Determination of second-order association constants by global analysis of 1H and 13C NMR chemical shifts. Application to the complexation of sodium fusidate and potassium helvolate by β- and γ-cyclodextrin

Steroids

Volumn 68, Issue 1, 2003, Pages 43-53

  Al Soufi, Wajih ^a   Ramos Cabrer, Pedro ^a   Jover, Aida ^a   Budal, Rosane M ^b   Vázquez Tato, José ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

Author keywords

Association constants; Computer program; Cyclodextrin; Global analysis; NMR; Steroids

Indexed keywords

BETA CYCLODEXTRIN; FUSIDATE SODIUM; GAMMA CYCLODEXTRIN; STEROID; ANTIINFECTIVE AGENT; BETA CYCLODEXTRIN DERIVATIVE; CARBON; CYCLODEXTRIN; DRUG DERIVATIVE; FUSIDIC ACID; GAMMA CYCLODEXTRIN DERIVATIVE; GAMMA-CYCLODEXTRIN; HELVOLIC ACID; PROTON;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; COMPUTER PROGRAM; CONFIDENCE INTERVAL; PROTON NUCLEAR MAGNETIC RESONANCE; STOICHIOMETRY; CHEMICAL MODEL; CHEMISTRY; DRUG DELIVERY SYSTEM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; THEORETICAL MODEL;

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

EID: 0037211341     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(02)00114-9     Document Type: Article

References (77)

