Cyclodextrin based novel drug delivery systems

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 62, Issue 1-2, 2008, Pages 23-42

  Vyas, Amber ^a   Saraf, Shailendra ^a   Saraf, Swarnlata ^a  

^a PT RAVISHANKAR SHUKLA UNIVERSITY   (India)

Author keywords

Beads; Complexed; Cyclodextrin; Hydrogels; Liposomes; Nanogels nanoassemblies; Nanoparticles; Nanosponges; Novel drug delivery

Indexed keywords

EID: 51649106621     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-008-9456-y     Document Type: Article

References (188)

1. Connors, K.A.: Population characteristics of cyclodextrin complex stabilities in aqueous solution. J. Pharm. Sci. 84, 843-848 (1995)
2. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743-1753 (1998)
3. Ueda, H., Endo, T.: Large-ring cyclodextrins. In: Dodziuk, H. (ed.) Cyclodextrins and their Complexes. Chemistry, Analytical Methods, Applications, pp. 370-380. Wiley-VCH Verlag, Weinheim (2006)
4. Larsen, K.L.: Large cyclodextrins. J. Incl. Phenom. Macrocycl. Chem. 43, 1-13 (2002)
5. Loftsson, T., Brewester, M.: Pharmaceutical applications of cyclodextrins. Drug solubilization and stabilization. J. Pharm. Sci. 85, 1017-1025 (1996)
6. Szejtli, J.: Cyclodextrin Technology. Kluwer Academic, Dordrecht (1988)
7. Szente, L., Szejtli, J.: Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development. Adv. Drug Deliv. Rev. 36, 17-38 (1999)
8. Matsuda, H., Arima, H.: Cyclodextrins in transdermal and rectal delivery. Adv. Drug Deliv. Rev. 36, 81-99 (1999)
9. Hirayama, F., Uekama, K.: Cyclodextrin-based controlled drug release system. Adv. Drug Deliv. Rev. 36, 125-141 (1999)
10. Bilati, U., Allémann, E., Doelker, E.: Strategic approaches for overcoming peptide and protein instability within biodegradable nano- and microparticles. Eur. J. Pharm. Biopharm. 59, 375-388 (2005)
11. Uekama, K., et al.: Sustained release of buserelin, a luteinizing hormone-releasing hormone agonist, from an injectable oily preparation utilizing ethylated β-cyclodextrin. J. Pharm. Pharmacol. 41, 874-876 (1989)
12. Loftsson, T., Brewster, M.E., Másson, M.: Role of cyclodextrins in improving oral drug delivery. Am. J. Drug Deliv. 2(4), 261-275 (2004)
13. Rajewski, R.A., Stella, V.J.: Pharmaceutical applications of cyclodextrins in vivo drug delivery. J. Pharm. Sci. 85, 1142-1168 (1996)
14. Irie, T., Uekama, K.: Pharmaceutical applications of cyclodextrins: III. Toxicological issues and safety evaluation. J. Pharm. Sci. 86(2), 147-162 (1997)
15. Uekama, K., Hirayama, F., Irie, T.: Cyclodextrin drug carrier systems. Chem. Rev. 98, 2045-2076 (1998)
16. Thompson, D.O.: Cyclodextrins-enabling excipients: their present and future use in pharmaceuticals. Crit. Rev. Ther. Drug Carrier Syst. 14, 1-104 (1997)
17. Szejtli, J.: Past, present, and future of cyclodextrin research. Pure Appl. Chem. 76(10), 1825-1845 (2004)
18. Loftsson, T., Duchêne, D.: Historical perspectives: cyclodextrins and their pharmaceutical applications. Int. J. Pharm. 329, 1-11 (2007)
19. Schardinger, F.: Bildung kristallisierter Polysaccharide (Dextrine) aus Stärkekleister durch Microben. Zentralbl. Bakteriol. Parasitenk. Abt. 29(II), 188-197 (1911)
20. Freudenberg, K., Cramer, F.: Die Konstitution der Schardinger-Dextrine α, β und γ. Z. Naturforsch. 3b, 464 (1948)
21. Szejtli, J.: Medicinal applications of cyclodextrins. Res. Rev. 14, 353-386 (1994)
22. Frömming, K.H., Szejtli, J.: Cyclodextrins in Pharmacy. Kluwer Academic, Dordrecht (1994)
23. Soliman, O.A.E., Kimura, K., Hirayama, F., Uekama, K., El-Sabbagh, H.M., El-Gawad, A.E.-G.H., Hashim, F.M.: Amorphous spironolactone-hydroxypropylated cyclodextrin complexes with superior dissolution and oral bioavailability. Int. J. Pharm. 149, 73-83 (1997)
24. Savolainen, J., Jarvinen, K., Taipale, H., Jarho, P., Loftsson, T., Jarvinen, T.: Coadministration of a water-soluble polymer increases the usefulness of cyclodextrins in solid oral dosage forms. Pharm. Res. 15(11), 1696-1701 (1998)
25. Wong, J.W., Yuen, K.H.: Improved oral bioavailability of artemisinin through inclusion complexation with β- and γ-cyclodextrin. Int. J. Pharm. 227, 177-185 (2001)
26. Kikuchi, M., Hirayama, F., Uekama, K.: Improvement of oral and rectal bioavailabilities of carmofur by methylated β-cyclodextrin complexations. Int. J. Pharm. 38, 191-198 (1987)
27. Evrard, B., Chiap, P., DeTullio, P., Ghalmi, F., Piel, G., Van Hees, T., Crommen, J., Losson, B., Delattre, L.: Oral bioavailability in sheep of albendazole from a suspension and from a solution containing hydroxypropyl-β-cyclodextrin. J. Control. Release 85(1-3), 45-50 (2002)
