Binding constants for aromatic amino acids and their derivatives with sulfobutyl ether β-cyclodextrin determined using capillary electrophoresis

Journal of Drug Delivery Science and Technology

Volumn 14, Issue 5, 2004, Pages 383-387

  Miyajima, M ^a,b   Ozeki, T ^a,c   Stella, V J ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b DAIICHI SANKYO CO   (Japan)

^c TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Aromatic amino acid; Binding constant; Capillary electrophoresis; Peptide; Sulfobutyl ether cyclodextrin

Indexed keywords

AROMATIC AMINO ACID; BETA CYCLODEXTRIN SULFOBUTYL ETHER; DIPEPTIDE; FUNCTIONAL GROUP; GLYCINE DERIVATIVE; GLYCYLPHENYLALANINE; GLYCYLTRYPTOPHAN; GLYCYLTYROSINE; N ACETYLTRYPTOPHAN; N ACETYLTRYPTOPHAN ETHYL ESTER; PHENYLALANINE; PHENYLALANYLGLYCINE; PHOSPHATE; TRYPTOPHAN DERIVATIVE; TRYPTOPHAN ETHYL ESTER; TRYPTOPHYLLGLYCINE; TYROSYLGLYCINE; UNCLASSIFIED DRUG;

ACIDITY; ALKALINITY; ARTICLE; BINDING AFFINITY; CAPILLARY ELECTROPHORESIS;

EID: 5644227599     PISSN: 11571489     EISSN: None     Source Type: Journal    
DOI: 10.1016/s1773-2247(04)50067-9     Document Type: Article

References (21)

1. ARAKAWA T., PRESTRELSKI S.J., KENNEY W.C., CARPENTER J.F. - Factors affecting short-term and long-term stabilities of proteins. - Adv. Drug Del. Rev., 46, 307-326, 2001.
2. BRANCHU S., FORBES R.T., YORK P., NYQVIST H. - A central composite design to investigate the thermal stabilization of lysozyme. - Pharm. Res., 16, 702-708, 1999.
3. KATAM M., BANGA A.K. - Aggregation of proteins and its prevention by carbohydrate excipients: albumins and gamma-globulin. - J. Pharm. Pharmacol., 47, 103-107, 1995.
4. CUETO M., DORTA M.J., MUNGUIA O., LLABRES M. - New approach to stability assessment of protein solution formulations by differential scanning calorimetry. - Int. J. Pharm., 252, 159-166, 2003.
5. NISHIJO J., TSUCHITANI M. - Interaction of L-tryptophan with alpha-cyclodextrin: studies with calorimetry and proton nuclear magnetic resonance spectroscopy. - J. Pharm. Sci., 90, 134-140, 2001.
6. MATSUBARA K., IRIE T., UEKAMA K. - Spectroscopic characterization of the inclusion complex of a luteinizing hormone-releasing hormone agonist, buserelin acetate, with dimethyl-beta-cyclodextrin. - Chem. Pharm. Bull., 45, 378-383, 1997.
7. SABBAH S., SCRIBA G.K. - Separation of dipeptide and tripeptide enantiomers in capillary electrophoresis using carboxymethyl-beta-cyclodextrin and succinyl-beta-cyclodextrin: influence of the amino acid sequence, nature of the cyclodextrin and pH. - Electrophoresis, 22, 1385-1393, 2001.
8. SABBAH S., SUSS F., SCRIBA G.K. - pH-dependence of complexion constants and complex mobility in capillary electrophoresis separations of dipeptide enantiomers. - Electrophoresis, 22, 3163-3170, 2001
9. MATSUBARA K., ANDO Y., IRIE T., UEKAMA K. - Protection afforded by maltosyl-beta-cyclodextrin against alpha-chymotrypsin-catalyzed hydrolysis of a luteinizing hormone-releasing hormone agonist, buserelin acetate. - Pharm. Res., 14, 1401-1405, 1997.
10. JOHNSON M.D., HOESTEREY B.L., ANDERSON B.D. - Solubilization of a tripeptide HIV protease inhibitor using a combination of ionization and complexation with chemically modified cyclodextrins. - J. Pharm. Sci., 83, 1142-1146, 1994.
11. JORGENSON J.W., LUKACS K.D. - Capillary zone electrophoresis. - Science, 222, 266-272, 1983.
12. TAIT R.J., SKANCHY D.J., THOMPSON D.P., CHETWYN N.C., DUNSHEE D.A., RAJEWSKI R.A., STELLA V.J., STOBAUGH J.F. - Characterization of sufphoalkyl ether derivatives of β-cyclodextrin by capillary electrophoresis with indirect UV detection. - J. Pharm. Biomed. Anal., 10, 615-622, 1992.
13. WINZOR D.J. - Measurement of binding constants by capillary electrophoresis. - J. Chromatogr. A., 696, 160-163, 1995.
14. PENN S.G., BERGSTROM E.T., KNIGHTS I., LIU G., RUDDICK A., GOODALL D.M. - Capillary electrophoreses as a method for determining binding constants: application to the binding of cyclodextrins and nitrophenolates. - J. Phys. Chem., 99, 3875-3880, 1995.
15. SHIBUKAWA A., LLOYD D.K., WAINTER I.W. - Simultaneous chiral separation of leucovorin and its major metabolite 5-methyltetrahydrofolate by capillary electrophoresis using cyclodextrins as chiral selectors - estimation of the formation constant and mobility of solute-cyclodextrin complexes. - Chromatographia, 35, 419-429, 1993.
16. SKANCHY D.J. - Capillary electrophoresis methodologies for solving problems in pharmaceutical analysis. - Ph.D. Dissertation, The University of Kansas, Lawrence, KS, USA, Chapter 4, pp. 134-184, 1996.
17. COHEN A.S., PAULUS A., KARGER B.L. - High-performance capillary electrophoresis using open tubes and gels. - Chromatographia, 24, 15-24, 1987.
18. GUTTMAN A., PAULUS A., COHEN S.A., GRINBERG N., KARGER B. L. - Use of complexing agents for selective separation in high-performance capillary electrophoresis - chiral resolution via cyclodextrins incorporated within polyacrylamide-gel columns. - J. Chromatogr., 448, 41-53, 1988.
19. WREN S.A.C., ROWE R.C. - Theoretical aspects of chiral separation in capillary electrophoresis. 1. Initial evaluation of a model. - J. Chromatogr., 603, 235-241, 1992.
20. The Merck Index 12th Edition, pp. 7428, 9930, 9971, Merck & Co., Inc. NJ, USA.
21. VALLAT P., GAILLARD P., CARRUPT P.A., TSAI R.S., TESTA B. - Structure-lipophilicity and structure-polarity relationships of amino acids and peptides. - Helv. Chim. Acta., 78, 471-485, 1995.