Cyclodextrins and their derivatives in drug delivery: A review

Current Trends in Biotechnology and Pharmacy

Volumn 6, Issue 3, 2012, Pages 255-279

  Palem, Chinna Reddy ^a   Siva Chaitanya Chopparapu, Karthik ^b   Subrahmanyam, P V R S ^a   Yamsani, Madhusudan Rao ^c  

^a HETERO LABS LTD   (India)

^b KAKATIYA UNIVERSITY   (India)

^c Vaagdevi Group of Pharmacy Colleges   (India)

Author keywords

Bioavailability; Cyclodextrins; Drug delivery; Formulation; Solubility; Stability

Indexed keywords

ANDROSTENEDIOL; ATORVASTATIN; BECLOMETASONE DIPROPIONATE; BERMOPROFEN; BETAMETHASONE; CALCITONIN; CARVEDILOL; CLOMIPRAMINE; CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; DANAZOL; DEXAMETHASONE; DIHYDROERGOTAMINE; DILTIAZEM; DIPIVEFRINE; ECONAZOLE; ESTRADIOL; FELODIPINE; GLICLAZIDE; GLYMESASON; ITRACONAZOLE; KETOCONAZOLE; MOLSIDOMINE; MORPHINE; NIFEDIPINE; PILOCARPINE; PIROXICAM; PREDNISOLONE; TIAPROFENIC ACID; TOLBUTAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOCOMPATIBILITY; CHEMICAL STRUCTURE; COMPLEX FORMATION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG CEREBROSPINAL FLUID LEVEL; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG PENETRATION; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; DRUG TOLERABILITY; GENE DELIVERY SYSTEM; HUMAN; LIPOSOMAL DELIVERY; NONHUMAN; PHYSICAL CHEMISTRY; TEMPERATURE; TIME TO MAXIMUM PLASMA CONCENTRATION;

ANIMALIA;

EID: 84864775721     PISSN: 09738916     EISSN: 22307303     Source Type: Journal    
DOI: None     Document Type: Article

References (111)