28. Carrier, R.L., Miller, L.A., Ahmed, I.: The utility of cyclodextrins for enhancing oral bioavailability. J. Control. Release 123, 78-99 (2007)
29. Gibaud, S., Zirar, S.B., Mutzenhardt, P., Fries, I., Astier, A.: Melarsoprol-cyclodextrins inclusion complexes. Int. J. Pharm. 306, 107-121 (2005) (ref 01)
30. Szejtli, J., Szente, L.: Elimination of bitter, disgusting tastes of drugs and foods by cyclodextrins. Eur. J. Pharm. Biopharm. 61, 115-125 (2005)
31. Weiszfeiler, V., Szejtli, J.: Bitterness reduction with beta-cyclodextrin. In: Huber, O., Szejtli, J. (eds.) Proc. Int. Symp. Cyclodextrins. Kluwer, Dordrecht, Neth. (1988) (CA:112:104658)
32. Andersen, F.M., Bundgaard, H., Mengel, H.B.: Formation, bioavailability and organoleptic properties of an inclusion complex of femoxetine with beta-cyclodextrin. Int. J. Pharm. 21, 51-60 (1984) (CA101:235497)
33. Uekama, K., Oh, K., Otagiri, M., Seo, H., Tsuruoka, M.: Improvement of some pharmaceutical properties of clofibrate by cyclodextrin complexation. Pharm. Acta Helv. 58, 338-342 (1983)
34. Ragnoa, G., Cione, E., Garofalo, A., Genchi, G., Ioele, G., Risoli, A., Spagnoletta, A.: Design and monitoring of photostability systems for amlodipine dosage forms. Int. J. Pharm. 265, 125-132 (2003)
35. Chen, X., Chen, R., Guo, Z., Li, C., Li, P.: The preparation and stability of the inclusion complex of astaxanthin with β-cyclodextrin. Food Chem. 101, 1580-1584 (2007)
36. Karathanos, V.T., Mourtzinos, I., Yannakopoulou, K., Andrikopoulos, N.K.: Study of the solubility, antioxidant activity and structure inclusion complex of vanillin with β-cyclodextrin. Food Chem. 101, 652-658 (2007)
37. Ayala-Zavala, J.F., Soto-Valdez, H., González-León, A., Álvarez-Parrilla, E., Martín-Belloso, O., González-Aguilar, G.A.: Microencapsulation of cinnamon leaf (Cinnamomum zeylanicum) and garlic (Allium sativum) oils in β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 60(3-4), 359-368 (2008)
38. Lindner, K.: Using cyclodextrin aroma complexes in the catering. Food/Nahrung. 26(7-8), 675-680 (2006)
39. Lucas-Abellán, C., Fortea, I., López-Nicolás, J.M., Núñez-Delicado, E.: Cyclodextrins as resveratrol carrier system. Food Chem. 104(1), 39-44 (2007)
40. Kim, J.H., Lee, S.K., Ki, M.H., Choi, W.K., Ahn, S.K., Shin, H.J., Il Hong, C.: Development of parenteral formulation for a novel angiogenesis inhibitor, CKD-732 through complexation with hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 272, 79-89 (2004)
41. Szejtli, J.: Cyclodextrin complexed generic drugs are generally not bio-equivalent with the reference products: therefore the increase in number of marketed drug/cyclodextrin formulations is so slow. J. Incl. Phenom. Macrocycl. Chem. 52, 1-11 (2005)
42. Tasic, L.M., Jovanovic, M.D., Djuric, Z.R.: The influence of beta-cyclodextrin on the solubility and dissolution rate of paracetamol solid dispersions. J. Pharm. Pharmacol. 44, 52-55 (1992)
43. Connors, K.A.: Measurement of cyclodextrin complex stability constants. In: Szejtli, J., Osa, T. (eds.) Cyclodextrins. Comprehensive Supramolecular Chemistry, vol. 3, pp. 205-241. Elsevier Sciences, Oxford (1996)
44. Challa, R., Ahuja, A., Ali, J., Khar, R.K.: Cyclodextrins in drug delivery: an updated review. AAPS PharmSciTech. 6(2), E329-E357 (2005)
45. Becket, G., Schep, L.J., Tan, M.Y.: Improvement of the in vitro dissolution of praziquantal by complexation with alpha, beta and gamma-cyclodextrins. Int. J. Pharm. 179, 65-71 (1999)
46. Cavallari, C., Abertini, B., Rodriguez, M.L.G., Rodriguez, L.: Improved dissolution behavior of steam granulated piroxicam. Eur. J. Pharm. Biopharm. 54, 65-73 (2002)
47. Ghorab, M.K., Adeyeye, M.C.: Enhancement of ibuprofen dissolution via wet granulation with beta cyclodextrin. Pharm. Dev. Technol. 6, 305-314 (2001)
48. Sanghavi, N.M., Choudhari, K.B., Matharu, R.S., Viswanathan, L.: Inclusion complexation of Lorazepam with beta-cyclodextrin. Drug Dev. Ind. Pharm. 19, 701-712 (1993)
49. Ahn, H.J., Kim, K.M., Choi, S.J., Kim, C.K.: Effects of cyclodextrin derivatives on bioavailability of ketoprofen. Drug Dev. Ind. Pharm. 23, 397-401 (1997)
50. Chowdary, K.P.R., Nalluri, B.N.: Nimesulide and beta-cyclodextrin inclusion complexes: physicochemical characterization and dissolution rate studies. Drug Dev. Ind. Pharm. 26, 1217-1220 (2000)
