama, K. Kajiya, T. Hishiya, and M. Kimiyama Molecular imprinting of cyclodextrin in water for the recognition of nanometer-scaled guests Analytica Chimica Acta 435 2001 25 33
4. H. Asanuma, M. Shibata, M. Kakazu, T. Hishiya, and M. Kimiyama Molecularly imprinted polymer of β-cyclodextrin for the efficient recognition of cholesterol Chemical Communications 20 1997 1971 1972
5. R. Auzely, and M. Rinaudo Chitosan derivatives bearing pendant cyclodextrin cavities: Synthesis and inclusion performance Macromolecules 34 2001 3574 3580
6. R. Auzely, and M. Rinaudo New supramolecular assemblies of a cyclodextrin-grafted chitosan through specific complexation Macromolecules 35 2002 7955 7962
7. R. Auzely, and M. Rinaudo Controlled chemical modifications of chitosan. Characterization and investigation of original properties Macromolecular Bioscience 3 2003 562 565
8. Awad, A. C., & Smith, D. M. (1996). Method for reduction of cholesterol in egg materials. US Patent No. 5484624.
9. H.J. Buschmann, D. Knittel, and E. Schollmeyer New textile applications of cyclodextrins Journal of Inclusion Phenomena and Macrocyclic Chemistry 40 2001 169 172
10. S. Chen, and Y. Wang Study on β-cyclodextrin grafting with chitosan and slow release of its inclusion complex with radioactive iodine Journal of Applied Polymer Science 82 2001 2414 2421
11. S.H. Chiu, T.W. Chung, R. Giridhar, and W.T. Wu Immobilization of β-cyclodextrin in chitosan beads for separation of cholesterol from egg yolk Food Research International 37 2004 217 223
12. S.Y. Choi, Y.J. Lee, Y.S. Park, K. Ha, and K.B. Yoon Monolayer assembly of zeolite crystals on glass with fullerene as the covalent linker Journal of the American Chemical Society 122 2000 5201 5203
13. D.J. Costain, R. Kennedy, C. Ciona, V.C. McAlister, and T.D.G. Lee Prevention of post surgical adhesions with N, O-carboxymethyl chitosan: Examination of the most efficacious preparation and the effect of N, O-carboxymethyl chitosan on post surgical healing Surgery 121 1997 314 319
14. V. Crescenzi, G. Paradossi, P. Desideri, M. Dentini, F. Cavalieri, and E. Amici New hydrogels based on carbohydrate and on carbohydrate-synthetic polymer networks Polymer Gels and Networks 5 1997 225 239
15. G. Crini Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment Progress in Polymer Science 30 2005 38 70
16. Y. Fang, G.H. Ning, J.R. Lu, and D.D. Hu Synthesis and solvent-sensitive fluorescence properties of a novel surface-functionalized chitosan film: Potential materials for reversible information storage Journal of Photochemistry and Photobiology A: Chemistry 135 2000 141 145
17. E. Furusaki, Y. Ueno, N. Sakairi, N. Nishi, and S. Tokura Facile preparation and inclusion ability of a chitosan derivative bearing carboxymethyl-β-cyclodextrin Carbohydrate Polymers 29 1996 29 34
18. M.A. Gaffar, S.M.E. Rafie, and K.F.E. Tahlawy Preparation and utilization of ionic exchange resin via graft copolymerization of β-CD itaconate with chitosan Carbohydrate Polymers 56 2004 387 396
19. J.F. Grcic, D. Voinovich, M. Moneghini, M.B. Lacan, L. Magarotto, and I. Jalsenjak Chitosan microspheres with hydrocortisone and hydrocortisone- hydroxypropyl-β-cyclodextrin inclusion complex European Journal of Pharmaceutical Sciences 9 2000 373 379
20. A. Harada, M. Okada, and M. Kamachi Preparation and characterization of inclusion complexes of poly(propylene glycol) with cyclodextrins Macromolecules 28 1995 8406 8411
21. P.R. Hari, T. Chandy, and C.P. Sharma Chitosan/calcium-alginate beads for oral delivery of insulin Journal of Applied Polymer Science 59 1996 1795 1801
22. S. Hirano, Y. Ohe, N. Metsuda, and Metsuda 2-Deoxy-2-nicotinamido derivatives of some mono-saccharides, oligo-saccharides, and poly-saccharides Carbohydrate Research 60 2 1978 404 406
23. S. Hirano, K. Tobetto, M. Hasagawn, and N.J. Matsuda Permeability properties of gels and membranes derived from chitosan Journal of Biomedical Materials Research 14 1980 477 486
24. A. Hoffman Hydrogels for biomedical applications Advanced Drug Delivery Reviews 54 2002 3 12
25. K.M. Huh, Y.W. Cho, H. Chung, I.C. Kwon, S.Y. Jeong, and T. Ooya Supramolecular hydrogel formation based on inclusion complexation between poly(ethylene glycol)-modified chitosan and α-cyclodextrin Macromolecular Bioscience 4 2004 92 99
