Characterization of site I of human serum albumin using spectroscopic analyses: Locational relations between regions Ib and Ic of site I

Journal of Pharmaceutical Sciences

Volumn 93, Issue 12, 2004, Pages 3004-3012

  Yamasaki, Keishi ^a   Maruyama, Toru ^a   Takadate, Akira ^b   Suenaga, Ayaka ^a   Kragh Hansen, Ulrich ^c   Otagiri, Masaki ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b DAIICHI UNIVERSITY OF PHARMACY   (Japan)

^c AARHUS UNIVERSITY   (Denmark)

Author keywords

Albumin; Circular dichroism; Drug interaction; Fluorescence spectroscopy; Protein binding; Transition

Indexed keywords

4 AMINOBENZOIC ACID DERIVATIVE; AMINO ACID DERIVATIVE; ASPARAGINE DERIVATIVE; DANSYL ASPARAGINE; DANSYL CHLORIDE; SERUM ALBUMIN; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; BINDING AFFINITY; BINDING SITE; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DRUG BINDING; DRUG PROTEIN BINDING; FLUORESCENCE ANALYSIS; PH; PH MEASUREMENT; SPECTROSCOPY;

EID: 10644282198     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20203     Document Type: Article

References (45)

1. Sellers EM, Koch-Weser J. 1977. Clinical implications of drug-albumin interaction. In: Rosenoer VM, Oratz M, Rothschild MA, editors. Albumin structure, function and uses. Oxford, UK: Pergamon Press, pp 159-182.
2. Vallner JJ. 1977. Binding of drugs by albumin and plasma protein. J Pharm Sci 66:447-465.
3. McMenamy RP. 1977. Albumin binding sites. In: Rosenoer VM, Oratz M, Rothschild MA, editors. Albumin structure, function and uses. Oxford, UK: Pergamon Press, pp 143-158.
4. Sudlow G, Birkett DJ, Wade DN. 1975. The characterization of two specific drug binding sites on human serum albumin. Mol Pharmacol 11:824-832.
5. Sudlow G, Birkett DJ, Wade DN. 1976. Further characterization of specific drug binding sites on human serum albumin. Mol Pharmacol 12:1052-1061.
6. Sjöholm I, Ekman B, Kober A, Ljungstedt-Pahlman I, Serving B, Sjödin T. 1979. Binding of drugs to human serum albumin. XI. The specificity of three binding sites as studied with albumin immobilized in microparticles. Mol Pharmacol 16:767-777.
7. He XM, Carter DC. 1992. Atomic structure and chemistry of human serum albumin. Nature 358:209-215.
8. Carter DC, Ho JX. 1994. Structure of serum albumin. Adv Protein Chem 45:153-201.
9. Petitpas I, Bhattacharya AA, Twine S, East M, Curry S. 2001. Crystal structure analysis of warfarin binding to human serum albumin: Anatomy of drug site I. J Biol Chem 276:22804-22809.
10. Bos OJ, Remijn JP, Fischer MJ, Wilting J, Janssen LH. 1988. Location and characterization of the warfarin binding site of human serum albumin. A comparative study of two large fragments. Biochem Pharmacol 37:3905-3909.
11. Bos OJ, Fischer MJ, Wilting J, Janssen LH. 1989. Mechanism by which warfarin binds to human serum albumin. Stopped-flow kinetic experiments with two large fragments of albumin. Biochem Pharmacol 38:1979-1984.
12. Dockal M, Carter DC, Ruker F. 1999. The three recombinant domains of human serum albumin. Structural characterization and ligand binding properties. J Biol Chem 274:29303-29310.
13. Dockal M, Chang M, Carter DC, Ruker F. 2000. Five recombinant fragments of human serum albumin-tools for the characterization of the warfarin binding site. Protein Sci 9:1455-1465.
14. Fehske KJ, Schlafer U, Wollert U, Müller WE. 1982. Characterization of an important drug binding area on human serum albumin including the high-affinity binding sites of warfarin and azapropazone. Mol Pharmacol 21:387-393.
15. Maruyama K, Nishigori H, Iwatsuru M. 1985. Characterization of the benzodiazepine binding site (diazepam site) on human serum albumin. Chem Pharm Bull 33:5002-5012.
16. Noctor TAG, Pham CD, Kaliszan R, Wainer IW. 1992. Stereochemical aspects of benzodiazepine binding to human serum albumin. I. Enantioselective high performance liquid affinity chromatographic examination of chiral and achiral binding interactions between 1,4-benzodiazepines and human serum albumin. Mol Pharmacol 42:506-511.
17. Kaliszan R, Noctor TAG, Wainer IW. 1992. Stereochemical aspects of benzodiazepine binding to human serum albumin. II. Quantitative relationships between structure and enantioselective retention in high performance liquid affinity chromatography. Mol Pharmacol 42:512-517.
18. Kragh-Hansen U. 1988. Evidence for a large and flexible region of human serum albumin possessing high affinity binding sites for salicylate, warfarin, and other ligands. Mol Pharmacol 34:160-171.
19. Yamasaki K, Maruyama T, Kragh-Hansen U, Otagiri M. 1996. Characterization of site I on human serum albumin: Concept about the structure of a drug binding site. Biochim Biophys Acta 1295:147-157.
20. Yamasaki K, Miyoshi T, Maruyama T, Takadate A, Otagiri M. 1994. Characterization of region Ic in site I on human serum albumin. Microenvironmental analysis using fluorescence spectroscopy. Biol Pharm Bull 17:1656-1662.