51. Pose-Vilarnovo, B., Perdomo-Lopez, I., Echezarreta-Lopez, M., Schroth-Pardo, P., Estrada, E., Torres-Labandeira, J.J.: Improvement of water solubility of sulfamethizole through its complexation with β- and hydroxypropyl-β-cyclodextrin-characterization of the interaction in solution and in solid state. Eur. J. Pharm. Sci. 13, 325-331 (2001)
52. Lotter, J., Krieg, H.M., Keizer, K., Breytenbach, J.C.: The influence of beta-cyclodextrin on the solubility of chlorthalidone and its enantiomers. Drug Dev. Ind. Pharm. 25, 879-884 (1999)
53. Askrabic, J.M., Rajic, D.S., Tasic, L., Djuric, S., Kasa, P., Hodi, K.P.: Etodolac and solid dispersion with β-cyclodextrin. Drug Dev. Ind. Pharm. 23, 1123-1129 (1997)
54. Chowdary, K.P.R., Rao, S.S.: Investigation of dissolution of itraconazole by complexation with β-, and hydroxypropyl-β cyclodextrins. Indian J. Pharm. Sci. 63, 438-441 (2001)
55. Arias, M.J., Moyano, J.R., Munoz, P., Gines, J.M., Justo, A., Giordano, F.: Study of omeprazole-gamma-cyclodextrin complexation in the solid state. Drug Dev. Ind. Pharm. 26, 253-259 (2000)
56. Uekama, K., Fujinaga, T., Hirayama, F., Otagiri, M., Yamasaki, M., Seo, H., Hashimoto, T., Tsuruoka, M.: Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. J. Pharm. Sci. 72, 1338-1341 (1983)
57. Kang, J., Kumar, V., Yang, D., Chowdhury, P.R., Hohl, R.J.: Cyclodextrin complexation: influence on the solubility, stability, and cytotoxicity of camptothecin, an antineoplastic agent. Eur. J. Pharm. Sci. 15, 163-170 (2002)
58. Bettinetti, G., Gazzaniga, A., Mura, P., Giordano, F., Setti, M.: Thermal behavior and dissolution properties of naproxen in combinations with chemically modified beta-cyclodextrins. Drug Dev. Ind. Pharm. 18, 39-53 (1992)
59. Nagase, Y., Hirata, M., Wada, K., Arima, H., Hirayama, F., Irie, T., Kikuchi, M., Uekama, K.: Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether beta-cyclodextrin. Int. J. Pharm. 229, 163-172 (2001)
60. Loftsson, T., Peterson, D.S.: Cyclodextrin solubilization of ETH-615, a zwitterionic drug. Drug Dev. Ind. Pharm. 24, 365-370 (1998)
61. McCandless, R., Yalkowsky, S.H.: Effect of hydroxypropyl-betacyclodextrin and pH on the solubility of levemopamil HCl. J. Pharm. Sci. 87, 1639-1642 (1998)
62. Castillo, J.A., Canales, J.P., Garcia, J.J., Lastres, J.L., Bolas, F., Torrado, J.J.: Preparation and characterization of albendazole beta-cyclodextrin complexes. Drug Dev. Ind. Pharm. 25, 1241-1248 (1999)
63. Arima, H., Yunomae, K., Miyake, K., Irie, T., Hirayama, F., Uekama, K.: Comparative studies of the enhancing effects of cyclodextrins on the solubility and oral bioavailability of tacrolimus in rats. J. Pharm. Sci. 90, 690-701 (2001)
64. Zhao, L., Li, P., Yalkowsky, S.H.: Solubilization of fluasterone. J. Pharm. Sci. 88, 967-969 (1999)
65. Kaukonen, A.M., Lennernas, H., Mannermaa, J.P.: Water-soluble beta cyclodextrin in paediatric oral solutions of spiranolactone: preclinical evalution of spiranolactone bioavailability from solutions of beta cyclodextrin derivatives in rats. J. Pharm. Pharmacol. 50, 611-619 (1998)
66. Jain, A.C., Adeyeye, M.C.: Hygroscopicity, phase solubility and dissolution of various substituted sulfobutylether beta-cyclodextrins (SBE) and danazol-SBE inclusion complexes. Int. J. Pharm. 212, 177-186 (2001)
67. Londhe, V., Nagarsenker, M.: Comparison between Hydroxypropyl-β- cyclodextrin and polyvinyl pyrrolidine as carriers for carbamazepine solid dispersions. Indian J. Pharm. Sci. 61, 237-240 (1999)
68. Loftsson, T., Stefánsson, E.: Effect of cyclodextrins on topical drug delivery to the eye. Drug Dev. Ind. Pharm. 23, 473-481 (1997)
69. Van Dorne, H.: Interaction between cyclodextrins and ophthalmic drugs. Eur. J. Pharm. Biopharm. 39, 133-139 (1993)
70. Uekama, K., Hirayama, F., Arima, H.: Recent aspect of cyclodextrin-based drug delivery system. J. Incl. Phenom. Macrocycl. Chem. 56, 3-8 (2006)
71. Davis, M.E., Brewster, M.E.: Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov. 3, 1023-1035 (2004)
72. Uekama, K.: Design and evaluation of cyclodextrin-based drug formulation. Chem. Pharm. Bull. 52, 900-915 (2004)
73. Miyake, K., Arima, H., Hiramaya, F.: Improvement of solubility and oral bioavailability of rutin by complexation with 2-hydroxypropyl-β- cyclodextrin. Pharm. Dev. Technol. 5, 399-407 (2000)
74. Memisoglu, E., Bochot, A., Sen, M., Charon, D., Duchene, D., Hincal, A.A.: Amphiphilic beta-cyclodextrins modified on the primary face: synthesis, characterization, and evaluation of their potential as novel excipients in the preparation of nanocapsules. J. Pharm. Sci. 91, 1214-1224 (2002)
