Improvement of Drug Properties by Cyclodextrins

The Practice of Medicinal Chemistry

Volumn , Issue , 2008, Pages 813-840

  Uekama, Kaneto ^a   Hirayama, Fumitoshi ^a  

^a SOJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84882465202     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-12-374194-3.00040-8     Document Type: Chapter

References (170)

1. Szejtli J. Cyclodextrins and Their Inclusion Complexes 1982, Akademiai Kiadó, Budapest.
2. Saenger W. Cyclodextrin inclusion compounds in research and industry. Angew. Chem. Int. Ed. Engl. 1980, 19:344-362.
3. Szejtli J. Cyclodextrin Technology 1988, Kluwer Academic Publishers, Dordrecht, The Netherlands.
4. Uekama K. Pharmaceutical applications of cyclodextrin complexations. Yakugaku. Zasshi 1981, 101:857-873.
5. Duchêne D. Cyclodextrins and Their Industrial Uses 1987, Editions de Sante, Paris.
6. Uekama K., Otagiri M. Cyclodextrins in drug carrier systems. CRC Crit. Rev. Ther. Drug Carr. Syst. 1987, 3:1-40.
7. Duchêne D. New Trends in Cyclodextrins and Their Derivatives 1991, Editions de Sante, Paris.
8. Uekama K., Hirayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 1998, 98:2045-2076.
9. Szejtli J. Dimethyl-β-cyclodextrin as parent drug carrier. J. Inclusion Phenom. 1983, 1:135-150.
10. Uekama K. Pharmaceutical applications of methylated cyclodextrins. Pharm. Int. 1985, 6:61-65.
11. Pitha J., Pitha J. Amorphous water-soluble derivatives of cyclodextrins, non-toxic dissolution enhancing excipients. J. Pharm. Sci. 1985, 74:987-990.
12. Müller B.W., Brauns U. Solubilization of drugs by modified β-cyclodextrins. Int. J. Pharm. 1985, 26:77-88.
13. Yoshida A., Arima H., Uekama K., Pitha J. Pharmaceutical evaluation of hydroxyalkyl ethers of β-cyclodextrins. Int. J. Pharm. 1988, 46:217-222.
14. Yoshida A., Yamamoto M., Irie T. Some pharmaceutical properties of 3-hydroxypropyl- and 2,3-dihydroxypropyl-β-cyclodextrins and their solubilizing and stabilizing abilities. Chem. Pharm. Bull. 1989, 37:1059-1063.
15. Brewster M.E., Simpkins J.W., Hora M.S., Stern W.C., Bodor N. The potential use of cyclodextrins in parenteral formulations. J. Parent. Sci. Techn. 1989, 43:231-240.
16. Koizumi K., Utamura T., Sato M., Yagi Y. Isolation and characterization of branched cyclodextrins. Carbohyd. Res. 1986, 153:55-67.
17. Yamamoto M., Yoshida A., Hirayama F., Uekama K. Some physicochemical properties of branched β-cyclodextrins and their inclusion characteristics. Int. J. Pharm. 1989, 49:163-171.
18. Hirayama F. Development and pharmaceutical evaluation of hydrophobic derivatives as modified-release drug carrier. Yakugaku. Zasshi 1993, 113:425-437.
19. Hirayama F., Kurihara M., Horichi Y. Preparation of heptakis(2,6-di-O-ethyl)-[3-cyclodextrin and its nuclear magnetic resonance spectroscopic characterization. Pharm. Res. 1993, 10:208-213.
20. Uekama K., Arima H., Irie T. Sustained release of buserelin acetate, a luteinizing hormone-releasing hormone agonist, from the injectable oily preparation utilizing ethylated β-cyclodextrin. J. Pharm. Pharmacol. 1989, 41:874-876.
21. Uekama K., Horiuchi Y., Irie T., Hirayama F. O-Carboxymethyl-O-ethyl-cyclomaltoheptaose as a delayed-release type drug carrier. Improvement of the oral bioavailability of diltiazem. Carbohyd. Res. 1989, 192:323-330.
22. Folkman J., Weisz P.B., Joullie M.M. Control of angiogenesis with synthetic heparin substitutes. Science 1989, 243:1490-1493.
23. Uekama K. Cyclodextrin inclusion compounds: effects on stability and bio-pharmaceutical properties. Topics in Pharmaceutical Sciences 1987, 181-194. Elsevier, Amsterdam. D.D. Breimer, P. Speiser (Eds.).
24. Coleman A.W., Nicolis I., Keller N., Dalbiez J.P. Aggregation of cyclodextrins: an explanation of the abnormal solubility of β-cyclodextrin. J. Inclusion Phenom. 1992, 13:139-143.
