Functional and physicochemical properties of cyclodextrins

Starch-Based Polymeric Materials and Nanocomposites: Chemistry, Processing, and Applications

Volumn , Issue , 2012, Pages 183-230

  Zhao, Jun ^a,b   Yao, Shan Jing ^b  

^a ZHEJIANG UNIVERSITY   (China)

^b HUAQIAO UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOLOGY; INDUSTRIAL RESEARCH; MOLECULES;

BACILLUS MACERANS; CYCLIC STRUCTURES; FREUDENBERG; GLUCANOTRANSFERASE; PHYSICOCHEMICAL PROPERTY; PREPARATION METHOD; RESEARCH GROUPS;

CYCLODEXTRINS;

EID: 84962659872     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/b11848     Document Type: Chapter

References (235)

1. Szejtli, J. 1998. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98: 1743-1753.
2. Hedges, A. R. 1998. Industrial applications of cyclodextrins. Chem. Rev. 98: 2035-2044.
3. 2O. Chem. Lett. 19: 739-742.
4. Takaha, T., Yanase, M., Takata, H., Okada, S., and Smith, S. M. 1996. Potato d-enzyme catalyzes the cyclization of amylose to produce cycloamylose, a novel cyclic glucan. J. Biol. Chem. 271: 2902-2908.
5. Jacob, J., Gessler, K., Hoffmann, D., Sanbe, H., Koizumi, K., Smith, S. M., Takaha, T., and Saenger, W. 1998. Strain-induced “band flips” in cyclodecaamylose and higher homologues. Angew. Chem. Int. Ed. 37: 605-609.
6. Larsen, K. L. 2002. Large cyclodextrins. J. Inclusion Phenom. Macrocyclic Chem. 43: 1-13.
7. Taira, H., Nagase, H., Endo, T., and Ueda, H. 2006. Isolation, purification and characterization of large-ring cyclodextrins (CD36-CD39). J. Inclusion Phenom. Macrocyclic Chem. 56: 23-28.
8. Sundararajan, P. R. and Rao, V. S. R. 1970. Conformational studies on cycloamyloses. Carbohydr. Res. 13: 351-358.
9. Valle, M. D. E. M. 2004. Cyclodextrins and their uses: A review. Process Biochem. 39: 1033-1046.
10. Saenger, W., Jacob, J., Gessler, K., Steiner, T., Hoffmann, D., Sanbe, H., Koizumi, K., Smith, S. M., and Takaha, T. 1998. Structures of the common cyclodextrins and their larger analogues-Beyond the doughnut. Chem. Rev. 98: 1787-1802.
11. Harata, K. 1998. Structural aspects of stereodifferentiation in the solid state. Chem. Rev. 98: 1803-1827.
12. Lindner, K. and Saenger, W. 1982. Crystal and molecular structure of cyclohepta-amylose dodecahydrate. Carbohydr. Res. 99: 103-115.
13. Harata, K. 1987. The structure of the cyclodextrin complex. XX. Crystal structure of uncomplexed hydrated γ-cyclodextrin. Bull. Chem. Soc. Jpn. 60: 2763-2767.
14. Connors, K. A. 1997. The stability of cyclodextrin complexes in solution. Chem. Rev. 97: 1325-1357.
15. Jozwiakowskia, M. J. and Connors, K. A. 1985. Aqueous solubility behavior of three cyclodextrins. Carbohydr. Res. 143: 51-59.
16. Khan, A. R., Forgo, P., Stine, K. J., and D’Souza, V. T. 1998. Methods for selective modifications of cyclodextrins. Chem. Rev. 98: 1977-1996.
17. Li, S. and Purdy, W. C. 1992. Cyclodextrins and their applications in analytical chemistry. Chem. Rev. 92: 1457-1470.
18. Hybl, A., Rundle, R. E., and Williams, D. E. 1965. The crystal and molecular structure of the cyclohexaamylose-potassium acetate complex. J. Am. Chem. Soc. 87: 2779-2788.
19. Saenger, W., Noltemeyer, M., Manor, P. C., Hingerty, B., and Klar, B. 1976. “Induced-fit”-type complex formation of the model enzyme α-cyclodextrin. Bioorg. Chem. 5: 187-195.
20. Rong, D. and D’Souza, V. T. 1990. A convenient method for functionalization of the 2-position of cyclodextrins. Tetrahedron Lett. 31: 4275-4278.
21. Cramer, F., Mackensen, G., and Kensse, K. 1969. Über einschlußverbindungen, XX. ORD-spektren und konformation der glucose-einheiten in cyclodextrinen. Chem. Ber. 102: 494-508.
22. Takeo, K., Ueraura, K., and Mitoh, H. 1988. Derivatives of α-cyclodextrin and the synthesis of 6-O-α-Dglucopyranosyl-α-cyclodextrin. J. Carbohydr. Chem. 7: 293-308.
23. Boger, J., Brenner, D. G., and Knowles, J. R. 1979. Symmetrical triamino-per-O-methyl-α-cyclodextrin: Preparation and characterization of primary trisubstituted α-cyclodextrins. J. Am. Chem. Soc. 101: 7630-7631.
24. Takahashi, K., Hattori, K., and Toda, F. 1984. Monotosylated α-and β-cyclodextrins prepared in an alkaline aqueous solution. Tetrahedron Lett. 25: 3331-3334.
25. Fujita, K., Nagamura, S., and Imoto, T. 1984. Convenient preparation and effective separation of the C-2 and C-3 tosylates of α-cyclodextrin. Tetrahedron Lett. 25: 5673-5676.
26. Boger, J., Corcoran, R. J., and Lehn, J.-M. 1978. Cyclodextrin chemistry. Selective modification of all primary hydroxyl groups of α-and β-cyclodextrins. Helv. Chim. Acta 61: 2190-2218.
27. Szejtli, J. 1988. Cyclodextrin Technology. Dordrecht, the Netherlands: Kluwer.
28. Szejtli, J. 1977. Interaction of hydrochloric acid with cyclodextrin. Stärke 29: 410-413.
29. Marshall, J. J. and Miwa, I. 1981. Kinetic difference between hydrolyses of gamma-cyclodextrin by human salivary and pancreatic alpha-amylases. Biochim. Biophys. Acta 661: 142-147.
30. Rajewski, R. A. and Stella, V. J. 1996. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J. Pharm. Sci. 85: 1142-1169.
31. Uekama, K., Hirayama, F., and Irie, T. 1998. Cyclodextrin drug carrier systems. Chem. Rev. 98: 2045-2076.
32. Andersen, G. H., Robbins, F. M., Domingues, F. J., Moores, R. G., and Long, C. L. 1963. The utilization of Schardinger dextrins by the rat. Toxicol. Appl. Pharmacol. 5: 257-266.