1. Avdeef, A., Bendels, S., Tsinman, O., Tsinman, K. and Kansy, M. (2007). Solubility excipient classification gradient maps. Pharm. Res, 24: 530-545.
2. Kim, C., Park, J. (2004). Solubility enhancers for oral drug delivery. Am. J. Drug Deliv, 2: 113-130.
3. Loftsson, T., Jarho, P., Masson, M. and Jarvinen, T. (2005). Cyclodextrins in drug delivery. Expert Opin. Drug Deliv, 2: 335-351.
4. Szejtli, J. and Szente, L. (2005). Elimination of bitter, disgusting tastes of drugs and foods by cyclodextrins. Eur. J. Pharm. Biopharm. 61: 115-125.
5. Lantz, A., Rodriguez, M., Wetterer, S. and Armstrong, D. (2006). Estimation of association constants between oral malodor components and various native and derivatized cyclodextrins. Anal. Chim. Acta, 557: 184-190.
6. Shimpi, S., Chauhan B. and Shimpi P. (2005). Cyclodextrins: Application in different routes of drug administration. Acta Pharm, 55: 139-156.
7. Loftsson, T. and Brewster, M.E. (1996). Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J. Pharm. Sci, 85: 1017-1025.
8. Uekama, K., Hirayama, F. and Irie, T. (1998). Cyclodextrin drug carrier systems. Chem. Rev, 98: 2045-2076.
9. Schmid, G. (1989). Cyclodextrin glycosyltransferase production-yield enhancement by over expression of cloned genes. Tibtech, 7: 244-248.
10. Schmid, G. (1991). Preparation and application of γ-cyclodextrin. In: Duchêne D, ed. New trends in cyclodextrins and derivatives, Editions de Santé, Paris, 25-54.
11. Winkler, R.G., Fioravanti, S., Ciccotti, G., Margheritis, C. and Villa, M. (2000). Hydration of β-cyclodextrin: a molecular dynamics simulation study. J. Comput. Aided Mol. Des, 14: 659-667.
12. Szejtli, J. (2004). Past, present and future of cyclodextrin research. Pure Appl. Chem, 76(10): 1825-1845.
13. Hashimoto, H. (1991). Preparation, structure, property and application of branched cyclodextrins. In: Duchêne D, ed. New trends in cyclodextrins and derivatives, Editions de Santé, Paris, 97-156.
14. Pitha, J., Milecki, J., Fales, H., Pannell, L. and Uekama, K. (1986). Hydroxypropyl-β- cyclodextrin preparation and characterization: effects on solubility of drugs. Int. J. Pharm, 29: 73-82.
15. Irie, T. and Uekama, K. (1997). Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J. Pharm. Sci, 86:147-162.
16. Thompson, D. (1997). Cyclodextrinsenabling excipients: their present and future use in pharmaceuticals. Crit. Rev. Ther. Drug Carrier Syst, 14:1-104.
17. Szente, L., Szejtli, J. and Kis, G. (1998). Spontaneous opalescence of aqueous γ- cyclodextrin solutions: complex formation or self-aggregation. J.Pharm.Sci, 87:778-781.
18. Muñoz-Botella, S., del Castillo, B. and Martyn, M.A. (1995). Cyclodetrin properties and applications of inclusion complex formation. Ars Pharm, 36:187-198.
19. Loftsson, T. and Brewster, M.E. (1996). Pharmaceutical applications of cyclodextrins: 1. Drug solubilisation and stabilization. J Pharm Sci, 85:1017-1025.
20. Schneiderman, E. and Stalcup, A.M. (2000). Cyclodextrins: a versatile tool in separation science. J Chromatogr B, 745:83-102.
21. Higuchi, T. and Connons, K.A. (1965). Advances in Analytical Chemistry and Instrumentation, vol. 4, Wiley-Interscience, New York, 117-212.
22. Connons, K.A. (1996). Measurement of cyclodextrin complex stability constants, in: J. Szejtli, T. Osa (Eds.), Comprehensive Supramolecular Chemistry, vol. 3, Elsevier, Oxford, UK, 205-241.
23. Brewster, M. and Loftsson, T. (1999). Complexation - use of cyclodextrins to improve pharmaceutical properties of intramuscular formulations, in: P. Gupta, G. Brazeau (Eds.), Injectable drug development-techniques to reduce pain and irritation, Interpharm Press, Buffalo Grove, IL, 307-336.
