Phase solubility and FTIR-ATR studies of idebenone/sulfobutyl ether β-cyclodextrin inclusion complex

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 75, Issue 3-4, 2013, Pages 255-262

  Cannava C ^a   Crupi, V ^a   Guardo, M ^a   Majolino, D ^a   Stancanelli, R ^a   Tommasini, S ^a   Ventura, C A ^a   Venuti, V ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

FTIR ATR spectroscopy; Idebenone; Inclusion complex; Phase solubility; Sulfobutyl ether cyclodextrin

Indexed keywords

EID: 84878520995     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-012-0110-3     Document Type: Conference Paper

References (30)

1. Degli Esposti, M.; Ngo, A.; Ghelli, A.; Benelli, B.; Carelli, V.; McLennan, H.; Linnane, A.W.: The interaction of Q analogs, particularly hydroxydecyl benzoquinone (idebenone), with the respiratory complexes of heart mitochondria. Arch. Biochem. Biophys. 330, 395-400 (1996)
2. Geromel, V.; Darin, N.; Chrétien, D.; Bénit, P.; DeLonlay, P.; Rötig, A.; Munnich, A.; Rustin, P.: Coenzyme Q(10) and idebenone in the therapy of respiratory chain diseases: rationale and comparative benefits. Genet. Metab. 77, 21-30 (2002)
3. Gutzmann, H.; Hadler, D.: Sustained efficacy and safety of idebenone in the treatment of Alzheimer's disease: update on a 2-year double-blind multicentre study. J. Neural Transm. Suppl. 54, 301-310 (1998)
4. Thal, L.J.; Grundman, M.; Berg, J.; Ernstrom, K.; Margolin, R.; Pfeiffer, E.; Weiner, M.F.; Zamrini, E.; Thomas, R.G.: Idebenone treatment fails to slow cognitive decline in Alzheimer's disease. Neurology 61, 1498-1502 (2003)
5. Schols, L.; Meyer, C.h.; Schmid, G.; Wilhelms, I.; Przuntek, H.: Therapeutic strategies in Friedreich's ataxia. J. Neural Transm. Suppl. 68, 135-145 (2004)
6. Genova, M.L.; Pich, M.M.; Biondi, A.; Bernacchia, A.; Falasca, A.; Bovina, C.; Formiggini, G.; Parenti Castelli, G.; Lesnaz, G.: Mitochondrial production of oxygen radical species and the role of coenzyme Q as an antioxidant. Exp. Biol. Med. 228, 506-513 (2003)
7. Gillis, J.C.; Benefield, P.; McTavish, D.: Idebenone. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in age-related cognitive disorders. Drugs Aging 5, 133-152 (1994)
8. Loftsson, T.; Jarho, P.; Masson, M.; Jarvinen, T.: Cyclodextrins in drug delivery. Expert. Opin. Drug Deliv. 2, 335-351 (2005)
9. Frank, D.W.; Gray, J.E.; Weaver, R.N.: Cyclodextrin nephrosis in the rat. Am. J. Pathol. 83, 367-382 (1976)
10. Irie, T.; Uekama, K.: Pharmaceutical application of cyclodextrins. III. Toxicological issues and safety evaluation. J. Pharm. Sci. 86, 147-162 (1997)
11. Rajewski, R.A.; Traiger, G.; Bresnahan, J.; Jaberaboansari, P.; Stella, V.J.; Thompson, D.O.: Preliminary safety evaluation of parenterally administered sulfoalkyl ether β-cyclodextrin derivatives. J. Pharm. Sci. 84, 927-932 (1995)
12. Stella, V.J.; Rajewski, R.A.: Cyclodextrins: their future in drug formulation and delivery. Pharm. Res. 14, 556-567 (1997)
13. Luna, E.; Vander Velde, D.G.; Tait, R.J.; Thompson, D.O.; Rajewski, R.A.; Stella, V.J.: Isolation and characterization by NMR spectroscopy of three monosubstituted 4-sulfobutyl ether derivatives of cyclomaltoheptaose (β-cyclodextrin). Carbohydr. Res. 299, 111-118 (1997)
14. Holvoet, C.; Heyden, Y.V.; Plaizier-Vercammen, J.: Inclusion complexation of diazepam with different cyclodextrins in formulations for parenteral use. Pharmazie 60, 598-603 (2005)