33. Szejtli, J. and Sebestyen, G. 1979. Resorption, metabolism and toxicity studies on the peroral application of β-cyclodextrin. Stärke 31: 385-389.
34. Irie, T. and Uekama, K. 1997. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J. Pharm. Sci. 86: 147-162.
35. Frank, D. W., Gray, J. E., and Weaver, R. N. 1976. Cyclodextrin nephrosis in the rat. Am. J. Pathol. 83: 367-382.
36. Munro, I. C., Newberne, P. M., Young, R. R., and Bär, A. 2004. Safety assessment of γ-cyclodextrin. Regul. Toxicol. Pharm. 39: 3-13.
37. Loftsson, T. and Duchêne, D. 2007. Cyclodextrins and their pharmaceutical applications. Int. J. Pharm. 329: 1-11.
38. Leroy-Lechat, F., Wouessidjewe, D., Andreux, J.-P., Puisieux, F., and Duchêne, D. 1994. Evaluation of the cytotoxicity of cyclodextrins and hydroxypropylated derivatives. Int. J. Pharm. 101: 97-103.
39. Frijlink, H. W., Eissens, A. C., Hefting, N. R., Poelstra, K., Lerk, C. F., and Meijer, D. K. F. 1991. The effect of parenterally administered cyclodextrins on cholesterol levels in the rat. Pharm. Res. 8: 9-16.
40. Szejtli, J., Cserhati, T., and Szogyi, M. 1986. Interactions between cyclodextrins and cell membrane phospholipids. Carbohydr. Polym. 6: 35-49.
41. Gould, S. and Scott, R. C. 2005. 2-Hydroxypropyl-β-cyclodextrin (HP-β-CD): A toxicology review. Food Chem. Toxicol. 43: 1451-1459.
42. Yoshida, A., Arima, H., Uekama, K., and Pitha, J. 1988. Pharmaceutical evaluation of hydroxyalkyl ethers of β-cyclodextrins. Int. J. Pharm. 46: 217-222.
43. Rajewski, R. A., Traiger, G., Bresnahan, J., Jaberaboansari, P., and Stella, V. J. 1995. Preliminary safety evaluation of parenterally administered sulfoalkyl ether β-cyclodextrin derivatives. J. Pharm. Sci. 84: 927-932.
44. Lehn, J.-M. 1978. Cryptates: Inclusion complexes of macropolycyclic receptor molecules. Pure Appl. Chem. 50: 871-892.
45. Lehn, J.-M. 1988. Supramolecular chemistry-Scope and perspectives molecules, supermolecules, and molecular devices. Angew. Chem. Int. Ed. 27: 89-112.
46. Lehn, J.-M. 1993. Supramolecular chemistry. Science 260: 1762-1763.
47. Lehn, J.-M. 1994. Supramolecular chemistry. J. Chem. Sci. 106: 915-922.
48. Lehn, J.-M. 1995. Supramolecular Chemistry-Concepts and Perspectives. Weinheim, Germany: VCH.
49. Ariga, K. and Kunitake, T. 2006. Supramolecular Chemistry-Fundamentals and Applications. Berlin, Heidelberg, New York: Springer-Verlag.
50. Lehn, J.-M. 2007. From supramolecular chemistry towards constitutional dynamic chemistry and adaptive chemistry. Chem. Soc. Rev. 36: 151-160.
51. Brewster, M. E. and Loftsson, T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev. 59: 645-666.
52. Yuan, H.-N., Yao, S.-J., Shen, L.-Q., and Mao, J.-W. 2009. Preparation and characterization of inclusion complexes of β-cyclodextrin-BITC and β-cyclodextrin-PEITC. Ind. Eng. Chem. Res. 48: 5070-5078.
53. 2 inclusion complex. J. Am. Chem. Soc. 96: 3630-3639.
54. Rekharsky, M. V. and Inoue, Y. 1998. Complexation thermodynamics of cyclodextrins. Chem. Rev. 98: 1875-1917.
55. Wang, Y.-L., Qiao, X.-N., Li, W.-C., Zhou, Y.-H., Jiao, Y., Yang, C., Dong, C., Inoue, Y., and Shuang, S.-M. 2009. Study on the complexation of isoquercitrin with β-cyclodextrin and its derivatives by spectroscopy. Anal. Chim. Acta 650: 124-130.
56. Tabushi, I., Kiyosuke, Y., Sugimoto, T., and Yamamura, K. 1978. Approach to the aspects of driving force of inclusion by α-cyclodextrin. J. Am. Chem. Soc. 100: 916-919.
57. Yan, C.-L., Li, X.-H., Xiu, Z.-L., and Hao, C. 2006. A quantum-mechanical study on the complexation of β-cyclodextrin with quercetin. J. Mol. Struct. (Theochem) 764: 95-100.
58. Yan, C.-L., Xiu, Z.-L., Li, X.-H., Teng, H., and Hao, C. 2007. Theoretical study for quercetin/β-cyclodextrin complexes: Quantum chemical calculations based on the PM3 and ONIOM2 method. J. Inclusion Phenom. Macrocyclic Chem. 58: 337-344.
59. Pralhad, T. and Rajendrakumar, K. 2004. Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J. Pharm. Biomed. Anal. 34: 333-339.
60. Schwingel, L., Fasolo, D., Holzschuh, M., Lula, I., Sinisterra, R., Koester, L., Teixeira, H., and Bassani, V. L. 2008. Association of 3-O-methylquercetin with β-cyclodextrin: complex preparation, characterization and ex vivo skin permeation studies. J. Inclusion Phenom. Macrocyclic Chem. 62: 149-159.
61. Ding, H.-Y., Chao, J.-B., Zhang, G.-M., Shuang, S.-M., and Pan, J.-H. 2003. Preparation and spectral investigation on inclusion complex of β-cyclodextrin with rutin. Spectrochim. Acta Part A 59: 3421-3429.
62. Shuang, S.-M., Pan, J.-H., Guo, S.-Y., Cai, M.-Y., and Liu, C.-S. 1997. Fluorescence study on the inclusion complexes of rutin with β-cyclodextrin, hydroxypropyl-β-cyclodextrin and γ-cyclodextrin. Anal. Lett. 30: 2261-2270.
63. Zheng, Y., Haworth, I. S., Zuo, Z., Chow, M. S. S., and Chow, A. H. L. 2005. Physicochemical and structural characterization of quercetin-β-cyclodextrin complexes. J. Pharm. Sci. 94: 1079-1089.
64. Jullian, C., Moyano, L., Yanez, C., and Olea-Azar, C. 2007. Complexation of quercetin with three kinds of cyclodextrins: An antioxidant study. Spectrochim. Acta Part A 67: 230-234.