75. Okimoto, K., Ohike, A., Ibuki, R., Ohnishi, N., Rajewski, R.A., Stella, V.J., Irie, T., Uekama, K.: Design and evaluation of an osmotic pump tablet (OPT) for chlorpromazine using (SBE)7 m-beta-CD. Pharm. Res. 16, 549-554 (1999)
76. Kamada, M., Hirayama, F., Udo, K., Yano, H., Arima, H., Uekama, K.: Cyclodextrin conjugate-based controlled release system: repeated- and prolonged-releases of ketoprofen after oral administration in rats. J. Control. Release 82, 407-416 (2002)
77. Hwang, S.J., Bellocq, N.C., Davis, M.E.: Effects of structure of β-cyclodextrin-containing polymers on gene delivery. Bioconjug. Chem. 12, 280-290 (2001)
78. Gonzalez, H., Hwang, S.J., Davis, M.E.: New class of polymers for the delivery of macromolecular therapeutics. Bioconj. Chem. 10, 1068 (1999)
79. Hwang, S.J., Bellocq, N.C., Davis, M.E.: Effects of Structure of beta-cyclodextrin-containing polymers on gene delivery. Bioconj. Chem. 12(2), 280-290 (2001)
80. Pun, S.H., Davis, M.E.: Development of a non-viral gene delivery vehicle for systemic application. Bioconj. Chem. 13, 630 (2002)
81. Kihara, F., Arima, H., Tsutsumi, T., Hirayama, F., Uekama, K.: Effects of structure of polyamidoamine dendrimer on gene transfer efficiency of the dendrimer conjugate with alpha-cyclodextrin. Bioconjug. Chem. 13, 1211-1219 (2002)
82. Nicolazzi, C., Venard, V., Le Faou, A., Finance, C.: In vitro antiviral activity of the gancyclovir complexed with beta cyclodextrin on human cytomegalovirus strains. Antiviral Res. 54, 121-127 (2002)
83. Blanchard, J., Ugwu, S.O., Bhardwaj, R., Dorr, R.T.: Development and testing of an improved of phenytoin using 2-hydroxypropyl-betacyclodextrin. Pharm. Dev. Technol. 5, 333-338 (2000)
84. Scalia, S., Villani, S., Casolari, A.: Inclusion complexation of the sunscreening agent 2-ethyl hexyl-p-dimethyl aminobenzoate with hydroxypropyl-β-cyclodextrin: effect on photostability. J. Pharm. Pharmacol. 51, 1367-1374 (1999)
85. Loftsson, T., Jarvinen, T.: Cyclodextrins in ophthalmic drug delivery. Adv. Drug Deliv. Rev. 36, 59-79 (1999)
86. Ueda, H., Ou, D., Endo, T., Nagase, H., Tomono, K., Nagai, T.: Evaluation of a sulfobutyl ether beta-cyclodextrin as a solubilizing/stabilizing agent for several drugs. Drug Dev. Ind. Pharm. 24, 863-867 (1998)
87. Lutka, A., Koziara, J.: Interaction of trimeprazine with cyclodextrins in aqueous solution. Chem. Pharm. Bull. 57, 369-374 (2000)
88. Lutka, A.: Investigation of interaction of promethazine with cyclodextrins in aqueous solution. Acta Pol. Pharm. 59, 45-51 (2002)
89. Babu, R., Pandit, J.K.: Effect of aging on the dissolution stability of glibenclamide/beta cyclodextrin complex. Drug Dev. Ind. Pharm. 25, 1215-1219 (1999)
90. Cwiertnia, B., Hladon, T., Stobiecki, M.: Stability of diclofenac sodium in the inclusion complex in the beta cyclodextrin in the solid state. J. Pharm. Pharmacol. 51, 1213-1218 (1999)
91. Li, J., Guo, Y., Zografi, G.: The solid-state stability of amorphous quinapril in the presence of beta-cyclodextrins. J. Pharm. Sci. 91, 229-243 (2002)
92. Croyle, M.A., Cheng, X., Wilson, J.M.: Development of formulations that enhance physical stability of viral vectors for gene therapy. Gene Ther. 8, 1281-1290 (2001)
93. Singla, A.K., Garg, A., Aggarwal, D.: Paclitaxel and its formulations. Int. J. Pharm. 235, 179-192 (2002)
94. McCormack, B., Geegoriadis, G.: Drugs-in-cyclodextrins-in liposomes: a novel concept in drug delivery. Int. J. Pharm. 112, 249-258 (1994)
95. McCormack, B., Gregoriadis, G.J.: Entrapment of cyclodextrin drug complexes into liposomes: potential advantages in drug delivery. Drug Target. 2, 449-454 (1994)
96. McCormack, B., Gregoriadis, G.: Comparative studies of the fate of free and liposome-entrapped hydroxypropyl-/3-cyclodextrin/drug complexes after intravenous injection into rats: implications in drug delivery. Biochim. Biophys. Acta 1291, 237-244 (1996)
97. McCormack, B., Gregoriadis, G.: Drugs-in-cyclodextrins-in-liposomes: an approach to controlling the fate of water insoluble drugs in vivo. Int. J. Pharm. 162, 59-69 (1998)
98. Fatouros, D.G., Hatzidimitriu, K., Antimisiaris, S.G.: Liposomes encapsulating prednisolone-cyclodextrin complexes: comparison of membrane integrity and drug release. Eur. J. Pharm. Sci. 13, 287-296 (2001)
99. Skalko, N., Brandl, M., Ladan, M.B., Grid, J.F., Genjak, I.J.: Liposomes with nifedipine and nifedipine-cyclodextrin complex: calorimetrical. Eur. J. Pharm. Sci. 4, 359-366 (1996)
100. Skalko-Basnet, N., Pavelic, Z., Becirevic-Lacan, M.: Liposomes containing drug and cyclodextrin prepared by the one-step spray-drying method. Drug Dev. Ind. Pharm. 26, 1279-1284 (2000)