24. Diaz, D., Bernad, M.J.B., Mora, J.G., Llaons, C.M.E. (1999). Solubility, 1H-NMR, and molecular mechanics of mebendazole with different cyclodextrins. Drug Dev Ind Pharm. 25:111-115.
25. Chowdary, K.P.R., Nalluri, B.N. (2000). Nimesulide and beta-cyclodextrin inclusion complexes: physicochemical characterization and dissolution rate studies. Drug Dev Ind Pharm. 26:1217-1220.
26. Palmeiri, G.F., Angeli, D.G., Giovannnucci, G., Martelli, S. (1997). Inclusion of methoxytropate in β- and hydroxylpropyl β- cyclodextrins: Comparision of preparation methods. Drug Dev Ind Pharm. 23:27-37.
27. Miyake, K., Irie T., Arima, H. (1999). Characterization of itraconazole/ 2- hydroxypropyl- β-cyclodextrin inclusion complex in aqueous propylene glycol solution. Int J Pharm. 179:237-245.
28. Loftsson, T., Brewster, M. and Masson, M. (2004). Role of cyclodextrins in improving oral drug delivery. Am. J. Drug Deliv, 2: 261-275.
29. Davis, M.E. and Brewster, M. (2004). Cyclodextrin-based pharmaceutics: past, present and future. Nat. Rev. Drug Discov, 3:1023-1035.
30. Loftsson, T. and Masson, M. (2001). Cyclodextrins in topical drug formulations: theory and practice. Int. J. Pharm, 225:15-30.
31. Rajewski, R.A. and Stella, V.J. (1996). Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci, 85:1142-1168.
32. Hirayama, F. and Uekama, K. (1999). Cyclodextrin-based controlled drug release system. Adv. Drug Deliv. Rev, 36:125-141.
33. Brewster, M.E., Anderson, W.R., Estes, K.S. and Bodor, N. (1991). Development of aqueous parenteral formulations for carbamazepine through the use of modified cyclodextrins. J. Pharm. Sci, 80:380-383.
34. Esclusa-Diaz, M.T., Gayo-Otero, M., Perez- Marcos, M.B., Vila-Jato, J.L. and Torres Labandeira, J.J. (1996). Preparation and evaluation of ketoconazole-β-cyclodextrin multicomponent complexes. Int. J. Pharm, 142:183-187.
35. Pedersen, M., Bjerregaard, S., Jacobson, J., Larsen, A.R. and Sorensen, A.M. (1998). An econazole β-cyclodextrin inclusion complex: an unusual dissolution rate, supersaturation, and biological efficacy example. Int. J. Pharm, 165:57-68.
36. Chinna Reddy, P., Shweta, P. and Varsha Pokharkar. (2009). Solubility and Stability Enhancement of Atorvastatin by Cyclodextrin Complexation. PDA J Pharm Sci Technol, 63: 217-225.
37. Chinna Reddy, P., Shweta, P., Vinod V. and Varsha Pokharkar. (2009). Influence of atorvastatin calcium-cyclodextrin complexation on solubility, stability and pharmacodynamic activity. Acta Pharm. Sciencia, 51: 297-312.
38. Uekama, K., Fujinaga, T., Hirayama, F., Otagiri, M., Yamasaki, M., Seo, H., Hashimoto, T. and Tsuruoka, M. (1983). Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. J. Pharm. Sci, 72:1338-1341.
39. Betlach, C.J., Gonzalez, M.A., Mckiernan, B.C., Neff-Davis, C. and Bodor, N. (1993). Oral pharmacokinetics of carbamazepine in dogs from commercial tablets and a cyclodextrin complex. J. Pharm. Sci, 82:1058-1060.
40. Yamamoto, M., Hirayama, F. and Uekama, K. (1992). Improvement of stability and dissolution of prostaglandin E1 by maltosyl- β-cyclodextrin in lyophilized formulation. Chem. Pharm. Bull, 40:747-751.
41. Jarvinen, T., Jarvinen, K., Schwarting, N. and Stella, V.J. (1995). β-Cyclodextrin derivatives, SBE-β-CD and HB-â-CD, increase the oral bioavailability of cinnarizine in beagle dogs. J. Pharm. Sci, 84: 295-299.