1. Marzona M., Carpignano R., Quagliotto P., Quantitative structure-stability relationships in the inclusion complexes of steroids with cyclodextrins. Ann. Chim. 82:1992;517-537.
2. Albers E., Muller B.W., Complexation of steroid hormones with cyclodextrins derivatives: substituent effects of the guest molecule on solubility and stability in aqueous solution. J. Pharm. Sci. 81(8):1992;756-761.
3. Breslow R., Zhang B., Cholesterol recognition and binding by cyclodextrin dimers. J. Am. Chem. Soc. 118:1996;8495-8496.
4. Asanuma H, Kakazu M, Shibata M, Hishiva T, Komivama M. Molecularly imprinted polymer of β -cyclodextrin for the efficient recognition of cholesterol. Chem Commun 1997:1971.
5. Ravichandran R., Divakar S., Inclusion of ring a of cholesterol inside the. β -cyclodextrin cavity: evidence from oxidation reactions and structural studies J. Inclusion Phenom. Mol. Recognit. Chem. 30:1998;253-270.
6. Taneva S., Ariga K., Okahata Y., Tagaki W., Association between amphiphilic cyclodextrins and cholesterol in mixed insoluble monolayers at the air-water interface. Langmuir. 5:1989;111-113.
7. Karuppiah N., Kaufman P.B., Kapustka S.A., Sharma A., Use of cyclodextrin-cholesterol complex as a primary standard in cholesterol analysis. Microchem. J. 47:1993;325-329.
8. Frijlink H.W., Eissens A.C., Hefting N.R., Poelstra K., Lerk C.F., Meijer D.K.F., The effect of parenterally administered cyclodextrins on cholesterol levels in the rat. Pharm. Res. 8:1991;9-16.
9. Claudy P., Letoffe J.M., Germain P., Bastide J.P., Bayol A., Blasquez S., et al. Physicochemical characterization of cholesterol-beta cyclodextrin inclusion complexes. J. Therm. Anal. 37:1991;2497-2506.
10. Sreenivasan K., Solvent effect on the interaction of steroids with a novel methyl. β -cyclodextrin polymer J. Appl. Polym. Sci. 68(11):1998;1857-1861.
11. 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(17):1999;5489-5495.
12. Saito H, Yonemura H, Nakamura H, Matsuo T. Stability and exchange properties of through-ring cyclodextrin complexes. Effects of chain length in polymethylene bis[1-pyridinium] as guest molecules. Chem Lett 1990:535-8.
13. Abadie C., Hug M., Kubli C., Gains N., Effect of cyclodextrins and undigested starch on the loss of chenodeoxycholate in the faeces. Biochem. J. 299:1994;725-730.
14. Boehler N., Riottot M., Ferezou J., Souidi M., Milliat F., Serougne C., et al. Antilithiasic effect of. β -cyclodextrin in LPN hamster: comparison with cholestyramine J. Lipid Res. 40:1999;726-734.
15. Nakanishi K., Masada M., Nadai T., Miyajima K., Effect of the interaction of drug-. β -cyclodextrin complex with bile salts on the drug absorption from rat small intestinal lumen Chem. Pharm. Bull. 37(1):1989;211-214.
16. Irie T, Fukunaga K, Garwood MK, Carpenter TO, Pitha J. Hydroxypropylcyclodextrins in parenteral use. II. Effects on transport and disposition of lipids in rabbit and humans. J Pharm Sci 81:524-8.
17. Armstrong D.W., DeMond W., Alak A., Hinze W.L., Riehl T.E., Bui K.H., Liquid chromatographic separation of diastereomers and structural isomers on cyclodextrin-bonded phases. Anal. Chem. 14(11):1991;234-237.
18. Shimada K., Nonaka M., Utility of cyclodextrin in mobile phase for high-performance liquid chromatographic separation of C21 steroids. J. Liq. Chromatogr. 14(11):1991;2109-2117.
19. Shimada K., Oe T., Hirose Y., Komine Y., Retention behavior of cardiac steroids using cyclodextrin in the mobile phase in high-performance liquid chromatography. J. Chromatogr. 478(2):1989;339-347.
20. Okafo G.N., Bintz C., Clarke S.E., Camilleri P., Micellar electrokinetic capillary chromatography in a mixture of taurodeoxycholic acid and. β -cyclodextrin J. Chem. Soc., Chem. Commun. 17:1992;1189-1192.
21. Aumatell A., Wells R.J., Enantiomeric differentiation of a wide range of pharmacologically active substances by cyclodextrin-modified micellar electrokinetic capillary chromatography using a bile salt. J. Chromatogr. A. 688:1994;329-337.
22. Castelnovo P., Albanesi C., Determination of the enantiomeric purity of N-propionyl-6,7-dimethoxy-2-aminotetralin by cyclodextrin-modified micellar electrokinetic chromatography. Electrophoresis. 18(6):1997;996-1001.
23. Sadlej-Sosnowska N., Influence of the structure of steroid hormones on their association with cyclodextrins: a high-performance liquid chromatography study. J. Inclusion Phenom. Mol. Recognit. Chem. 27(1):1997;31-40.
24. Sadlej-Sosnowska N., Inclusion complexes of steroid hormones with cyclodextrins studied by the Hummel-Dreyer method using reversed-phase liquid chromatography. J. Pharm. Biomed. Anal. 13(4/5):1995;701-704.