101. Loukas, Y.L., Jayasekera, P., Gregoriadis, G.: Novel liposome-based multicomponent systems for the protection of photolabile agents. Int. J. Pharm. 117, 85-94 (1995)
102. Loukas, Y.L., Vraka, V., Gregoriadis, G.: Drugs, in cyclodextrins, in liposomes: a novel approach to the chemical stability of drugs sensitive to hydrolysis. Int. J. Pharm. 162, 137-142 (1998)
103. Sukegawa, T., Furuike, T., Niikura, K., Yamagishi, A., Monde, K., Nishimura, S.: Erythrocyte-like liposomes prepared by means of amphiphilic cyclodextrin sulfates. Chem. Commun. 5, 430-431 (2002)
104. Loftsson, T., Kristmundsdóttir, T., Ingvarsdóttir, K., Ólafsdóttir, B.J., Baldvinsdóttir, J.: Preparation and physical evaluation of microcapsules of hydrophilic drug-cyclodextrin complexes. J. Microencapsul. 9, 375-382 (1992)
105. Filipovic-Grcic, J., Laan, M.B., Skalko, N., Jalsenjak, I.: Chitosan microspheres of nifedipine and nifedipine-cyclodextrin inclusion complexes. Int. J. Pharm. 135, 183-190 (1996)
106. Filipovic-Grcic, J., Voinovich, D., Moneghini, M., Becirevic-Lacan, M., Magarotto, L., Jalsenjak, I.: Chitosan microspheres with hydrocortisone and hydrocortisone hydroxypropyl-β-cyclodextrin inclusion complex. Eur. J. Pharm. Sci. 9, 373-379 (2000)
107. Quaglia, F., De Rosa, G., Granata, E., Ungaro, F., Fattal, E., La Rotonda, M.I.: Feeding liquid, non-ionic surfactant and cyclodextrin affect the properties of insulin-loaded poly (lactide-co-glycolide) microspheres prepared by spray-drying. J. Control. Release 86, 267-278 (2003)
108. Pariot, N., Levy, F.E., Andry, M.C., Levy, M.C.: Cross-linked betacyclodextrin microcapsules.II. Retarding effect on drug release through semi-permeable membranes. Int. J. Pharm. 232, 175-181 (2002)
109. Duchênea, D., Ponchel, G., Wouessidjewe, D.: Cyclodextrins in targeting Application to nanoparticles. Adv. Drug Del. Rev. 36, 29-40 (1999)
110. Memisoglu, E., Bochot, A., Sen, M., Duchene, D., HIncal, A.A.: Non-surfactant nanospheres of progesterone inclusion complexes with amphiphilic β-cyclodextrins. Int. J. Pharm. 251, 143-153 (2003)
111. Silveira, M.A., Ponchel, G., Puisieux, F., Duchene, D.: Combined poly (isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs. Pharm. Res. 15, 1051-1055 (1998)
112. Silveira, A.M.: Formulation et caractérisation de nanoparticules combinées de poly(cyanoacrylate d'isobutyle) et de cyclodextrines destinées à l'admininistration de principes actifs faiblement solubles dans l'eau. Thesis, University of Paris XI (1998)
113. Boudad, H., Legrand, P., Lebas, G., Cheron, M., Duchene, D., Ponchel, G.: Combined hydroxypropyl-beta-cyclodextrin and poly (alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir. Int. J. Pharm. 218, 113-124 (2001)
114. Cavalli, R., Peira, E., Caputo, O., Gasco, M.R.: Solid lipid nanoparticles as carriers of hydrocortisone and progesterone complexes with betacyclodextrins. Int. J. Pharm. 182, 59-69 (1999)
115. Memisoglu, E., Bochot, A., Ozalp, M., Sen, M., Duchene, D., Hincal, A.A.: Direct formation of nanospheres from amphiphilic beta-cyclodextrin inclusion complexes. Pharm. Res. 20, 117-125 (2003)
116. National Institute of Health: NIH Consens Statement Online. Sunlight, Ultraviolet Radiation, and the Skin. http://text.nlm.nih.gov/nih/cdc/www/74txt. html. Accessed 6 Feb. 2000 (1989)
117. Fenyvesi, É., Otta, K., Kolbe, I., Novák, C., Szejtli, J.: Cyclodextrin complexes of UV filters. J. Incl. Phenom. Macrocycl. Chem. 48, 117-123 (2004)
118. Schwack, W., Rudolph, T.: Photochemistry of dibenzoylmethane UV-A filters. J. Photochem. Photobiol. B Biol. 28, 229-234 (1995)
119. Scalia, S., Villani, S., Scatturin, A., Vandelli, M.A., Forni, F.: Complexation of the sunscreen agent, butyl-methoxydibenzoylmethane, with hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 175, 205-213 (1998)
120. Tarras-Wahlberg, N., Stenhagen, G., Larkö, O., Rosén, A., Wennberg, A.M., Wennerström, O.: Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation. J. Invest. Dermatol. 113, 547-553 (1999)
121. Chatelain, E., Gabard, B.: Photostabilization of butyl methoxydibenzoylmethane (Avobenzone) and ethylhexyl methoxycinnamate by bisethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter. Photochem. Photobiol. 74, 401-406 (2001)
122. Scalia, S., Molinari, A., Casolari, A., Maldotti, A.: Complexation of the sunscreen agent, phenylbenzimidazole sulphonic acid with cyclodextrins: effect on stability and photo-induced free radical formation. Eur. J. Pharm. Sci. 22, 241-249 (2004)
