Solubility and mass and nuclear magnetic resonance spectroscopic studies on interaction of cyclosporin A with dimethyl-α- and -β-cyclodextrins in aqueous solution

Journal of Pharmaceutical Sciences

Volumn 88, Issue 1, 1999, Pages 39-45

  Miyake, Kouzou ^a   Hirayama, Fumitoshi ^a   Uekama, Kaneto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CYCLODEXTRIN DERIVATIVE; AMINO ACID; BETA CYCLODEXTRIN DERIVATIVE; CHLOROFORM; CHLORPROMAZINE; CYCLOSPORIN A; METHANOL; WATER;

AQUEOUS SOLUTION; ARTICLE; DRUG SOLUBILITY; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032936547     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js980284+     Document Type: Article

References (22)

1. Bender, M. L., Komiyama, M., Eds. Cyclodextrin Chemistry; Springer-Verlag: Berlin, 1978.
2. Connors, K. A. The stability of cyclodextrin complexes in solution. Chem. Rev. 1997, 97, 1325-1357.
3. Hirayama, F.; Uekama, K. Methods of investigating and preparing inclusion compounds. In Cyclodextrins and their industrial uses; Duchêne, D., Ed.; Edition de Santê: Paris, 1987; pp 131-172.
4. Vincenti, M. Host-guest chemistry in the mass spectrometer. J. Mass Spectrom. 1995, 30, 925-939.
5. Camilleri, P.; Haskins, N. J.; New, A. P.; Saunders, M. R. Analysing the complexation of amino acids and peptides with β-cyclodextrin using electrospray ionization mass spectrometry. Rapid Commun. Mass Spectrom. 1993, 7, 949-952.
6. Camilleri, P.; Haskins, N. J.; Howlett, D. R. β-Cyclodextrin interacts with the Alzheimer amyloid β-A4 peptide. FEBS Lett. 1994, 341, 256-258.
7. Tokihiro, K.; Irie, T.; Hirayama, F.; Uekama, K. Mass spectroscopic evidence on inhibiting effect of maltosyl-β-cyclodextrin on insulin self-association. Pharm. Sci. 1996, 2, 519-522.
8. Fahr, A. Cyclosporin clinical pharmacokinetics. Clin. Pharmacokinet. 1993, 24, 472-495.
9. Lampen, A.; Christians, U.; Bader, A.; Hackbarth, I.; Sewing, K. F. Drug interaction and interindividual variability of ciclosporin metabolism in the small intestine. Pharmacology 1996, 52, 159-168.
10. Miyake, K.; Irie, T.; Hirayama, F.; Uekama, K. Improvements of gastrointestinal absorption and lymphatic transfer of cyclosporin A by various cyclodextrins. Drug Delivery Syst. 1998, 13, 369-375.
11. Spencer, C. M.; Stoddart, J. F.; Zarzycki, R. Structural mapping of an unsymmetrical chemically modified cyclodextrin by high-field nuclear magnetic resonance spectroscopy. J. Chem. Soc., Perkin Trans. 2, 1987, 1323-1336.
12. Higuchi, T.; Connors, K. A. Phase-solubility techniques. Adv. Anal. Chem. Instr. 1965, 4, 117-212.
13. Higuchi, T.; Kristiansen, H. Binding specificity between small organic solutes in aqueous solution: classification of some solutes into two groups according to binding tendencies. J. Pharm. Sci. 1970, 59, 1601-1608.
14. Ishida, K.; Hoshino, T.; Irie, T.; Uekama, K. Alleviation of chlorpromazine-photosensitized contact dermatitis by β-cyclodextrin derivatives and their possible mechanisms. Xenobiot. Metab. Dispos. (in Japanese). 1988, 3, 377-386.
15. Shiotani, K.; Uehata, K.; Irie, T.; Hirayama, F.; Uekama, K. Characterization and the inclusion mode of β-cyclodextrin sulfate and its effect on the chlorpromazine-induced hemolysis of rabbit erythrocytes. Chem. Pharm. Bull. 1994, 42, 2332-2337.
16. 6 by a combination of homo- and heteronuclear two-dimensional techniques. Helv. Chem. Acta 1985, 68, 661-681.
17. Ko, S. Y.; Dalvit, C. Conformation of cyclosporin A in polar solvent. Int. J. Pept. Protein Res. 1992, 40, 380-382.
18. Hasumi, H.; Nishikawa, T.; Ohtani, H. Effect of temperature on molecular structure of cyclosporin A. Biochem. Mol. Biol. Int. 1994, 32, 505-511.
19. Utsuki, T.; Imamura, K.; Hirayama, F.; Uekama, K. Stoichiometry-dependent changes of solubility and photoreactivity of an antiulcer agent, 2′-carboxymethoxy-4,4′-bis(3-methyl-2-butenyloxy)chalcone, in cyclodextrin inclusion complexes. Eur. J. Pharm. Sci. 1993, 1, 81-87.
20. 1H NMR study of conformation of formay-L-phenylalanyl-6-deoxy-6-amino-cyclomaltoheptaose that has excellent ability of chiral recognition. Bull. Chem. Soc. Jpn. 1990, 63, 3175-3180.
21. 1H NMR spectroscopy to determine the enantioselective mechanism of neutral and anionic cyclodextrins in capillary electrophresis. J. Pharm. Biomed. Anal. 1997, 15, 1603-1619.
22. 1H NMR study of intramolecular hydrogen-bonding interaction in cyclodextrins and their di-O-methylated derivatives. Bull. Chem. Soc. Jpn. 1988, 61, 4015-4021.