Spectra and structure of complexes formed by sodium fusidate and potassium helvolate with β- and γ-cyclodextrin

Steroids

Volumn 68, Issue 1, 2003, Pages 55-64

  Jover, Aida ^a   Budal, Rosane M ^b   Al Soufi, Wajih ^a   Meijide, Francisco ^a   Vázquez Tato, José ^a   Yunes, Rosendo A ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Cyclodextrin; Inclusion compounds; NMR; Potassium helvolate; Sodium fusidate; Steroids

Indexed keywords

ANTIBIOTIC AGENT; BETA CYCLODEXTRIN; FUSIDATE SODIUM; GAMMA CYCLODEXTRIN; POTASSIUM HELVOLATE; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; BETA CYCLODEXTRIN DERIVATIVE; CYCLODEXTRIN; DRUG DERIVATIVE; FUSIDIC ACID; GAMMA CYCLODEXTRIN DERIVATIVE; GAMMA-CYCLODEXTRIN; HELVOLIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; DRUG STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STRUCTURE ANALYSIS; BINDING SITE; CHEMICAL MODEL; CHEMISTRY; DRUG DELIVERY SYSTEM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; THEORETICAL MODEL;

ANTI-BACTERIAL AGENTS; BETA-CYCLODEXTRINS; BINDING SITES; CYCLODEXTRINS; DRUG DELIVERY SYSTEMS; FUSIDIC ACID; GAMMA-CYCLODEXTRINS; MODELS, CHEMICAL; MODELS, THEORETICAL; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

EID: 1842856243     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(02)00115-0     Document Type: Article

References (33)

