The self-association of the drug acemetacin and its interactions and stabilization with β-cyclodextrin in aqueous solution as inferred from NMR spectroscopy and HPLC studies

Carbohydrate Research

Volumn 337, Issue 15, 2002, Pages 1387-1395

  Zouvelekis, Dimitris ^a   Yannakopoulou, Konstantina ^a   Mavridis, Irene M ^a   Antoniadou Vyza, Ekaterini ^b  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

^b UNIVERSITY OF ATHENS   (Greece)

Author keywords

Cyclodextrin; Acemetacin; HPLC; Multiple equilibria; NMR; Self association

Indexed keywords

CONFORMATIONAL EQUILIBRIA;

CRYSTALS; DRUG DOSAGE; ISOMERS; NUCLEAR MAGNETIC RESONANCE; SOLUTIONS; TITRATION;

CARBOHYDRATES;

ACEMETACIN; BETA CYCLODEXTRIN; BUFFER; NONSTEROID ANTIINFLAMMATORY AGENT; BETA CYCLODEXTRIN DERIVATIVE; CYCLODEXTRIN; DRUG; DRUG DERIVATIVE; FOOD ADDITIVE; INDOMETACIN;

AQUEOUS SOLUTION; ARTICLE; COMPLEX FORMATION; CRYSTAL; DRUG HYDROLYSIS; DRUG STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERISM; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTION AND SOLUBILITY; STRUCTURE ACTIVITY RELATION;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BETA-CYCLODEXTRINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLODEXTRINS; DRUG STABILITY; FOOD ADDITIVES; INDOMETHACIN; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037014989     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(02)00174-X     Document Type: Article

References (34)

1. Matsuki Y., Ito T., Kojima M., Katsumura H., Ono H. Chem. Pharm. Bull. 31:1983;2033-2038.
2. Szejtli J. Cyclodextrin Technology. 1988;Kluwer Academic, Dordrecht.
3. Szejtli J., Szente L. Pharmazie. 36:1981;694-698.
4. Hoshino T., Tagawa T., Hirayama F., Otagiri M., Uekama K. Yakagaru Zasshi. 102:1982;1184-1190.
5. Szente L., Apostol I., Gerloczy A., Szejtli J. Pharmazie. 40:1985;406-407.
6. Tarimci N., Celebi N. Pharmazie. 43:1988;323-325.
7. Croft A.K., Easton C.J., Lincoln S.M., May M.L., Papageorgiou J. Aust. J. Chem. 50:1997;857-860.
8. Fini A., Fernandez-Hervas M.J., Holgado M.A., Rodriguez L., Cavallari C., Passerini N., Caputo O. J. Pharm. Sci. 86:1997;1303-1309.
9. Ueda H., Ou D., Endo T., Nagase H., Tomono K., Nagai T. Drug Dev. Ind. Pharm. 27:1998;863-867.
10. Fronza G., Mele A., Rendeti E., Ventura P. J. Org. Chem. 61:1996;909-914.
11. Djedaini F., Lin S.Z., Perly B., Wouessidjewe D. J. Pharm. Sci. 79:1990;643-646.
12. See special issue: Cyclodextrins in Drug Delivery Systems; Adv. Drug Deliv. Rev. 1999, 36, 1
13. see special issue: S.T.P. Pharm. Sci. 1999, 9, 225;
14. Benes, E.; Szejtli, J. Proc. Int. Symp. Cyclodextrins 9th; Santiago de Compostela, Spain, 1998.
15. Djedaïni, F., Perly B. Nuclear Magnetic Resonance of Cyclodextrins, Derivatives, and Inclusion Compounds. In New trends in Cyclodextrins and Derivatives; Duchêne D., Ed.; Editions de Santé Paris, France, 1991;
16. th; Paris, France, 1990; pp. 130
17. Eliadou K., Yannakopoulou K., Rontoyianni A., Mavridis I.M. J. Org. Chem. 64:1999;6217-6226.
18. Shetty A.S., Zhang J., Moore J.S. J. Am. Chem. Soc. 118:1996;1019-1027.
19. Petter R.C., Salek J.S., Sikorski C.T., Kumaravel G., Lin F.-T. J. Am. Chem. Soc. 112:1990;3860-3868.
20. Connors K.A. Binding Constants. 1987;Wiley, New York.
21. Attwood D., Waigh R., Blundell R., Bloor D., Thevand A., Boitard E., Dubes J.-P., Tachoire H. Magn. Reson. Chem. 32:1996;468-472.
22. Steullet V., Dixon D.W. J. Chem. Soc., Perkin Trans. 2. 1999;1547-1558.
23. Kistenmacher T.J., Marsh R.E. J. Am. Chem. Soc. 94:1972;1340-1345.
24. Gund P., Shen T.Y. J. Med. Chem. 20:1977;1146-1152.
25. Mitra A., Seaton P.J., Assarpour R.A., Williamson T. Tetrahedron. 54:1998;15489-15498.
26. Houbiers C., Lima J.C., Macanita A.L., Santos H. J. Phys. Chem. B. 102:1998;3578-3585.
27. Duffy C.P., Elliot C.J., O'Connor R.A., Heenan M.M., Coyle S., Cleary I.M., Kavanagh K., Verhaegen S., O'Loughlin C.M., NicAmhlaoibh R., Clynes M. Eur. J. Cancer. 34:1998;1250-1259.
28. Burger A., Lettenbichler A. Pharmazie. 48:1993;262-272.
29. Botsi A., Yannakopoulou K., Perly B., Hadjoudis E. J. Org. Chem. 60:1995;4017-4023.
30. Rozou S., Antoniadou-Vyza E. J. Pharm. Biomed. Anal. 18:1998;899-905.
31. Notarianni L.J., Collins A.J. J. Chromatogr. 413:1987;305-308.
32. Schöllnhammer G., Dell H.D., Doersing K., Kamp R. J. Chromatogr. 375:1986;331-338.
33. Battista H.J., Wehinger G., Henn R. J. Chromatogr. 345:1985;77-89.
34. Kahn A.H., Jensen P.B., Mørk N., Bundgaard H. Acta Pharm. Nord. 1:1989;327-336.