25. Okada Y., Kubota Y., Koizumi K. Some properties and inclusion behaviour of branched cyclodextrins. Chem. Pharm. Bull. 1988, 36:2176-2185.
26. Arima H., Kondo T., Irie T. Use of water-soluble β-cyclodextrin derivatives as carriers of anti-inflammatory drug biphenylylacetic acid in rectal delivery. Yakugaku. Zasshi 1992, 112:65-72.
27. Horiuchi Y., Hirayama F., Uekama K. Improvement of stability and bioavailability of 1-hexylcarbamoyl-5-fluorouracil (HCFU) by O-carboxymethyl-O-ethyl-β-cyclodextrin. Yakugaku. Zasshi 1991, 111:592-599.
28. Bender M.L., Komiyama M. Cyclodextrin Chemistry 1978, Springer-Verlag, Berlin.
29. Hirayama F., Kurihara M., Utsuki T., Uekama K. Inhibitory effect of guest molecules on acid-catalyzed ring-opening of β-cyclodextrin. J. Chem. Soc. Chem. Commun. 1993, 1578-1580.
30. Marshall J.J., Miwa I. Kinetic difference between hydrolyses of γ-cyclodextrin by human salivary and pancreatic α-amylases. Biochim. Biophys. Acta. 1981, 661:142-147.
31. Yamamoto M., Aritomi H., Irie T. Biopharmaceutical evaluation of maltosyl-β-cyclodextrin as a parenteral drug carrier. STP Pharm. Sci. 1991, 1:397-402.
32. Brewster M.E., Estes K.S., Bodor N. An intravenous toxicity of study of 2-hydroxypropyl-β-cyclodextrin, a useful drug solubilizer, in rats and monkeys. Int. J. Pharm. 1990, 59:231-243.
33. Frijlink H.W., Visser J., Hefting N.R. The pharmacokinetics of β-cyclodextrin and hydroxypropyl-β-cyclodextrin in the rat. Pharm. Res. 1990, 7:1248-1252.
34. Frank D.W., Gray J.E., Weaver R.N. Cyclodextrin nephrosis in the rat. Am. J. Pathol. 1976, 83:367-382.
35. Irie T., Uekama K. Pharmaceutical application of cyclodextrins III. Toxicological issues and safety. J. Pharm. Sci. 1997, 86:147-162.
36. Ohtani Y., Irie T., Uekama K. Differential effects of α-, β-, and γ-cyclodextrins on human erythrocytes. Eur. J. Biochem. 1989, 186:17-22.
37. 14C-β-cyclodextrin in rats. Arznei.-Forschung. 1985, 35:1042-1047.
38. Poelma F.G.J., Tukker J.J., Hilbers H.W., Jansen A.C.A. Intestinal absorption of drugs II. The effects of inclusion in cyclodextrins on the absorption of dantrolene. J. Inclusion Phenom. 1989, 7:423-430.
39. Arima H., Kondo T., Irie T., Uekama K. Enhanced rectal absorption and reduced local irritation of anti-inflammatory drug ethyl 4-biphenylyl acetate in rats by complexation with water-soluble β-cyclodextrin derivatives and formulations as oleaginous suppository. J. Pharm. Sci. 1992, 81:1119-1125.
40. Uekama K., Imai T., Maeda T. Improvement of dissolution and suppository release characteristics of flurbiprofen by inclusion complexation with heptakis(2,6-di-O-methyl)-β-cyclodextrin. J. Pharm. Sci. 1985, 74:841-845.
41. Arima H., Adachi H., Irie T. Enhancement of the anti-inflammatory effect of ethyl 4-biphenylylacetate in ointment by β-cyclodextrin derivatives: increased absorption and localized activation of the prodrug in rats. Pharm. Res. 1990, 7:1152-1156.
42. Zhang M.-Q., Rees D.C. A review of recent application of cyclodextrins for drug discovery. Expert. Opin. Ther. Pat. 1999, 9:1697-1717.
43. Dietzel K., Estes K.S., Brewster M.E. The use of 2-hydroxypropyl-β-cyclodextrin as a vehicle for intravenous administration of dexamethasone in dogs. Int. J. Pharm. 1990, 59:225-230.
44. Hoshino T., Uekama K., Pitha J. Increase in temperature enhances solubility of drugs in aqueous solutions of hydroxypropylcyclodextrins. Int. J. Pharm. 1993, 98:239-242.
45. Brewster M.E., Estes K.S., Loftsson T. Improved delivery through biological membranes XXXI: Solubilization and stabilization of an estradiol chemical delivery system by modified β-cyclodextrins. J. Pharm. Sci. 1988, 77:981-985.