65. Jullian, C., Orosteguis, T., Pérez-Cruz, F., Sánchez, P., Mendizabal, F., and Olea-Azar, C. 2008. Complexation of morin with three kinds of cyclodextrin: A thermodynamic and reactivity study. Spectrochim. Acta Part A 71: 269-275.
66. Cragg, P. J. 2010. Supramolecular Chemistry-From Biological Inspiration to Biomedical Applications. Dordrecht, the Netherlands; London, U.K.: Springer.
67. Breslow, R. 2005. Artificial Enzymes. Weinheim, Germany: WILEY-VCH.
68. Breslow, R. and Overman, L. E. 1970. An “artificial enzyme” combining a metal catalytic group and a hydrophobic binding cavity. J. Am. Chem. Soc. 92: 1075-1077.
69. D’Souza, V. T., Hanabusa, K., O’Leary, T., Gadwood, R. C., and Bender, M. L. 1985. Synthesis and evaluation of a miniature organic model of chymotrypsin. Biochem. Biophys. Res. Commun. 129: 727-732.
70. D’Souza, V. T. and Bender, M. L. 1987. Miniature organic models of enzymes. Acc. Chem. Res. 20: 146-152.
71. Breslow, R. 1982. Artificial enzymes. Science 218: 532-537.
72. Breslow, R. and Dong, S. D. 1998. Biomimetic reactions catalyzed by cyclodextrins and their derivatives. Chem. Rev. 98: 1997-2011.
73. Breslow, R. 1991. How do imidazole groups catalyze the cleavage of RNA in enzyme models and in enzymes? Evidence from “negative catalysis.” Acc. Chem. Res. 24: 317-324.
74. Anslyn, E. and Breslow, R. 1989. Proton inventory of a bifunctional ribonuclease model. J. Am. Chem. Soc. 111: 8931-8932.
75. Breslow, R., Doherty, J. B., Guillot, G., and Lipsey, C. 1978. β-Cyclodextrinylbisimidazole, a model for ribonuclease. J. Am. Chem. Soc. 100: 3227-3229.
76. Breslow, R. and Schmuck, C. 1996. Goodness of fit in complexes between substrates and ribonuclease mimics: Effects on binding, catalytic rate constants, and regiochemistry. J. Am. Chem. Soc. 118: 6601-6605.
77. Dong, S. D. and Breslow, R. 1998. Bifunctional cyclodextrin metalloenzyme mimics. Tetrahedron Lett. 39: 9343-9346.
78. Breslow, R., Hammond, M., and Lauer, M. 1980. Selective transamination and optical induction by a β-cyclodextrin-pyridoxamine artificial enzyme. J. Am. Chem. Soc. 102: 421-422.
79. Breslow, R., Canary, J. W., Varney, M., Waddell, S. T., and Yang, D. 1990. Artificial transaminases linking pyridoxamine to binding cavities: Controlling the geometry. J. Am. Chem. Soc. 112: 5212-5219.
80. Breslow, R. and Czarnik, A. W. 1983. Transaminations by pyridoxamine selectively attached at C-3 in β-cyclodextrin. J. Am. Chem. Soc. 105: 1390-1391.
81. 6 enzyme for chiral aminotransfer reaction. J. Am. Chem. Soc. 107: 5545-5546.
82. Weiner, W., Winkler, J., Zimmerman, S. C., Czarnik, A. W., and Breslow, R. 1985. Mimics of tryptophan synthetase and of biochemical dehydroalanine formation. J. Am. Chem. Soc. 107: 4093-4094.
83. Breslow, R., Brown, A. B., McCullough, R. D., and White, P. W. 1989. Substrate selectivity in epoxidation by metalloporphyrin and metallosalen catalysts carrying binding groups. J. Am. Chem. Soc. 111: 4517-4518.
84. Breslow, R., Zhang, X.-J., Xu, R., Maletic, M., and Merger, R. 1996. Selective catalytic oxidation of substrates that bind to metalloporphyrin enzyme mimics carrying two or four cyclodextrin groups and related metallosalens. J. Am. Chem. Soc. 118: 11678-11679.
85. Breslow, R., Zhang, X.-J., and Huang, Y. 1997. Selective catalytic hydroxylation of a steroid by an artificial cytochrome P-450 enzyme. J. Am. Chem. Soc. 119: 4535-4536.
86. Breslow, R., Huang, Y., Zhang, X.-J., and Yang, J. 1997. An artificial cytochrome P450 that hydroxylates unactivated carbons with regio-and stereoselectivity and useful catalytic turnovers. Proc. Natl. Acad. Sci. USA 94: 11156-11158.
87. Breslow, R., Gabriele, B., and Yang, J. 1998. Geometrically directed selective steroid hydroxylation with high turnover by a fluorinated artificial cytochrome P-450. Tetrahedron Lett. 39: 2887-2890.
88. Yang, J. and Breslow, R. 2000. Selective hydroxylation of a steroid at C-9 by an artificial cytochrome P-450. Angew. Chem. Int. Ed. 39: 2692-2694.
89. Breslow, R., Yang, J., and Yan, J.-M. 2002. Biomimetic hydroxylation of saturated carbons with artificial cytochrome P-450 enzymes-Liberating chemistry from the tyranny of functional groups. Tetrahedron 58: 653-659.
90. Yang, J., Gabriele, B., Belvedere, S., Huang, Y., and Breslow, R. 2002. Catalytic oxidations of steroid substrates by artificial cytochrome P-450 enzymes. J. Org. Chem. 67: 5057-5067.
91. Breslow, R. 2001. Biomimetic selectivity. Chem. Rec. 1: 3-11.
92. Breslow, R., Yan, J.-M., and Belvedere, S. 2002. Catalytic hydroxylation of steroids by cytochrome P-450 mimics. Hydroxylation at C-9 with novel catalysts and steroid substrates. Tetrahedron Lett. 43: 363-365.
93. Rotruck, J. T., Pope, A. L., Ganther, H. E., Swanson, A. B., Hafeman, D. G., and Hoekstra, W. G. 1973. Selenium: Biochemical role as a component of glutathione peroxidase. Science 179: 588-590.
94. Epp, O., Ladenstein, R., and Wendel, A. 1983. The refined structure of the selenoenzyme glutathione peroxidase at 0.2-nm resolution. Eur. J. Biochem. 133: 51-69.
95. Ren, B., Huang, W.-H., Åkesson, B., and Ladenstein, R. 1997. The crystal structure of seleno-glutathione peroxidase from human plasma at 2.9 Å resolution. J. Mol. Biol. 268: 869-885.
96. Müller, A., Cadenas, E., Graf, P., and Sies, H. 1984. A novel biologically active seleno-organic compound-1: Glutathione peroxidase-like activity in vitro and antioxidant capacity of PZ 51 (Ebselen). Biochem. Pharmacol. 33: 3235-3239.
