The fluorescent probe Prodan characterizes the warfarin binding site on human serum albumin

Photochemistry and Photobiology

Volumn 69, Issue 1, 1999, Pages 8-15

  Moreno, F ^b   Cortijo, M ^b   Gonzalez Jimenez J ^a,b  

^a INSTITUTO PLURIDISCIPLINAR   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 NAPHTHYLAMINE; DRUG DERIVATIVE; FLUORESCENT DYE; PRODAN; SERUM ALBUMIN; WARFARIN;

ARTICLE; BINDING SITE; CIRCULAR DICHROISM; FLUORESCENCE POLARIZATION; HUMAN; IN VITRO STUDY; METABOLISM; PROTEIN BINDING;

2-NAPHTHYLAMINE; BINDING SITES; CIRCULAR DICHROISM; FLUORESCENCE POLARIZATION; FLUORESCENT DYES; HUMANS; PROTEIN BINDING; SERUM ALBUMIN; WARFARIN;

EID: 0032603482     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1999.tb05299.x     Document Type: Article

References (35)

1. Brock, A. (1975) Binding of digitoxin to human serum proteins: influence of pH on the binding of digitoxin to human albumin. Acta Pharmacol. Toxicol. 36, 13-24.
2. Fehske, K. J., W. E. Muller and U. Wollert (1978) The modification of the lone tryptophan residue in human serum albumin by 2-hydroxy-5-nitrobenzyl bromide. Characterization of the modified protein and the binding of L-tryptophan and benzodiazepines to the tryptophan modified albumin. Z. Physiol. Chem. 359, 709-717
3. Kragh-Hansen, U. (1981) Molecular aspects of ligand binding to serum albumin. Pharmacol Rev. 33, 17-53.
4. Kremaer, J. H. M., J. Wilting and L. H. M. Jassen (1988) Drug binding to human alpha-1-acid glycoprotein in health and disease. Pharmacol. Rev. 40, 1-17.
5. Kragh-Hansen, U. (1985) Relations between high-affinity binding sites of markers for binding regions on human serum albumin. Biochem. J. 225, 629-638.
6. Weber, G. and F. J. Farris (1979) Synthesis and spectral properties of a hydrophobic fluorescent probe: 6-propionyl-2-(dimethylamino)naphthalene. Biochemistry 18, 3075-3078.
7. McGregor, R. B. and G. Weber (1986) Estimation of the polarity of the protein interior by optical spectroscopy. Nature 319, 70-73.
8. Cowley, D. J. (1986) Polar pocket with nonpolar lining. Nature 319, 14-15.
9. Catalan, J., P. Perez, J. Laynez and F. Garcia-Blanco (1991) Analysis of the solvent effect on the photophysics properties of 6-propionyl-2-dimethylaminonaphthalene (Prodan). J. Fluoresc. 4, 215-223.
10. Chong, P. L. G. and G. Weber (1983) Pressure dependence of 1,6-diphenyl-1,3,5-hexatrine fluorescence in single-component phosphatidylcholine liposomes. Biochemistry 22, 5544-5551.
11. Chong, P. L. G. (1988) Effects of hydrostatic pressure on the location of Prodan in lipid bilayers and cellular membranes. Biochemistry 27, 399-404 .
12. Massey, P. M., H. S. She and H. J. Pownall (1985) Intrafacial properties of model membranes and plasma lipoproteins containing ether lipids. Biochemistry 24, 6973-3083.
13. Zechel, K. (1993) The interaction of 6-propionyl-2-(NN-dimethyl)aminonaphthalene (Prodan)-labelled actin with actin-binding proteins. Biochem. J. 290, 411-417.
14. Peters, T., Jr. (1975) The Plasma Proteins, Vol. 1. Academic Press, New York.
15. Mazzini, A., P. Cavatorta, M. Iori, R. Favilla and G. Sartor (1992) The binding of 4′,6-diamidino-2-phenylindole to bovine serum albumin. Biophys. Chem. 42, 101-106.