26. K.M. Huh, H. Tomita, T. Ooya, W.K. Lee, S. Lee, and S. Sasaki pH dependence of inclusion complexation between cationic poly(ε-lysine) and α-cyclodextrin Macromolecules 35 2002 3775 3777
27. T. Ichi, J. Watanabe, T. Ooya, and N. Yui Controllable erosion time and profile in poly(ethylene glycol) hydrogels by supramolecular structure of hydrolyzable polyrotaxane Biomacromolecules 2 2001 204 210
28. L. Illum Chitosan and its use as a pharmaceutical excipient Pharmaceutical Research 15 1998 1326 1331
29. P. Indra, B. Bhesh, and D. Bruce Evaluation of various extraction methods of encapsulated oil from β-cyclodextrin-lemon oil complex powder Journal of Food Composition and Analysis 13 2000 59 70
30. H. Ishigami, T. Okemoto, K. Arai, S. Yoshida, K. Sato, and I. Yamamoto Japanese Kokai Tokkyo Koho 6 1995 (JP07173201)
31. V. Jimenez, J. Belmar, and J.B. Alderete Determination of the association constant of 6-thiopurine and chitosan grafted β-cyclodextrin Journal of Inclusion Phenomena and Macrocyclic Chemistry 47 2003 71 75
32. B. Krajewska, M. Leszko, and W. Zoborska Urease immobilized on chitosan membrane - preparation and properties Journal of Chemical Technology and Biotechnology 48 1990 337 350
33. V. Laine, C.A. Sarguet, A. Gadelle, J. Defaye, B. Perly, and D.F. Pilard Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin Journal of the Chemical Society, Perkin Transactions 2 1995 1479 1485
34. T. Lecourt, P. Sinay, C. Chassenieux, M. Rinaudo, and R. Auzely Complexation between a hydrophobically modified chitosan and cyclodextrin homodimers singly or doubly connected through their primary sides: Effects of their molecular architecture on the polymer properties in solution Macromolecules 37 2004 4635 4642
35. J. Li, A. Harada, and M. Kamachi Sol-gel transition during inclusion complex formation between α-cyclodextrin and high molecular weight poly(ethylene glycol)s in aqueous solution Polymer Journal 26 1994 1019 1025
36. T. Loftsson, and M.E. Brewster Pharmaceutical applications of cyclodextrins: Drug solubilization and stabilization Journal of Pharmaceutical Sciences 85 10 1996 1017 1025
37. B. Martel, M. Devassine, G. Crini, M. Weltrowski, M. Bourdonneau, and M. Morcellet Preparation and sorption properties of a β-cyclodextrin-linked chitosan derivative Journal of Polymer Science: Part A: Polymer Chemistry 39 2001 169 176
38. F.L. Mi, S.S. Shyu, C.T. Chen, and J.Y. Schoung Porous chitosan microsphere for controlling the antigen release of Newcastle disease vaccine: Preparation of antigen-adsorbed microsphere and in vitro release Biomaterials 20 1999 1603 1612
39. Y. Mine, and M. Bergougnoux Adsorption properties of cholesterol-reduced egg yolk low-density lipoprotein at oil-in-water interfaces Journal of Agricultural and Food Chemistry 46 1998 2153 2158
40. S. Miyazaki, K. Ishii, and T. Nadai The use of chitin and chitosan as drug carriers Chemical and Pharmaceutical Bulletin 29 10 1981 3067 3069
41. 2 with adsorption on alumina International Journal of Food Science and Technology 33 1998 445 454
42. R.S. Mohamed, M.D.A. Saldana, F.H. Socantaype, and T.G. Kieckbusch Reduction in the cholesterol content of butter oil using supercritical ethane extraction and adsorption on alumina Journal of Supercritical Fluids 16 2000 225 233
43. L.R. Moses, K.J. Dileep, and C.P. Sharma Beta cyclodextrin-insulin- encapsulated chitosan/alginate matrix: Oral delivery system Journal of Applied Polymer Science 75 2000 1089 1096
44. R. Muzzarell, G. Biagini, and A. Paugnaloni Reconstruction of parodontal tissue with chitosan Biomaterials 10 1989 598 603
45. R.A. Nash Handbook of pharmaceutical excipients 1994 American Pharmaceutical Association & Pharmaceutical Press London p. 145
46. S. Nishimura, Y. Miyura, L. Ren, M. Sato, A. Yamagishi, and N. Nishi An efficient method for the syntheses of novel amphiphilic polysaccharides by regioselective and thermoselective modifications of chitosan Chemistry Letters 1993 1623 1626
47. M. Ohring The materials science of thin films 1992 Academic Press Boston, MA P. 124
48. R.S.R. Pablo, J.R. Isasi, and G.G. Gaitano Binding of dibenzofuran and its derivatives to water-soluble β-cyclodextrin polymers Journal of Photochemistry and Photobiology A: Chemistry 173 2005 248 257
49. 1H NMR relaxation study of a chitosan-cyclodextrin network Carbohydrate Research 300 1997 77 84
50. G. Paradossi, E. Chiessi, F. Cavalieri, D. Moscone, and V. Crescenzi Networks based on chitosan and oxidized cyclodextrin-II. Structural and catalytic features of a copper (II)-loaded network Polymer Gels and Networks 5 1997 525 540