97. Wilson, S. R., Zucker, P. A., Huang, R. R. C., and Spector, A. 1989. Development of synthetic compounds with glutathione peroxidase activity. J. Am. Chem. Soc. 111: 5936-5939.
98. Cotgreave, I. A., Moldeus, P., Brattsand, R., Hallberg, A., Andersson, C. M., and Engman, L. 1992. α-(Phenylselenenyl)acetophenone derivatives with glutathione peroxidase-like activity: A comparison with ebselen. Biochem. Pharmacol. 43: 793-802.
99. Ren, X.-J., Liu, J.-Q., Luo, G.-M., Zhang, Y., Luo, Y.-M., Yan, G.-L., and Shen, J.-C. 2000. A novel selenocysteine-β-cyclodextrin conjugate that acts as a glutathione peroxidase mimic. Bioconjug. Chem. 11: 682-687.
100. Ren, X.-J., Xue, Y., Liu, J.-Q., Zhang, K., Zheng, J., Luo, G.-M., Guo, C.-H., Mu, Y., and Shen, J.-C. 2002. A novel cyclodextrin-derived tellurium compound with glutathione peroxidase activity. ChemBioChem 3: 356-363.
101. Dong, Z.-Y., Liu, J.-Q., Mao, S.-Z., Huang, X., Luo, G.-M., and Shen, J.-C. 2006. A glutathione peroxidase mimic 6,6′-ditellurobis (6-deoxy-β-cyclodextrin) with high substrate specificity. J. Inclusion Phenom. Macrocyclic Chem. 56: 179-182.
102. 1H NMR study on the inclusion complex of glutathione with a glutathione peroxidase mimic, 2,2′-ditelluro-bridged β-cyclodextrins. J. Inclusion Phenom. Macrocyclic Chem. 54: 171-175.
103. Dong, Z.-Y., Huang, X., Mao, S.-Z., Liang, K., Liu, J.-Q., Luo, G.-M., and Shen, J.-C. 2006. Cyclodextrinderived mimic of glutathione peroxidase exhibiting enzymatic specificity and high catalytic efficiency. Chem. Eur. J. 12: 3575-3579.
104. Yu, S.-J., Huang, X., Miao, L., Zhu, J.-Y., Yin, Y.-Z., Luo, Q., Xu, J.-Y., Shen, J.-C., and Liu, J.-Q. 2010. A supramolecular bifunctional artificial enzyme with superoxide dismutase and glutathione peroxidase activities. Bioorg. Chem. 38: 159-164.
105. Dodziuk, H. 2006. Cyclodextrins and Their Complexes-Chemistry, Analytical Methods, Applications. Weinheim, Germany: WILEY-VCH.
106. Harada, A. 2001. Cyclodextrin-based molecular machines. Acc. Chem. Res. 34: 456-464.
107. Amabilino, D. B. and Stoddart, J. F. 1995. Interlocked and intertwined structures and superstructures. Chem. Rev. 95: 2725-2828.
108. Nepogodiev, S. A. and Stoddart, J. F. 1998. Cyclodextrin-based catenanes and rotaxanes. Chem. Rev. 98: 1959-1976.
109. Harada, A. and Kamachi, M. 1990. Complex formation between poly(ethylene glycol) and α-cyclodextrin. Macromolecules 23: 2821-2823.
110. Harada, A., Li, J., and Kamachi, M. 1993. Preparation and properties of inclusion complexes of poly(ethylene glycol) with α-cyclodextrin. Macromolecules 26: 5698-5703.
111. Ceccato, M., Lo Nostro, P., and Baglioni, P. 1997. α-Cyclodextrin/polyethylene glycol polyrotaxane: A study of the threading process. Langmuir 13: 2436-2439.
112. Lo Nostro, P., Lopes, J. R., and Cardelli, C. 2001. Formation of cyclodextrin-based polypseudorotaxanes: Solvent effect and kinetic study. Langmuir 17: 4610-4615.
113. Pozuelo, J., Mendicuti, F., and Mattice, W. L. 1997. Inclusion complexes of chain molecules with cycloamyloses. 2. Molecular dynamics simulations of polyrotaxanes formed by poly(ethylene glycol) and α-cyclodextrins. Macromolecules 30: 3685-3690.
114. Harada, A., Li, J., Kamachi, M., Kitagawa, Y., and Katsube, Y. 1998. Structures of polyrotaxane models. Carbohydr. Res. 305: 127-129.
115. Harada, A., Okada, M., Li, J., and Kamachi, M. 1995. Preparation and characterization of inclusion complexes of poly(propylene glycol) with cyclodextrins. Macromolecules 28: 8406-8411.
116. Harada, A. 1996. Preparation and structures of supramolecules between cyclodextrins and polymers. Coord. Chem. Rev. 148: 115-133.
117. Kamitori, S., Matsuzaka, O., Kondo, S., Muraoka, S., Okuyama, K., Noguchi, K., Okada, M., and Harada, A. 2000. A novel pseudo-polyrotaxane structure composed of cyclodextrins and a straight-chain polymer: Crystal structures of inclusion complexes of β-cyclodextrin with poly(trimethylene oxide) and poly(propylene glycol). Macromolecules 33: 1500-1502.
118. Harada, A., Suzuki, S., Okada, M., and Kamachi, M. 1996. Preparation and characterization of inclusion complexes of polyisobutylene with cyclodextrins. Macromolecules 29: 5611-5614.
119. Harada, A., Li, J., and Kamachi, M. 1994. Double-stranded inclusion complexes of cyclodextrin threaded on poly(ethylene glycol). Nature 370: 126-128.
120. Harada, A., Nishiyama, T., Kawaguchi, Y., Okada, M., and Kamachi, M. 1997. Preparation and characterization of inclusion complexes of aliphatic polyesters with cyclodextrins. Macromolecules 30: 7115-7118.
121. Steinbrunn, M. B. and Wenz, G. 1996. Synthesis of water-soluble inclusion compounds from polyamides and cyclodextrins by solid-state polycondensation. Angew. Chem. Int. Ed. 35: 2139-2141.
122. Liu, Y., Zhao, Y.-L., Zhang, H.-Y., and Song, H.-B. 2003. Polymeric rotaxane constructed from the inclusion complex of β-cyclodextrin and 4,4′-dipyridine by coordination with nickel(II) ions. Angew. Chem. Int. Ed. 42: 3260-3263.
123. Ogino, H. 1981. Relatively high-yield syntheses of rotaxanes. Syntheses and properties of compounds consisting of cyclodextrins threaded by α,ω-diaminoalkanes coordinated to cobalt(III) complexes. J. Am. Chem. Soc. 103: 1303-1304.
124. Ogino, H. and Ohta, K. 1984. Syntheses and properties of rotaxane complexes. 2. Rotaxane consisting of α-or β-cyclodextrin threaded by (µ-α,ω-diaminoalkane)bis[chlorobis-(ethylenediamine)-cobalt(III)] complexes. Inorg. Chem. 23: 3312-3316.
