Complexation thermodynamics of cyclodextrins

Chemical Reviews

Volumn 98, Issue 5, 1998, Pages 1875-1917

  Rekharsky, Mikhail V ^a   Inoue, Yoshihisa ^a  

^a NONE

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[No Author keywords available]

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EID: 4243778369     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr970015o     Document Type: Article

References (288)

1. Li, S.; Purdy, W. C. Chem. Rev. 1992, 92, 1457-1490.
2. Szejtli, L. Cyclodextrin Technology; Kluwer Academic: Dordecht, The Netherlands, 1988.
3. Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry; Springer-Verlag: Berlin, 1978.
4. Lehn, J. M. Supramolecular Chemistry; VCH: Weinheim, Germany, 1995.
5. Bergeron, R. J. In Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Academic: London, 1984; Vol. 3, pp 391-443.
6. Cramer, F. Einscblussverbindungen; Springer: Berlin, 1954.
7. Saenger, W. In Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Academic Press: London, 1984; Vol. 2, pp 231-259.
8. Hallén, D.; Schön, A.; Shehatta, L; Wadsö, I. J. Chem. Soc., Faraday Trans. 1992, 88, 2859-2863.
9. Rekharsky, M. V.; Mayhew, M. P.; Goldberg, R. N.; Ross, P. D.; Yamashoji, Y.; Inoue, Y.; A J. Phys. Chem. 1997, 101, 87-100.
10. Ross, P. D.; Rekharsky, M. V. Biophys. J. 1996, 71, 2144-2154.
11. Matsui, Y.; Mochida, K. Bull. Chem. Soc. Jpn. 1979, 52, 2808-2814.
12. Rekharsky, M. V.; Schwarz, F. P.; Tewari, Y. B.; Goldberg, R. N.; Tanaka, M.; Yamashoji, Y. J. Phys. Chem. 1994, 98, 4098-4103.
13. Rekharsky, M. V.; Goldberg, R. N.; Schwarz, F. P.; Tewari, Y. B.; Ross, P. D.; Yamashoji, Y.; Inoue, Y. J. Am. Chem. Soc. 1995, 117, 8830-8840.
14. Inoue, Y.; Hakushi, T.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 475-481.
15. Wood, D. J.; Hruska, F. E.; Saenger, W. J. Am. Chem. Soc. 1977, 99, 1735-1740.
16. Hamilton, J. A.; Sabesan, M. N.; Steirauf, L. K.; Geddes, A. Biochem. Biophys. Res. Commun. 1976, 73, 659-664.
17. Barone, G.; Castronuovo, G.; Del Vecchio, P.; Elia, V.; Muscetta, M. J. Chem. Soc., Faraday Trans. 1 1986, 82, 2089-2101.
18. Fujiwara, H.; Arakawa, H.; Murata, S.; Sasaki, Y.; Bull. Chem. Soc. Jpn. 1987, 60, 3891-3894.
19. Saenger, W. Angew. Chem., Int. Ed. Engl. 1980, 19, 344-362.
20. Sanemasa I.; Osajima, T.; Deguchi, T. Bull. Chem. Soc. Jpn. 1990, 63, 2814-2818.
21. Harrison, J. C.; Eftink, M. R. Biopolymers 1982, 21, 1153-1166.
22. Tabushi, I.; Kiyosuke, Y.; Sugimoto, T.; Yamamura, K. J. Am. Chem. Soc. 1978, 100, 916-919.
23. Szejtli, J. In Inclusion Compounds. Volume 3: Physical Properties and Applications; Adwood, J. L., Davies, J. E. D., MacNicol, D. D., Eds.; Academic: New York, 1984; pp 331-390.
24. Schurig, V.; Jung, M. Recent Advances in Chiral Separations. In Proceedings of the Chromatography Society International Symposium Chiral Separation, 2nd Meeting; Stevenson, D.; Wilson, I. D., Eds.; Plenum: New York, 1991; pp 117-133.
25. Amato, M. E.; Djedaini-Pilard, F.; Perly, B.; Scarlata, G. J. Chem. Soc., Perkin Trans. 2 1992, 2065-2069.
26. Berthod, A.; Li, W.; Armstrong D. W. Anal. Chem. 1992, 64, 873-879.
27. Yamashoji, Y.; Ariga, T.; Asano, S.; Tanaka, M. Anal. Chim. Acta 1992, 268, 39-47.
28. Wishnia, A.; Lappi, S. J. J. Mol. Biol. 1974, 82, 77-89.
29. Tucker, E. E.; Christian, S. D. J. Am. Chem. Soc. 1984, 106, 1942-1945.
30. Sasaki, K. J.; Christian, S. D.; Tucker, E. E. Fluid Phase Equilib. 1989, 49, 281-289.
31. Andini, S.; Castronuovo, G.; Elia, V.; Gallotta, E. Carbohydr. Res. 1991, 217, 87-97.
32. Rekharsky, M. V.; Schwarz, F. P.; Tewari, Y. B.; Goldberg, R. N. J. Phys. Chem. 1994, 98, 10282-10288.
33. Bastos, M.; Briggner, L.-E.; Shehatta, I.; Wadsö, I. J. Chem. Thermodyn. 1990, 22, 1181-1190.
34. Kinoshita, T.; Iinuma, F.; Tsuji, A. Chem. Pharm. Bull. 1974, 22, 2413-2420.
35. Castronuovo, G.; Elia, V.; Fessas, D.; Giordano, A.; Velleca, F. Carbohydr. Res. 1995, 272, 31-39.
36. Mwakibete, H.; Bloor, D. M.; Wyn-Jones, E. J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 10, 497-505.
37. Danil de Namor, A. F.; Blackett, P. M.; Cabaleiro, M. C.; Al Rawl, J. M. A. J. Chem. Soc., Faraday Trans. 1994, 90, 845-847.