46. Millard W.J., Romano T.M., Bodor N., Simpkins J.W. Growth hormone (GH) secretory dynamics in animals administered estradiol utilizing a chemical delivery system. Pharm. Res. 1990, 7:1011-1018.
47. Merkus F.W.H.M., Verhoef J.C., Romeijn S.G., Schipper N.G.M. Absorption enhancing effect of cyclodextrins on intranasally administered insulin in rats. Pharm. Res. 1991, 8:588-592.
48. Kurihara M., Hirayama F., Uekama K., Yamasaki M. Improvement of some pharmaceutical properties of nocloprost by β and β-cyclodextrin complexations. J. Inclusion Phenom. 1990, 8:363-373.
49. 9-bis(3-methyl-2-butenyloxy) chalcone, in cyclodextrin inclusion complexes. Eur. J. Pharm. Sci. 1993, 1:81-87.
50. 2 by inclusion complexation with methylated β-cyclodextrins. Chem. Pharm. Bull. 1984, 32:4237-4240.
51. 1 by maltosyl-β-cyclodextrin in lyophilized formulation. Chem. Pharm. Bull. 1992, 40:747-751.
52. Hirayama F., Kurihara M., Uekama K. Improvement of chemical instability of prostacyclin in aqueous solution by complexation with methylated cyclodextrins. Int. J. Pharm. 1987, 35:193-199.
53. Uekama K., Fujinaga T., Hirayama F. Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. J. Pharm. Sci. 1983, 72:1338-1341.
54. Yoshida A., Yamamoto M., Hirayama F., Uekama K. Improvement of chemical instability of digitoxin in aqueous solution by complexation with β-cyclodextrin derivatives. Chem. Pharm. Bull. 1988, 36:4075-4080.
55. Uekama K., Fujinaga T., Hirayama F. Effects of cyclodextrins on the acid hydrolysis of digoxin. J. Pharm. Pharmacol. 1982, 34:627-630.
56. Seo H., Uekama K. Enhanced bioavailability of digoxin by γ-cyclodextrin complexation: evaluation for sublingual and oral administrations in human. Yakugaku. Zasshi 1989, 109:778-782.
57. Brittain H.G. Polymorphism in Pharmaceutical Solids 1999, Marcel Dekker, New York.
58. Bernstein J. Polymorphism in Molecular Crystals 2002, Oxford University Press, Oxford.
59. Davey R.J., Cardew P.T., McEwan D. Rate controlling processes in solvent-mediated phase transformation. J. Cryst. Growth 1986, 79:648-653.
60. Ostwald W. Studien uber die Bildung und Umwandlung Fester Korper. Z. Physik. Chem. 1987, 22:289-302.
61. Sonoda Y., Hirayama F., Arima H. Cyclodextrin-based isolation of Ostwald's metastable polymorphs occurring during crystallization. Chem. Commun. 2007, 517-519.
62. Sonoda Y., Hirayama F., Arima H. Selective crystallization of the metastable form IV polymorph of tolbutamide in the presence of 2,6-di-O-methyl-β-cyclodextrin in aqueous solution. Cryst. Growth Des. 2007, 6:1181-1185.
63. Sugimoto I., Kuchiki K., Nakagawa H. Stability of nifedipine-polyvinylpyrrolidone coprecipitate. Chem. Pharm. Bull. 1981, 29:1715-1723.
64. Uekama K., Ikegami K., Wang Z. Inhibitory effect of 2-hydroxypropyl-β-cyclodextrin on crystal-growth of nifedipine during storage: superior dissolution and oral bioavailability compared with polyvinylpyrrtolidone K-30. J. Pharm. Pharmacol. 1992, 44:73-78.
65. Kikuchi M., Hirayama F., Uekama K. Improvement of chemical instability of carmofur in β-cyclodextrin solid complex by utilizing some organic acids. Chem. Pharm. Bull. 1987, 35:315-319.
66. Kikuchi M., Uemura Y., Hirayama F. Improvement of some pharmaceutical properties of carmofur by cyclodextrin complexation. J. Inclusion Phenom. 1984, 2:623-630.
67. Kikuchi M., Hirayama F., Uekama K. Improvement of oral and rectal bioavailability of carmofur by methylated β-cyclodextrin complexations. Int. J. Pharm. 1987, 38:191-198.
68. Hirayama F., Hirashima N., Abe K. Utilization of diethyl-β-cyclodextrin as a sustained-release carrier for isosorbide dinitrate. J. Pharm. Sci. 1988, 77:233-236.
69. Uekama K., Hirashima N., Horiuchi Y. Ethylated β-cyclodextrins as hydrophobic drug carriers: sustained release of diltiazem in the rat. J. Pharm. Sci. 1987, 76:660-661.
