Predicting plasma protein binding of drugs: A new approach

Biochemical Pharmacology

Volumn 64, Issue 9, 2002, Pages 1355-1374

  Kratochwil, Nicole A ^a   Huber, Walter ^a   Müller, Francis ^a   Kansy, Manfred ^a   Gerber, Paul R ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

ADME modeling; Albumin binding prediction; Human serum albumin; Lipophilicity; Plasma protein binding; Therapeutic drugs

Indexed keywords

ACETYLSALICYLIC ACID; CAMPTOTHECIN; CARBENOXOLONE; CEFACLOR; CEFADROXIL; CEFAMANDOLE; CEFOPERAZONE; CEFOTAXIME; CEFOXITIN; CEFSULODIN; CEFTRIAXONE; CEFUROXIME; CHLOROTHIAZIDE; CHLORPROMAZINE; DOXYCYCLINE; FENTIAZAC; HUMAN SERUM ALBUMIN; IMIPRAMINE; LORAZEPAM; NAPROXEN; NORTRIPTYLINE; PHENYTOIN; PLASMA PROTEIN; PRACTOLOL; PROMAZINE; SOTALOL; UNINDEXED DRUG; URAPIDIL; VALPROIC ACID; VERAPAMIL;

ACCURACY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CORRELATION ANALYSIS; DRUG PROTEIN BINDING; HUMAN; LIPOPHILICITY; MODEL; PHYSICAL CHEMISTRY; PLASMA PROTEIN BINDING; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; REGRESSION ANALYSIS;

HUMANS; MODELS, BIOLOGICAL; PHARMACEUTICAL PREPARATIONS; PROTEIN BINDING; REPRODUCIBILITY OF RESULTS; SERUM ALBUMIN; STATISTICS;

EID: 0036828938     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(02)01074-2     Document Type: Article

References (219)