38. Lin, S.-F.; Connors, K. A. J. Pharm. Sci. 1983, 72, 1333-1338.
39. Bertrand, G. L.; Faulkner, J. R.; Han, S. M.; Armstrong, D. W. J. Phys. Chem. 1989, 93, 6863-6867.
40. Hilbers, H. W.; Jansen, A. C. A.; Janssen, L. H. M. In Procedings of 5th Minutes International Symposium on Cyclodextrins; Puchene, J., Ed.; Sante: Paris, 1990; pp 213-216.
41. Yoshida, N.; Seiyama, A.; Fujimoto, M. J. Phys. Chem. 1990, 94, 4246-4253.
42. Cramer, F.; Saenger, W.; Spatz, H.-C. J. Am. Chem. Soc. 1967, 89, 14-20.
43. Danil de Namor, A. F.; Traboulssi, R.; Lewis, D. F. V. J. Am. Chem. Soc. 1990, 112, 8442-8447.
44. Yoshida, N.; Seiyama, A.; Fujimoto, M. Chem. Lett. 1984, 703-706.
45. Connors, K. A.; Lin, S.-F.; Wong, A. B. J. Pharm. Sci. 1982, 71, 217-222.
46. Wong, A. B.; Lin, S.-F.; Connors, K. A. J. Pharm. Sci. 1983, 72, 388-390.
47. Connors, K. A.; Paulson, A.; Toledo-Velasquez, D. J. Org. Chem. 1988, 53, 2023-2026.
48. Orienti, I.; Fini, A.; Bertasi, V.; Zecchi, V. Eur. J. Pharm. Biopharm. 1991, 37, 110-112.
49. Menard, F. A.; Dedhiya, M. G.; Rhodes, C. T. Drug Dev. Ind. Pharm. 1990, 16, 91-113.
50. Miyaji, T.; Kurono, Y.; Uekama, K.; Ikeda, K. Chem. Pharm. Bull. 1976, 24, 1155-1159.
51. Min, S. H. J. Pharm. Soc. Korea 1971, 15, 8-15.
52. Hardee, G. E.; Otagiri, M.; Perrin, J. H. Acta Pharm. Suec. 1978, 15, 188-199.
53. Danil de Namor, A. F.; Tanaka, D. A. P.; Regueira, L. N.; Gómez-Orellana, I. J. Chem. Soc., Faraday Trans. 1992, 88, 1665-1668.
54. Zhang, B.; Breslow, R. J. Am. Chem. Soc. 1993, 115, 9353-9354.
55. Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644.
56. Liu, Y.; Zhang, Y.-M.; Sun, S.-X.; Li, Y.-M.; Chen, R.-T. J. Chem. Soc., Perkin Trans. 2 1997, 1609-1613.
57. Liu, Y.; Zhang, Y.-M.; Sun, S.-X.; Zhang, Z.-H.; Chen, R.-T. Acta Chim. Sin. 1997, in press.
58. (58) Briggner, L.-E.; Wadsö, I. J. Chem. Thermodyn. 1990, 22, 1067-1074.
59. Bilal, M.; De Brauer, C.; Claudy, P.; Germain, P.; Letoffe, J. M. Thermochim. Acta 1995, 249, 63-74.
60. De Brauer, C.; Claudy, P.; Diot, M.; Germain, P.; Letoffe, J. M. In Proceedings of the Eighth Interanational Symposium on Cyclodextrins; Szejtli, J., Szente, L., Eds.; Kluwer Academic: The Netherlands, 1996; pp 21-24.
61. French, D. Adv. Carbohydr. Chem. 1957, 12, 189-263.
62. Jozwiakowski, M. J.; Connors, K. A. Carbohydr. Res. 1985, 143, 51-59.
63. Wiedenhof, N.; Lammers, J. N. J. J. Carbohydr. Res. 1968, 7, 1-6.
64. Tewari, Y. B.; Goldberg, R. N.; Sato, M. Carbohydr. Res. 1997, 301, 11-22.
65. Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. Bioorg. Chem. 1982, 11, 274-280.