51. M. Prabaharan, and J.F. Mano Chitosan-based particles as controlled drug delivery systems Drug Delivery 12 2005 41 57
52. R.A. Rajewski, and V.G. Stella Pharmaceutical applications of cyclodextrins: In vivo drug delivery Journal of Pharmaceutical Sciences 85 1996 1142 1169
53. S. Rossi, F. Ferrari, M.C. Bonferoni, and C. Caramella Characterization of chitosan hydrochloride-mucin interaction by means of viscosimetric and turbidimetric measurements European Journal of Pharmaceutical Sciences 10 2000 251 257
54. S. Rozou, S. Michaleas, and E.A. Vyza Study of structural features and thermodynamic parameters, determining the chromatographic behaviour of drug-cyclodextrin complexes Journal of Chromatography A 1087 2005 86 94
55. N.G. Schipper, S.G. Romeijn, J.C. Verhoef, and F.W. Merkus Nasal insulin delivery with dimethyl-β-cyclodextrin as an absorption enhancer in rabbits: Powder more effective than liquid formulations Pharmaceutical Research 10 1993 682 686
56. A.B. Schnurch, M. Hornof, and T. Zoidl Thiolated polymers - thiomers: Synthesis and in vitro evaluation of chitosan - 2-iminothiolane conjugates International Journal of Pharmaceutics 260 2003 229 237
57. B. Schnurch The use of inhibitory agents to overcome the enzymatic barrier to perorally administered therapeutic peptides and proteins Journal of Controlled Release 52 1998 1 16
58. B. Sellergren, J. Wieschemeyer, K.S. Boos, and D. Seidel Imprinted polymers for selective adsorption of cholesterol from gastrointestinal fluids Chemistry of Materials 10 1998 4037 4046
59. L. Shahabeddin, O. Damour, and F. Bethod Reconstructed skin from cocultured human keratinocytes and fibroblasts on a chitosane cross-linked collagen-gag matrix Journal of Materials Science Materials in Medicine 2 1991 222 226
60. T.C. Shi, Y.M. Jing, and D.X. Sui Affinity chromatography of trypsin using chitosan as ligand support Journal of Chromatography 742 1996 107 112
61. Y. Shigeno, and K. Takemot Functional monomers and polymers on the adsorption of iodine onto chitosan Journal of Applied Polymer Science 25 1980 731 738
62. Y. Song, H. Onishi, and Y. Machida Synthesis and drug-release characteristics of the conjugates of mitomycin-c with n-succinyl-chitosan and carboxymethyl-chitin Chemical and Pharmaceutical Bulletin 40 1992 2822 2825
63. K. Sreenivasan Synthesis and preliminary studies on a β-cyclodextrin-coupled chitosan as a novel adsorbent matrix Journal of Applied Polymer Science 69 1998 1051 1055
64. J. Szejtli Cyclodextrin technology 1988 Kluwer Academic London p. 167
65. F. Tanida, T. Tojima, S.M. Han, N. Nishi, S. Tokura, and N. Sakairi Novel synthesis of a water-soluble cyclodextrin-polymer having a chitosan skeleton Polymer 39 1998 5261 5263
66. T. Tojima, H. Katsura, S.M. Han, F. Tanida, N. Nishi, and S. Tokura Preparation of an α-cyclodextrin-linked chitosan derivative via reductive amination strategy Journal of Polymer Science: Part A: Polymer Chemistry 36 1998 1965 1968
67. T. Tojima, H. Katsura, M. Nishiki, N. Nishi, S. Tokura, and N. Sakairi Chitosan beads with pendant α-cyclodextrin: Preparation and inclusion property to nitrophenolates Carbohydrate Polymers 40 1999 17 22
68. K. Uekama Recent aspects of pharmaceutical application of cyclodextrins Journal of Inclusion Phenomena and Macrocyclic Chemistry 44 2002 3 7
69. L.G. Wade Organic chemistry 1999 Prentice Hall International Englewood Cliffs, NJ p. 822
70. H. Wang, Y. Fang, L. Ding, L. Gao, and D. Hu Preparation and nitromethane sensing properties of chitosan thin films containing pyrene and β-cyclodextrin units Thin Solid Films 440 2003 255 260
71. H. Wang, Y. Fang, D.D. Hu, Y.L. Cui, and G.L. Gao Fluorescence properties of immobilized pyrene on quartz surface Materials Chemistry and Physics 77 2002 185 191
72. K.D. Yao, T. Peng, Y. Yin, and M. Xu Microcapsules-microspheres related to chitosan Journal of Macromolecular Science, Reviews in Macromolecular Chemistry and Physics 35 1995 155 180
73. J. Zhai, T.X. Wei, and C.H. Huang Fabrication of a new photoelectric conversion system by using a self-assembling technique Thin Solid Films 370 2000 248 252
74. X. Zhang, Y. Wang, and Y. Yi Synthesis and characterization of grafting α-cyclodextrin with chitosan Journal of Applied Polymer Science 94 2004 860 864