Cyclodextrins as oral drug carrier molecular devices: Origins, reasons and in-vitro model applications

Current Organic Chemistry

Volumn 16, Issue 20, 2012, Pages 2365-2378

  Perchyonok, Victoria T ^a   Oberholzer, Theunis ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

Cyclodextrin; Drug delivery systems; Host guest chemistry; In vitro models

Indexed keywords

BIOCHEMISTRY; BIOCOMPATIBILITY; CONTROLLED DRUG DELIVERY; TARGETED DRUG DELIVERY;

CYCLIC OLIGOMERS; DRUG CARRIER; DRUG-DELIVERY SYSTEMS; HOSTGUEST CHEMISTRY; IN-VITRO MODELS; INCLUSION COMPLEX; MODEL APPLICATION; MOLECULAR DEVICE; SMALL MOLECULES; WATERSOLUBLE;

CYCLODEXTRINS;

EID: 84872534682     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212803520119     Document Type: Article

References (101)

1. Dressman, J.; Butler, J.; Hempenstall, J.; The BCS: where do we go from here? Pharm Tech North Am, 2001, 25, 68-76
2. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Experimental and computational approaches to estimate solubility and permeability in drug discovery and sufficient lipophilicity to partition into and then permeate through development settings., Adv Drug Deliv Rev, 2001, 46, 3-26
3. Duchene, D.; editor. New trends in cyclodextrins and derivatives.; Paris, Editions de Santé, 1991
4. Duchene, D.; Cyclodextrins and their industrial uses.; Paris, Editions de Sant́e, 1987.
5. Szejtli, J.; Cyclodextrin technology.; Kluwer.; Academic Publisher, 1988
6. Fromming, K. H.; Szejtli, J.; Cyclodextrins in pharmacy.; Dordrecht, Kluwer Academic Publishers, 1994
7. Loftsson, T.; Brewster, M. E.; Pharmaceutical applications of cyclodextrins: 1. Drug solubilization and stabilization, J Pharm Sci, 1996, 85, 1017-25
8. Rajewski, R. A.; Stella, V. J.; Pharmaceutical applications of cyclodextrins: 2. In vivo drug delivery. J Pharm Sci, 1996, 85, 1142-68
9. Irie, T.; Uekama, K.; Pharmaceutical applications of cyclodextrins: III. Toxicological issues and safety evaluation. J Pharm Sci., 1997, 86, 147-62
10. Stella, V.J.; Rajewski, R. A.; Cyclodextrins: their future in drug formulation and delivery, Pharm Res, 1997, 14, 556-67
11. Uekama, K.; Cyclodextrins in drug delivery, Adv Drug Deliv Rev, 1999, 36, 1-141
12. D'Souza, V. T.; Lipkowitz, K. B.; Cyclodextrins: introduction., Chem Rev, 1998, 98, 1741-1742
13. Loftsson, T.; Brewster, M. E.; Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J. Pharm. Sci., 1996, 85, 1017-1025.
14. Rajewski, R. A.; Stella, V. J.; Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery, J. Pharm. Sci., 1996, 85, 1142-1168.
15. Irie, T.; Uekama, K.; Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation, J. Pharm. Sci., 1997, 86, 147-162.
16. Loftsson, T.; Cyclodextrins and the biopharmaceutics classification system of drugs, J. Incl. Phenom. Macroc. Chem., 2003, 44, 123-129
17. Loftsson, T.; Methods to enhance the complexation efficiency of cyclodextrins, S.T.P. Pharma Sci., 1999, 9, 237-242.
18. Eds Anderson, P. O.; Handbook of Clinical Drug Data, Appelton & Lange. 1999, 9th Ed.
19. Loftsson, T.; Brewster, M. E.; Cyclodextrins as Pharmaceutical Excipients. Pharm. Technol. Europe, 1997, 9, 26-33.
20. Redenti, E.; Drug/cyclodextrin/hydroxy acid multicomponent systems. Properties and pharmaceutical applications, J. Pharm. Sci., 2000, 89, 1-8.