66. Gelb, R. I.; Schwartz, L. M.; Bradshaw, J. J.; Laufer, D. A. Bioorg. Chem. 1980, 9, 299-304.
67. Linert, W.; Margl, P.; Renz, F. Chem. Phys. 1992, 161, 327-338.
68. Linert, W.; Han, L.-F.; Likovits, I. Chem. Phys. 1989, 139, 441-455.
69. Sakurai, M.; Kitagawa, M.; Hoshi, H.; Inoue, Y. Chem. Lett. 1988, 895.
70. Yang, C. P. ITC Data Analysis in Origin v.2.9; MicroCal Inc.: Northampton, MA, 1993.
71. Gelb, R. I.; Schwartz, L. M. J. Inclusion Phenom. Mol. Recognit. Chem. 1989, 7, 465-476.
72. Aversa, A.; Etter, W.; Gelb, R. I.; Schwartz, L. M. J. Inclusion Phenom. Mol. Recognit. Chem. 1990, 9, 277-285.
73. Siimer, E.; Kurvits, M. Thermochim. Acta 1989, 140, 161-168.
74. Tong, W.-Q.; Lach, J. L.; Chin, T.-F.; Guillory, J. K. Pharm. Res. 1991, 8, 951-957.
75. Briggner, L.-E.; Ni, X.-R.; Tempesti, F.; Wadsö, I. Thermochim. Acta 1986, 109, 139-143.
76. Jobe, D. J.; Verrall, R. E.; Palepu, R.; Reinsborough, V. C. J. Phys. Chem. 1988, 92, 3582-3586.
77. Boromo, R. P.; Cucinotta, V.; D'Alessandro, F.; Impellizzeri, G.; Maccarrone, G.; Vecchio, G.; Rizzarelli, E. Inorg. Chem. 1991, 30, 2708-2713.
78. Herrmann, W.; Wehrle, S.; Wenz, G. Chem. Commun. 1997, 1709.
79. Alberty, R. A. Biophys. Chem. 1992, 43, 239-254.
80. Landau, S.; Grushka, E. Isr. J. Chem. 1990, 30, 271-279.
81. Eftink, M. R.; Andy, M. L.; Byström, K.; Perlmutter, H. D.; Kristol, D. S. J. Am. Chem. Soc. 1989, 111, 6765-6772.
82. Menard, F. A.; Dedhiya, M. G.; Rhodes, C. T. Pharm. Acta Helv. 1989, 64, 76-81.
83. Lammers, J. N. J. J.; Koole, J. L.; Van Diemen, A. J. G. Recl. Trav. Chim. Pays-Bas 1972, 91, 483-498.
84. Weickenmeter, M.; Wenz, G. Macromol. Rapid Commun. 1996, 17, 731-736.
85. Kotake, Y.; Janzen, E. G. J. Am. Chem. Soc. 1989, 111, 7319-7323.
86. Turro, N. J.; Okubo, T.; Chung, C.-J. J. Am. Chem. Soc. 1982, 104, 1789-1794.
87. Hersey, A.; Robinson, B. H. J. Chem. Soc., Faraday Trans. 1 1984, 80, 2039-2052.
88. Turco Liveri, V.; Cavallaro, G.; Giammona, G.; Pitarresi, G.; Puglisi, G.; Ventura, C. Thermochim. Acta 1992, 199, 125-132.
89. Tagaki, S.; Maeda, M. J. Inclusion Phenom. 1984, 2, 775-780.
90. Tagaki, S.; Kimura, T.; Maeda, M. Thermochim. Acta 1985, 88, 247-254.
91. Fujisawa, M.; Kimura, T.; Tagaki, S. Netsu Sokutei 1991, 18, 71-76.
92. Wiseman, T.; Williston, S.; Brandts, J. F.; Lin, L.-N. Anal. Biochem. 1989, 179, 131-137.
93. Gorman-Nordmark, M.; Laynez, J.; Schön, A.; Suurkuusk, J.; Wadsö, I. J. Biochem. Biophys. Methods 1984, 10, 187-202.
94. Darrington, R. T.; Xiang, T.-X.; Anderson, B. D. Int. J. Pharm. 1990, 59, 35-44.
95. Kitamura, K.; Imayoshi, N. Anal. Sci. 1992, 8, 497-501.
96. Ebel, S.; Karger, A. Chemom. Intell. Lab. Syst. 1989, 6, 301-311.
97. Kano, K.; Yoshiyasu, K.; Yasuoka, H.; Hata, S.; Hashimoto, S. J. Chem. Soc., Perkin Trans. 2 1992, 1265-1269.
98. Harata, K. Bull. Chem. Soc. Jpn. 1979, 52, 1807-1812.
99. Sokolov, V. I.; Bondareva, V. L.; Shustov, G. V. Metalloorg. Khim. 1991, 4, 697-699 (in Russian).
100. Ueno, A.; Chen, Q.; Suzuki, I.; Osa, T. Anal. Chem. 1992, 64, 1650-1655.
101. Hamasaki, K.; Ikeda, H.; Nakamura, A.; Ueno, A.; Toda, F.; Suzuki, I.; Osa, T. J. Am. Chem. Soc. 1993, 115, 5035-5040.