123. Scalia, S., Tursilli, R., Sala, N., Iannuccelli, V.: Encapsulation in lipospheres of the complex between butyl methoxydibenzoylmethane and hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 320, 79-85 (2006)
124. Lo Nostro, P., Fratoni, L., Baglioni, P.: Modification of a cellulosic fabric with β-cyclodextrin for textile finishing applications. J. Incl. Phenom. Macrocycl. Chem. 44, 423-427 (2002)
125. Martel, B., Morcellet, M., Ruffin, D., Vinet, F., Weltrowski, M.: Capture and controlled release of fragrances by CD finished textiles. J. Incl. Phenom. Macrocycl. Chem. 44, 439-442 (2002)
126. Scalia, S., Tursilli, R., Bianchi, A., Lo Nostro, P., Bocci, E., Ridi, F., Baglioni, P.: Incorporation of the sunscreen agent, octyl methoxycinnamate in a cellulosic fabric grafted with β-cyclodextrin. Int. J. Pharm. 308, 155-159 (2006)
127. Reuscher, H., Hinsenkorn, R.: Cavasol W7 MCT-new ways in surface modification. J. Incl. Phenom. Mol. Recogn. Chem. 25, 191-196 (1996)
128. Liu, Y.Y., Fan, X.D., Hu, H., Tang, Z.H.: Release of chlorambucil from poly(N-isopropylacrylamide) hydrogels with β-cyclodextrin moieties. Macromol. Biosci. 4, 729-736 (2004)
129. Liu, Y.Y., Fan, X.D., Kang, T., Sun, L.: A cyclodextrin microgel for controlled release driven by inclusion effects. Macromol. Rapid Commun. 25, 1912-1916 (2004)
130. Kanjickal, D., Lopina, S., Evancho-Chapman, M.M., Schmidt, S., Donovan, D.: Improving delivery of hydrophobic drugs from hydrogels through cyclodextrins. J. Biomed. Mater. Res. 74A, 454-460 (2005)
131. Liu, Y.Y., Fan, X.D., Zhao, Y.B.: Synthesis and characterization of a poly(N isopropylacrylamide) with β-cyclodextrin as pendant groups. J. Polym. Sci. A Polym. Chem. 43, 3516-3524 (2005)
132. Siemoneit, U., Schmitt, C., Alvarez-Lorenzo, C., Luzardo, A., Otero-Espinar, F., Concheiro, A., Blanco-Mendez, J.: Acrylic/cyclodextrin hydrogels with enhanced drug loading and sustained release capability. Int. J. Pharm. 312, 66-74 (2006)
133. Rodriguez-Tenreiro, C., Alvarez-Lorenzo, C., Rodriguez-Perez, A., Concheiro, A., Torres-Labandeira, J.J.: Estradiol sustained release from high affinity cyclodextrin hydrogels. Eur. J. Pharm. Biopharm. 66, 55-62 (2007)
134. Higashi, T., Hirayama, F., Arima, H., Uekama, K.: Polypseudorotaxanes of pegylated insulin with cyclodextrins: application to sustained release system. Bioorg. Med. Chem. Lett. 17(7), 1871-1874 (2007)
135. Cavalli, R., Trotta, F., Tumiatti, W.: Cyclodextrin-based nanosponges for drug delivery. J. Incl. Phenom. Macrocycl. Chem. 56, 209-213 (2006)
136. Woodley, J.F.: Liposomes for oral administration of drugs. Crit. Rev. Ther. Drug Carrier Syst. 2, 1-18 (1985)
137. Mayer, C.: Nanocapsules as drug delivery systems. Int. J. Artif. Organs 28, 1163-1171 (2005)
138. Bummer, P.M.: Physical chemical considerations of lipid-based oral drug delivery-solid lipid nanoparticles. Crit. Rev. Ther. Drug Carrier Syst. 21, 1-20 (2004)
139. Uner, M.: Preparation, characterization and physico-chemical properties of solid lipid nanoparticles (SLN) and nanostructured lipid carriers (NLC): their benefits as colloidal drug carrier systems. Pharmazie 61, 375-386 (2006)
140. Bochot, A., Trichard, L., Le Bas, G., Alphandary, H., Grossiord, J.L., Duchêne, D., Fattal, E.: α-cyclodextrin/oil beads: an innovative self-assembling system. Int. J. Pharm. 339, 121-129 (2007)
141. Trichard, L., Fattal, E., Besnard, M., Bochot, A.: α-cyclodextrin/ oil beads as a new carrier for improving the oral bioavailability of lipophilic drugs. J. Control. Release 122, 47-53 (2007)
142. Glass, J.E. (ed.): Associative Polymers in Aqueous Solutions. ACS Symp. Am. Chem. Soc, Washington DC (2000)
143. Landoll, L.M.: Nonionic polymer surfactants. J. Polym. Sci. Polym. Chem. Ed. 20, 443-455 (1982)
144. Rouzes, C., Durand, A., Leonard, M., Dellacherie, E.: Surface activity and emulsification properties of hydrophobically modified dextrans. J. Colloid Interface Sci. 253, 217-223 (2002)
145. Rotureau, E., Dellacherie, E., Durand, A.: Viscosity of aqueous solutions of polysaccharides and hydrophobically modified polysaccharides: application of Fedors equation. Eur. Polym. J. 42, 1086-1092 (2006)
146. Esquenet, C., Bulher, E.: Phase behavior of associating polyelectrolyte polysaccharides. 1. Aggregation process in dilute solution. Macromolecules 34, 5287-5294 (2001)
147. Esquenet, C., Terech, P., Boué, F., Buhler, E.: Structural and rheological properties of hydrophobically modified polysaccharide associative networks. Langmuir 20, 3583-3592 (2004)