21. Redenti, E.; "Cyclodextrin complexes of salts of acidic drugs. Thermodynamic properties, structural features, and pharmaceutical applications", J. Pharm. Sci., 2001, 90, 979-986.
22. Loftsson, T.; Increasing the cyclodextrin complexation of drugs and drug bioavailability through addition of water-soluble polymers, Pharmazie, 1998, 53, 733-740.
23. Loftsson, T.; The effects of cyclodextrins on topical delivery of hydrocortisone: the aqueous diffusion layer, S.T.P. Pharma Sci., 2003, 13, 145-161
24. Suzuki, M.; 2H NMR study of the self-assembly of an azo dyecyclomaltooctanose (g-cyclodextrin) complex, Carbohydr. Res., 1994, 264, 223-230.
25. Mele, A.; Non-covalent associations of cyclomaltooligosaccharides (cyclodextrins) with trans-b-carotene in water: evidence for the formation of large aggregates by light scattering and NMR spectroscopy, Carboh. Res., 1998, 310, 261-267.
26. Loftsson, T.; Cyclodextrins and drug permeability through semi-permeable cellophane membranes, Int. J. Pharm., 2001, 24, 165-178.
27. Loftsson, T.; Self-association and cyclodextrin solubilization of drugs, J. Pharm. Sci., 2002, 91, 2307-2316.
28. Loftsson, T.; The effect of water-soluble polymers on drug-cyclodextrin complexation, Int. J. Pharm., 1994, 110, 169-177.
29. Valero, M.; Effect of PVP K-25 on the formation of naproxen:b-cyclodextrin complex, Int. J. Pharm., 2003, 253, 97-110.
30. Loftsson, T.; Fririksdóttir, H.; The effect of water-soluble polymers on the aqueous solubility and complexing abilities of b-cyclodextrin, Int. J. Pharm., 1998, 163, 115-121.
31. Villiers, A.; Compt Rendu., 1891, 112, 536.
32. Szetjli, J.; Introduction and general overview of cyclodextrin chemistry, Chem Rev, 1998, 98, 1743-1753.
33. Muñoz-Botella, S.; del Castillo, B.; Martyn, M. A.; Cyclodextrin properties and applications of inclusion complex formation, Ars Pharm, 1995, 36,187-198.
34. Loftsson, T.; Brewster, M. E.; Pharmaceutical applications of cyclodextrins: 1. Drug solubilisation and stabilization, J Pharm Sci, 1996, 85, 1017-1025.
35. Schneiderman, E.; Stalcup, A.M.; Cyclodextrins: a versatile tool in separation science, J Chromatogr B, 2000, 745, 83-102.
36. Schmid, G.; Cyclodextrin glucanotransferse production: yield enhancement by overexpression of cloned genes, Trends Biotechnol, 1989, 7, 244-248.
37. Fujishima, N.; Kusaka, K.; Umino, T.; Urushinata, T.; Terumi, K.; Flour based foods containing highly branched cyclodextrins, Japanese Patent JP, 2001, 136, 898-902.
38. Bhardwaj, R.; Dorr, R. T.; Blanchard, J.; Approaches to reducing toxicity of parenteral anticancer drug formulations using cyclodextrins, J Pharm Sci Technol, 2000, 54, 233-239.
39. Holland, L.; Rizzi, G.; Malton, P.; Cosmetic compositions comprising cyclic oligosaccharides and fragrance, PCT Int Appl WO, 1999, 67, 716.
40. Lezcano, M.; Ai-Soufi, W.; Novo, M.; Rodriguez-Nunez, E.; Tato, J. V.; Complexation of several benzimidazole-type fungicides with alpha and betacyclodextrins., J Agric Food Chem, 2002, 50, 108-112.
41. Dufosse, L.; Souchon, I.; Feron, G.; Latrasse, A.; Spinnler, H. E.; In situ detoxification of the fermentation medium during gamma-decalactone production with the yeast Sporidiobolus salmonicolor, Biotechnol Prog, 1999, 15, 135-139.