21. Sakai T, Yamasaki K, Sako T, Kragh-Hansen U, Suenaga A, Otagiri M. 2001. Interaction mechanism between indoxyl sulfate, a typical uremic toxin bound to site II, and ligands bound to site I of human serum albumin. Pharm Res 18:520-524.
22. Yamasaki K, Maruyama T, Yoshimoto K, Tsutsumi Y, Narazaki R, Fukuhara A, Kragh-Hansen U, Otagiri M. 1999. Interactive binding to the two principal ligand binding sites of human serum albumin: Effect of the neutral-to-base transition. Biochim Biophys Acta 1432:313-323.
23. Chen RF. 1967. Removal of fatty acids from serum albumin by charcoal treatment. J Biol Chem 242:173-181.
24. Kadaba PK, Carr M, Tribo M, Triplett J, Glasser AC. 1969. Boron trifluoride ethyl ether as an effective catalyst in the synthesis of alkyl p-amino-benzoates. J Pharm Sci 58:1422-1423.
25. Dash D, Rao GR. 1990. Characterization of the effects of propranolol on the physical state of platelet membrane. Arch Biochem Biophys 276:343-347.
26. Chen RF, Bowman RL. 1965. Fluorescence polarization: Measurement with ultraviolet-polarizing filters in a spectrophotofluorometer. Science 147:729-732.
27. Yamaoka K, Tanigawara Y, Nakagawa T, Uno T. 1981. A pharmacokinetic analysis program (multi) for microcomputer. J Pharmacobiodyn 4:879-885.
28. Maruyama T, Otagiri M, Takadate A. 1990. Characterization of drug binding sites on alpha 1-acid glycoprotein. Chem Pharm Bull 38:1688-1691.
29. Miyoshi T, Yamamichi R, Maruyama T, Takadate A, Otagiri M. 1992. Further characterization of reversal of signs of induced cotton effects of dicumarol derivatives-alpha 1-acid glycoprotein systems by protriptyline. Biochem Pharmacol 43:2161-2167.
30. Chignell CF. 1969. Optical studies of drug-protein complexes. II. Interaction of phenylbutazone and its analogues with human serum albumin. Mol Pharmacol 5:244-252.
31. Chignell CF. 1969. Optical studies of drug-protein complexes. 3. Interaction of flufenamic acid and other N-arylanthranilates with serum albumin. Mol Pharmacol 5:455-462.
32. Chignell CF. 1970. Optical studies of drug-protein complexes. IV. The interaction of warfarin and dicoumarol with human serum albumin. Mol Pharmacol 6:1-12.
33. Chignell CF, Starkweather DK. 1971. Optical studies of drug-protein complexes. V. The interaction of phenylbutazone, flufenamic acid, and dicoumarol with acetylsalicylic acid-treated human serum albumin. Mol Pharmacol 7:229-237.
34. Shinitzky M, Barenholz Y. 1978. Fluidity parameters of lipid regions determined by fluorescence polarization. Biochim Biophys Acta 515:367-394.
35. Wilting J, van der Gielsen WF, Jansen LHM, Weideman MM, Otagiri M, Perrin JH. 1980. The effect of albumin conformation on the binding of warfarin to human serum albumin. The dependence of the binding of warfarin to human serum albumin on the hydrogen, calcium, and chloride ion concentrations as studied by circular dichroism, fluorescence, and equilibrium dialysis. J Biol Chem 255:3032-3037.
36. Wanwimolruk S, Birkett DJ. 1982. The effects of N-B transition of human serum albumin on the specific drug-binding sites. Biochim Biophys Acta 709:247-255.
37. Kasai-Morita S, Horie T, Awazu S. 1987. Influence of the N-B transition of human serum albumin on the structure of the warfarin-binding site. Biochim Biophys Acta 915:277-283.
38. Dockal M, Carter DC, Ruker F. 2000. Conformational transitions of the three recombinant domains of human serum albumin depending on pH. J Biol Chem 275:3042-3050.
39. Bos OJ, Labro JF, Fischer MJ, Wilting J, Janssen LH. 1989. The molecular mechanism of the neutral-to-base transition of human serum albumin. Acid/base titration and proton nuclear magnetic resonance studies on a large peptic and a large tryptic fragment of albumin. J Biol Chem 264:953-959.
40. Wilting J, Weideman MN, Roomer ACJ, Perrin JH. 1979. Conformational changes in human serum albumin around the neutral pH from circular dichroic measurements. Biochim Biophys Acta 579:469-473.
41. t'Hart BJ, Wilting J, de Gier JJ. 1986. Evidence for distinct consecutive steps in the neutral to base transition of human serum albumin. Biochem Pharmacol 35:1005-1009.
42. Peters T Jr. 1996. All about albumin: Biochemistry, genetics, and medical applications. San Diego: Academic Press.
43. Leonard WJ, Vijai KK, Foster JF. 1963. A structural transformation in bovine and human plasma albumins in alkaline solution as revealed by rotatory dispersion studies. J Biol Chem 238:1984-1988.
44. Dröge JH, Janssen LH, Wilting J. 1985. A study on the allosteric interaction between the major binding sites of human serum albumin using microcalorimetry. Biochim Biophys Acta 827:396-402.
45. Hagag NG, Bimbaum DW, Darnall DW. 1982. Distances between Tyr-411 and Trp-214 of human serum albumin measured by fluorescence energy transfer: Effects of pH and fatty acids. Fed Proc 41:1189.