125. Yamanari, K. and Shimura, Y. 1983. Stereoselective formation of rotaxanes composed of polymethylene-bridged dinuclear cobalt(III) complexes and α-or β-cyclodextrin. Bull. Chem. Soc. Jpn. 56: 2283-2289.
126. Yamanari, K. and Shimura, Y. 1984. Stereoselective formation of rotaxanes composed of polymethylenebridged dinuclear cobalt(III) complexes and α-cyclodextrin. II. Bull. Chem. Soc. Jpn. 57: 1596-1603.
127. Wylie, R. S. and Macartney, D. H. 1992. Self-assembling metal rotaxane complexes of α-cyclodextrin. J. Am. Chem. Soc. 114: 3136-3138.
128. Rao, T. V. S. and Lawrence, D. S. 1990. Self-assembly of a threaded molecular loop. J. Am. Chem. Soc. 112: 3614-3615.
129. Harada, A., Li, J., and Kamachi, M. 1997. Non-ionic [2]rotaxanes containing methylated α-cyclodextrins. Chem. Commun. 18: 1413-1414.
130. Kawaguchi, Y. and Harada, A. 2000. An electric trap: A new method for entrapping cyclodextrin in a rotaxane structure. J. Am. Chem. Soc. 122: 3797-3798.
131. Murakami, H., Kawabuchi, A., Kotoo, K., Kunitake, M., and Nakashima, N. 1997. A light-driven molecular shuttle based on a rotaxane. J. Am. Chem. Soc. 119: 7605-7606.
132. Stanier, C. A., Alderman, S. J., Claridge, T. D. W., and Anderson, H. L. 2002. Unidirectional photoinduced shuttling in a rotaxane with a symmetric stilbene dumbbell. Angew. Chem. Int. Ed. 41: 1769-1772.
133. Kawaguchi, Y. and Harada, A. 2000. A cyclodextrin-based molecular shuttle containing energetically favored and disfavored portions in its dumbbell component. Org. Lett. 2: 1353-1356.
134. Harada, A., Li, J., and Kamachi, M. 1992. The molecular necklace: A rotaxane containing many threaded α-cyclodextrins. Nature 356: 325-327.
135. Harada, A., Li, J., Nakamitsu, T., and Kamachi, M. 1993. Preparation and characterization of polyrotaxanes containing many threaded α-cyclodextrins. J. Org. Chem. 58: 7524-7528.
136. Shigekawa, H., Miyake, K., Sumaoka, J., Harada, A., and Komiyama, M. 2000. The molecular abacus: STM manipulation of cyclodextrin necklace. J. Am. Chem. Soc. 122: 5411-5412.
137. Harada, A., Li, J., and Kamachi, M. 1994. Preparation and characterization of a polyrotaxane consisting of monodisperse poly(ethylene glycol) and α-cyclodextrins. J. Am. Chem. Soc. 116: 3192-3196.
138. Harada, A., Li, J., and Kamachi, M. 1993. Synthesis of a tubular polymer from threaded cyclodextrins. Nature 364: 516-518.
139. Harada, A., Takashima, Y., and Yamaguchi, H. 2009. Cyclodextrin-based supramolecular polymers. Chem. Soc. Rev. 38: 875-882.
140. Araki, J., Zhao, C.-M., and Ito, K. 2005. Efficient production of polyrotaxanes from α-cyclodextrin and poly(ethylene glycol). Macromolecules 38: 7524-7527.
141. Sakamoto, K., Takashima, Y., Yamaguchi, H., and Harada, A. 2007. Preparation and properties of rotaxanes formed by dimethyl-β-cyclodextrin and oligo(thiophene)s with β-cyclodextrin stoppers. J. Org. Chem. 72: 459-465.
142. Wu, J.-Y., He, H.-K., and Gao, C. β-Cyclodextrin-capped polyrotaxanes: One-pot facile synthesis via click chemistry and use as templates for platinum nanowires. Macromolecules 43: 2252-2260.
143. Ooya, T., Eguchi, M., and Yui, N. 2001. Enhanced accessibility of peptide substrate toward membrane-bound metalloexopeptidase by supramolecular structure of polyrotaxane. Biomacromolecules 2: 200-203.
144. Loethen, S., Ooya, T., Choi, H. S., Yui, N., and Thompson, D. H. 2006. Synthesis, characterization, and pH-triggered dethreading of α-cyclodextrin-poly(ethylene glycol) polyrotaxanes bearing cleavable endcaps. Biomacromolecules 7: 2501-2506.
145. Frömming, K.-H. and Szejtli, J. 1994. Cyclodextrins in Pharmacy. Dordrecht, the Netherlands: Kluwer.
146. Mocanu, G., Vizitiu, D., and Carpov, A. 2001. Cyclodextrin polymers. J. Bioact. Compat. Pol. 16: 315-342.
147. Solms, J. and Egli, R. H. 1965. Harze mit Einschlusshohlräumen von Cyclodextrin-Strucktur, Helv. Chim. Acta 48: 1225-1228.
148. Fenyvesi, E., Szilasi, M., Zsadon, B., Szejtli, J., and Tudos, F. 1981. Water-soluble cyclodextrin polymers and their complexing properties. In Proceedings of the 1st International Symposium on Cyclodextrins, Budapest, Hungary, 1981, pp. 345-356.
149. Crini, G. and Morcellet, M. 2002. Synthesis and applications of adsorbents containing cyclodextrins. J. Sep. Sci. 25: 789-813.
150. Kobayashi, N., Shirai, H., and Hojo, N. 1989. Virtues of a poly-cyclodextrin for the de-aggregation of organic molecules in water. J. Polym. Sci., Part C: Polym. Lett. 27: 191-195.
151. Wiedenhof, N., Lammers, J. N. J. J., and van Panthaleon van Eck, C. L. 1969. Properties of cyclodextrins. III. Cyclodextrin-epichlorohydrin resins. Preparation and analysis. Stärke 21: 119-123.
152. Wiedenhof, N. 1969. Properties of cyclodextrins. IV. Features and use of insoluble cyclodextrinepichlorohydrin resins. Stärke 21: 163-166.
153. Wiedenhof, N. and Trieling, R. G. 1971. Properties of cyclodextrins. V. Inclusion isotherm and kinetics of inclusion of benzoic acid and m-chlorobenzoic acid on β-E25 cyclodextrin-epichlorohydrin resin. Stärke 23: 129-132.
154. Nussstein, P., Staudinger, G., and Kreuzer, F.-H. 1994. Cyclodextrin polymers and process for their preparation. US patent 5360899.
155. Szejtli, J., Fenyvesi, E., Zoltan, S., Zsadon, B., and Tudos, F. 1980. Cyclodextrin-poly(vinyl alcohol) polymeric compositions in film, fiber, bead, and block polymers. DE patent 2 927 733.
