Biantennary glycans as well as genetic variants of α1-acid glycoprotein control the enantioselectivity and binding affinity of oxybutynin

Pharmaceutical Research

Volumn 23, Issue 5, 2006, Pages 1038-1042

  Kimura, Tomoko ^a   Shibukawa, Akimasa ^b   Matsuzaki, Katsumi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b CHIBA INSTITUTE OF SCIENCE   (Japan)

Author keywords

1 acid glycoprotein; Biantennary branching glycan; Genetic variants; High performance frontal analysis; Oxybutynin; Protein binding; Sugar chain

Indexed keywords

CARBOHYDRATE CONFORMATION; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; MANDELIC ACIDS; MUSCARINIC ANTAGONISTS; OROSOMUCOID; POLYMORPHISM, GENETIC; POLYSACCHARIDES; PROTEIN BINDING; PROTEIN CONFORMATION; PROTEIN ISOFORMS; STEREOISOMERISM;

EID: 33646891086     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-006-9777-8     Document Type: Article

References (39)

1. R. H. Levy T. A. Moreland 1984 Rationale for monitoring free drug levels Clin. Pharmacokinet. 9 1 9
2. J. D. Wright F. D. Boudinot M. R. Ujhelyi 1996 Measurement and analysis of unbound drug concentrations Clin. Pharmacokinet. 30 445 462
3. T. Noctor I. W. Wainer 1993 Drug Stereochemistry 2 Dekker New York
4. G. T. Tucker M. S. Lennard 1990 Enantiomer specific pharmacokinetics Pharmacol. Ther. 45 309 329
5. A. Shibukawa Y. Yoshikawa T. Kimura T. Nakagawa I. W. Wainer 2002 Binding study of desethyloxybutynin using high-performance frontal analysis method J. Chromatogr. B 768 189 197
6. A. Shibukawa N. Ishizawa T. Kimura T. Nakagawa I. W. Wainer 2002 Plasma protein binding study of oxybutynin by high-performance frontal analysis J. Chromatogr. B. 768 177 188
7. A. Shibukawa T. Nakagawa N. Nishimura M. Miyake H. Tanaka 1989 Determination of free drug in protein binding equilibrium by high-performance frontal analysis using internal-surface reversed-phase silica support Chem. Pharm. Bull. 37 707 711
8. A. Shibukawa N. Nishimura K. Nomura Y. Kuroda T. Nakagawa 1990 Simultaneous determination of the free and total carbamazepine concentrations in human plasma by high-performance frontal analysis using an internal-surface reversed-phase silica support Chem. Pharm. Bull. 38 443 447
9. A. Shibukawa M. Nagao Y. Kuroda T. Nakagawa 1990 Stereoselective determination of free warfarin concentration in protein binding equilibrium using direct sample injection and an on-line liquid chromatographic system Anal. Chem. 62 712 716
10. A. Shibukawa A. Terakita J. He T. Nakagawa 1992 High-performance frontal analysis-high-performance liquid chromatographic system for stereoselective determination of unbound ketoprofen enantiomers in plasma after direct sample injection J. Pharm. Sci. 81 710 715
11. T. Kimura K. Nakanishi T. Nakagawa A. Shibukawa K. Matsuzaki 2005 High-performance frontal analysis of the binding of thyroxine enantiomers to human serum albumin Pharm. Res. 22 667 675
12. T. Kimura K. Nakanishi T. Nakagawa A. Shibukawa K. Matsuzaki 2005 Simultaneous determination of unbound thyroid hormones in human plasma using high performance frontal analysis with electrochemical detection J. Pharm. Biomed. Anal. 15 204 209
13. A. Shibukawa Y. Kuroda T. Nakagawa 1999 High-performance frontal analysis for drug-protein binding study J. Pharm. Biomed. Anal. 18 1047 1055
14. G. A. Turner 1992 N-Glycosylation of serum proteins in disease and its investigation using lectins Clin. Chim. Acta 208 149 171
15. J. M. H. Kremer 1988 Drug binding to human alpha-1-acid glycoprotein in health and disease Pharmacol. Rev. 40 1 47
16. W. Dijk 1995 Alpha 1-acid glycoprotein (orosomucoid): pathophysiological changes in glycosylation in relation to its function Glycoconjugate J. 12 227 233
17. L. Dente A. Metspalu 1987 Structure and expression of the genes coding for human alpha 1-acid glycoprotein EMBO J. 6 2289 2296
18. I. Yuasa K. Suenaga K. Umetsu K. Ito M. Robinet-Levy 1987 Orosomucoid (ORM) typing by isoelectric focusing: evidence for gene duplication of ORM1 and genetic polymorphism of ORM2 Hum. Genet. 77 255 258
19. C. B. Eap P. Baumann 1988 Isoelectric focusing of alpha-1 acid glycoprotein (orosomucoid) in immobilized pH-gradients with 8M urea: detection of its desialylated variants using an alkaline phosphatase-linked secondary antibody system Electrophoresis 9 650 654