42. Hedges, R. A.; Industrial applications of cyclodextrins, Chem Rev, 1998, 98, 2035-2044.
43. Frömming, K.H.; Szejtli, J.; Cyclodextrins in pharmacy, Topics in inclusion science. Dordrecht: Kluwer Academic Publishers, 1994.
44. Hirayama, F.; Uekama, K.; Methods of investigating and preparing inclusion compounds, Duchene D, Ed, Cyclodextrins and their industrial uses, Paris: Editions de Santé, 1987, 131-172.
45. Higuchi, T.; Connors, K.A.; Phase-solubility techniques, Adv. Anal. Chem. Instrum., 1965, 4, 117-212.
46. Sigurdardottir, A.M.; Loftsson, T.; The effect of polyvinylpyrrolidone on cyclodextrin complexation of hydrocortisone and its diffusion through hairless mouse skin, Int J Pharm, 1995, 126, 73-78.
47. Hussain, M. A.; Diluccio, R. C.; Maurin, M. B.; Complexation of moricizine with nicotinamide and evaluation of the complexation constants by various methods, J Pharm Sci, 1993, 82, 77-79.
48. Loftsson, T.; Effects of cyclodextrins on chemical stability of drugs in aqueous solutions, Drug Stabil, 1995, 1, 22-33.
49. Másson, M.; Loftsson, T.; Jónsdóttir, S.; Fridriksdóttir, H.; Petersen, D.S.; Stabilisation of drugs through complexation with non-ionic and ionic cyclodextrins, Int J Pharm, 1998, 164, 45-55.
50. Liu, F.; Kildsig, D. O.; Mitra, A.K.; Cyclodextrin/weak-electrolyte complexation: interpretation and estimation of association constants from phase solubility diagrams, Pharm Res, 1992, 9, 1671-1672.
51. Suzuki, M.; Ito, K.; Fushimi, C.; Kondo, T.; The freezing point depression method for the determination of binding parameters of drugs by polyvinylpyrrolidone and polyoxyethylene n-dodecylether, Chem Pharm Bull., 1993, 41, 1616-1620.
52. Connors, K. A.; The stability of cyclodextrin complexes in solution, Chem Rev, 1997, 97, 1325-1357.
53. Connors, K. A.; Population characteristics of cyclodextrin complex stabilities in aqueous solution, J. Pharm Sci, 1995, 84, 843-848.
54. Higuchi, T.; Connors, K. A.; Phase-solubility techniques, Adv. Anal. Chem. Instrum, 1965, 4, 117-212.
55. Martin, A.; Physical pharmacy, 4th ed. Philadelphia: Lea & Fedbiger; 1993.
56. Bergeron, R. J.; Cycloamylose-substrate binding, Inclusion Compounds, London, Academic Press, 1984.
57. Loftsson, T.; Brewster, M. E.; Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J Pharm Sci., 1996, 85, 1017-1025.
58. Loftsson, T.; Ólafsdóttir, B. J.; Fridriksdóttir, H.; Jónsdóttir, S.; Cyclodextrin complexation of NSAIDS: physicochemical characteristics, Eur J Pharm Sci 1993, 1, 95-101.
59. Pitha, J.; Hoshino, T.; Effects of ethanol on formation of inclusion complexes of hydroxypropylcyclodextrins with testosterone or with methyl organe, Int J Pharm, 1992, 80, 243-51.
60. Loftsson, T.; Stefansdottir, Ó.; Fridriksdottir, H.; Gudmundsson, Ö.; Interaction between preservatives and 2-hydroxypropyl-b-cyclodextrin, Drug Devel Ind Pharm, 1992, 18, 1477-1484.
61. Furuta, T.; Yoshii, H.; Miyamoto, A.; Yasunishi, A.; Hirano, H.; Effects of water of inclusion complexes of d-limonene and cyclodextrins., Supramol Chem 1993, 1, 321-5.
62. Torres-Labandeira, J. J.; Davignon, P.; Pitha, J.; Oversaturated solutions of drug in hydroxypropylcyclodextrins: parenteral preparation of pancratistatin, J Pharm Sci, 1990, 80, 384-6.