25. Sadlej-Sosnowska N., Molecular complexation: β -cyclodextrin and steroid hormones inclusion complexes studied by high-performance liquid chromatography Eur. J. Pharm. Sci. 3(1):1995;1-5.
26. Flood K.G., Reynolds E.R., Snow N.H., Characterization of inclusion complexes of betamethasone-related steroids with cyclodextrins using high-performance liquid chromatography. J. Chromatogr. 903(1/2):2000;49-65.
27. Flood K.G., Reynolds E.R., Snow N.H., Determination of apparent association constants of steroid-cyclodextrin inclusion complexes using a modification of the Hummel-Dreyer method. J. Chromatogr. A. 913(1/2):2001;261-268.
28. Hirayama F., Uekama K., Cyclodextrin-based controlled drug release system. Adv. Drug Delivery Rev. 36(1):1999;125-141.
29. Uekama K., Hirayama F., Irie T., Cyclodextrin drug carrier systems. Chem. Rev. 98(5):1998;2045-2076.
30. Pitha J., Harman S.M., Michel M.E., Hydrophilic cyclodextrin derivatives enable effective oral administration of steroidal hormones. J. Pharm. Sci. 75(2):1986;165-167.
31. Seo H., Tsuruoka M., Hashimoto T., Fujinaga T., Otagiri M., Uekama K., Enhancement of oral bioavailability of spironolactone by. β - and γ -cyclodextrin complexations Chem. Pharm. Bull. 31(1):1983;286-291.
32. Uekama K., Otagiri M., Uemura Y., Fujinaga T., Arimori K., Matsuo N., et al. Improvement of oral bioavailability of prednisolone by. β -cyclodextrin complexation in humans J. Pharmacobiol. Dyn. 6(2):1983;124-127.
33. Yano H., Hirayama F., Kamada M., Arima H., Uekama K., Colon-specific delivery of prednisolone-appended. α -cyclodextrin conjugate: alleviation of systemic side effect after oral administration J. Controlled Release. 79(1-3):2002;103-112.
34. Otagiri M., Fujinaga T., Sakai A., Uekama K., Effects of. β - and γ -cyclodextrins on release of betamethasone from ointment bases Chem. Pharm. Bull. 32(6):1984;2401-2405.
35. Uekama K., Arimori K., Sakai A., Masaki K., Irie T., Otagiri M., Improvement in percutaneous absorption of prednisolone by. β - and γ -cyclodextrin complexations Chem. Pharm. Bull. 35(7):1987;2910-2913.
36. Uekama K., Otagiri M., Sakai A., Irie T., Matsuo N., Matsuoka Y., Improvement in the percutaneous absorption of beclomethasone dipropionate by. γ -cyclodextrin complexation J. Pharm. Pharmacol. 37(8):1985;532-535.
37. Arimori K., Sakai A., Otagiri M., Uekama K., Improvement in biopharmaceutics of prednisolone by. β - and γ -cyclodextrins J. Inclusion Phenom. 1(4):1984;387-394.
38. Worth GM, Thomas M, Farr SJ, Taylor G. Steroid/cyclodextrin complexes for pulmonary delivery. In: Proceedings of the 24th International Symposium on Controlled Release Bioactivity Materials; 1997, p. 747-8.
39. Pitha J., Anaissie E.J., Uekama K. β -Cyclodextrin:testosterone complex suitable for sublingual administration J. Pharm. Sci. 76(10):1987;788-790.
40. Uekama K., Hieda Y., Hirayama F., Arima H., Sudoh M., Yagi A., et al. Stabilizing and solubilizing effects of sulfobutyl ether. β -cyclodextrin on prostaglandin e1 analogue Pharm. Res. 18(11):2001;1578-1585.
41. Ohvo H., Slotte J.P., Cyclodextrin-mediated removal of sterols from monolayers: effects of sterol structure and phospholipids on desorption rate. Biochemistry. 35(24):1996;8018.
42. Yoshida A., Yamamoto M., Irie T., Hirayama F., Uekama K., Some pharmaceutical properties of 3-hydroxypropyl- and 2,3-dihydroxypropyl-. β -cyclodextrins and their solubilizing and stabilizing abilities Chem. Pharm. Bull. 37(4):1989;1059.
43. Bayol A, Frankinet J, Gonzalez B, Maffrand J-P. Porcédé d'élimination de composés contenus dans une substance d'origine biologique. European Patent EP 0326469 A1; 1989.
44. Roderbourg H, Dalemans D, Bouhon R. Procédé de Réduction de la Teneur En Cholestérol et En Acides Gras Libres D'une Matiére Grasse D'origine Animale et Matiére Grasse Asinsi Obtenue. European Patent EP 0-387-708-A1; 1990.
45. Oakenfull DG, Sidhu GS, Rooney ML. Cholesterol removal. Australian Patent AU-A-54768/90; 1989.
46. Courregelongue J, Maffrand J-P. Procédé d'elimination du cholesterérol contenu dans une matière grasse d'origine animale et matière grasse appaurvrie en cholestérol obtenue. European Patent EP 0-256-911-A1; 1988.
47. Kempfle M.A., Mueller R.F., Palluk R., Winkler H.A., The binding of fluorescent 4,6,8(14)-triene-3-one steroids to cyclodextrins as a model for steroid-protein interactions. Biochim. Biophys. Acta. 923(1):1987;83-87.
48. 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(16):2000;2856-2858.
49. 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. 14(5):2002;397-404.
