Characterization, molecular dynamics, and encapsulation ability of β-cyclodextrin polymers crosslinked by polyethylene glycol

Carbohydrate Polymers

Volumn 128, Issue , 2015, Pages 11-23

  Kono, Hiroyuki ^a   Nakamura, Taichi ^a   Hashimoto, Hisaho ^a   Shimizu, Yuuichi ^a  

^a TOMAKOMAI NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

Author keywords

Adsorption isotherm; Cyclodextrin polymer; Encapsulation ability; Epoxy functionalized PEG; Molecular dynamics

Indexed keywords

ADSORPTION ISOTHERMS; ALIPHATIC COMPOUNDS; CHAIN LENGTH; CYCLODEXTRINS; ETHERS; ETHYLENE; ETHYLENE GLYCOL; MOLECULAR DYNAMICS; POLYETHYLENE GLYCOLS; POLYETHYLENES; REACTION KINETICS;

CROSS LINKING AGENTS; CYCLODEXTRIN POLYMER; ETHYLENE GLYCOL DIGLYCIDYL ETHERS; FUNCTIONALIZED; GLYCOL DIGLYCIDYL ETHERS; RELAXATION MEASUREMENTS; SHORT CHAIN LENGTHS; STRUCTURAL HOMOGENEITY;

CROSSLINKING;

4,4' ISOPROPYLIDENEDIPHENOL; BENZHYDRYL DERIVATIVE; BETA CYCLODEXTRIN; BETA CYCLODEXTRIN DERIVATIVE; CROSS LINKING REAGENT; EPOXY RESIN; MACROGOL DERIVATIVE; PHENOL DERIVATIVE; QUETOL 651;

CHEMISTRY; MOLECULAR DYNAMICS;

BENZHYDRYL COMPOUNDS; BETA-CYCLODEXTRINS; CROSS-LINKING REAGENTS; EPOXY RESINS; MOLECULAR DYNAMICS SIMULATION; PHENOLS; POLYETHYLENE GLYCOLS;

EID: 84928527141     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2015.04.009     Document Type: Article

References (55)