63. Loftsson, T.; Sigfusson, S. D.; Sigurosson, H. H.; Masson, M.; The Effects of cyclodextrins on topical delivery of Hydrocortisone: the aqueous diffusion layer, STP Pharma Sci., 2003, 13, 125-131.
64. Irie, T.; Wakamatsu, K.; Arima, H.; Aritomi, H.; Uekama, K.; Enhancing Effects of cyclodextrins on nasal absorption of insulin in rats., Int J Pharm., 1992, 84, 129-139.
65. Loftsson, T.; Masson, M.; Cyclodextrins in topical drug formulations: Theory and practice, Int J Pharm, 2001, 225, 15-30
66. Szejtli, J.; Cyclodextrins and their Inclusion Complexes, Akademiai Kiado, Budapest, 1982.
67. Uekama, K.; Otagiri, M.; Drug Carrier System-A Review, Crit Rev Ther Drug Car Sys, 1987, 3, 1-12.
68. Uekama, K.; Ikegami, K.; Wang, Z.; Horiuchi, Y.; Hirayama, F.; Inhibitory effect of 2-hydroxypropyl-β-cyclodextrin on crystal-growth of nifedipine during storage: superior dissolution and oral bioavailability compared with polyvinylpyrrolidone K-30, J Pharm Pharmacol, 1992, 44, 73-78.
69. Loftsson, T.; Brewster, M. E.; Masson, M.; Role of cyclodextrins in improving oral drug delivery, Am J Drug Deliv, 2004, 2, 261-275.
70. Carrier, R. L.; Miller, L. A.; Ahmed, I.; The utility of cyclodextrins for enhancing oral bioavailability, J Contr Rel., 2007, 123, 78-99.
71. Harrs, D.; Robinson, J. R.; Drug delivery via the mucous membranes of the oral cavity, J Pharm Sci, 1992, 82, 1-10.
72. Hoon, T. J.; Dawood, M. Y.; Khan-Dawood, F. S.; Ramos, J.; Batenhorst, R. L.; Bioequivalence of 17β-Estradiol Hydroxypropyl-β-cyclodextrin complex in postmenopausal women, J Clin Pharmacol, 1993, 33, 1116-1121.
73. Brown, G.A.; Martin, E.R.; Roberts, B. S.; Vukovich, M.D.; King, D. S.; Acute hormonal response to sublingual androstenediol in young men. J Appl Physiol., 2002, 92, 142-146.
74. Yoo, S. D.; Yoon, B.M.; Lee, H. S.; Lee, K. C.; Increased bioavailability of clomipramine after sublingual administration in rats, J Pharm Sci, 1999, 88, 1119-1121.
75. Badawy, S.; Ghorab, M. M.; Adeyeye, C. M.; Bioavailability of danazolhydroxypropyl-β-cyclodextrin complex by different routes of administration, Int J Pharm, 1996, 145, 137-143.
76. Mannila, J.; Jarvinen, T.; Lehtonen, M.; 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, 2003.
77. 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 Contr Rel, 2002, 82, 407-416.
78. Sukegawa, T.; Furuike, T.; Niikura, K.; Yamagishi, A.; Monde, K.; Nishimura, S.; Erythrocyte-like liposomes prepared by means of amphiphilic cyclodextrin Sulfates, Chem Commun., 2002, 5, 430-431.
79. Jicsinszky, L.; Petrikovics, I.; Petro, M.; Horvath, G.; Szejtli, J.; Way, J. L.; Improved drug delivery by conjugation with cyclodextrins. Proceedings of 14th European Carbohydrate Symposium, September 2-7, Lubeck, Germany, 2007.
80. Lim, H.J.; Cho, E. C.; Shim, J.; Kim, D. H.; An, E. J.; Polymer-associated liposomes as a novel delivery system for cyclodextrin bound drugs. J Colloid Interface Sci., 2008, 2, 460-468.
81. Duchene, D.; Ponchel, G., Wouessidjewe, D., Cyclodextrins in targeting: Application to nanoparticles, Adv Drug Del Rev, 1999, 36, 29-40.