20. L. Tomei C. B. Eap P. Baumann L. Dente 1989 Use of transgenic mice for the characterization of human alpha 1-acid glycoprotein (orosomucoid) variants Hum. Genet. 84 89 91
21. F. Herve E. Gomas J. P. Tillement 1996 Binding of disopyramide, methadone, dipyridamole, chlorpromazine, lignocaine and progesterone to the two main genetic variants of human alpha 1-acid glycoprotein: evidence for drug-binding differences between the variants and for the presence of two separate drug-binding sites on alpha 1-acid glycoprotein Pharmacogenetics 6 403 415
22. 1- acid glycoprotein variants Br. J. Clin. Pharmacol. 56 664 669
23. H. Shiono A. Shibukawa T. Nakagawa 1997 Effect of sialic acid residues of human alpha 1-acid glycoprotein on stereoselectivity in basic drug-protein binding Chirality 9 291 296
24. N. F. Fraeyman C. D. Dello F. M. Belpaire 1988 Alpha 1-acid glycoprotein concentration and molecular heterogeneity: relationship to oxprenolol binding in serum from healthy volunteers and patients with lung carcinoma or cirrhosis Br. J. Clin. Pharmacol. 25 733 740
25. 1-acid glycoprotein in the native form by chromatography on an immobilized copper (II) affinity adsorbent: heterogeneity of the separate variants by isoelectrofocusing and by concanavalin A affinity chromatography J. Chromatogr. B. 615 47 57
26. 1- acid glycoprotein and of their pharmacokinetics in the rat J. Chromatogr. B. 798 283 294
27. 1-acid glycoprotein Its application to the purification of rare phenotype samples of the protein and their study by chromatography on immobilized metal chelate affinity adsorbent J. Chromatogr. B. 678 1 14
28. M. F. Bierhuizen W. V. Dijk 1988 Glycosylation of three molecular forms of human alpha 1-acid glycoprotein having different interactions with concanavalin A. Variations in the occurrence of di-, tri-, and tetraantennary glycans and the degree of sialylation Eur. J. Biochem. 175 387 394
29. I. Nicollet J. P. Lebreton M. Hiron 1981 Evidence for alpha-1-acid glycoprotein populations of different pI values after concanavalin A affinity chromatography. Study of their evolution during inflammation in man Biochem. Biophys. Acta 668 235 245
30. E. R. Smith S. E. Wright G. Aberg Y. Fang J. R. [tmp] McCullough 1998 Comparison of the antimuscarinic and antispasmodic actions of racemic oxybutynin and desethyloxybutynin and their enantiomers with those of racemic terodiline Arzneim.-Forsch. 48 1012 1018
31. D. R. P. Gray 2003 Clinical pharmacokinetics of drugs used to treat urge incontinence Clin. Pharmacokinet. 42 1243 1285
32. N. A. L. Mohamed Y. Kuroda A. Shibukawa T. Nakagawa S. E. Samia E. Gizawy F. A. Hassan M. E. E. Kommos 2000 Enantioselective binding analysis of verapamil to plasma lipoproteins by capillary electrophoresis-frontal analysis J. Chromatogr. A. 875 447 453
33. F. Herve M. C. Millot 1992 pH titration curves of the desialylated human alpha 1-acid glycoprotein variants by combined isoelectrofocusing- electrophoresis: utilization in the development of a fractionation method for the protein variants by chromatography on immobilized metal affinity adsorbent J. Chromatogr. 577 43 59
34. 1-acid glycoprotein in malignant mesothelioma J. Chromatogr. B. 715 111 123
35. W. V. Dijk O. Pos L. Dente P. Baumann C. B. Eap 1991 Inflammation-induced changes in expression and glycosylation of genetic variants of alpha 1-acid glycoprotein. Studies with human sera, primary cultures of human hepatocytes and transgenic mice Biochem. J. 276 343 347
36. A. Mackiewicz K. Mackiewicz 1995 Glycoforms of serum alpha 1-acid glycoprotein as markers of inflammation and cancer Glycoconjugate J. 12 241 247
37. I. Nicollet J.-P. Lebreton M. Fontaine M. Hiron 1981 Evidence for alpha-1-acid glycoprotein populations of different pI values after concanavalin A affinity chromatography. Study of their evolution during inflammation in man Biochim. Biophys. Acta 668 235 245
38. F. Herve 1993 Evidence for differences in the binding of drugs to the two main genetic variants of human alpha 1-acid glycoprotein Br. J. Clin. Pharmacol. 36 241 249
39. O. Pos W. Dijk 1990 Con A-nonreactive human alpha 1-acid glycoprotein (AGP) is more effective in modulation of lymphocyte proliferation than Con A-reactive AGP serum variants Inflammation 14 133 141