148. Duval-Terrie, C., Huguet, J., Muller, G.: Self-assembly and hydrophobic clusters of amphiphilic polysaccharides. Colloids Surf. A Physicochem. Eng. Asp. 220, 105-115 (2003)
149. Henni, W., Deyme, M., Stchakovsky, M., Le Cerf, D., Picton, L., Rosilio, V.: Aggregation of hydrophobically modified polysaccharides in solution and at the air-water interface. J. Colloid Interface Sci. 281, 316-324 (2005)
150. Harada, A., Kamachi, M.: Complex formation between poly (ethylene glycol) and α-cyclodextrin. Macromolecules 23, 2821-2823 (1990)
151. Harada, A.: Preparation and structures of supramolecules between cyclodextrins and polymers. Coord. Chem. Rev. 148, 115-133 (1996)
152. Harada, A.: Construction of supramolecular structures from cyclodextrins, polymers. Carbohydr. Polym. 34, 183-188 (1997)
153. Huh, K.M., Ooya, T., Lee, W.K., Sasaki, S., Kwon, I.C., Jeong, S.Y., Yui, N.: Supramolecular-structured hydrogels showing a reversible phase transition by inclusion complexation between poly(ethylene glycol) grafted dextran and α-cyclodextrin. Macromolecules 34, 8657-8662 (2001)
154. Huh, K.M., Cho, Y.W., Chung, H., Kwon, I.C., Jeong, S.Y., Ooya, T., Lee, W.K., Sasaki, S., Yui, N.: Supramolecular hydrogel formation based on inclusion complexation between poly(ethylene glycol)-modified chitosan and α-cyclodextrin. Macromol. Biosci. 4, 92-99 (2004)
155. Daoud-Mahammed, S., Couvreur, P., Gref, R.: Novel self-assembling nanogels: stability and lyophilisation studies. Int. J. Pharm. 332, 185-191 (2007)
156. Davis, M.E., Bellocq, N.C.: Cyclodextrin-containing polymers for gene delivery. J. Incl. Phenom. Macrocycl. Chem. 44, 17-22 (2002)
157. Maestrelli, F., Luísa González-Rodríguez, M., Rabasco, A.M., Mura, P.: Preparation and characterisation of liposomes encapsulating ketoprofen-cyclodextrin complexes for transdermal drug delivery. Int. J. Pharm. 298, 55-67 (2005)
158. Lee, E.S., Kwon, M.J., Lee, H., Kim, J.J.: Stabilization of protein encapsulated in poly(lactide-co-glycolide) microspheres by novel viscous S/W/O/W method. Int. J. Pharm. 331, 27-37 (2007)
159. Devarakond, B., Hill, R.A., Liebenberg, W., Brits, M., de Villiers, M.M.: Comparison of the aqueous solubilization of practically insoluble niclosamide by polyamidoamine (PAMAM) dendrimers and cyclodextrins. Int. J. Pharm. 304, 193-209 (2005)
160. Yu, H., Wei, H., Hou, D., Zhang, A.Y., Feng, Z.G.: Composite hydrogels filled with inclusion complexes made from β-cyclodextrins with poly(propylene glycol) bisamine. Curr. Appl. Phys. 7, e116-e119 (2007)
161. Trapani, A., Laquintana, V., Denora, N., Lopedota, A., Cutrignelli, A., Franco, M., Trapani, G., Liso, G.: Eudragit RS 100 microparticles containing 2-hydroxypropyl-β-cyclodextrin and glutathione: physicochemical characterization, drug release and transport studies. Eur. J. Pharm. Sci. 30, 64-74 (2007)
162. Maestrelli, F., Garcia-Fuentes, M., Mura, P., Alonso, M.J.: A new drug nanocarrier consisting of chitosan and hydoxypropylcyclodextrin. Eur. J. Pharm. Biopharm. 63, 79-86 (2006)
163. Lemos-Senna, E., Wouessidjewe, D., Lesieur, S., Duchêne, D.: Preparation of amphiphilic cyclodextrin nanospheres using the emulsification solvent evaporation method. Influence of the surfactant on preparation and hydrophobic drug loading. Int. J. Pharm. 170, 119-128 (1998)
164. Sajeesh, S., Sharma, C.P.: Cyclodextrin-insulin complex encapsulated polymethacrylic acid based nanoparticles for oral insulin delivery. Int. J. Pharm. 325, 147-154 (2006)
165. Cappello, B., De Rosa, G., Giannini, L., La Rotonda, M.I., Mensitieri, G., Miro, A., Quaglia, F., Russo, R.: Cyclodextrin-containing poly(ethyleneoxide) tablets for the delivery of poorly soluble drugs: potential as buccal delivery system. Int. J. Pharm. 319, 63-70 (2006)
166. Ungaro, F., De Rosa, G., Miro, A., Quaglia, F., La Rotonda, M.I.: Cyclodextrins in the production of large porous particles: development of dry powders for the sustained release of insulin to the lungs. Eur. J. Pharm. Sci. 28, 423-432 (2006)
167. Rosa, G.D., Larobina, D., La Rotonda, M.I., Musto, P., Quaglia, F., Ungaro, F.: How cyclodextrin incorporation affects the properties of protein-loaded PLGA-based microspheres: the case of insulin/hydroxypropyl- β-cyclodextrin system. J. Control. Release 102, 71-83 (2005)
168. Sortino, S., Mazzagliab, A., Scolaroc, L.M., Merlod, F.M., Valverid, V., Sciortinod, M.T.: Nanoparticles of cationic amphiphilic cyclodextrins entangling anionic porphyrins as carrier-sensitizer system in photodynamic cancer therapy. Biomaterials 27, 4256-4265 (2006)