156. Thuaud, N., Sebille, B., Deratani, A., and Lelievre, G. 1991. Retention behavior and chiral recognition of β-cyclodextrin-derivative polymer adsorbed on silica for warfarin, structurally related compounds and Dns-amino acids. J. Chromatogr. 555: 53-64.
157. Zhao, J., Lin, D.-Q., Wang, Y.-C., and Yao, S.-J. 2010. A novel β-cyclodextrin polymer/tungsten carbide composite matrix for expanded bed adsorption: Preparation and characterization of physical properties. Carbohydr. Polym. 80: 1085-1090.
158. Smolková-Keulemansová, E. 1982. Cyclodextrins as stationary phases in chromatography. J. Chromatogr. 251: 17-34.
159. Zsadon, B., Szilasi, M., Tudos, F., Fenyvesi, E., and Szejtli, J. 1979. Inclusion chromatography of amino acids on beta-cyclodextrin-polymer gel beds. Stärke 31: 11-12.
160. Hoffman, J. L. 1973. Chromatography of nucleic acids on cross-linked cyclodextrin gels having inclusion-forming capacity. J. Macromol. Sci. Chem. A7: 1147-1157.
161. Moon, J.-Y., Jung, H.-J., Moon, M. H., Chung, B. C., and Choi, M. H. 2008. Inclusion complexbased solid-phase extraction of steroidal compounds with entrapped β-cyclodextrin polymer. Steroids 73: 1090-1097.
162. Harada, A., Furue, M., and Nozakura, S.-I. 1978. Optical resolution of mandelic acid derivatives by column chromatography on crosslinked cyclodextrin gels. J. Polym. Sci. Polym. Chem. Ed. 16: 189-196.
163. Zsadon, B., Decsei, L., Szilasi, M., Tudos, F., and Szejtli, J. 1983. Inclusion chromatography of enantiomers of indole alkaloids on a cyclodextrin polymer stationary phase. J. Chromatogr. 270: 127-134.
164. Zsadon, B., Szilasi, M., Decsei, L., Ujhazy, A., and Szejtli, J. 1986. Variation of the selectivity in the resolution of alkaloid enantiomers on cross-linked cyclodextrin polymer stationary phases. J. Chromatogr. 356: 428-432.
165. He, X.-L., Tan, T.-W., Xu, B.-Z., and Janson, J.-C. 2004. Separation and purification of puerarin using β-cyclodextrin-coupled agarose gel media. J. Chromatogr. A 1022: 77-82.
166. Yang, L., Zhu, Y., Yan, T.-W., and Janson, J.-C. 2007. Coupling oligo-β-cyclodextrin on polyacrylate beads media for separation of puerarin. Process Biochem. 42: 1075-1083.
167. Yang, L. and Tan, T.-W. 2008. Enhancement of the isolation selectivity of isoflavonoid puerarin using oligo-β-cyclodextrin coupled polystyrene-based media. Biochem. Eng. J. 40: 189-198.
168. Xu, J., Zhang, G.-F., Tan, T.-W., and Janson, J.-C. 2005. One-step purification of epigallocatechin gallate from crude green tea extracts by isocratic hydrogen bond adsorption chromatography on β-cyclodextrin substituted agarose gel media. J. Chromatogr. B 824: 323-326.
169. Yang, L., Tan, T.-W., and Zhang, L.-Q. 2009. Process utilized oligo-β-cyclodextrin substituted agarose gel medium for efficient purification of paclitaxel from Taxus cuspidata. Sep. Purif. Technol. 68: 119-124.
170. Xu, J., Sandström, C., Janson, J.-C., and Tan, T. W. 2006. Chromatographic retention of epigallocatechin gallate on oligo-β-cyclodextrin coupled Sepharose media investigated using NMR. Chromatographia 64: 7-11.
171. Yang, L., Zhang, H.-Y., Tan, T.-W., and Rahman, A. U. 2009. Thermodynamic and NMR investigations on the adsorption mechanism of puerarin with oligo-β-cyclodextrin-coupled polystyrene-based matrix. J. Chem. Technol. Biotechnol. 84: 611-617.
172. Mannen, T., Yamaguchi, S., Honda, J., Sugimoto, S., and Nagamune, T. 2001. Expanded-bed protein refolding using a solid-phase artificial chaperone. J. Biosci. Bioeng. 91: 403-408.
173. Zhao, J., Lin, D.-Q., and Yao, S.-J. 2009. Expansion and hydrodynamic properties of β-cyclodextrin polymer/tungsten carbide composite matrix in an expanded bed. J. Chromatogr. A 1216: 7840-7845.
174. Mizobuchi, Y., Tanaka, M., and Shono, T. 1980. Preparation and sorption behaviour of cyclodextrin polyurethane resins. J. Chromatogr. 194: 153-161.
175. Mizobuchi, Y., Tanaka, M., and Shono, T. 1981. Separation of aromatic amino acids on β-cyclodextrin polyurethane resins. J. Chromatogr. 208: 35-40.
176. Tang, S.-W., Kong, L., Ou, J.-J., Liu, Y.-Q., Li, X., and Zou, H.-F. 2006. Application of cross-linked β-cyclodextrin polymer for adsorption of aromatic amino acids. J. Mol. Recognit. 19: 39-48.
177. Carbonnier, B., Janus, L., Lekchiri, Y., and Morcellet, M. 2004. Coating of porous silica beads by in situ polymerization/crosslinking of 2-hydroxypropyl β-cyclodextrin for reversed-phase high performance liquid chromatography applications. J. Appl. Polym. Sci. 91: 1419-1426.
178. Kim, I. W., Choi, H. M., Yoon, H. J., and Park, J. H. 2006. β-Cyclodextrin-hexamethylene diisocyanate copolymer-coated zirconia for separation of racemic 2,4-dinitrophenyl amino acids in reversed-phase liquid chromatography. Anal. Chim. Acta 569: 151-156.
179. Bhaskar, M., Aruna, P., Jeevan, R. J. G., and Radhakrishnan, G. 2004. β-Cyclodextrin-polyurethane polymer as solid phase extraction material for the analysis of carcinogenic aromatic amines. Anal. Chim. Acta 509: 39-45.
180. Yamasaki, H., Makihata, Y., and Fukunaga, K. 2008. Preparation of crosslinked β-cyclodextrin polymer beads and their application as a sorbent for removal of phenol from wastewater. J. Chem. Technol. Biotechnol. 83: 991-997.
181. Yamasaki, H., Makihata, Y., and Fukunaga, K. 2006. Efficient phenol removal of wastewater from phenolic resin plants using crosslinked cyclodextrin particles. J. Chem. Technol. Biotechnol. 81: 1271-1276.