1. Arigoni D., von Daehne W., Godtfredsen W.O., Marquet A., Melera A. Location of the ring C hydroxyl group in fusidic acid. Experientia. 19:1963;521-522.
2. Carey M.C., Montet J.C., Small D.M. Surface and solution properties of steroid antibiotics: 3-acetoxylfusidic acid, cephalosporin P1 and helvolic acid. Biochemistry. 14:1975;4896-4905.
3. Carey M.C., Small D.M. Micelle formation by bile salts. Physical-chemical and thermodynamic considerations. Arch. Intern. Med. 130:1972;506-527.
4. Coello A., Meijide F., Rodríguez Núñez E., Vázquez Tato J. Aggregation behavior of sodium fusidate in aqueous solution. J. Pharm. Sci. 83:1994;828-832.
5. Carey M.C., Small D.M. Micellar properties of sodium fusidate, a steroid antibiotic structurally resembling the bile salts. J. Lipid Res. 12:1971;604-613.
6. Richard A.J. Ultracentrifugal study of effect of sodium chloride on micelle size of fusidate sodium. J. Pharm. Sci. 64:1975;873-875.
7. Wilkinson J.D. Fusidic acid in dermatology. Br. J. Dermatol. Suppl. 139:1998;37-40.
8. Roholt I. Comparative efficacy of sodium fusidate ointment and two formulations of mupirocin ointment against experimentally induced wound infections in mice. Curr. Therap. Res. 51:1992;390-395.
9. Turnidge J. Fusidic acid pharmacology, pharmacokinetics and pharmacodynamics. Int. J. Antimicrob Agents. 12:1999;S23-S34.
10. Christiansen K. Fusidic acid adverse drug reactions. Int. J. Antimicrob. Agents. 12:1999;S3-S9.
11. Güttler R., Tybring L., Engerg-Pedersen H. Interaction of albumin and fusidic acid. Br. J. Pharmacol. 43:1971;151-160.
12. Rolinson G.N., Sutherland R. The binding of antibiotics to serum proteins. Br. J. Clin. Pharmacol. 25:1965;638-650.
13. Rieutord R., Bourget P., Troche G., Zazzo J.F. In vitro study of the protein binding of fusidic acid: a contribution to the comprehension of its pharmacokinetic behaviour. Int. J. Pharm. 119:1995;57-64.
14. Brodersen R. Fusidic acid binding to serum albumin and interaction with binding of bilirubin. Acta Paed. Scand. 74:1985;874-880.
15. Bourget P., Quinquis-Desmaris V., Hulin A., Peter J.D., Jehl F. Study of the protein binding of fusidic acid in cholestatic individuals and comparison with in vitro findings. Int. J. Pharm. 128:1996;223-228.
16. von Daehne W., Godtfredsen W.O., Rasmussen P.R. Adv. Appl. Microbiol. 25:1979;95-146.
17. Shinohara C., Hasumi K. Endo A inhibition of oxidized low-density lipoprotein metabolism in macrophage J774 by helvolic acid. Biochim. Biophys. Acta. 1167:1993;303-306.
18. Amitani R., Taylor G., Elezis E.N., Llewellyn-Jones C., Mitchell J., Kuze F.et al. Purification and characterization of factors produced by Aspergillus fumigatus which affect human ciliated respiratory epithelium. Infection Infect. Immun. 63:1995;3266-3271.
19. Tschen J.S.-M., Chen L.-L., Hsieh S.-T., Wu T.-S. Isolation and phytotoxic effects of helvolic acid from plant pathogenic fungus Sarocladium oryzae. Bot. Bull. Acad. Sin. 38:1997;251-256.
20. Szejtli J. Cyclodextrin technology. Dordrecht: Kluwer; 1988.
21. Otero Espinar F.J., Anguiano Igea S., Blanco Mendez J., Vila Jato J.L. Reduction in the ulcerogenicity of naproxen by complexation with β-cyclodextrin. Int. J. Pharm. 70:1991;35-41.
22. Ramos Cabrer P., Alvarez-Parrilla E., Meijide F., Seijas J.A., Rodríguez Núñez E., Vázquez Tato J. Complexation of sodium cholate and sodium deoxycholate by β-cyclodextrin and derivatives. Langmuir. 15:1999;5489-5495.
23. Alvarez-Parrilla E, Ramos Cabrer P, Singh A-P, Al-Soufi W, Meijide F, Rodríguez Núñez E, et al. Supramolecular linear conglomerates formed by β-cyclodextrin dimers and sodium deoxycholate. Supramol Chem, in press.
24. Alvarez Parrilla E., Ramos Cabrer P., Al-Soufi W., Meijide F., Rodríguez Núñez E., Vázquez Tato J. Dendritic growth of a supramolecular complex. Angew. Chem. Int. Ed. 39:2000;2856-2858.
25. Ramos Cabrer P, Alvarez-Parrilla E, Al-Soufi W, Meijide F, Rodríguez Núñez E, Vázquez Tato, J. Complexation of bile salts by natural cyclodextrins. Supramol Chem, in press.
26. Forgo P., D'Souza V.T. The application of selective ROE experiments to study solution structures of cyclomaltooligosacharide derivatives and complexes. Carbohydr. Res. 306:1998;473-478.
27. Barber J., Lian L., Morris G.A., Tehrani M.H. Full assignments of the proton and carbon-13 NMR spectra of sodium fusidate in organic and aqueous media. Magn. Reson. Chem. 27:1989;740-747.
28. Iwasaki S, Sair MI, Igarashi H, Okuda S. Revised structure of helvolic acid. J Chem Soc D 1970;1119-20.
29. Okuda S, Iwasaki S, Sair MI, Machida Y, Inoue A, Tsuda K. Stereochemistry of helvolic acid. Tetrahedron Lett. 1967;2295-302.
30. Oxley P. Cephalosporin P1 and helvolic acid. Chem Commun 1966;729-30.
31. Palepu R., Reinsborough V.C. Surfactant-cyclodextrin interactions by conductance measurements. Can. J. Chem. 66:1988;325-328.
32. Gil V.M.S., Oliveira N.C. On the use of the method of continuous variations. J. Chem. Educ. 67:1990;473-478.
33. Cameron K.S., Fielding L. NMR diffusion spectroscopy as a measure of host-guest complex association constants and as a probe of complex size. J. Org. Chem. 66:2001;6891-6895.