42. Horikawa, T., Hirayama, F. and Uekama, K. (1995). In vivo and in vitro correlation for delayed-release behavior of a molsidomine/O-carboxymethyl-O-ethyl-β- cyclodextrin complex in gastric aciditycontrolled dogs. J. Pharm. Pharmacol, 47:124-127.
43. Uekama, K. (1993). In Vitro and In Vivo Evaluation of Delayed-Release Behavior of Diltiazem from its O-Carboxymethyl-OEthyl- β-Cyclodextrin Complex. J. Contl. Rel. 25:99-109.
44. M. Vakiley, F. Khorasheh, and F. Jamali, "Dependency of Gastrointestinal Toxicity on Release Rate of Tiaprofenic Acid: A Novel Pharmacokinetic-Pharmacodynamic Model," Pharm. Res. 16 (1), 123-129 (1999)
45. Wang, Z., Hirayama, F. and Uekama, K. (1994). In vivo and in vitro evaluations of a modified-release oral dosage form of nifedipine by hybridization of hydroxypropyl- β-cyclodextrin and hydroxypropyl celluloses in dogs. J. Pharm. Pharmacol, 46: 505-507.
46. Okimoto, K., Rajewski, R.A., Uekama, K., Jana, J.A. and Stella, V.J. (1996). The interaction of charged and uncharged drugs with neutral (HB-β-CD) and anionically charged (SBE-β-CD) β-cyclodextrins. Pharm. Res, 13: 256-264.
47. Hoon, T., Dawood, M., Khan-Dawood, F., Ramos, J. and Batenhorst, R. (1993). Bioequivalence of 17 β-Estradiol Hydroxypropyl-β- Cyclodextrin Complex in Postmenopausal Women. J. Clin. Pharmacol, 33:1116-1121.
48. Brown, G., Martin, E., Roberts, B., Vukovich, M. and King, D. (2002). Acute hormonal response to sublingual androstenediol in young men. J. Appl. Physiol, 92:142-146.
49. Yoo, S., Yoon, B., Lee, H. and Lee, K. (1999). Increased bioavailability of clomipramine after sublingual administration in rats. J. Pharm. Sci, 88:1119-1121.
50. Badawy, S., Ghorab, M. and Adeyeye, C. (1996). Bioavailability of danazol hydroxypropyl-β-cyclodextrin complex by different routes of administration. Int. J. Pharm, 145:137-143.
51. Mannila, J., Järvinen, T. and Lehtonen, M. (2003). Effects of RM-α-CD on bioavailability of THC. Proceedings of the AAPS annual meeting and exposition, Salt Palace Convention Center, Salt Lake City, USA.
52. Jug, M. and Becirevic-Lacan, M. (2004). Influence of hydroxypropyl-β-cyclodextrin complexation on piroxicam release from buccoadhesive tablets. Eur. J. Pharm. Sci, 21: 251-260.
53. Cappello, B., Giuseppe, D., Lucia, G., Maria, I.L.R., Giuseppe, M., Agnese, M., Fabiana, Q. and Roberto, R. (2006). Cyclodextrin-containing poly (ethyleneoxide) tablets for the delivery of poorly soluble drugs: Potential as buccal delivery system. Int. J. Pharm, 319: 63-70.
54. Chinna Reddy, P., Sunil Kumar, B., Ramesh, G., Vamshi Vishnu, Y., Michael A.R. and Madhusudan Rao, Y. (2011). Role of cyclodextrin complexation in felodipinesustained release matrix tablets intended for oral transmucosal delivery: in vitro and ex vivo characterization. Pharm. Dev. Tech, 1-12.
55. Loftsson, I. and Stefansson, E. (1997). Effect of cyclodextrins on topical drug delivery to the eye, Drug Devel. Ind. Pharm, 23: 473-481.
56. Loftsson, T., Stefansson, E., Kristinsson, J.K., Fridriksdottir, H., Sverrisson, T., Gudmundsdottir, G. and Thorisdottir, S. (1996). Topically effective acetazolamide eye-drop solution in man, Pharm. Sci. 6: 277-279.
57. Jarho, P., Jarvinen, K., Urtti, A., Stella, V.J. and Jarvinen, T. (1996). Modified β- cyclodextrin (SBE7-β-CyD) with viscous vehicle improves the ocular delivery and tolerability of pilocar pine prodrug in rabbits, J. Pharm. Pharmacol, 48: 264-270.
58. Jarvinen, T., Jarvinen, K., Urtti, A., Thompson, D. and Stella, V.J. (1995). Sulfobutyl ether-β-cyclodextrin (SBE-β-CD) in eye drops improves the tolerability of a topically applied pilocarpine prodrug in rabbits. J. Ocular Pharmacol. Ther, 11: 95-106.