182. Ozmen, E. Y., Sezgin, M., Yilmaz, A., and Yilmaz, M. 2008. Synthesis of β-cyclodextrin and starch based polymers for sorption of azo dyes from aqueous solutions. Bioresour. Technol. 99: 526-531.
183. Yilmaz, E., Memon, S., and Yilmaz, M. 2010. Removal of direct azo dyes and aromatic amines from aqueous solutions using two β-cyclodextrin-based polymers. J. Hazard. Mater. 174: 592-597.
184. Asanuma, H., Hishiya, T., and Komiyama, M. 2000. Tailor-made receptors by molecular imprinting. Adv. Mater. 12: 1019-1030.
185. Asanuma, H., Kakazu, M., Shibata, M., and Hishiya, T. 1997. Molecularly imprinted polymer of β-cyclodextrin for the efficient recognition of cholesterol. Chem. Commun. 1971-1972.
186. Asanuma, H., Kakazu, M., Shibata, M., Hishiya, T., and Komiyama, M. 1998. Synthesis of molecularly imprinted polymer of β-cyclodextrin for the efficient recognition of cholesterol. Supramol. Sci. 5: 417-421.
187. Hishiya, T., Shibata, M., Kakazu, M., Asanuma, H., and Komiyama, M. 1999. Molecularly imprinted cyclodextrins as selective receptors for steroids. Macromolecules 32: 2265-2269.
188. Hishiya, T., Asanuma, H., and Komiyama, M. 2002. Spectroscopic anatomy of molecular-imprinting of cyclodextrin. Evidence for preferential formation of ordered cyclodextrin assemblies. J. Am. Chem. Soc. 124: 570-575.
189. Osawa, T., Shirasaka, K., Matsui, T., Yoshihara, S., Akiyama, T., Hishiya, T., Asanuma, H., and Komiyama, M. 2006. Importance of the position of vinyl group on β-cyclodextrin for the effective imprinting of amino acid derivatives and oligopeptides in water. Macromolecules 39: 2460-2466.
190. Song, S.-H., Shirasaka, K., Katayama, M., Nagaoka, S., Yoshihara, S., Osawa, T., Sumaoka, J., Asanuma, H., and Komiyama, M. 2007. Recognition of solution structures of peptides by molecularly imprinted cyclodextrin polymers. Macromolecules 40: 3530-3532.
191. Yang, Y., Long, Y.-Y., Cao, Q., Li, K.-A., and Liu, F. 2008. Molecularly imprinted polymer using β-cyclodextrin as functional monomer for the efficient recognition of bilirubin. Anal. Chim. Acta 606: 92-97.
192. Zhang, W., Qin, L., He, X.-W., Li, W.-Y., and Zhang, Y.-K. 2009. Novel surface modified molecularly imprinted polymer using acryloyl-β-cyclodextrin and acrylamide as monomers for selective recognition of lysozyme in aqueous solution. J. Chromatogr. A 1216: 4560-4567.
193. Muk Ng, S. and Narayanaswamy, R. 2009. Molecularly imprinted β-cyclodextrin polymer as potential optical receptor for the detection of organic compound. Sens. Actuators B 139: 156-165.
194. Roche, P. J. R., Muk Ng, S., Narayanaswamy, R., Goddard, N., and Page, K. M. 2009. Multiple surface plasmon resonance quantification of dextromethorphan using a molecularly imprinted β-cyclodextrin polymer: A potential probe for drug-drug interactions. Sens. Actuators B 139: 22-29.
195. Pariot, N., Edwards-Lévy, F., Andry, M.-C., and Lévy, M.-C. 2000. Cross-linked β-cyclodextrin microcapsules: Preparation and properties. Int. J. Pharm. 211: 19-27.
196. Constantin, M., Fundueanu, G., Bortolotti, F., Cortesi, R., Ascenzi, P., and Menegatti, E. 2004. Preparation and characterisation of poly(vinyl alcohol)/cyclodextrin microspheres as matrix for inclusion and separation of drugs. Int. J. Pharm. 285: 87-96.
197. Girek, T., Kozlowski, C. A., Koziol, J. J., Walkowiak, W., and Korus, I. 2005. Polymerisation of β-cyclodextrin with succinic anhydride. Synthesis, characterisation, and ion flotation of transition metals. Carbohydr. Polym. 59: 211-215.
198. Zhao, D., Zhao, L., Zhu, C.-S., Huang, W.-Q., and Hu, J.-L. 2009. Water-insoluble β-cyclodextrin polymer crosslinked by citric acid: Synthesis and adsorption properties toward phenol and methylene blue. J. Inclusion Phenom. Macrocyclic Chem. 63: 195-201.
199. Zhao, D., Zhao, L., Zhu, C.-S., Tian, Z.-B., and Shen, X.-Y. 2009. Synthesis and properties of waterinsoluble β-cyclodextrin polymer crosslinked by citric acid with PEG-400 as modifier. Carbohydr. Polym. 78: 125-130.
200. Harada, A., Furue, M., and Nozakura, S.-I. 1976. Cyclodextrin-containing polymers. 1. Preparation of polymers. Macromolecules 9: 701-704.
201. Harada, A., Furue, M., and Nozakura, S.-I. 1976. Cyclodextrin-containing polymers. 2. Cooperative effects in catalysis and binding. Macromolecules 9: 705-710.
202. Janus, L., Crini, G., El-Rezzi, V., Morcellet, M., Cambiaghi, A., Torri, G., Naggi, A., and Vecchi, C. 1999. New sorbents containing beta-cyclodextrin. Synthesis, characterization, and sorption properties. React. Funct. Polym. 42: 173-180.
203. Nielsen, A. L., Steffensen, K., and Larsen, K. L. 2009. Self-assembling microparticles with controllable disruption properties based on cyclodextrin interactions. Colloids Surf. B 73: 267-275.
204. Vretblad, P. 1974. Immobilization of ligands for biospecific affinity chromatography via their hydroxyl groups. The cyclohexaamylose-β-amylase system. FEBS Lett. 47: 86-89.
205. Subbaramaiah, K. and Sharma, R. 1984. Polarimetric determination of substitution of oxirane groups on Epoxy-activated Sepharose 6B gel by cyclodextrins. J. Biochem. Biophys. Methods 10: 65-68.
206. Tanaka, M., Mizobuchi, Y., Sonoda, T., and Shono, T. 1981. Retention behaviour of benzene derivatives on chemically bonded β-cyclodextrin phases. Analy. Lett. 14: 281-290.
207. Tanaka, M., Kawaguchi, Y., Nakae, M., Mizobuchi, Y., and Shono, T. 1982. Separation of disubstituted benzene isomers on chemically bonded cyclodextrin stationary phases. J. Chromatogr. 246: 207-214.