102. Hamai, S. Bull. Chem. Soc. Jpn. 1986, 59, 2979-2982.
103. Herkstroeter, W. G.; Martic, P. A.; Farid, S. J. Chem. Soc., Perkin Trans. 2 1984, 1453-1457.
104. Nelson, G.; Patonay, G.; Warner, I. M. J. Inclusion Phenom. 1988, 6, 277-289.
105. Hashimoto, S.; Thomas, J. K. J. Am. Chem. Soc. 1985, 107, 4655-4662.
106. Bright, F. V.; Keimig, T. L.; McGown, L. B. Anal. Chim. Acta 1985, 175, 189-201.
107. Casy, A. F. Trends Anal. Chem. 1993, 12, 185-189.
108. Hansen, P. E.; Dettman, H. D.; Sykes, B. D. J. Magn. Reson. 1985, 62, 487-496.
109. Brown, S. E.; Coates, J. H.; Lincoln, S. F.; Coghlan, D. R.; Easton, C. J. J. Chem. Soc., Faraday Trans. 1991, 87, 2699-2703.
110. Greatbanks, D.; Pickford, R. Magn. Reson. Chem. 1987, 25, 208-215.
111. Brereton, I. M.; Spotswood, T. M.; Lincoln, S.; Williams, E. H. J. Chem. Soc., Faraday Trans. 1 1984, 80, 3147-3156.
112. Suzuki, M.; Sasaki, Y. Chem. Pharm. Bull. 1984, 32, 832-838.
113. Michon, J.; Rassat, A. J. Am. Chem. Soc. 1979, 101, 4337-4339.
114. Eastman, M. P.; Freiha, C. C.; Hsu, C. C.; Lum, K. C.; Chang, C. A. J. Phys. Chem. 1987, 91, 1953-1956.
115. Ito, K.; Kikuchi, K.; Okazaki, N.; Kobayashi, S. Agric. Biol. Chem. 1988, 52, 2763-2769.
116. Vazquez, M. L.; Franco, C. M.; Cepeda, A.; Prognon, P.; Mahuzier, G. Anal. Chim. Acta 1992, 269, 239-247.
117. Mohseni, R. M.; Hurtubise, R. J. J. Chromatogr. 1991, 537, 61-71.
118. Korpela, T. K.; Himanen, J.-P. J. Chromatogr. 1984, 290, 351-361.
119. Uekama, K.; Hirayama, F.; Nasu, S.; Matsuo, N.; Irie, T. Chem. Pharm. Bull. 1978, 26, 3477-3484.
120. Rawjee, Y. Y.; Staerk, D. U.; Vigh, G. J. Chromatogr. 1993, 635, 291-306.
121. Penn, S. G.; Berstrom, E. D.; Goodall, D. M.; Loran, J. S. Anal. Chem. 1994, 66, 2866-2873.
122. Gareil, P.; Pernin, D.; Gramond, J.-P.; Guyon, F. J. High Res. Chromatogr. 1993, 16, 195-197.
123. Valsami, G. N.; Koupparis, M. A.; Macheras, P. E. Pharm. Res. 1992, 9, 94-100.
124. Valsami, G. N.; Macheras, P. E.; Koupparis, M. A. J. Pharm. Sci. 1990, 79, 1087-1094.
125. Komiyama, M.; Bender, M. L. J. Am. Chem. Soc. 1978, 100, 2259-2260.
126. Komiyama, M.; Bender, M. L. J. Am. Chem. Soc. 1978, 100, 4576-4579.
127. Van Hooidonk, C.; Breebaart-Hansen, J. C. A. E. Recl. Trav. Chim. Pays-Bas 1971, 90, 680-686.
128. Cohen, J.; Lach, J. L. J. Pharm. Sci. 1963, 52, 132-136.
129. Lach, J. L.; Cohen, J. J. Pharm. Sci. 1963, 52, 137-142.
130. Lach, J. L.; Chin, T.-F.; J. Pharm. Sci. 1964, 53, 69-73.
131. Pauli, W. A.; Lach, J. L. J. Pharm. Sci. 1965, 54, 1745-1750.
132. Lach, J. L.; Pauli, W. A. J. Pharm. Sci. 1966, 55, 32-38.
133. Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. Bioorg. Chem. 1980, 9, 450-461.
134. Li, G.-N.; Jin, H.; Zhang, L.-F. Acta Chim. Sin. 1987, 45, 159-165 (in Chinese).
135. Grime, J. K. Analytical Solution Chemistry; Wiley: New York, 1985.
136. Inoue, Y.; Liu, Y. In Comprehensive Supramolecular Chemistry; Pergamon: Oxford, U.K., 1996; Vol. 8, Chapter 10, Section 4.1.
137. Kano, K.; Tamiya, Y.; Hashimoto, S. J. Inclusion Phenom. Mol. Recognit. Chem. 1992, 13, 287-293.
138. Nakatani, H.; Shibata, K.-I.; Kondo, H.; Hiromi, K. Biopolymers 1977, 16, 2363-2370.
139. Tabushi, I.; Kuroda, Y.; Mizutani, T. J. Am. Chem. Soc. 1986, 108, 4514-4518.
140. Guo, Q. X.; Zheng, X. Q.; Luo, S. H.; Liu, Y. C. Chin. Chem. Lett. 1996, 7, 357-360.
141. Hacket, F.; Coteron, J.-M.; Schneider, H.-J.; Kazachenko, V. P. Can. J. Chem. 1997, 75, 52-55.
142. Nishijo, J.; Nagai, M.; Yasuda, M. Carbohydr. Res. 1993, 245, 43-56.
143. Catena, G. C.; Bright, F. V. Anal. Chem. 1989, 61, 905-909.
144. Bekos, E. J.; Gardella, J. A.; Bright, F. V. J. Inclusion Phenom. Mol. Recognit. Chem. 1996, 26, 185-195.
145. Bright, F. V.; Catena, G. C.; Huang, J.; Zagrobelny, J.; Zhang, J. In Advances in Multidimensional Luminescence; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 85-99.