59. Lee, V.H.L. and Robinson J.R. (1986). Topical ocular drug delivery: recent developments and future challenges. J. Ocular Pharmacol, 2: 67-108.
60. Loftsson, T. (2002). Cyclodextrins and the Biopharmaceutics Classification System of Drugs. J. Incl. Phenom. Macrocycl. Chem, 44: 63-67.
61. Hermens, W A.J.J., Belder, C.W.J., Merkus, J.M.W.M., Hooymans, P.M., Verhoef, J. and Merkus, F.W.H.M. (1992). Intranasal administration of estradiol in combination with progesterone to oophorectomized women: a pilot study. Eur. J. Obstet. Gynecol. Reprod. Biol, 43: 65-70.
62. Kondo, T., Nishimura, K., Hirata, M., Irie, T. and Uekama, K. (1996). Effects of cyclodextrins on nasal absorption and analgesic activity of opioids in rats. In: Szejtli J, Szente L, ed. Proceedings of the Eighth International Symposium on Cyclodextrins, Kluwer Academic Publishers, Dordrecht, 387-390.
63. Marttin, E., Romeijn, S.G., Verhoef, J.C. and Merkus, F.W.H.M. (1997). Nasal absorption of dihydroergotamine from liquid and powder formulations in rabbits. J. Pharm. Sci, 86: 802-807.
64. Matsubara, K., Abe, K., Irie, T. and Uekama, K. (1995). Improvement of nasal bioavailability of luteinizing hormonereleasing hormone agonist, buserelin by cyclodextrin derivatives in rats. J. Pharm. Sci, 84: 1295-1300.
65. Adjei, A., Sundberg, D., Miller, J. and Chun, A. (1992). Bioavailability of leuprolide acetate following nasal and inhalation delivery to rats and healthy humans. Pharm. Res, 9: 244-249.
66. Schipper, N.G.M., Verhoef, J.C., Romeijn, S.G. and Merkus, F.W.H.M. (1995). Methylated â cyclodextrins are able to improve the nasal absorption of salmon calcitonin. Calcif. Tissue Int, 56: 280-282.
67. Sakr, F.M. (1996). Nasal administration of glucagon combined with dimethyl-β- cyclodextrin: comparison of pharmacokinetics and pharmacodynamics of spray and powder formulations. Int. J. Pharm, 132: 189-194.
68. Schipper, N.G.M., Romeijn, S.G., Verhoef, J.C. and Merkus, F.W.H.M. (1993). Nasal insulin delivery with dimethyl-β-cyclodextrin as an absorption enhancer in rabbits: powder more effective than liquid formulations. Pharm. Res, 10: 682-686.
69. Romeijn, S.G., Verhoef, J.C., Marttin, E., Merkus F.W.H.M. (1996). The effect of nasal drug formulations on ciliary beating in vitro. Int. J. Pharm, 135:137-145.
70. Loftsson, T., Sigfússon, S.D., Sigurdsson, H.H. and Másson, M. (2003). The effects of cyclodextrins on topical delivery of hydrocortisone: the aqueous diffusion layer. S.T.P. Pharma Sci, 13:125-131.
71. Otagiri, M., Fujinaga, T., Sakai, A. and Uekama, K. (1984). Effects of β- and β- cyclodextrins on release of betamethasone from ointment bases. Chem. Pharm. Bull, 32: 2401-2405.
72. Uekama, K., Otagiri, M., Sakai, A., Irie, T., Matsuo, N. and Matsuoka, Y. (1985). Improvement in the percutaneous absorption of beclomethasone dipropionate by β-cyclodextrin complexation. J. Pharm. Pharmacol, 37: 532-535.
73. Uekama, K., Masaki, K., Arimori, K., Irie, T. and Hirayama, F. (1987). Effects of β- and dimethyl-β-cyclodextrins on release and percutaneous absorption behaviors of prednisolone from some ointment bases. Yakugaku Zasshi, 107: 449-456; ref. Chem. Abstr, 107:120965t.
74. Lin, S.Z., Wouessidjewe, D., Poelman, M.C. and Duchene, D. (1994). In vivo evaluation of indomethacin/ cyclodextrin complexes gastrointestinal tolerance and dermal anti-inflammatory activity. Int. J. Pharm, 106: 63-67.
75. Roy, S.D. and De, G.J. (1994). Percutaneous absorption of nafarelin acetate, an LHRH analog, through human cadaver skin and monkey skin. Int. J. Pharm, 110:137-145.