70. Uekama K., Horikawa T., Yamanaka M., Hirayama F. Peracylated β-cyclodextrin as novel sustained-release carrier for water-soluble drug, molsiodomine. J. Pharm. Pharmacol. 1994, 46:714-717.
71. Uekama K., Horikawa T., Horiuchi Y., Hirayama F. In vitro andin vivo evaluation of delayed-release behaviour of diltiazem from its O-carboxymethyl-O-ethyl-β-cyclodextrin complex. J. Control Release 1993, 25:99-106.
72. Horiuchi Y., Abe K., Hirayama F., Uekama K. Control of theophylline by β-cyclodextrin derivatives: hybridizing of hydrophilic and ionizable β-cyclodextrin complexes. J. Control Release 1991, 15:177-182.
73. Matsubara K., Kuriki T., Arima H. Possible use of diethyl-β-cyclodextrin in preparation of sustained release oily injection of busenelin acetate (LHRH agonist). Drug Deliver. Syst. 1990, 5:95-99.
74. Matsubara K., Irie T., Uekama K. Controlled-release of the LHRH agonist buserelin acetate from injectable suspensions containing triacetylated cyclodextrins in the oil vehicle. J. Control Release 1994, 31:173-180.
75. Uekama K., Hirayama F., Irie T. Application of cyclodexterin. Absorption Enhancement: Concept, Possibilities and Limitations 1994, Vol. 3:411-456. Harwood Publishers, Amsterdam. A.G. Boer (Ed.).
76. Tokumura T., Nanba M., Tsushima Y. Enhancement of bioavailability of cinnarizine from its β-cyclodextrin complex on oral administration with DL-phenylalanine as a competing agent. J. Pharm. Sci. 1986, 75:391-394.
77. Seo H., Tsuruoka M., Hashimoto T. Enhancement of oral bioavailability of spironolactone by β- and γ-cyclodextrin complexations. Chem. Pharm. Bull. 1983, 31:286-291.
78. Uekama K., Fujinaga T., Otagiri M. Improvement of dissolution and chemical stability of proscillaridin by cyclodextrin complexations. Acta Pharm. Suec. 1983, 20:287-294.
79. Uekama K., Otagiri M., Uemura Y. Improvement of oral bioavailability of prednisolone by β-cyclodextrin complexation in humans. J. Pharmacobio-Dynam. 1983, 6:124-127.
80. Uekama K., Narisawa S., Hirayama F., Otagiri M. Improvement of dissolution and absorption characteristics of benzodiazepines by cyclodextrin complexation. Int. J. Pharm. 1983, 16:327-338.
81. Uekama K., Matsuo N., Hirayama F. Enhanced bioavailability of acetohexamide by β-cyclodextrin complexation. Yakugaku. Zasshi 1980, 100:903-909.
82. Miyaji T., Inoue Y., Acarrurk F. Improvement of oral bioavailability of fenbufen by cyclodextrin complexations. Acta Pharm. Nord. 1992, 4:17-22.
83. Irie T., Tsunenari Y., Uekama K., Pitha J. Effect of bile on the intestinal absorption of α-cyclodextrin in rats. Int. J. Pharm. 1988, 43:41-44.
84. Nakanishi K., Nadai T., Masada M., Masada M. Effect of cyclodextrins on biological membrane II. Mechanism of enhancement of the intestinal absorption of non-absorbable drug by cyclodextrins. Chem. Pharm. Bull. 1992, 40:1252-1256.
85. Horiuchi Y., Kikuchi M., Hirayama F. Improvement of bioavailability of menaquinone-4 by dimethyl-β-cyclodextrin complexation following oral administration. Yakugaku. Zasshi 1988, 108:1093-1100.
86. Ueno M., Ijitsu T., Horiuchi Y. Improvement of dissolution and absorption characteristics of ubidecarenone by dimethyl-β-cyclodextrin complexation. Acta Pharm. Nord. 1989, 2:99-104.
87. Otagiri M., Imai T., Uekama K. Enhanced oral bioavailability of anti-inflammatory drug flurbiprofen in rabbits by tri-O-methyl-β-cyclodextrin complexation. J. Pharmacobio-Dynam. 1982, 5:1027-1029.
88. Nakai Y., Yamamoto K., Terada K. Interaction of tri-O-methyl-β-cyclodextrin with drugs, enhanced bioavailability of ketoprofen in rats when administered with tri-O-methyl-β-cyclodextrin. Chem. Pharm. Bull. 1983, 31:3745-3747.