146. Voet, D.; Voet, J. G. Biochemistry; Wiley: New York, 1990; pp 175-181.
147. Corrodini, R.; Impellizzeri, G.; Marchelli, R.; Rizzarelli, E.; Vecchio, R. In Chemistry and Properties of Biomolecular Systems; Rizzarelli, E., Theophanides, T., Eds.; Kluwer Academic Publisher: Netherlands, 1991; pp 209-221.
148. Uekama, K.; Hirayama, F.; Otagiri, M.; Otagiri, Y.; Ikeda, K. Chem. Pharm. Bull. 1978, 26, 1162-1167.
149. Naghibi, H.; Tamura, A.; Sturtevant, J. M. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 5597-5599.
150. Smithrud, D. B.; Wyman, T. B.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420-5426.
151. Stauffer, D. A.; Richard E. Barrans, J.; Dougherty, D. A. J. Org. Chem. 1990, 55, 2762-2767.
152. Gómez-Orellana, I.; Hallén, D. Thermochim. Acta 1993, 221, 183-193.
153. StöDeman, M.; Wadsö, I. Pure Appl. Chem. 1995, 67, 1059-1068.
154. King, E. J. Acid Base Equilibria; Pergamon: Oxford, U.K., 1965; pp 184-217.
155. Hallén, D. Pure Appl. Chem. 1993, 65, 1527-1532.
156. Molecular Recognition: Chemical and Biological Problems II; Roberts, S. M., Ed.; Royal Society of Chemistry: Cambridge, U.K., 1992.
157. Searle, M. S.; Westwell, M. S.; Williams, D. H. J. Chem. Soc., Perkin Trans. 2 1995, 141-151.
158. Inoue, Y.; Wada, T. In Advances in Supramolecular Chemistry; Gokel, G. W., Ed.; JAI Press: Greenwich, CT, 1997; Vol. 4, pp 55-96.
159. Tanford, C. The Hydrophobic Effect; Formation of Micelles and Biological Membranes, 2nd ed.; Krieger Publ.: Malabar, FL, 1991 (reprint edition; the original 2nd ed. was published in 1980 by Wiley).
160. Hansch, C.; Leo, A. Substitutent Constants for Correlation Analysis in Chemistry and Biology; Wiley-Interscience: New York, 1979.
161. Manor, P. C.; Saenger, W. J. Am. Chem. Soc. 1974, 96, 3630-3639.
162. Lindner, K.; Saenger, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 694-695.
163. Hallén, D.; Nilsson, S.-O.; Rotschild, W.; Wadsö, I. J. Chem. Thermodyn. 1986, 18, 429-442.
164. Nilsson, S.-O.; Wadsö, I. J. Chem. Thermodyn. 1986, 18, 673-681.
165. Konicek, J.; Wadsö, I. Acta Chem. Scand. 1971, 25, 1541-1551.
166. Nichols, N.; Sköld, R.; Spink, C.; Wadsö, I. J. Chem. Thermodyn. 1976, 8, 993-999.
167. Behr, J. P.; Lehn, J. M. J. Am. Chem. Soc. 1976, 98, 1743-1747.
168. Spencer, J. N.; Mihalick, J. E.; Paul, I. M.; Petigara, B.; Wu, Z.; Chen, S.; Yoder, C. H. J. Solution Chem. 1996, 25, 747-756.
169. Hamai, S. Bull. Chem. Soc. Jpn. 1992, 65, 2323-2327.
170. Watanabe, M.; Nakamura, H.; Matsuo, T. Bull. Chem. Soc. Jpn. 1992, 65, 164-169.
171. Castronuovo, G.; Elia, V.; Velleca, F.; Viscardi, G. Thermochim. Acta 1997, 292, 31-37.
172. Gelb, R. I.; Schwartz, L. M.; Johnson, R. F.; Laufer, D. A. J. Am. Chem. Soc. 1979, 101, 1869-1874.
173. Toda, F. Bioorg. Chem. 1991, 19, 157-168.
174. Kauzmann, W. Adv. Protein Chem. 1959, 14, 1-63.
175. Frank, H. S.; Evans, M. W. J. Chem. Phys. 1945, 13, 507-532.
176. Pimentel, G. C.; McClellan, A. L. The Hydrogen Bond; Freeman: San Francisco, CA, 1960; pp 220-221.
177. Gelb, R. I.; Schwartz, L. M.; Cardelino, B.; Fuhrman, H. S.; Johnson, R. F.; Laufer, D. A. J. Am. Chem. Soc. 1981, 103, 1750-1757.