76. Felton, L.A., Wiley, C.J. and Godwin, D.A. (2002). Influence of hydroxypropyl-β- cyclodextrin on transdermal permeation and skin accumulation of oxybenzone. Drug Dev. Ind. Pharm, 28:1117-1124.
77. Loftsson, T., Masson, M., Sigurdsson, H.H., Magnusson, P. and Goffic, F.L. (1998). Cyclodextrins as co-enhancers in dermal and transdermal drug delivery. Pharmazie. 53: 137-139.
78. Uekama, K., Irie, T., Sunada, M., Otagiri, M., Arimatsu, Y. and Nomura, S. (1982). Alleviation of prochlorperazine induced primary irritation of skin by cyclodextrin complexation. Chem. Pharm. Bull, 30: 3860-3862.
79. Matsuda, H. and Arima, H. (1999). Cyclodextrins in transdermal and rectal delivery. Adv. Drug Del. Rev., 36:81-99.
80. Takahashi, T., Kagami, I., Kitamura, K., Nakanishi, Y. and Imasato, Y. (1986). Stabilization of AD-1590, a non-steroidal anti-inflammatory agent, in suppository bases by β-cyclodextrin complexation. Chem. Pharm. Bull, 34: 1770-1774.
81. Watanabe, Y, Matsumoto, Y., Seki, M., Takase, M. and Matsumoto, M. (1992). Absorption enhancement of polypeptide drugs by cyclodextrins. I. Enhanced rectal absorption of insulin from hollow-type suppositories containing insulin and cyclodextrins in rabbits. Chem. Pharm. Bull, 40: 3042-3047.
82. Watanabe, Y., Kiriyama, M. and Ito, R. (1996). Pharmacodynamics and pharmacokinetics of recombinant human granulocyte colony-stimulating factor (rhGCSF) after administration of a rectal dosage vehicle. Biol. Pharm. Bull, 19: 1059-1063.
83. Arima, H., Kondo, T., Irie, T. and Uekama, K. (1992). Enhanced rectal absorption and reduced local irritation of the antiinflammatory drug ethyl 4-biphenylylacetate in rats by complexation with water-soluble β-cyclodextrin derivatives and formulation as oleaginous suppository. J. Pharm. Sci, 81: 1119-1125.
84. Arima, H., Kondo, T., Irie, T., Hirayama, F., Uekama, K., Miyaji, T. and Inoue, Y. (1992). Use of water-soluble β-cyclodextrin derivatives as carriers of anti-inflammatory drug biphenyl-acetic acid in rectal delivery. Yakugaku Zasshi, 112:65-72.
85. Washington, N., Washington, C. and Wilson, C.G. (2001). Pulmonary drug delivery. In: Physiological Pharmaceutics. Barriers to drug absorption, 2nd Edition, Taylor & Francis, London, UK, 221-247.
86. Cabral Marques, H.M., Hadgraft, J., Kellaway, I.W. and Taylor, G. (1991). Studies of cyclodextrin inclusion complexes. III. The pulmonary absorption of β-, DM-β- and HP- β- cyclodextrins in rabbits. Int. J. Pharm., 77: 297-302.
87. Prime, D., Atkins, P.J., Slater, A. and Sumby, B. (1997). Review of dry powder inhalers. Adv. Drug Deliv. Rev, 26: 51-58.
88. Leite Pinto, J.M.C. and Cabral Marques, H.M. (1999). Beclomethasone/cyclodextrin inclusion complex for dry powder inhalation. S.T.P. Pharma Sci, 9:253-256.
89. Shao, Z.J., Li, Y. and Mitra, A.K. (1994). Cyclodextrins as mucosal absorption promoters of insulin. III. Pulmonary route of delivery. Eur. J. Pharm. Biopharm, 40: 283-288.
90. Shao, Z.J. and Mitra, A.K. (1996). Pulmonary absorption of recombinant human growth hormone in rats. Eur. J. Pharm. Biopharm, 42:199-203.
91. Wall, D.A., Marcello, J., Pierdomenico, D. and Farid, A. (1994). Administration as hydroxypropyl β-cyclodextrin complexes does not slow rates of pulmonary drug absorption in rats. S.T.P.Pharma Sci, 4:63-68.
92. Kinnarinen, T., Jarho, P., Järvinen, K. and Järvinen, T. (2003). Pulmonary deposition of a budesonide/γ-cyclodextrin complex in vitro. J. Control. Rel, 90(2):197-205.