1. Krueger-Thiemer E, Buenger P. The role of the therapeutic regimen in dosage design. Chemotherapia 1965;10:61-73, 129-44.
2. Benet LZ, Kroetz DL, Sheiner LB. Pharmacokinetics. The dynamics of drug absorption distribution and elimination In: Goodman GA, Gilman, editors. The pharmacological basis of therapeutics. 9th ed. New York: McGraw-Hill, 1996. p. 3-27.
3. Goodman GA, Gilman. The pharmacological basis of therapeutics. 9th ed. New York: McGraw-Hill, 1996.
4. Peters Jr T. All about albumin: biochemistry genetics and medical applications. San Diego: Academic Press, 1996.
5. Fehske K.J., Müller W.E., Wollert U. The location of drug binding sites in human serum albumin. Biochem. Pharmacol. 30:1981;687-692.
6. Vorum H. Reversible ligand binding to human serum albumin. Dan. Med. Bull. 46:1999;379-399.
7. Kragh-Hansen U. Structure and ligand binding properties of human serum albumin. Dan. Med. Bull. 37:1990;57-84.
8. Curry S., Brick P., Franks N.P. Fatty acid binding to human serum albumin: new insights from crystallographic studies. Biochim. Biophys. Acta. 1441:1999;131-140.
9. Curry S., Mandelkow H., Brick P., Franks N. Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat. Struct. Biol. 5:1998;827-835.
10. Sugio S., Kashima A., Mochizuki S., Noda M., Kobayashi K. Crystal structure of human serum albumin at 25 Å resolution. Protein Eng. 12:1999;439-446.
11. He X.M., Carter D.C. Atomic structure and chemistry of human serum albumin. Nature. 358:1992;209-215.
12. Carter D.C., Ho J.X. Structure of serum albumin. Adv. Protein Chem. 45:1994;153-203.
13. Bhattacharya A.A., Grune T., Curry S. Crystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J. Mol. Biol. 303:2000;721-732.
14. Watanbe H., Tanase S., Nakajou K., Maruyama T., Kragh-Hansen U., Otagiri M. Role of Arg-410 and Tyr-411 in human serum albumin for ligand binding and esterase-like activity. Biochem. J. 349:2000;813-819.
15. Bhattacharya A.A., Curry S., Franks N.P. Binding of the general anesthetics propofol and halothane to human serum albumin: high-resolution crystal structures. J. Biol. Chem. 275:2000;38731-38738.
16. Petitpas I., Bhattacharya A.A., Twine S., East M., Curry S. Crystal structure analysis of warfarin binding to human serum albumin anatomy of drug site I. J. Biol. Chem. 276:2001;22804-22809.
17. Morris JJ, Bruneau PP. Prediction of physicochemical properties. In: Böhm H-J, Schneider G, editors. Virtual screening for bioactive molecules. Weinheim: Wiley-VCH Verlag GmbH, 2000. p. 33-56.
18. Dollery C. Therapeutic drugs. 2nd ed. Edinburgh: Churchill Livingstone, 1999.
19. Rowley M., Kulagowski J.J., Watt A.P., Rathbone D., Stevenson G.I., Carling R.W., Baker R., Marshall G.R., Kemp J.A., Foster A.C., Grimwood S., Hargreaves R., Hurley C., Saywell K.L., Tricklebank M.D., Leeson P.D. Effect of plasma protein binding on in vivo activity and brain penetration of glycine/NMDA receptor antagonists. J. Med. Chem. 40:1997;4053-4068.
20. Fingerprint toolkit version 47, Daylight CIS Inc., http://www.Daylight.com.
21. Mtprgn, Mtprsml, Moloc. Gerber Molecular Design, Switzerland, http://www.moloc.ch.
22. TSAR version 3.21, Oxford Molecular Ltd, Oxford England, http://www.oxmol.com/software/tsar/.
23. So S.-S., Karplus M. Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks 2 applications. J. Med. Chem. 40:1997;4360-4371.
24. So S.S., Karplus M. Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks 2. Method and validations. J. Med. Chem. 40:1997;4347-4359.
25. SIMCA-P version 8.0, Umetrics AB, UmeÅ Sweden, http://www.umetrics.com.
26. Marengo E., Todeschini R. A new algorithm for optimal distance-based experimental design. Chemomet. Intell. Lab. Syst. 16:1992;37-44.
27. GOLPE version 4.5.11, Molecular Discovery Ltd, Oxford London, http://www.moldiscovery.com and http://www.miasrl.com.
28. Lipinski C.A., Lombardo F., Dominy B.W., Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46:2001;3-26.
29. Plotting the HSA association constants of all the 105 commercial drugs against the available log D-values (non ion-corrected phosphate buffer pH 74) from the MedChem database gave rise to a similar correlation factor The MedChem Project and BioByte Corp. in Claremont CA maintains the MedChem database, http://www.Daylight.com/products/databases/Medchemhtml.