178. Barone, G.; Castronuovo, G.; Elia, V.; Muscetta, M. J. Solution Chem. 1986, 15, 129-140.
179. Otagiri, M.; Miyaji, T.; Uekama, K.; Ikeda, K. Chem. Pharm. Bull. 1976, 24, 1146-1154.
180. Schellman, J. A. C. R. Trav. Lab. Carlsberg, Ser. Chim. 1955, 29, 223-229.
181. Kreshek, G. C.; Scheraga, H. A. J. Phys. Chem. 1965, 69, 1704-1706.
182. Klotz, I. M.; Franzen, J. S. J. Am. Chem. Soc. 1962, 84, 3461-3466.
183. Susi, H.; Timasheff, S. N.; Ard, J. S. J. Biol. Chem. 1964, 239, 3051-3054.
184. Susi, H.; Ard, J. S. Arch. Biochem. Biophys. 1966, 117, 147-151.
185. Schrier, E. E.; Pottle, M.; Scheraga, H. A. J. Am. Chem. Soc. 1964, 86, 3444-3449.
186. Gill, S. J.; Noll, L. J. Phys. Chem. 1972, 76, 3065-3068.
187. Murphy, K. P.; Gill, S. J. J. Chem. Thermodyn. 1989, 21, 903-913.
188. Rudiger, V.; Eliseev, A.; Simova, S.; Schneider, H.-J.; Blandamer, M. J.; Cullis, P. M.; Meyer, A. J. J. Chem. Soc., Perkin Trans. 2 1996, 2119-2123.
189. Connors, K. A.; Lin, S.-F.; Wong, A. B. J. Pharm. Sci. 1982, 71, 217-222.
190. Connors, K. A.; Pendergast, D. D. J. Am. Chem. Soc. 1984, 106, 7607-7614.
191. Hirayama, F.; Kurihara, M.; Uekama, K. Int. J. Pharm. 1987, 35, 193-199.
192. Lewis, E. A.; Hansen, L. D. J. Chem. Soc., Perkin Trans. 2 1973, 2081-2085.
193. Eftink, M. R.; Harrison, J. C. Bioorg. Chem. 1981, 10, 388-398.
194. Harata, K. Bioorg. Chem. 1981, 10, 255-265.
195. Davies, D. M.; Savage, J. R. J. Chem. Res. (S) 1993, 94-95; (M) 666-671.
196. Davies, D. M.; Deary, M. E. J. Chem. Soc., Perkin Trans. 2 1995, 1287-1995.
197. Guo, Q.-X.; Luo, S.-H.; Wang, H.; Zhang, M.-S.; Liu, Y.-C. J. Chem. Res. (S) 1996, 38-39.
198. Guo, Q.-X.; Zheng, X.-Q.; Ruan, X.-Q.; Luo, S.-H.; Liu, Y.-C J. Inclusion Phenom. Mol. Recognit. Chem. 1996, 26, 175-183.
199. Guo, Q.-X.; Luo, S.-H.; Liu, Y.-C. J. Inclusion Phenom. Mol. Recognit. Chem. 1997, in press.
200. Guo, Q.-X.; Chu, S.-D.; Wang, Y.-M.; Pan, Z.-X.; Zhang, M.-S.; Liu, Y.-C. Chin. Chem. Lett. 1997, 8, 145-148.
201. Barone, G.; Castronuovo, G.; di Ruocco, V.; Elia, V.; Giancola, C. Carbohydr. Res. 1989, 192, 331-341.
202. Cooper, A.; MacNicol, D. D. J. Chem. Soc., Perkin Trans. 2 1978, 760-763.
203. Kano, K.; Kato, Y.; Kodera, M. J. Chem. Soc., Perkin Trans. 2 1996, 1211-1217.
204. Kano, K. Yukagaku (J. Jpn. Oil Chem. Soc.) 1994, 43, 868-877 (in Japanese).
205. Gelb, R. I.; Schwartz, L. M. J. Inclusion Phenom. Mol. Recognit. Chem. 1989, 7, 537-543.
206. Gelb, R. I.; Raso, S.; Alper, J. S. Supramol. Chem. 1995, 4, 279-285.
207. Harata, K.; Tsuda, K.; Uekama, K.; Otagiri, M.; Hirayama, F. J. Inclusion Phenom. 1988, 6, 135-142.
208. Kano, K.; Ishimura, T.; Negi, S. J. Inclusion Phenom. Mol. Recognit. Chem. 1995, 22, 285-298.
209. Godínez, L. A.; Schwartz, L.; Criss, C. M.; Kaifer, A. E. J. Phys. Chem. B 1997, 101, 3376-3380.
210. Harata, K. Bioorg. Chem. 1981, 9, 530-539.
211. Bergeron, R. J.; Pillor, D, M.; Gibeily, G.; Roberts, W. P. Bioorg. Chem. 1978, 7, 263-271.
212. VanEtten, R. L.; Sebastian, J. F.; Clowes, G. A.; Bender, M. L. J. Am. Chem. Soc. 1967, 89, 3242-3253.
213. Gill, S. J.; Nichols, N. F.; Wadsö, I. J. Chem. Thermodyn. 1976, 8, 445-452.
214. Leffler, J. E. J. Org. Chem. 1955, 20, 1202-1231.
215. (a) Leffler, J. E.; Grunwald, E. Rates and Equilibria of Organic Reactions; Wiley: New York, 1963 (reprinted version from Dover: New York, 1989).