50. Djedaini F., Perly B., Nuclear magnetic resonance investigation of the stoichiometries in. β -cyclodextrin-steroid inclusion complexes J. Pharm. Sci. 80(12):1991;1157-1161.
51. Rudiger V., Schneider H.-J., The use of complexation induced proton NMR chemical shifts for structural analysis of host-guest complexes in solution. Chem. Eur. J. 6(20):2000;3771-3776.
52. 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.
53. a ) from solution NMR data Tetrahedron. 56(34):2000;6151-6170.
54. 13 C nuclear magnetic resonance spectroscopic study on amorphous solid complexes of tolbutamide with 2-hydroxypropyl- α - and - β -cyclodextrins Pharm. Res. 16(11):1999;1729-1734.
55. Connors KA. Binding constants: the measurement of molecular complex stability. New York: Wiley; 1987.
56. 3, a lanthanide shift reagent, and organic molecules J. Am. Chem. Soc. 95(11):1973;3534-3540.
57. Johnston M.D. Jr., Shapiro B.L., Shapiro M.J., Proulx T.W., Godwin A.D., Pearce H.L., Lanthanide-induced shifts in proton nuclear magnetic resonance spectra. XI. Equilibrium constants and bound shifts for cyclohexanones and cyclohexanols. J. Am. Chem. Soc. 97(3):1975;542-554.
58. Kneeland DM, Ariga K, Lynch M, Vincent, Huang C-Y, Anslyn EV. Bis(alkylguanidinium) receptors for phosphodiesters: effect of counterions, solvent mixtures, and cavity flexibility on complexation. J Am Chem Soc 1993;115(22):10042-55.
59. Gonzalez-Gaitano G., Compostizo A., Sanchez-Martin L., Tardajos G., Speed of sound, density, and molecular modeling studies on the inclusion complex between sodium cholate and. β -cyclodextrin Langmuir. 13:1997;2235-2241.
60. Beechem J.M., Global analysis of biochemical and biophysical data. Meth. Enzymol. 210:1992;37-54.
61. Gelb R.I., Schwartz L.M., Laufer D.A., Complexation chemistry of cyclohexaamyloses. 2. p -Methylcinnamate anion J. Am. Chem. Soc. 100(18):1978;5875-5879.
62. Brereton I.M., Spotswood T.M., Lincoln S.F., Williams E.H., Fluorine-19 nuclear magnetic resonance study of the inclusion of fluoro- and difluoro-trans-cinnamates by. α -cyclodextrin J. Chem. Soc., Faraday Trans. I. 80:1984;3147-3156.
63. Frassineti C., Ghelli S., Gans P., Sabatini A., Moruzzi M.S., Vacca A., Nuclear magnetic resonance as a tool for determining protonation constants of natural polyprotic bases in solution. Anal. Biochem. 231:1995;374-382.
64. Laouenan A., Suet E., MICMAC-Un Programme General et Rigoureux D'Affinement Multiparametrique Pour la Determination de Constantes D'Equilibre a Partir de Methodes Physiques Variees. Talanta. 32(4):1985;245-255.
65. Petti M.A., Shepodd T.J., Barrans R.E. Jr., Dougherty D.A., "Hidrophobic" binding of water-soluble guests by high-symmetry, chiral hosts. An electron-rich receptor site with a general affinity for quaternary ammonium compounds and electron-deficient. π systems J. Am. Chem. Soc. 110(20):1988;6825-6840.
66. Barrans R., Dougherty D.A., An improved method for determining bimolecular association constants from NMR titration experiments. Supramol. Chem. 4:1994;121-130.
67. Lenkinski R.E., Elgavish G.A., Reuben J., Criteria and algorithms for the characterization of weak molecular complexes of 2:1 stoichiometry from nuclear magnetic resonance data. Applications to a shift reagent system. J. Magn. Reson. 32:1978;367-376.
68. Tsukube H, Furuta H, Odani A, Takeda Y, Kudo Y, Inoue Y, et al. Determination of stability constants. In: Atwood JL, Davies JED, Macnicol DD, Vögtle F, editors. Comprehensive supramolecular chemistry, vol. 8. Pergamon Press, Oxford; 1996, Chapter 10, p. 425.
69. 13 C NMR spectroscopy J. Incl. Phenom. Macro. 37(1-4):2000;423-440.
70. Wolfram Research Inc. Champaign, IL, USA, http://www.wolfram.com.
71. Microcal Software Inc. Northampton, MA, USA, http://www.OriginLab.com.
72. Herbison-Evans D. Solving quartics and cubics for graphics. In: Paeth A, editor. Graphics Gems V, Academic Press, Chesnut Hill; 1995, p. 3-15. Available on the WEB as Technical Report TR94-487, Basser Department of Computer Science, University of Sydney, Australia.
73. Bevington PR, Robinson DK. Data reduction and error analysis for the physical sciences. McGraw-Hill, New York; 1994.
74. Johnson M.L., Faunt L.M., Parameter estimation by least-squares methods. Meth. Enzymol. 210:1992;1-37.
75. Johnson M.L., Evaluation and propagation of confidence intervals in nonlinear, asymmetrical variance spaces. Analysis of ligand-binding data. Biophys. J. 44(1):1983;101-106.
76. Johnson M.L., Frasier S.G., Nonlinear least-squares analysis. Meth. Enzymol. 117(Pt. J):1985;301-342.
77. Johnson M.L., Parameter correlations while curve fitting. Meth. Enzymol. 321:2000;424-446.