Cyclodextrins as solubilizers: Formation of complex aggregates

Journal of Pharmaceutical Sciences

Volumn 99, Issue 2, 2010, Pages 719-729

  Jansook, Phatsawee ^a   Kurkov, Sergey V ^a   Loftsson, Thorsteinn ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

Author keywords

Activity coefficient; Aggregate; Complex; Cyclodextrin; Permeation; TEM

Indexed keywords

2 HYDROXYPROPYL GAMMA CYCLODEXTRIN; AMPHOTERICIN B; CYCLODEXTRIN; DICLOFENAC; GAMMA CYCLODEXTRIN; HYDROCORTISONE; MONOMER; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; HYDRATION; TRANSMISSION ELECTRON MICROSCOPY;

EID: 74049133227     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21861     Document Type: Article

References (36)

1. Loftsson T, Duchêne D. 2007. Cyclodextrins and their pharmaceutical applications. Int J Pharm 329:1-11.
2. Dodziuk H, editor. 2006. Cyclodextrins and their complexes. 1st edition. Weinheim: Wiley-VCH Verlag.
3. Kajtár M, Vikmon M, Morlin E, Szejtli J. 1989. Aggregation of amphotericin B in the presence of γ-cyclodextrin. Biopolymers 28:1585-1596.
4. Coleman AW, Nicolis I, Keller N, Dalbiez JP. 1992. Aggregation of cyclodextrins: An explanation of the abnormal solubility of β-cyclodextrin. J Incl Phenom Macroc Chem 13:139-143.
5. Andronati SA, Shapiro YE, Yakubovskaya LN, Gorbatyuk VY, Andronati KS, Krasnoschekaya SP. 1996. Inclusion compounds of psychotropic agents and cyclodextrins. J Incl Phenom Macroc Chem 24:175-186.
6. Gabelica V, Galic N, De Pauw E. 2002. On the specificity of cyclodextrin complexes detected by electrospray mass spectrometry. J Am Soc Mass Spectrom 13:946-953.
7. Correia I,Bezzenine N, RonzaniN,Platzer N, Beloeil J-C, Doan B-T. 2002. Study of inclusion complexes of acridine with b- and (2,6-di-O-methyl)-β- cyclodextrin by use of solubility diagrams and NMR spectroscopy. J Phys Org Chem 15:647-659.
8. Loftsson T, Másson M, Brewster ME. 2004. Selfassociation of cyclodextrins and cyclodextrin complexes. J Pharm Sci 93:1091-1099.
9. Bikádi Z, Kurdi R, Balogh S, Szemán J, Hazai E. 2006. Aggregation of cyclodextrins as an important factor to determine their complexation behavior. Chem Biodiv 3:1266-1276.
10. Yan P, Tang J-N, Xiao J-X. 2007. Interaction between b-cyclodextrin and mixed cationic-anionic surfactants (2): Aggregation behavior. J Dispers Sci Technol 28:623-626.
11. Szente L, Szejtli J, Kis GL. 1998. Spontaneous opalescence of aqueous γ-cyclodextrin solutions: Complex formation or self-aggregation. J Pharm Sci 87:778-781.
12. Wu A, Shen X, He Y. 2006. Investigation of gcyclodextrin nanotube induced by N,N'-diphenyl-benzidine molecule. J Coll Interf Sci 297:525-533.
13. Wu A, Shen X, He Y. 2006. Micrometer-sized rod-like structure formed by the secondary assembly of cyclodextrin nanotube. J Coll Interf Sci 302:87-94.
14. Bonini M, Rossi S, Karlsson G, Almgren M, Lo Nostro P, Baglioni P. 2006. Self-assembly of b-cyclodextrin in water. Part 1.Cryo-TEManddynamic and static light scattering. Langmuir 22: 1478-1484.
15. Loftsson T, Magnúsdóttir A, Másson M, Sigurjónsdóttir JF. 2002. Self-association and cyclodextrin solubilization of drugs. J Pharm Sci 91:2307-2316.
16. Loftsson T, Másson M, Sigurdsson HH. 2002. Cyclodextrins and drug permeability through semi-permeable cellophane membranes. Int J Pharm 232:35-43.