216. (b) Grunwald, E.; Steel, C. J. Am. Chem. Soc. 1995, 117, 5687.
217. Exner, O. Correlation Analysis of Chemical Data, Plenum: New York, 1988.
218. Chen, R. T. Correlation Analysis in Coordination Chemistry; Anhui Educational Publishing: Hefei, China, 1995 (in Chinese).
219. Petersen, R. C. J. Org. Chem. 1964, 29, 3133-3135.
220. Exner, O. Nature 1964, 201, 488-490.
221. Exner, O. Nature 1970, 227, 366-367.
222. Exner, O. Prog. Phys. Org. Chem. 1973, 10, 411-482.
223. Wold, S.; Exner, O. Chem. Scr. 1973, 3, 5-11.
224. Leffler, J. E. Nature 1965, 205, 1101-1102.
225. Krug, R. R.; Hunter, W. G.; Grieger, R. A. J. Phys. Chem. 1976, 80, 2335-41.
226. Krug, R. R.; Hunter, W. G.; Grieger, R. A. J. Phys. Chem. 1976, 80, 2341-51.
227. Danil de Namor, A. F.; Ritt, M.-C.; Schwing-Weill, M.-J.; Arnaud-Neu, F.; Lewis, D. F. V. J. Chem. Soc., Faraday Trans. 1991, 87, 3231-3239.
228. Inoue, Y.; Hakushi, T. J. Chem. Soc., Perkin Trans. 2 1985, 935.
229. Inoue, Y.; Hakushi, T.; Liu, Y. In Cation Binding by Macrocycles; Inoue, Y.,; Gokel, G. W., Eds.; Marcel Dekker: New York, 1990; Chapter 1.
230. Inoue, Y.; Wada, T. In Molecular Recognition Chemistry; Tsukube, H., Ed.; Sankyo Shuppan: Tokyo, Japan, 1996; Chapter 2 (in Japanese).
231. Ikeda, K.; Uekama, K.; Otagiri, M. Chem. Pharm. Bull. 1975, 23, 201-208.
232. Yoshida, N.; Seiyama, A.; Fujimoto, M. J. Phys. Chem. 1987, 91, 6691-6695.
233. Hirsch, W.; Muller, T.; Pizer, R.; Ricatto, P. J. Can. J. Chem. 1995, 73, 12-15.
234. Cyclodextrin, Ueno, A., Ed.; Sangyo Tosho: Tokyo, 1995 (in Japanese).
235. Whitesides, G. M.; Simanek, E. E.; Mathias, J. P. Acc. Chem. Res. 1995, 28, 37.
236. Gelb, R. I.; Schwartz, L. M.; Radeods, M.; Edmonds, R. B.; Laufer, D. A. J. Am. Chem. Soc. 1982, 104, 6283-6288.
237. Han, L. F.; Linert, W. Orient. J. Chem. 1988, 4, 338-343.
238. Cromwell, W. C.; Byström, K.; Eftink, M. R. J. Phys. Chem. 1985, 89, 326-332.
239. Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. J. Chem. Soc., Perkin Trans. 2 1984, 15-21.
240. Gómez-Orellana, I.; Hallén, D.; StöDeman, M. J. Chem. Soc., Faraday Trans. 1994, 90, 3397-3400.
241. Chun, I. K.; Lee, M. H. Yakche Hakhoechi (J. Korlan Pharm. Sci.) 1989, 19, 71-79 (in Korean).
242. Blyshak, L. A.; Warner, I. M.; Patonay, G. Anal. Chim. Acta 1990, 232, 239-243.
243. Siimer, E.; Kõbu, M.; Kurvits, M. Thermochim. Acta 1990, 170, 89-95.
244. Spencer, J. N.; DeGarmo, J.; Paul, I. M.; He, Q.; Ke, X.; Wu, Z.; Yoder, C. H.; Chen, S.; Mihalick, J. E. J. Solution Chem. 1995, 24, 601-609.
245. Takagi, S.; Fujisawa, M.; Kimura, T. Thermochim. Acta 1991, 183, 289-297.
246. Shehatta, I. React. Funct. Polym. 1996, 28, 183-190.
247. Castronuovo, G.; Elia, V.; Fessas, D.; Velleca, F.; Viscardi, G. Carbohydr. Res. 1996, 287, 127-138.
248. Barone, G.; Castronuovo, G.; Elia, V.; Muscetta, M. Thermochim. Acta 1985, 85, 443-446.
249. Yonemura, H.; Kasahara, M.; Saito, H.; Nakamura, H.; Matsuo, T. J. Phys. Chem. 1992, 96, 5765-5770.
250. Alston, D. R.; Aston, P. R.; Lilley, T. H.; Stoddart, F.; Zarzycki, R. Carbohydr. Res. 1989, 192, 259-281.
251. Hersey, A.; Robinson, B. H.; Kelly, H. C. J. Chem. Soc., Faraday Trans. 1 1986, 82, 1271-1287.
252. Godínez, L. A.; Patel, S.; Criss, C. M.; Kaifer, A. E. J. Phys. Chem. 1995, 99, 17449-17455.
253. Harada, A.; Saeki, K.; Takahashi, S. Carbohydr. Res. 1989, 192, 1-7.
254. Ueda, H.; Perrin, J. H. J. Pharm. Biomed. Anal. 1986, 4 107-110.
255. Godínez, L. A.; Schulze-Fiehn, B. G.; Patel, S.; Criss, C. M.; Evanseck, J. D.; Kaifer, A. E. Supramol. Chem. 1996, 8, 17-22.