1. 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
2. G. Astray, C. Gonzalez-Barreiro, J.C. Mejuto, R. Rial-Otero, and J. Simal-Gándara A review on the use of cyclodextrins in food Food Hydrocolloid 23 2009 1631 1640
3. V.G. Avakyan, V.B. Nazarov, M.V. Alfimov, A.A. Bagaturyants, and N.I. Voronezheva The role of intra- and intermolecular hydrogen bonds in the formation of β-cyclodextrin head-to-head and head-to-tail dimers. The results of ab initio and semiempirical quantum-chemical calculations Russian Chemical Bulletin 50 2001 206 216
4. 4/cyclodextrin polymer nanocomposites for selective heavy metals removal from industrial wastewater Carbohydrate Polymers 91 2013 322 332
5. F.E. Bailey Jr., and J.V. Koleske Poly(ethylene oxide) 1976 Academic Press New York
6. F.E. Bailey Jr., and J.V. Koleske Alkylene oxides and their polymers: Surfactant science series Vol. 35 1991 Marcel Dekker New York
7. 13C NMR study of per(3,6-anhydro)-α-cyclodextrin based polymers and of their chromium complexes Carbohydrate Polymers 61 2005 88 94
8. L.C. Cesteros, C.A. Ramírez, A. Peciña, and I. Katime Poly(ethylene glycol-β-cyclodextrin) gels: Synthesis and properties Journal of Applied Polymer Science 102 2006 1162 1166
9. H.A. Chase Prediction of the performance of preparative affinity chromatography Journal of Chromatography A 297 1984 179 202
10. D.Q.M. Craig The mechanisms of drug release from solid dispersions in water-soluble polymers International Journal of Pharmaceutics 231 2002 131 144
11. G. Crini Recent developments in polysaccharide-based materials used as adsorbents in wastewater treatment Progress in Polymer Science 30 2005 38 70
12. G. Crini Kinetic and equilibrium studies on the removal of cationic dyes from aqueous solution by adsorption onto a cyclodextrin polymer Dyes and Pigments 77 2008 415 426
13. G. Crini, S. Bertini, G. Torri, A. Naggi, D. Sforzini, C. Vecchi, et al. Sorption of aromatic compounds in water using insoluble cyclodextrin polymers Journal of Applied Polymer Science 68 1998 1973 1978
14. G. Crini, and M. Morcellet Synthesis and applications of adsorbents containing cyclodextrins Journal of Separation Science 25 2002 789 813
15. G. Crini, H.N. Peindy, F. Gimbert, and C. Robert Removal of C.I. Basic Green 4 (Malachite Green) from aqueous solutions by adsorption using cyclodextrin-based adsorbent: Kinetic and equilibrium studies Separation and Purification Technology 53 2007 97 110
16. M. Dalaran, S. Emik, G. Güçlü, T.B. ̄yim, and S. Özgümüş Study on a novel polyampholyte nanocomposite superabsorbent hydrogels: Synthesis, characterization and investigation of removal of indigo carmine from aqueous solution Desalination 279 2011 170 182
17. A. Domján, J. Bajdik, and K. Pintye-Hódi Understanding of the plasticizing effects of glycerol and PEG 400 on chitosan films using solid-state NMR spectroscopy Macromolecules 42 2009 4667 4673
18. D.G. Duff, S.M.C. Ross, and D.H. Vaughan Adsorption from solution: An experiment to illustrate the Langmuir adsorption isotherm Journal of Chemical Education 65 1988 815 816
19. F. Fuertges, and A. Abuchowski The clinical efficacy of poly(ethylene glycol)-modified proteins Journal of Controlled Release 11 1990 139 148
20. B.M. Fung, A.K. Khitrin, and K. Ermolaev An improved broadband decoupling sequence for liquid crystals and solids Journal of Magnetic Resonance 142 2000 97 101
21. G. Gerbaud, S. Hediger, A. Gadelle, and M. Bardet Synthesis and solid-state NMR study of chromium complexes of per(3,6-anhydro)-α-cyclodextrin based polymers Carbohydrate Polymers 73 2008 64 73
22. T. Gu, G.-J. Tsai, and G.T. Tsao Synthesis of rigid cyclodextrin-containing polymeric resins for adsorption Journal of Inclusion Phenomena and Macrocyclic Chemistry 56 2006 375 379
23. A. Harada, M. Furue, and S.-I. Nozakura Inclusion of aromatic compounds by a β-cyclodextrin-epichlorohydrin polymer Polymer Journal 13 1981 777 781
24. K. He, F. Qui, J. Qin, J. Yan, and D. Yang Selective adsorption of l-TA/d-TA by β-cyclodextrin derivative modified with l-tryptophan: Isotherm, kinetic and thermodynamics studies Journal of Industrial and Engineering Chemistry 20 2014 1293 1300
25. A.R. Hedges Industrial applications of cyclodextrins Chemical Reviews 98 1998 2035 2044
26. S. Hediger, L. Emsley, and M. Fischer Solid-state NMR characterization of hydration effects on polymer mobility in onion cell-wall material Carbohydrate Research 322 1999 102 112
27. Y.S. Ho, and G. McKay Sorption of die from aqueous solution by peat Chemical Engineering Journal 70 1998 115 124
28. Y.S. Ho, and G. McKay Pseudo-second order model for sorption processes Process Biochemistry 34 1999 451 465