30. Maggiora GM, Johnson MA. Concepts and applications of molecular similarity. New York: Wiley, 1990. p. 99-117.
31. Gerber PR. Topological pharmacophore description of chemical structures using MAB-force-field derived data and corresponding similarity measures. In: Carbó-Dorca, editor. Fundamentals of molecular similarity. New York: Kluwer Academic/Plenum Publishers, 2001. p. 67-82. Implemented in the software package MOLOC, http://www.moloc.ch.
32. Jarvis RA. Clustering using a similarity measure based on shared nearest neighbors. IEEE Trans Comput C-22: 1025-1034, 1973. Implemented in the software package Daylight, http://www.Daylight.com/dayhtml/doc/.
33. Gerber P.R., Müller K. MAB a generally applicable molecular force field for structure modelling in medicinal chemistry. J. Comput. Aided Mol. Des. 9:1995;251-268.
34. Gerber P.R. Charge distribution from a simple molecular orbital type calculation and non-bonding interaction terms in the force field MAB. J. Comput. Aided Mol. Des. 12:1998;37-51.
35. Wright J.D., Boudinot F.D., Ujhelyi M.R. Measurements and analysis of unbound drug concentration. Clin. Pharmacokin. 30:1996;445-462.
36. Frostell-Karlsson Å., Remaeus A., Roos H., Borg P., Hämäläinen M., Karlsson R. Biosensor analysis of the interaction between immobilized human serum albumin and drug compounds for prediction of human serum albumin binding levels. J. Med. Chem. 43:2000;1986-1992.
37. Schumacher J., Bühner K., WittLaido A. Determination of the free fraction and relative free fraction of drugs strongly bound to plasma proteins. J. Pharm. Sci. 89:2000;1008-1021.
38. Grandison M.K., Boudinot F.D. Age-related changes in protein binding of drugs. Implications for therapy. Clin. Pharmacokinet. 38:2000;271-290.
39. Holford NHG, Benet LZ. Pharmacokinetics & pharmacodynamic: dose selection & the time course of drug action. In: Katzung BG, editor. Basic & clinical pharmacology. Stamford, CT: Appleton & Lange, 1998. p. 34-9.
40. Benet LZ. Predicting the relevance or the lack of relevance of protein binding on drug disposition. In: International Symposium on Serum Albumin & a-1-Acid Glycoprotein. From Basic Sciences to clinical Applications, 2000 Oct 3-6; Kumamoto, Japan.
41. Samson LN, Evans AM. What is the true clinical significance of plasma protein binding displacement interactions? Drug Safety 1995;12:227-33.
42. Rolan PE. Plasma protein binding displacement interactions - why are they still regarded as clinically important? Br J Clin Pharmacol 1994;37:125-28.
43. Guerry P, Hartman PG, Locher H, Jolidon S, Broger C, Oefner C, Gmunder H, Then R. New inhibitors of trimethoprim-resistant Staphylococcal dihydrofolate reductase. Chem Biol Pteridines Folates Proc Int Symp Pteridines Folates 1997.
44. Guerry P, Hartman P G, Jolidon S, Locher H, Muller M, Pflieger P, Pirson W, Schmitt-Hoffmann A, Wyss P. Internal Roche progress report. No B-170'036, 1999.
45. Scholtan W. Die hydrophobe bindung der pharmaka an humanalbumin und ribonucleinsaeure. Arzneim-Forsch/Drug Res. 18:1968;505-517.
46. Scholtan W. Bestimmungsmethoden und gesetzmaessigkeiten der serumproteinbindung von arzneimitteln. Arzneim-Forsch/Drug Res. 28:1978;1037-1047.
47. Seydel JK, Schaper K-J. Quantitative Struktur-Pharmakokinetik Beziehungen. In: Seydel JK, Schaper K-J, editors. Chemische struktur und biologische aktivitaet von wirkstoffen, methoden der quantitativen struktur-wirkungs-analyse. Weinheim: Wiley-VCH Verlag GmbH, 1979. p. 223.
48. Seydel J.K., Schaper K.J. Quantitative structure-pharmacokinetic realtionships and drug design. Pharmacol. Therap. 15:1982;131-182.
49. Desmotes-Mainard F., Pehourcq F., Jagou M., Bannwarth B. J. Pharm. Biomed. Anal. 16:1997;223-229.
50. Deschamps-Labat L., Pehourcq F., Jagou M., Bannwarth B. Relationship between lipophilicity and binding to human serum albumin of arylpropionic acid non-steroidal antiinflammatory drugs. J. Pharm. Biomed. Anal. 16:1997;223-229.
51. Rahman M.H., Miyoshi T., Sukimoto K., Takadate A., Otagiri M. Interaction mode of dicumarol and its derivatives with human serum albumin alpha1-acid glycoprotein and asialo alpha1-acid glycoprotein. J. Pharmacobiol. Dyn. 15:1992;7-16.