82. Skalko, B. N., Pavelic, Z., Becirevic, L.M., Liposomes containing drug and cyclodextrin prepared by the one-step spray-drying method, Drug Dev Ind Pharm., 2000, 26, 1279-1284.
83. Fatouros, D. G.; Hatzidimitriu, K.; Antimisiaris, S. G.; Liposomes encapsulating prednisolone-cyclodextrin complexes: comparision of membrane integrity and drug release, Eur J Pharm Sci, 2001, 13, 287-296.
84. McClelland, G. A.; Sulton, S. C.; Engle, K.; Zentner, G. M.; The solubility-modulated osmotic pump: invitro / invivo release of diltiazem hydrochloride, Pharm Res, 1991, 8, 88-92.
85. Kharmnna, S. C.; Therapeutic system for sparingly soluble active ingredients. US patent, 1991, 4, 278.
86. Kuczynski, A. L.; Ayer, A. D.; Wong, P.S.; Dosage form for administering oral hypoglycemic glipizide, US patent 5, 1997, 413.
87. Geerke, J. H.; Method and apparatus for forming dispenser delivery ports, US patent 5, 1997, 658.
88. Okimoto, K.; Rajewski, R. A.; Stella, V. J.; Release of testosterone from an osmotic pump tablets utilizing (SBE) 7M-β-CD as both a solubilizing and an osmotic pump agent, J Control Rel., 1999, 58, 29-38.
89. Mehramizi, A.; Monfared, A. E.; Pourfarzib, M.; Bayati, K. H.; Dorkoosh, F. A.; Tehrani, R. M.; Influence of β-cyclodextrin complexation on lovastatin release from osmotic pump tablets (OPT), DAR, 2007, 15, 71-78.
90. Soares, A.; Francisca, C.; Rui de. A.; Francisco. V.; Oral administration of peptides and proteins: nanoparticles and cyclodextrins as biocompatible delivery systems, Nanomedicine, 2007, 2, 183-202.
91. Irie, T.; Uekama, K.; Cyclodextrins in peptide and protein delivery, Adv Drug Deliv Rev, 1999, 36, 101-123.
92. Sayani, A.; Chien, Y. W.; Systemic delivery of peptides and proteins across absorptive mucosae, Crit Rev Ther Drug Carrier Syst, 1996, 13, 85-184.
93. Hattori, Kenjiro., Synthesis and Evaluation of Novel Targeting Cyclodextrins as Drug Carrier. Program of 4th Asian Cyclodextrin Conference, May 18, 2007.
94. Wu, W. M., Wu, J., Bodor, N., Effect of 2-hydroxypropyl-betacyclodextrin on the solubility, stability, and pharmacological activity of the chemical delivery system of TRH analogs, Pharmazie, 2002, 57, 130-134.
95. Begley, D. J.; The Blood brain barrier: principles for targeting peptides and drugs to the central nervous system, J Pharm Pharmacol., 1996, 48, 136-140.
96. 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, 48, 715-720.
97. Eguchi, M.; Da, Y.Z.; Ogawa, Y.; Okada, T.; Yumoto, N.; Kodaka, M.; Effects of conditions for preparing nanoparticles composed of aminoethylcarbamoyl-β-cyclodextrin and ethylene glycol diglycidyl ether on trap efficiency of a guest molecule, Int J Pharm, 2006, 311, 215-222.
98. Perchyonok, V. T.; Towards Streamlining Conventional Radical Reactions Through Development of b-cyclodextrin based Batch, Flow-Through and "Teabag" Prototype Molecular Reactors, Current Nanoscience, 2011, in print
99. George, R.; Oberholzer, T.; Perchyonok, V. T.; Development of novel drug delivery prototypes devices for targeted delivery drug therapy at the molecular level in aqueous media, Current Drug Delivery, 2011, in print.
100. Perchyonok, V. T.; Lykakis, I. N.; Postigo, A.; Streamlining Free Radical Green Chemistry, RSC, 2011.
101. Martin Del Valle E. M., Process Biochemistry, 2004, 39(9), 1033-1046.