89. Kikuchi M., Uekama K. Enhancement of antitumor activity of carmofur (HCFU) by dimethyl-β-cyclodextrin complexation in P-388 leukemia-bearing mice. Xenobiotic Metab. Dispos. 1988, 3:267-273.
90. Uekama K., Horiuchi Y., Kikuchi M. Enhanced dissolution and oral bioavailability of α-tocopheryl esters by dimethyl-β-cyclodextrin complexations. J. Inclusion Phenom. 1988, 6:167-174.
91. Duchêne D., Wouessidjewe D., Poelman M.-C. Dermal uses of cyclodextrin and derivatives. New Trends in Cyclodextrins and Their Derivatives 1991, 447-481. Editions de Sante, Paris. D. Duchene (Ed.).
92. Otagiri M., Fujinaga T., Sakai A., Uekama K. Effects of β- and γ-cyclodextrins on release of betamethasone from ointment bases. Chem. Pharm. Bull. 1984, 32:2401-2405.
93. Orienti I., Zecchi V., Bettasi V., Fini A. Release of ketoprofen from dermal bases in presence of cyclodextrins: effect of the affinity constant determined in semisolid vehicles. Arch. Pharm. (Weinheim) 1991, 324:943-947.
94. Uekama K., Otagiri M., Sakai A. Improvement in the percutaneous absorption of beclomethasone dipropionate by γ-cyclodextrin complexation. J. Pharm. Pharmacol. 1985, 37:532-535.
95. Arima H., Adachi H., Irie T., Uekama K. Improved drug delivery through the skin by hydrophilic β-cyclodextrins: enhancement of anti-inflammatory effect of 4-biphenylylacetic acid in rats. Drug Invest. 1990, 2:155-161.
96. Uekama K., Maeda T., Arima H. Possible utility of β-cyclodextrin complexation in the preparation of biphenylylacetic acid suppository. Yakugaku. Zasshi 1986, 106:1126-1130.
97. Arima H., Irie T., Uekama K. Differences in the enhancing effects of water-soluble β-cyclodextrins on the release of ethyl 4-biphenylyl acetate, an anti-inflammatory agent from an oleaginous suppository base. Int. J. Pharm. 1989, 57:107-115.
98. Hermens W.A.J.J., Deurloo M.J.M., Romeyn S.G. Nasal absorption enhancement of 17β-estradiol by dimethyl-β-cyclodextrin in rabbits and rats. Pharm. Res. 1990, 7:500-503.
99. Schipper N.G.M., Hermens W.A.J.J., Romeyn S.G. Nasal absorption of 17β-estradiol and progesterone from a dimethyl-cyclodextrin inclusion formulation in rats. Int. J. Pharm. 1990, 64:61-66.
100. Stuenkel C.A., Dudley R.E., Yen S.S.C. Sublingual administration of testosterone-hydroxypropyl-β-cyclodextrin inclusion complex simulates episodic androgen release in hypogonadal men. J. Clin. Endocrinol. Metab. 1991, 72:1054-1059.
101. Schipper N.G.M., Verhoef J.C., Merkus F.W.H.M. The nasal mucociliary clearance: relevance to nasal drug delivery. Pharm. Res. 1991, 8:807-814.
102. Hermens W.A.J.J., Belder C.W.J., Merkus J.M.W.M. Intranasal estradiol administration to oophorectomized women. Eur. J. Obstet. Gynecol. Reprod. Biol. 1991, 40:35-41.
103. Yoshida A., Yamamoto M., Itoh T. Utility of 2-hydroxypropyl-β-cyclodextrin in an intramuscular injectable preparation of nimodipine. Chem. Pharm. Bull. 1990, 38:176-179.
104. Irie T., Otagiri M., Uekama K. Alleviation of the chlorpromazine-induced muscular tissue damage by β-cyclodextrin complexation. J. Inclusion Phenom. 1984, 2:637-644.
105. Imai T., Maeda T., Otagiri M., Uekama K. Improvement of absorption characteristics and reduction of irritation on stomach of flurbiprofen by complexation with various cyclodextrins. Xenobiotic Metab. Dispos. 1987, 2:657-664.
106. Ishida K., Hoshino T., Irie T., Uekama K. Alleviation of chlorpromazine-photosensitized contact dermatitis by β-cyclodextrin derivatives and their possible mechanisms. Xenobiotic Metab. Dispos. 1988, 3:377-386.
107. Hoshino T., Ishida K., Irie T. An attempt to reduce the photosensitizing potential of chlorpromazine with the simultaneous use of β- and dimethyl-β-cyclodextrins in guinea pigs. Arch. Dermatol. Res. 1989, 281:60-65.
108. Uekama K., Irie T., Hirayama F. Participation of cyclodextrin inclusion catalysis in photolysis of chlorpromazine to give promazine in aqueous solution. Chem. Lett. 1978, 1109-1112.