29. M. Kitaoka, and K. Hayashi Adsorption of bisphenol A by cross-linked β-cyclodextrin polymer Journal of Inclusion Phenomena and Macrocyclic Chemistry 44 2002 429 431
30. H. Kono Characterization and properties of carboxymethyl cellulose hydrogels crosslinked by polyethylene glycol Carbohydrate Polymers 106 2014 84 93
31. H. Kono, H. Hara, H. Hashimoto, and Y. Shimizu Nonionic gelation agents prepared from hydroxypropyl guar gum Carbohydrate Polymers 117 2015 638 643
32. H. Kono, and T. Nakamura Polymerization of β-cyclodextrin with 1,2,3,4-butanetetracarboxylic dianhydride: Synthesis, structural characterization, and bisphenol A adsorption capacity Reactive and Functional Polymers 73 2013 1096 1102
33. H. Kono, K. Onishi, and T. Nakamura Characterization and bisphenol A adsorption capacity of β-cyclodextrin-carboxymethylcellulose-based hydrogels Carbohydrate Polymers 98 2013 784 792
34. C.A. Kozlowski, and W. Sliwa The use of membranes with cyclodextrin units in separation processes: Recent advances Carbohydrate Polymers 74 2008 1 9
35. S. Lagergren Zur theorie der sogenannten adsorption gelöster stoffe Kungliga Svenska Vetenskapsakademiens Handlingar 24 1898 1 39
36. O.H. Lin, R.N. Kumar, H.D. Rozman, and M.A.M. Noor Grafting of sodium carboxymethyl cellulose (CMC) with glycidyl methacrylate and development of UV curable coatings from CMC-g-GMA induced by cationic photoinitiators Carbohydrate Polymers 59 2005 57 69
37. H. Liu, X. Cai, Y. Wang, and J. Chen Adsorption mechanism-based screening of cyclodextrin polymers for adsorption and separation of pesticides from water Water Research 45 2011 3499 3511
38. E.M. Martin Del Valle Cyclodextrins and their uses: A review Process Biochemistry 39 2004 1033 1046
39. T.T. Nielsen, V. Wintgens, K.L. Larsen, and C. Amiel Synthesis and characterization of poly(ethylene glycol) based β-cyclodextrin polymers Journal of Inclusion Phenomena and Macrocyclic Chemistry 65 2009 341 348
40. M.V. Rekharsky, and Y. Inoue Complexation thermodynamics of cyclodextrins Chemical Reviews 98 1998 1875 1918
41. R. Rodŕiguez, C. Alvarez-Lorenzo, and A. Concheiro Cationic cellulose hydrogels: Kinetics of the cross-linking process and characterization as pH-/ion-sensitive drug delivery systems Journal of Controlled Release 86 2003 253 265
42. S. Salmaso, A. Semenzato, S. Bersani, P. Matricardi, F. Rossi, and P. Caliceti Cyclodextrin/PEG based hydrogels for multi-drug delivery International Journal of Pharmaceutics 345 2007 42 50
43. K. Sreenivasan Synthesis and characterization of poly(vinyl alcohol)-β-cyclodextrin copolymer Die Angewandte Makromolekulare Chemie 235 1996 15 20
44. 1 values by a method which suppresses artifacts Journal of Magnetic Resonance 30 1978 613 616
45. V.P. Torchilin PEG-based micelles as carriers of contrast agents for different imaging modalities Advanced Drug Delivery Reviews 54 2002 235 252
46. 13C NMR European Journal of Biochemistry 239 1996 294 301
47. A.J.M. Valente, and O. Söderman The formation of host-guest complexes between surfactants and cyclodextrins Advances in Colloid and Interface Science 205 2014 156 176
48. F.S. von Saal, S.C. Nagel, B.L. Coe, B.M. Angle, and J.A. Taylor The estrogenic endocrine disrupting chemical bisphenol A (BPA) and obesity Molecular and Cellular Endocrinology 354 2012 74 84
49. X. Wang, H. Zeng, Y. Wei, and J.-M. Lin A reversible fluorescence sensor based on insoluble β-cyclodextrin polymer for direct determination of bisphenol A (BPA) Sensors and Actuators B: Chemical 114 2006 565 572
50. T.C. Werner, J.L. Iannacone, and M.N. Amoo The binding of pyrene and other probes to CD polymers Journal of Inclusion Phenomena and Macrocyclic Chemistry 25 1996 77 80
51. P.W. Wester, C.W. van der Heijden, G.J. Bisschop, and G.J. van Esch Carcinogenicity study with epichlorohydrin (CEP) by gavage in rats Toxicology 36 1985 325 339
52. P.K. Working, M.S. Newman, J. Johnson, and B. Cornacoff Safety of poly(ethylene glycol) and poly(ethylene glycol) derivatives J.M. Harris, S. Zalipsky, Polyethylene glycol chemistry and biological applications 1997 American Chemical Society Washington, DC 45 57
53. Z.-X. Yang, Y. Chen, and Y. Liu Inclusion complexes of bisphenol A with cyclomaltoheptaose (β-cyclodextrin): Solubilization and structure Carbohydrate Research 343 2008 2439 2442
54. S. Zalipsky Functionalized poly(ethylene glycols) for preparation of biologically relevant conjugates Bioconjugate Chemistry 6 1995 150 165
55. J. Zhao, D.-Q. Lin, and S.-J. Yao Adsorption of rutin with a novel β-cyclodextrin polymer adsorbent: Thermodynamic and kinetic study Carbohydrate Polymers 90 2012 1764 1770