17. Loftsson T, Másson M. 2004. The effects of water-soluble polymers on cyclodextrins and cyclodextrin solubilization of drugs. J Drug Del Sci Tech 14:35-43.
18. Redenti E, Szente L, Szejtli J. 2000. Drug/cyclodextrin/ hydroxy acid multicomponent systems. Properties and pharmaceutical applications. J Pharm Sci 89:1-8.
19. Yamakawa T, Nishimura S. 2003. Liquid formulation of a novel non-fluorinated topical quinolone, T-3912, utilizing the synergic solubilizing effect of the combined use of magnesium ions and hydroxypropyl-β- cyclodextrin. J Control Rel 86:101-113.
20. Jansook P, Loftsson T. 2008. gCD/HPgCD: Synergistic solubilization. Int J Pharm 363:217-219.
21. Loftsson T, Hreinsdóttir D, Másson M. 2005. Evaluation of cyclodextrin solubilization of drugs. Int J Pharm 302:18-28.
22. Higuchi T, Connors KA. 1965. Phase-solubility techniques. Adv Anal Chem Instrum 4:117-212.
23. Brewster ME, Loftsson T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59:645-666.
24. Saarinen-Savolainen P, Urtti A, Jarho P, Järvinen T. 1997. β-Cyclodextrin derivatives (2-HP-β-CD, SBE4-β-CD) decrease the amphiphilicity and membrane perturbing effects of pilocarpine prodrugs. Eur J Pharm Sci 5:89-96.
25. Bugler J, Sommerdijk NAJM, Visser AJWG, van Hoek A, Nolte RJM, Engbersen JFJ, Reinhoudt DN. 1999. Interconnective host-guest complexation of beta-cyclodextrin-calix[4]arene couples. J Am Chem Soc 121:28-33.
26. Magnusdottir A, Másson M, Loftsson T. 2002. Self association and cyclodextrin solubilization of NSAIDs. J Incl Phenom Macroc Chem 44:213-218.
27. Miyajima K, Sawada M, Nakagaki M. 1983. Viscosity B-coefficients, apparent molar volumes, and activity coefficients for α- and γ-cyclodextrins in aqueous solutions. Bull Chem Soc Jpn 56:3556-3560.
28. Terdale SS, Dagade DH, Patil KJ. 2006. Thermo-dynamic studies of molecular interactions in aqueous alpha-cyclodextrin solutions: Application of McMillan-Mayer and Kirkwood-Buff theories. J Phys Chem B 106:18583-18593.
29. Zannou EA, Streng WH, Stella VJ. 2001. Osmotic properties of sulfobutylether and hydroxypropyl cyclodextrins. Pharm Res 18:1226-1231.
30. Patil K, Pawar R, Dagade D. 2002. Studies of osmotic and activity coefficients in aqueous and CCl4 solutions of 18-Crown-6 at 258C. J Phys Chem A 106:9606-9611.
31. He W, Fu P, Shen XH, Gao HC. 2008. Cyclodextrin-based aggregates and characterization by micro-scopy. Micron 39:495-516.
32. Moffat AC, Osselton MD, Widdop B, editors. 2004. Clarke's Analysis of drugs and poisons. 3rd edition. London: Pharmaceutical Press.
33. Lavasanifar A, Samuel J, Kwon GS. 2002. The effect of fatty acid substitution on the in vitro release of amphotericin B from micelles composed of poly(ethylene oxide)-block-poly(N-hexyl stearate-L-aspartamide). J Control Rel 79:165-172.
34. Nokhodchi A, Javadzadeh Y, Siahi-Shadbad MR, Barzegar-Jalali M. 2005. The effect of type and concentration of vehicles on the dissolution rate of a poorly soluble drug (indomethacin) from liquisolid compacts. J Pharm Pharmaceut Sci 8:18-25.
35. Riess W, Stierlin H, Degen P, Faigle JW, Gerardin A, Moppert J, Sallmann A, Schmid K, Schweizer A, Sulc M, Theobald W, Wagner J. 1978. Pharmaco-kinetics and metabolism of the anti-inflammatory agent Voltaren. Scand J Rheumato Suppl 22:17-29.
36. Huang Y-B, Wu P-C, Ko H-M, Tsai Y-H. 1995. Cardamom oil as a skin permeation enhancer for indomethacin, piroxicam and diclofenac. Int J Pharm 126:111-117.