256. Ortona, O.; Paduano, L.; Costantino, L.; Vitagliano, V. J. Mol. Liq. 1995, 63, 291-302.
257. Takagi, S.; Fujisawa, M.; Kimura, T. Chem. Express 1991, 6, 93-96.
258. Uekama, K.; Otagiri, M.; Kanie, Y.; Tanaka, S.; Ikeda, K. Chem. Pharm. Bull. 1975, 23, 1421-1430.
259. Yoshida, N.; Fujimoto, M. J. Chem. Res. (S) 1985, 224-225.
260. Danil de Namor, A. F. Ind. J. Technol. 1992, 30, 593-603.
261. Rekharsky, M. V.; Nemykina, E. V.; Eliseev, A. V.; Yatsimirsky, A. K. Thermochim. Acta 1992, 202, 25-33.
262. Gelb, R. I.; Schwartz, L. M.; Radeos, M.; Laufer, D. A. J. Phys. Chem. 1983, 87, 3350-3354.
263. Gelb, R. I.; Schwartz, L. M.; Laufer, D. A. Carbohydr. Res. 1983, 118, 111-117.
264. El Gezawi, S.; Omar, N.; El Rabbat, N.; Ueda, H.; Perrin, J. H. J. Pharm. Biomed. Anal. 1988, 6, 399-406.
265. Tawarah, K. M. Dyes Pigments 1992, 19, 59-67.
266. Miyajima, K.; Komatsu, H.; Inoue, K.; Handa, T.; Nakagaki, M. Bull. Chem. Soc. Jpn. 1990, 63, 6-10.
267. Tawarah, K. M.; Khouri, S. J. Carbohydr. Res. 1993, 245, 165-173.
268. Harata, K. Bull. Chem. Soc. Jpn. 1978, 51, 2737-2738.
269. Gelb, R. I.; Schwartz, L. M.; Cardelino, B.; Laufer, D. A. Anal. Biochem. 1980, 103, 362-368.
270. Takeo, K.; Kuge, T. Stärke 1972, 24, 331-336.
271. Maeda, M.; Takagi, S. Natsu Sokutei 1983, 10, 103-107.
272. Matsuyama, K.; El-Gizawy, S.; Perrin, J. H. Drug Dev. Ind. Pharm. 1987, 13, 2687-2691.
273. Paduano, L.; Sartorio, R.; Vitagliano, V.; Castronuovo, G. Thermochim. Acta 1990, 162, 155-161.
274. Otagiri, M.; Fokkens, J. G.; Hardee, G. E.; Perrin, J. H. Pharm. Acta Helv. 1978, 53, 241-247.
275. Huang, J.; Bright, F. V. J. Phys. Chem. 1990, 94, 8457-8463.
276. Hu, C.-Q. Acta Chim. Sinica 1984, 42, 856-860 (in Chinese).
277. Moelands, D.; Karnik, N. A.; Prankerd, R. J.; Sloan, K. B.; Stone, H. W.; Perrin, J. H. Int. J. Pharm. 1992, 86, 263-265.
278. Siimer, E.; Kurvits, M.; Köstner, A. Thermochim. Acta 1987, 116, 249-256.
279. Sträub, T. S.; Bender, M. L. J. Am. Chem. Soc. 1972, 94, 8881-8888.
280. Takisawa, N.; Shirahama, K.; Tanaka, I. Colloid Polym. Sci. 1993, 271, 499-506.
281. Bowen, J. M.; Purdie, N. Anal. Chem. 1981, 53, 2239-2242.
282. Sadlej-Sosnowska, N. J. Chromatogr. A 1996, 728, 89-95.
283. Tong, L.-H.; Liu, Y. Youji Huaxue 1990, 10, 432-435 (in Chinese).
284. Maeda, M.; Takagi, S. Natsu Sokutei 1983, 10, 43-47 (in Japanese).
285. Menard, F. A.; Dedhiya, M. G.; Rhodes, C. T. Pharm. Acta Helv. 1988, 63, 303-308.
286. Höfler, T.; Wenz, G. J. Inclusion Phenom. Mol. Recognit. Chem. 1996, 25, 81-84.
287. Tong, W.-Q.; Lach, J. L.; Chin, T.-F.; Guillory, J. K. J. Pharm. Biomed. Anal. 1991, 9, 1139-1146.
288. Lammers, J. N. J. J.; Koole, J. L.; Hurkmans, J. Stärke 1971, 23, 167-171.