Effect of sialic acid residues of human α1-acid glycoprotein on stereoselectivity in basic drug-protein binding

Chirality

Volumn 9, Issue 3, 1997, Pages 291-296

  Shiono, Hiromitsu ^a   Shibukawa, Akimasa ^a   Kuroda, Yukihiro ^a   Nakagawa, Terumichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

capillary electrophoresis; high performance frontal analysis; propranolol; verapamil

Indexed keywords

OROSOMUCOID; PROPRANOLOL; SIALIC ACID; VERAPAMIL;

ARTICLE; BINDING AFFINITY; DRUG PROTEIN BINDING; DRUG STRUCTURE; PRIORITY JOURNAL; SIALYLATION; STRUCTURE ACTIVITY RELATION;

ADRENERGIC BETA-ANTAGONISTS; BLOOD PROTEINS; CALCIUM CHANNEL BLOCKERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; ELECTROPHORESIS, CAPILLARY; HUMANS; OROSOMUCOID; PROPRANOLOL; PROTEIN BINDING; SIALIC ACIDS; SPECTROMETRY, FLUORESCENCE; STEREOISOMERISM; VERAPAMIL;

EID: 0030992547     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1997)9:3<291::AID-CHIR15>3.0.CO;2-I     Document Type: Article

References (35)

1. Meyer, M.C., Gultman, D.E. The binding of drugs by plasma proteins. J. Pharm. Sci. 57:895-918, 1968.
2. Vallner, J.V. Binding of drugs by albumin and plasma protein. J. Pharm. Sci. 66:447-465, 1977.
3. Kwong, T.C. Free drug measurements: methodology and clinical significance. Clin. Chem. Acta 151:193-216, 1985.
4. Tucker, G.T., Lennard, M.S. Enantiomer specific pharmacokinetics. Pharmacol. Ther. 45:309-329, 1990.
5. Nocter, T. Enantioselective binding of drugs to plasma proteins. In: Drug Stereochemistry, 2nd ed. Wainer, I.W., ed. New York: Dekker 1993:337-364.
6. Bacchus, H. Serum seromucoid and acid mucopolysaccharide in malignant neoplastic diseases. Cancer 18:1285-1291, 1965.
7. Martyn, J.A., Abernethy, D.R., Greenblatt, D.J. Plasma protein binding of drugs after severe burn injury. Clin. Pharmacol. Ther. 35:535-540, 1984.
8. 1-acid glycoprotein in health and disease. Pharmacol. Rev. 40:1-47, 1988.
9. Schmid, K. The Plasma Proteins: Structure Function and Genetic Control, vol. 1. New York: Academic Press, 1975:184-228.
10. 1-acid glycoprotein. Biochem. Biophys. Acta. 492:291-302, 1977.
11. 1-acid glycoprotein. Biochem. J. 283:105-112, 1992.
12. 1-antitrypsin desialylation in liver disease. Hepatology 3:356-359, 1983.
13. 1-acid glycoprotein in liver disease. J. Hepatol. 2:245-252, 1986.
14. Wong, A.K.L., Hsia, J.C. In vitro binding of propranolol and progesterone to native and desialyated human orosomucoid. Can. J. Biochem. Cell. Biol. 61:1114-1116, 1983.
15. 1-acid glycoprotein for characterization of the progesterone binding site. Biochem. Biophys. Acta. 420:195-213, 1976.
16. 1acid glycoprotein. J. Pharmacobiol. Dynam. 14:7-16, 1992.
17. 1-acid glycoprotein. Int. J. Clin. Pharmacol. Ther. Toxcol. 21:271-276, 1983.
18. Friedman, M.L., Wermeling, J.R., Halsall, H.B. The influence of N-acetylneuraminic acid on the properties of human orosomucoid. Biochem. J. 236:149-153, 1986.
19. 1acid glycoprotein. J. Pharmacol. Exp. Ther. 234:703-707, 1985.
20. 1-acid glycoprotein. J. Pharm. Pharmacol. 44:28-33, 1992.
21. 1-acid glycoprotein on propranolol binding. J. Pharm. Sci. 74:473-475, 1985.
22. 1-acid glycoprotein as the chiral stationary phase. J. Chromatogr. 269:71-80, 1983.
23. 1-acid glycoprotein chiral stationary phase. Anal. Chem. 65:3684-3690, 1993.
24. 1-acid glycoprotein (orosomucoid), human serum albumin, and human serum. Further characterization of the "single drug binding site" of orosomucoid. J. Pharm. Pharmacol. 37:305-309, 1985.
25. 1-acid glycoprotein. NaunynSchmiedebergs Arch. Pharmacol. 322:170-173, 1983.
26. 1-acid glycoprotein and binding of basic drugs. Methods Find. Exp. Clin. Pharmacol. 5:635-648, 1983.
27. 1-acid glycoprotein (orosomucoid). Biochem. J. 280: 277-280, 1991.
28. Urien, S., Giroud, Y., Tsai, R.S. Carrupt, P.A.. BréE. F., Testa. B., Tillement, J.P. Biochem. J. 306:545-549, 1995.
29. Shibukawa, A., Yoshimoto, Y., Ohara, T., Nakagawa, T. High-performance capillary electrophoresis/frontal analysis for the study of protein binding of a basic drug. J. Pharm. SCi. 83:616-619, 1994.
30. Ohara, T. Shibukawa. A., Nakagawa, T. Capillary electrophoresis/ frontal analysis for microanalysis of enantioselective protein binding of a basic drug. Anal. Chem. 67:3520-3525, 1995.
31. 1acid glycoprotein and human plasma. Br. J. Clin. Pharmacol. 18:224-246, 1984.
32. Warren, L. The thiobarbituric acid assay of sialic acids. J. Biol. Chem. 234:1971-1975. 1959.
33. Hodge, J.F., Hofreiter, B.T. Methods in Carbohydrate Chemistry, vol. 1. Whistler, R.L., Wolfrom, M.L. eds. New York: Academic Press, 1962.
34. Hjerten, S. High-performance electrophoresis. Elimination of electroendosmosis and solute adsorption. J. Chromatogr. 347:191-198, 1985.
35. Gross, A.S., Heuer, B., Eichelbaum, M. Stereoselective protein binding of verapamil enantiomers. Biochem. Pharmacol. 37:4623-4627, 1988.