16. Scatchard, G. (1949) The attractions of proteins for small molecules and ions. Ann. N. Y. Acad. Sci. 51, 660-673.
17. Dixon, W. J. (1981) Biomedical Computer Programs. Univ. California Press, Berkeley.
18. González-Jiménez, J., G. Frutos, I. Cayre and M. Cortijo (1991) Chlorpheniramine binding to human serum albumin by fluorescence quenching measurements. Biochemie 73, 551-556.
19. Panjehshahin, M. R., C. J. Bowmer and M. S. Yates (1989) A pitfall in the use of double-reciprocal plots to estimate the intrinsic molar fluorescence of ligands bound to albumin. Biochem. Pharmacol. 38, 155-159.
20. Kaneo, Y., A. Nishikawa, Y. Kato and S. Kiryu (1979) Displacement of sulfonamides from bovine serum albumin by nonsteroidal anti-inflammatory drugs. Chem. Pharm. Bull. 6, 1335-1342.
21. Sudlow, G., D. J. Birkett and D. N. Wade (1975) The characterization of two specific drug binding sites on human serum albumin. Mol. Pharmacol. 11, 824-832.
22. González-Jiménez, J. (1994) Analysis of the binding of chlorpheniramine to human serum albumin by spectroscopic techniques. Chem. Biol. Interact. 91, 65-74 .
23. Chignell, C. F. (1969) Optical studies of drug-protein complexes. II. Interaction of phenylbutazone and its analogues with human serum albumin. Mol. Pharmacol. 5, 244-252.
24. Lakowicz, J. R. and G. Weber (1980) Nanosecond segmental mobilities of tryptophan residues in proteins observed by lifetime-resolved fluorescence anisotropies. Biophys. J. 32, 591-601.
25. Maes, V., Y. Engelborghs, J. Hoebeke, Y. Maras and A. Vercruysse (1981) Fluorimetric analysis of the binding of warfarin to human serum albumin. Mol. Pharmacol. 21, 100-107.
26. O'Reilly, R. A. and P. E. Kowitz (1967) Studies on the coumarin anticoagulant drugs: interaction of human plasma albumin and warfarin sodium. J. Clin. Invest. 46, 829-837.
27. Nemethy, G. and H. A. Scheraga (1962) The structure of water and hydrophobic bonding in proteins. The thermodynamic properties of hydrophobic bonds in proteins. J. Phys. Chem. 66, 1773-1789.
28. Timasheff, S. N. (1972) Thermodynamics of protein interactions. In Proteins of Biological Fluids (Edited by H. Peeters). Pergamon Press, Oxford.
29. Ross, P. D. and S. Subramanian (1981) Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 20, 3096-3102.
30. Levison, S. A. (1975) Fluorescence polarization kinetic studies of macromolecular reactions. In Biochemical Fluorescence Concepts. Vol. 1 (Edited by Chen and Edelhoch). Marcel Dekker, New York.
31. Rossen, A. (1970) The measurement of binding constants using circular dicroism. Binding of phenylbutazone and oxyphenbutazone. Biochem. Pharmacol. 19, 2075-2081.
32. Hervé, F., S. Urien, E. Albengres, J. C. Duché and J. P. Tillment (1994) Drugs binding in plasma. Clin. Pharmacokinet. Concepts 1, 44-58.
33. Brown, J. R. and P. Shockley (1982) Lipid-Protein Interactions, Vol. 1 (Edited by Jost and Griffith). John Wiley and Sons, New York.
34. Brodersen, R., T. Sjödin and I. Sjöholm (1977) Independent binding of ligands to human serum. J. Biol. Chem. 252, 5067-5072.
35. Roosdorp, N., B. Wänn and I. Sjöholm (1977) Correlation between arginyl residue modification and benzodiazepine binding to human serum albumin. J. Biol. Chem. 252, 3876-3880.