109. Hoshino T., Ishida K., Irie T. Reduction of photohemolytic activity of benoxaprofen by β-cyclodextrin complexation. J. Inclusion Phenom. 1988, 6:415-423.
110. Hoshino T., Ishida K., Irie T. Alleviation in protriptyline-photosensitized skin irritation by di-O-methyl-β-cyclodextrin complexation. Int. J. Pharm. 1987, 38:265-267.
111. Perrin J.H., Field F.P., Hansen D.A. beta;-Cyclodextrin as an aid to peritoneal dialysis. Renal toxicity of β-cyclodextrin in the rat. Res. Commun. Chem. Pathol. Pharmacol. 1978, 19:373-376.
112. Carpenter T.O., Pettifor J.M., Russell R.M. Severe hypervitaminosis A in siblings: evidence of variable tolerance to retinol intake. J. Pediatr. 1987, 111:507-512.
113. Irie T., Fukunaga K., Garwood M.K. Hydroxypropylcyclodextrins in parenteral use. II. Effects on transport and disposition of lipids in rabbits and humans. J. Pharm. Sci. 1992, 81:524-528.
114. Frijlink H.W., Eissen A.C., Hefting N.R. The effect of parenterally administered cyclodextrins on cholesterol levels in the rat. Pharm. Res. 1991, 8:9-16.
115. Irie T., Fukunaga K., Pitha J. Hydroxypropylcyclodextrins in parenteral use. I. Lipid dissolution and effects on lipid transfers in vitro. J. Pharm. Sci. 1992, 81:521-523.
116. Uekama K., Shiotani K., Irie T. Protective effects of cyclodextrin sulphates against gentamicin-induced nephrotoxicity in the rat. J. Pharm. Pharmacol. 1993, 45:745-747.
117. Shimamoto T. Pharmaceutical aspects: nasal and depot formulations of leuprolide. J. Androl. 1987, 8:S14-S16.
118. Irie T., Wakamatsu K., Arima H. Enhancing effects of cyclodextrins on nasal absorption of insulin. Int. J. Pharm. 1992, 84:129-139.
119. Schipper N.G.M., Verhoef J., Romeijn S.G., Merkus F.W.H.M. Absorption enhancers in nasal insulin delivery and their influence on nasal ciliary functioning. J. Control Release 1992, 21:173-186.
120. Irie T., Arima H., Abe K. Possible mechanisms of cyclodextrin-enhanced nasal absorption of peptide and protein drugs. Minutes of the 6th International Symposium on Cyclodextrins 1992, 503-508. Editions de Sante, Paris. A.R. Hedges (Ed.).
121. Maitani Y., Igawa T., Machida Y., Nagai T. Intranasal administration of β-interferon in rabbits. Drug Des. Deliver. 1986, 1:65-70.
122. Irie T., Abe K., Adachi H. Potential use of 2-hydroxypropyl-β-cyclodextrin in designing nasal preparations of insulin involving lipophilic absorption enhancer HPE-101. Drug Deliver. Syst. 1992, 7:91-95.
123. Brewster M.E., Hora M.S., Simpkins J.W., Bodor N. Use of 2-hydroxypropyl-β-cyclodextrin as a solubilizing and stabilizing excipient for protein drugs. Pharm. Res. 1991, 8:792-795.
124. 2a monoclonal antibody (MN12). Pharm. Res. 1992, 9:266-270.
125. Uekama K., Yamamoto M., Irie T., Hirayama F. Pharmaceutical evaluation of maltosyl-β-cyclodextrin as a drug carrier in parenteral formulation. Minutes of the 6th International Symposium on Cyclodextrins 1992, 491-496. Editions de Sante, Paris. A.R. Hedges (Ed.).
126. Fukunaga K., Hijikata S., Ishimura K. Aluminium β-cyclodextrin sulphate as a stabilizer and sustained-release carrier for basic fibroblast growth factor. J. Pharm. Pharmacol. 1994, 46:168-171.
127. Harris J.M., Chess R.B. Effects of pegylation on pharmaceuticals. Nat. Rev. Drug Discov. 2003, 2:214-221.
128. Veronese F.M., Harris J.M. Preface: introduction and overview of peptide and protein peglylation. Adv. Drug Deliver. Rev. 2002, 54:453-456.
129. Harada A. Cyclodextrin-based molecular machines. Acc. Chem. Res. 2001, 34:456-464.
130. Higashi T., Hirayama F., Arima H., Uekama K. Polypseudorotaxanes of pegylated insulin with cyclodextrins: application to sustained release system. Bioorg. Med. Chem. Lett. 2007, 17:1871-1874.