169. Gao, H., Yang, Y., Fan, Y., Ma, J.: Conjugates of poly(DL-lactic acid) with ethylenediamino or diethylenetriamino bridged bis(β cyclodextrin) s and their nanoparticles as protein delivery systems. J. Control. Release 112, 301-311 (2006)
170. Kang, F., Singh, J.: Conformational stability of a model protein (bovine serum albumin) during primary emulsification process of PLGA microspheres synthesis. Int. J. Pharm. 260, 149-156 (2003)
171. Fundueanua, G., Constantinb, M., Dalpiaza, A., Bortolottia, F., Cortesia, R., Ascenzic, P., Menegattia, E.: Preparation and characterization of starch/cyclodextrin bioadhesive microspheres as platform for nasal administration of Gabexate Mesylate (Foys) in allergic rhinitis treatment. Biomaterials 25, 159-170 (2004)
172. Memisoglu-Bilensoya, E., Vurala, T.I., Bochotb, A., Renoirb, J.M., Ducheneb, D., Hvncala, A.A.: Tamoxifen citrate loaded amphiphilic h-cyclodextrin nanoparticles: In vitro characterization and cytotoxicity. J. Control. Release 104, 489-496 (2005)
173. Francois, M., Snoeckx, E., Putteman, P., Wouters, F., Proost, E.D., Delaet, U., Peeters, J., Brewster, M.E.: A mucoadhesive, cyclodextrin-based vaginal cream formulation of itraconazole. AAPS PharmSci. 5(1), E5 (2003)
174. Wongmekiat, A., Yoshimatsu, S., Tozuka, Y., Moribe, K., Yamamoto, K.: Investigation of drug nanoparticle formation by co-grinding with cyclodextrins: studies for indomethacin, furosemide and naproxen. J. Incl. Phenom. Macrocycl. Chem. 56, 29-32 (2006)
175. Nishimura, K., Hidaka, R., Hirayama, F., Arima, H., Uekama, K.: Improvement of dispersion and release properties of nifedipine in suppositories by complexation with 2-hydroxypropyl-β-cyclodextrin. J. Incl. Phenom. Macrocycl. Chem. 56, 85-88 (2006)
176. Skiba, M., Bounoure, F., Barbot, C., Arnaud, P., Skiba, M.: Development of cyclodextrins microspheres for pulmonary drug delivery. J. Pharm. Pharm. Sci. 8(3), 409-418 (2005)
177. Evrarda, B., Bertholeta, P., Guedersc, M., Flamentb, M.P., Piela, G., Delattrea, L., Gayotb, A., Letermeb, P., Foidartc, J.M., Cataldo, D.: Cyclodextrins as a potential carrier in drug nebulization. J. Control. Release 96, 403-410 (2004)
178. Okimoto, K., Ohike, A., Ibuki, R., Aoki, O., Ohnishi, N., Rajewski, R.A., Stellab, V.J., Irie, T., Uekama, K.: Factors affecting membrane-controlled drug release for an osmotic pump tablet (OPT) utilizing (SBE)-β-CD as both a 7m solubilizer and osmotic agent. J. Control. Release 60, 311-319 (1999)
179. Wang, J., Cai, Z.: Incorporation of the antibacterial agent, miconazole nitrate into a cellulosic fabric grafted with β-cyclodextrin. Carbohydr. Polym. (in press). doi: 10.1016/j.carbpol.2007.10.019 (2008)
180. Smith, J.S., MacRaea, R.J., Snowden, M.J.: Effect of SBE7-b-cyclodextrin complexation on carbamazepine release from sustained release beads. Eur. J. Pharm. Biopharm. 60, 73-80 (2005)
181. Anadolu, R.Y., Sen, T., Tarimci, N., Birol, A., Erdem, C.: Improved efficacy and tolerability of retinoic acid in acne vulgaris: a new topical formulation with cyclodextrin complex. JEADV 18, 416-421 (2004)
182. Herrmann, S., Winter, G., Mohl, S., Siepmann, F., Siepmann, J.: Mechanisms controlling protein release from lipidic implants: effects of PEG addition. J. Control. Release 118, 161-168 (2007)
183. Mora, P.C., Cirri, Æ.M., Mura, Æ.P.: Development of a sustained-release matrix tablet formulation of DHEA as ternary complex with α-cyclodextrin and glycine. J. Incl. Phenom. Macrocycl. Chem. 57(1-4), 699-704 (2007)
184. Maestrelli, F., Corti, G., Mura, P., Cirri, M., Rangoni, C.: Development of fast-dissolving tablets of flurbiprofen-cyclodextrin complexes. Drug Dev. Ind. Pharm. 31, 697-707 (2005)
185. Martin, R., Nchez, I.S., Cao, R., Rieumont, J.: Solubility and kinetic release studies of naproxen and ibuprofen in soluble epichlorohydrin-β- cyclodextrin polymer. Supramol. Chem. 18(8), 627-631 (2006)
186. Jug, M., Bećirević-Laćan, M., Kwokal, A., Cetina-Cizmek, B.: Influence of cyclodextrin complexation on piroxicam gel formulations. Acta Pharm. 55, 223-236 (2005)
187. Babu, R.J., Pandit, J.K.: Effect of cyclodextrins on the complexation and transdermal delivery of bupranolol through rat skin. Int. J. Pharm. 271, 155-165 (2004)
188. Dias, M.M.R., Raghavan, S.L., Pellett, M.A., Hadgraft, J.: The effect of β-cyclodextrins on the permeation of diclofenac from supersaturated solutions. Int. J. Pharm. 263, 173-181 (2003)