93. Stevens, D.A. (1999). Itraconazole in cyclodextrin solution. Pharmacotherapy, 9:603-611.
94. Rajeswari, C., Alka, A., Javed, A. and Khar R.K. (2005). Cyclodextrins in Drug Delivery: An Updated Review AAPS Pharm. Sci.Tech, 6(2):Article 43.
95. Kim, Y., Oksanen, D.A., Massefski, W., Blake, J.F., Duffy, E.M. and Chrunyk, B. (1998). Inclusion complexation of ziprasidone mesylate with beta-cyclodextrin sulfobutyl ether. JPharm Sci, 87:1560-1567.
96. Boudad, H., Legrand, P., Lebas, G., Cheron, M., Duchene, D. and Ponchel, G. (2001). Combined hydroxypropyl-β-cyclodextrin and poly(alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir. Int. J. Pharm, 218:113-124.
97. Skalko, N., Brandl, M., Ladan, M.B., Grid, J.F. and Genjak, I.J. (1996). Liposomes with nifedipine and nifedipine-cyclodextrin complex: calorimetrical. Eur. J. Pharm. Sci, 4:359-366.
98. Skalko-Basnet, N., Pavelic, Z. And Becirevic-Lacan, M. (2000). Liposomes containing drug and cyclodextrin prepared by the one-step spray-drying method. Drug Dev. Ind. Pharm, 26:1279-1284.
99. Loukas, Y.L., Jayasekera, P. and Gregoriadis, G. (1995). Novel liposomebased multi component systems for the protection of photolabile agents. Int. J.Pharm, 117:85-94.
100. Kang, F., Jiang, G., Hinderliter, A., Luca, P.P.D. and Singh J. (2002). Lysozyme stability in primary emulsion for PLGA microsphere preparation: Effect of recovery methods and stabilizing excipients. Pharm Res, 19: 629-633.
101. Kang, F., Jiang, G., Hinderliter, A., Luca, P.P.D. and Singh, J. (2002). Lysozyme stability in primary emulsion for PLGA microsphere preparation: effect of recovery methods and stabilizing excipients. Pharm. Res, 19:629-633.
102. Kang, F. and Singh, J. (2003). Conformational stability of a model protein (bovine serum albumin) during primary emulsification process of PLGA microspheres synthesis. Int. J. Pharm, 260:149-156.
103. Hýncal, A.A. (2005). Recent advances in drug delivery using amphiphilic cyclodextrin nanoparticles. Eur. J. Pharm. Sci, 25S1: S3-S4.
104. Rodriguez-Tenreiro, C., Diez-Bueno, L., Concheiro, A., Torres-Labandeira, J.J. and Alvarez-Lorenzo, C. (2007). Cyclodextrin/ carbopol micro-scale interpenetrating networks (ms-IPNs) for drug delivery. J. Control. Rel, 123: 56-66.
105. Yano, H., Hirayama, F., Kamada, M., Arima, H. and Uekama, K. (2002). Colon specific delivery of prednisolone-appended alphacyclodextrin conjugate: alleviation of systemic side effect after oral administration. J Contr. Rel, 79:103-112.
106. Brewster, M.E. and Loftsson, T. (2002). The use of chemically modified cyclodextrins in the development of formulations for chemical delivery systems. Pharmazie, 57:94-101.
107. Arima, H., Yunomae, K., Hirayama, F. and Uekama, K. (2001). Contribution of Pglycoprotein to the enhancing effects of dimethyl-β-cyclodextrin on oral bioavailability of Tacrolimus. J. Pharm. Exp. Therapeutics, 297:547-555.
108. Hwang, S.J., Bellocq, N.C. and Davis, M.E. (2001). Effects of structure of β-cyclodextrin -containing polymers on gene delivery. Bioconjugate Chem, 12:280-290.
109. Loftsson, T., Masson, M. and Brewster, M.E. (2004). Self-Association of Cyclodextrins and Cyclodextrin Complexes. J. Pharm. Sci, 93:1091-1099.
110. Nagase, Y., Hirata, M. and Wada, K. (2001). Improvement of some pharmaceutical properties of DY-9760e by sulfobuty ether beta-cyclodextrin. Int J Pharam, 229:163-172.
111. Arias Blanco, M.J., Moyano, J.R., perez martinez, J.I. and Gines, J.M. (1998). Study of the inclusion of gliclazide in alpha - cyclodextrin. J pharm Biomed Anal, 18 (1-2):275-9.