131. Wang Z., Ikegami K., Hirayama F., Uekama K. Release characteristics of nifedipine from 2-hydroxypropyl-β-cyclodextrin complex during storage and its modification of hybridizing polyvinylpyrrolidone K-30. Chem. Pharm. Bull. 1993, 41:1822-1826.
132. Wang Z., Hirayama F., Uekama K. Design and in vitro evaluation of a modified-release oral dosage form of nifedipine by hybridization of hydroxypropyl-β-cyclodextrin and hydroxypropyl-cellulose. J. Pharm. Pharmacol. 1993, 45:942-946.
133. Wang Z., Hirayama F., Uekama K. In vivo and in vitro evaluation of modified-release oral dosage form of nifedipine by hybridization of hydroxypropyl-β-cyclodextrin and hydroxypropyl-celluloses in dog. J. Pharm. Pharmacol. 1994, 46:505-507.
134. 1 in fatty alcohol propylene glycol ointment by acidic cyclodextrin derivative, O-carboxymethyl-O-ethyl-β-cyclodextrin. Chem. Pharm. Bull. 1992, 40:1586-1591.
135. 1 through hairless mouse skin: combined use of carboxymethyl-ethyl-β-cyclodextrin and penetration enhancers. J. Pharm. Pharmacol. 1992, 44:119-121.
136. 1 in hairless mice. Eur. J. Pharm. Sci. 1993, 1:117-123.
137. 1 on laurate-induced peripheral vascular occlusive sequelae in rabbits: optimized topical formulation with β-cyclodextrin derivative and penetration enhancer HPE-101. J. Pharm. Pharmacol. 1992, 44:1033-1035.
138. Tobino Y., Torii H., Ikeda K. Release control of morphine hydrochloride in suppository. Kyushu Yakugaku-Kai Kaiho 1991, 45:15-20.
139. Uekama K., Kondo T., Nakamura K. Modification of rectal absorption of morphine from hollow-type suppositories with a combination of α-cyclodextrins and viscosity-enhancing polysaccharide. J. Pharm. Sci. 1995, 84:15-20.
140. König W.A., Lutz S., Wenz G. Modified cyclodextrins-novel, highly enantioselective stationary phases for gas chromatography. Angew. Chem. Int. Ed. Engl. 1988, 27:979-980.
141. Breslow R. Biomimetic chemistry artificial enzymes: catalysis by design. Acc. Chem. Res. 1995, 28:146-153.
142. Parrot-Lopez H., Djedaini F., Perly B. An approach to vectorization of pharmacologically active molecules: the covalent binding of Leuenkephalin to a modified β-cyclodextrin. Tetrahedron Lett. 1990, 31:1999-2002.
143. Tanaka H., Kominato K., Yamamoto R. Synthesis of doxorubicin-cyclodextrin conjugates. J. Antibiot. 1994, 47:1025-1029.
144. Karunaratne D.N., Farmer S., Hancock R.E.W. Synthesis of bulky β-lactams for inhibition of cell surface β-lactamase activity. Bioconjugate Chem. 1993, 4:434-439.
145. A-O-{2-[4-(2-methylpropyl)-phenyl] propanoyl}-β-cyclodextrin. J. Chem. Soc. Chem. Commun. 1991, 759-760.
146. Djedaini-Pilard F., Perly B., Dupas S. Specific interaction and stabilization between host and guest: complexation of ellipticine in a nucleobase functionalized cyclodextrin. Tetrahedron Lett. 1993, 34:1145-1148.
147. Flourie B., Molis C., Achour L. Fate of β-cyclodextrin in the human intestine. J. Nutr. 1993, 123:676-680.
148. Antenucci R., Palmer J.K. Enzymatic degradation of α-and β-cyclodextrins by bacteroides of the human colon. J. Agric. Food Chem. 1984, 32:1316-1321.
149. Hirayama F., Minami K. In vitro evaluation of biphenylylacetic acid-β-cyclodextrin conjugate as colon-targeting prodrug: drug release behavior in rat biological fluids. J. Pharm. Pharmacol. 1996, 48:27-31.
150. A [[(4-biphenylyl) acetyl]amino]-α-, -β-, and -γ-cyclodextrins: potential prodrugs for colon-specific delivery. J. Med. Chem. 1997, 40:2755-2761.
151. Minami K., Hirayama F., Uekama K. Colon-specific drug delivery based on a cyclodextrin prodrug: release behavior of biphenylylacetic acid from its cyclodextrin conjugates in rat intestinal tracts after oral administration. J. Pharm. Sci. 1998, 87:715-720.