208. Hattori, K., Takahashi, K., Mikami, M., and Watanabe, H. 1986. Novel high-performance liquid chromatographic adsorbents prepared by immobilization of modified cyclodextrins. J. Chromatogr. 355: 383-391.
209. Wang, H.-J., Ma, J.-B., Zhang, Y.-H., and He, B.-L. 1997. Adsorption of bilirubin on the polymeric β-cyclodextrin supported by partially aminated polyacrylamide gel. React. Funct. Polym. 32: 1-7.
210. Sreenivasan, K. 1996. Grafting of β-cyclodextrin-modified 2-hydroxyethyl methacrylate onto polyurethane. J. Appl. Polym. Sci. 60: 2245-2249.
211. Sreenivasan, K. 1998. Solvent effect on the interaction of steroids with a novel methyl β-cyclodextrin polymer. J. Appl. Polym. Sci. 69: 1419-1427.
212. Sreenivasan, K. 1998. Synthesis and evaluation of a beta cyclodextrin-based molecularly imprinted copolymer. J. Appl. Polym. Sci. 70: 15-18.
213. Crini, G., Janus, L., Morcellet, M., Torri, G., Naggi, A., Bertini, S., and Vecchi, C. 1998. Macroporous polyamines containing cyclodextrin: Synthesis, characterization, and sorption properties. J. Appl. Polym. Sci. 69: 1419-1427.
214. Auzely, R. and Rinaudo, M. 2001. Chitosan derivatives bearing pendant cyclodextrin cavities: Synthesis and inclusion performance. Macromolecules 34: 3574-3580.
215. Prabaharan, M. and Mano, J. F. 2006. Chitosan derivatives bearing cyclodextrin cavities as novel adsorbent matrices. Carbohydr. Polym. 63: 153-166.
216. Sreenivasan, K. 1998. Synthesis and preliminary studies on a β-cyclodextrin-coupled chitosan as a novel adsorbent matrix. J. Appl. Polym. Sci. 69: 1051-1055.
217. Chiu, S. H., Chung, T. W., Giridhar, R., and Wu, W. T. 2004. Immobilization of β-cyclodextrin in chitosan beads for separation of cholesterol from egg yolk. Food Res. Int. 37: 217-223.
218. Zha, F., Li, S.-G., and Chang, Y. 2008. Preparation and adsorption property of chitosan beads bearing β-cyclodextrin cross-linked by 1,6-hexamethylene diisocyanate. Carbohydr. Polym. 72: 456-461.
219. Furusaki, E., Ueno, Y., Sakairi, N., Nishi, N., and Tokura, S. 1996. Facile preparation and inclusion ability of a chitosan derivative bearing carboxymethyl-β-cyclodextrin. Carbohydr. Polym. 29: 29-34.
220. Aoki, N., Nishikawa, M., and Hattori, K. 2003. Synthesis of chitosan derivatives bearing cyclodextrin and adsorption of p-nonylphenol and bisphenol A. Carbohydr. Polym. 52: 219-223.
221. Zhang, X., Wang, Y., and Yi, Y. 2004. Synthesis and characterization of grafting α-cyclodextrin with chitosan. J. Appl. Polym. Sci. 94: 860-864.
222. Chen, S. and Wang, Y. 2001. Study on β-cyclodextrin grafting with chitosan and slow release of its inclusion complex with radioactive iodine. J. Appl. Polym. Sci. 82: 2414-2421.
223. Wang, H., Fang, Y., Ding, L., Gao, L., and Hu, D. 2003. Preparation and nitromethane sensing properties of chitosan thin films containing pyrene and β-cyclodextrin units. Thin Solid Films 440: 255-260.
224. Martel, B., Devassine, M., Crini, G., Weltrowski, M., Bourdonneau, M., and Morcellet, M. 2001. Preparation and sorption properties of a β-cyclodextrin-linked chitosan derivative. J. Polym. Sci. Part A: Polym. Chem. 39: 169-176.
225. Abdel-Halim, E. S., Abdel-Mohdy, F. A., Al-Deyab, S. S., and El-Newehy, M. H. 2010. Chitosan and monochlorotriazinyl-β-cyclodextrin finishes improve antistatic properties of cotton/polyester blend and polyester fabrics. Carbohydr. Polym. 82: 202-208.
226. El-Tahlawy, K., Gaffar, M. A., and El-Rafie, S. 2006. Novel method for preparation of β-cyclodextrin/grafted chitosan and its application. Carbohydr. Polym. 63: 385-392.
227. Krauland, A. H. and Alonso, M. J. 2007. Chitosan/cyclodextrin nanoparticles as macromolecular drug delivery system. Int. J. Pharm. 340: 134-142.
228. Teijeiro-Osorio, D., Remuñán-López, C., and Alonso, M. J. 2009. Chitosan/cyclodextrin nanoparticles can efficiently transfect the airway epithelium in vitro. Eur. J. Pharm. Biopharm. 71: 257-263.
229. Maestrelli, F., Garcia-Fuentes, M., Mura, P., and Alonso, M. J. 2006. A new drug nanocarrier consisting of chitosan and hydroxypropylcyclodextrin. Eur. J. Pharm. Biopharm. 63: 79-86.
230. Teijeiro-Osorio, D., Remunan-Lopez, C., and Alonso, M. J. 2009. New generation of hybrid poly/oligosaccharide nanoparticles as carriers for the nasal delivery of macromolecules. Biomacromolecules 10: 243-249.
231. Trapani, A., Lopedota, A., Franco, M., Cioffi, N., Ieva, E., Garcia-Fuentes, M., and Alonso, M. J. 2010. A comparative study of chitosan and chitosan/cyclodextrin nanoparticles as potential carriers for the oral delivery of small peptides. Eur. J. Pharm. Biopharm. 75: 26-32.
232. Prabaharan, M. and Gong, S.-Q. 2008. Novel thiolated carboxymethyl chitosan-g-β-cyclodextrin as mucoadhesive hydrophobic drug delivery carriers. Carbohydr. Polym. 73: 117-125.
233. Zhang, X.-G., Wu, Z.-M., Gao, X.-J., Shu, S.-J., Zhang, H.-J., Wang, Z., and Li, C.-X. 2009. Chitosan bearing pendant cyclodextrin as a carrier for controlled protein release. Carbohydr. Polym. 77: 394-401.
234. Prabaharan, M. and Jayakumar, R. 2009. Chitosan-graft-β-cyclodextrin scaffolds with controlled drug release capability for tissue engineering applications. Int. J. Biol. Macromol. 44: 320-325.
235. Ji, J.-G., Hao, S.-L., Liu, W.-Q., Wu, D.-J., Wang, T.-F., and Xu, Y. 2011. Preparation, characterization of hydrophilic and hydrophobic drug in combine loaded chitosan/cyclodextrin nanoparticles and in vitro release study. Colloids Surf. B 83: 103-107.