15. Järvinen, T.; Järvinen, K.; Urtti, A.; Thompson, D.; Stella, V.J.: Sulfobuthyl ether beta-cyclodextrin (SBE-beta-CD) in eyedrops improves the tolerability of a topically applied pilocarpine prodrug in rabbits. J. Ocul. Pharmacol. Ther. 11, 95-106 (1995)
16. Puglisi, G.; Ventura, C.A.; Fresta, M.; Vandelli, M.A.; Cavallaro, G.; Zappalà, M.: Preparation and physico-chemical study of inclusion complexes between idebenone and modified β-cyclodextrin. J. Incl. Phenom. 24, 193-210 (1996)
17. Higuchi, T.; Connors, K.A.: Phase solubility techniques. Adv. Anal. Chem. Instr. 4, 117-212 (1965)
18. Gibaud, S.; Zirar, S.B.; Mutzenhardt, P.; Fries, I.; Astier, A.: Melarsoprol-cyclodextrins inclusion complexes. Int. J. Pharm. 306, 107-121 (2005)
19. Maréchal, Y.: Observing the water molecule in macromolecules and aqueous media using infrared spectrometry. J. Mol. Struct. 648, 27-47 (2003)
20. Szejtli, J.: Cyclodextrins and their inclusion compounds. Akademiai Kiado, Budapest (1982)
21. Dotsikas, Y.; Kontopanou, E.; Allagiannis, C.; Loukas, Y.L.: Interaction of 6-p-toluidinylnaphthalene-2-sulphonate with β-cyclodextrin. J. Pharm. Biomed. Anal. 23, 997-1003 (2000)
22. Jara, F.; Dominquez, M.; Rezende, M.C.: The interaction of solvatochromic pyridiniophenolates with cyclodextrins. Tetrahedron 62, 7817-7823 (2006)
23. Aramǎ, C.; Nicolescu, C.; Nedelcu, A.; Monciu, C.M.: Synthesis and characterization of the inclusion complex between repaglinide and sulfobutylether-β-cyclodextrin (Captisol®). J. Incl. Phenom. Macrocycl. Chem. 70, 421-428 (2011)
24. Crupi, V.; Guella, G.; Majolino, D.; Mancini, I.; Rossi, B.; Stancanelli, R.; Venuti, V.; Verrocchio, P.; Viliani, G.: T-dependence of the vibrational dynamics of IBP/diME-β-CD in solid state: a FT-IR spectral and quantum chemical study. J. Mol. Struct. 972, 75-80 (2010)
25. Crupi, V.; Majolino, D.; Venuti, V.; Guella, G.; Mancini, I.; Rossi, B.; Verrocchio, P.; Viliani, G.; Stancanelli, R.: Temperature effect on the vibrational dynamics of cyclodextrin inclusion complexes: investigation by FTIR-ATR spectroscopy and numerical simulation. J. Phys. Chem. A 114, 6811-6817 (2010)
26. Gavira, J.M.; Hernanz, A.; Bratu, I.: Dehydration of β-cyclodextrin: an IR ν(OH) band profile analysis. Vib. Spectrosc. 32, 137-146 (2003)
27. Crupi, V.; Ficarra, R.; Guardo, M.; Majolino, D.; Stancanelli, R.; Venuti, V.: UV-vis and FTIR-ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins. J. Pharm. Biomed. Anal. 44, 110-117 (2007)
28. Stancanelli, R.; Ficarra, R.; Cannavà, C.; Guardo, M.; Calabrò, M.L.; Ficarra, P.; Ottanà, R.; Maccari, R.; Crupi, V.; Majolino, D.; Venuti, V.: UV-vis and FTIR-ATR characterization of 9-fluorenon-2-carboxyester/(2-hydroxypropyl)-β-cyclodextrin inclusion complex. J. Pharm. Biomed. Anal. 47, 704-709 (2008)
29. Cannavà, C.; Crupi, V.; Ficarra, P.; Guardo, M.; Majolino, D.; Stancanelli, R.; Venuti, V.: Physicochemical characterization of coumestrol/β-cyclodextrins inclusion complexes by UV-vis and FTIR-ATR spectroscopies. Vib. Spectrosc. 48, 172-178 (2008)
30. Bratu, I.; Veiga, F.; Fernandes, C.; Hernanz, A.; Gavira, J.M.: Infrared spectroscopic study of triacetyl-β-cyclodextrin and its inclusion complex with nicapiridine. Spectroscopy 18, 459-467 (2004)