152. Yano H., Hirayama F., Arima H., Uekama K. Hydrolysis behavior of prednisolone 21-hemisuccinate/β-cyclodextrin amide conjugate: involvement of intramolecular catalysis of amide group in drug release. Chem. Pharm. Bull. 2000, 48:1125-1128.
153. Yano H., Hirayama F., Arima H., Uekama K. Preparation of prednisolone-appended α-, β- and γ-cyclodextrins: substitution at secondary hydroxyl groups and in vitro hydrolysis behavior. J. Pharm. Sci. 2001, 90:493-503.
154. Yano H., Hirayama F., Arima H., Uekama K. Prednisolone-appended α-cyclodextrin: alleviation of systemic adverse effect of prednisolone after intracolonic administration in 2,4,6-trinitrobenzenesulfonic acid-induced colitis rats. J. Pharm. Sci. 2002, 90:2103-2112.
155. Yano H., Hirayama F., Kamada M. Colon-specific delivery of prednisolone-appended α-cyclodextrin conjugate: alleviation of systemic side effect after oral administration. J. Conrol Release 2002, 79:103-112.
156. Hirayama F., Ogata T., Yano H. Release characteristics of a short-chain fatty acid, n-butyric acid, from its β-cyclodextrin ester conjugate in rat biological media. J. Pharm. Sci. 2000, 89:1486-1495.
157. Kim C., MacKellar W.C., Cho N. Impermeant antitumor sulfonylurea conjugates that inhibit plasma membrane NADH oxidase and growth of HeLa cells in culture: identification of binding proteins from sera of cancer patients. Biochim. Biophys. Acta 1997, 1324:171-181.
158. Parrot-Lopez H., Leray E., Coleman A.W. New β-cyclodextrin derivatives possessing biologically active saccharide antennae. Supramol. Chem. 1993, 3:37-42.
159. Robertis L., Lancelon-Pin C., Driguez H. Synthesis of new oligosaccharidyl-thio-β-cyclodextrins (CDS): a novel family of potent drug-targeting vectors. Bioorg. Med. Chem. Lett. 1994, 4:1127-1130.
160. 0)-hexyl]amido-6-deo xy-cycloheptaamylose. J. Chem. Soc. Chem. Commun. 1995, 1019-1020.
161. Imata H., Kubota K., Hattori K. The specificity of association between concanavalin A and oligosaccharide-branched cyclodextrins with an optical biosensor. Bioorg. Med. Chem. Lett. 1997, 7:109-112.
162. Attioui F., Al-Omar A., Leray E. Recognition ability and cytotoxicity of some oligosaccharidyl substituted β-cyclodextrins. Biol. Cell 1994, 82:161-167.
163. Péan C., Wijkhuisen A., Djedaini-Pilard F. Pharmacological investigations of new peptide-cyclodextrins. Proceedings of the 9th International Symposium on Cyclodextrins 1998, 387-390. Kluwer Academic Press, Dordrecht. J.J. Torres Labandeira, J.L. Vila-Jato (Eds.).
164. Péan C., Fischer J., Doly A. In vitro and in vivo investigations of the specific binding of substance P-γ-cyclodextrin adducts (SB-γ-CD) to rat brain NK1 receptors. Proceedings of the 9th International Symposium on Cyclodextrins 1998, 403-406. Kluwer Academic Press, Dordrecht. J.J. Torres Labandeira, J.L. Vila-Jato (Eds.).
165. Schaschke N., Fiori S., Weyher E. Cyclodextrin as carrier of peptide hormones: conformational and biological properties of β-cyclodextrin/gastrin constructs. J. Am. Chem. Soc. 1998, 120:7030-7038.
166. Arima, H., Kihara, F., Hirayama, F., Uekama, K. Enhancement of gene expression by polyamidoamine dendrimer conjugates with α-, β-, and γ-cyclodextrin. Bioconjugate. Chem. 12: 476-484
167. Begley D.J. The blood-brain barrier: principles for targeting peptides and drugs to the central nervous system. J. Pharm. Pharmacol. 1996, 48:136-146.
168. Bodor N. Prodrugs versus soft drugs. Design of Prodrugs 1985, 333-354. Elsevier, Amsterdam. H. Bundgaard (Ed.).
169. Djedaini-Pilard F., Désalos J., Perly B. Synthesis of a new carrier: N (Leuenkephalin)yl-6-amino-6-deoxycyclomaltoheptaose. Tetrahedron Lett. 1993, 34:2457-2460.
170. Hristova-Kazmierski M.K., Horan P., Davis P. A new approach to enhance bioavailability of biologically active peptides: conjugation of a δ-opioid agonist to β-cyclodextrin. Bioorg. Med. Chem. Lett. 1993, 3:831-834.