52. Zlotos G., Bücker A., Kinzig-Schippers M., Sorgel F., Holzgrabe U. Plasma protein binding of gyrase inhibitors. J. Pharm. Sci. 87:1998;215-220.
53. Terasaki T., Nouda H., Tsuji A. Relationship between lipophilicity and binding affinity with human serum albumin for penicillin and cepham antibiotics. J. Pharmacobiol. Dyn. 15:1992;99-106.
54. Saiakhov R., Stefan L.R., Klopman G. Multiple computer-automated structure evaluation model of the plasma protein binding affinity of diverse drugs. Perspect. Drug Discov. Des. 19:2000;133-155.
55. van de Waterbeemd H., Smith D.A., Jones B.C. Lipophilicity in PK design: methyl ethyl futile. J. Comp. Aid. Mol. Des. 15:2001;273-286.
56. Bruneau P. Search for predictive generic models of protein binding and solubility. Informatics and computing support for early ADME & toxicology studies. In: IBC Global Conferences Limited, London, 1999. p. 1-34.
57. Ferrer J.M., Leiton M.J., Zaton A.M.L. The binding of benzopyranes to human serum albumin A structure-affinity study. J. Protein Chem. 17:1998;115-119.
58. Zaton A.M.L., Ferrer J.M., Ruiz de Gordoa J.C., Marquinez M.A. Binding of coumarins to site I of human serum albumin effect of fatty acids. Chem. Biol. Interact. 97:1995;169-174.
59. Tsutsumi Y., Maruyama T., Takadate A., Goto M., Matsunaga H., Otagiri M. Interaction between two dicarboxylate endogenous substances bilirubin and an uremic toxin 3-carboxyl-4-methyl-5-propyl-2-furanpropanoic acid on human serum albumin. Pharm. Res. 16:1999;916-923.
60. Kasai S., Horie T., Mizuma T., Awazu S. Fluorescence energy transfer study of the relationship between the lone tryptophan residue and drug binding sites in human serum albumin. J. Pharm. Sci. 76:1987;387-392.
61. Muller N., Lapique F., Drelon E., Netter P. Binding sites of fluorescent probes on human serum albumin. J. Pharm. Pharmacol. 46:1994;300-304.
62. Takikawa H., Sugiyama Y., Hanano M., Kurita M., Yoshida H., Sugimoto T. A novel binding site for bile acids on human serum albumin. Biochim. Biophys. Acta. 926:1987;145-153.
63. Tillement J.-P., Zini R., d'Athias P., Vassent G. Binding of certain acidic drugs to human albumin: theoretical and practical estimation of fundamental parameters. Eur. J. Clin. Pharmacol. 7:1974;307-313.
64. Yamasaki K., Maruyama T., Kragh-Hansen U., Otagiri M. Characterisation of site I on human serum albumin: concept about the structure of a drug binding site. Biochim. Biophys. Acta. 1295:1996;147-157.
65. Jusko W.J., Gretch M. Plasma and tissue protein binding of drugs in pharmacokinetics. Drug Metab. Rev. 5:1976;43-140.
66. Aarons L., Clifton P., Fleming G., Rowland M. Aspirin binding and the effect of albumin on spontaneous and enzyme-catalysed hydrolysis. J. Pharm. Pharmacol. 32:1980;537-543.
67. Aki H., Yamamoto M. Thermodynamic characterization of drug binding to human serum albumin by isothermal titration microcalorimetry. J. Pharm. Sci. 83:1994;1712-1716.
68. Bagatolli L.A., Kivatinitz S.C., Fidelio G.D. Interaction of small ligands with human serum albumin IIIA subdomain. How to determine the affinity constant using an easy steady state fluorescent method. J. Pharm. Sci. 85:1996;1131-1132.
69. Honore B., Brodersen R. Albumin binding of anti-inflammatory drugs: utility of a site-oriented versus a stochiometric analysis. Mol. Pharmacol. 25:1983;137-150.
70. Kragh-Hansen U. Evidence for a large and flexible region of human serum albumin possessing high affinity binding sites for salicylate warfarin and other ligands. Mol. Pharmacol. 34:1988;160-171.
71. Fehske K.J., Jaehnchen E., Mueller W.E., Stillbauer A. Azapropazone binding to human serum albumin. Naunyn-Schmiedeberg's Arch. Pharmacol. 313:1980;159-163.
72. Diana F.J., Veronich K., Kapoor A.L. Binding of nonsteroidal anti-inflammatory agents and their effects on binding of racemic warfarin and its enantiomers to human serum albumin. J. Pharm. Sci. 78:1989;195-199.
73. Petersen C.E., Ha C.E., Harohalli K., Feix J.B., Bhagavan N.V. A dynamic model for bilirubin binding to human serum albumin. J. Biol. Chem. 275:2000;20985-20995.
74. Jacobsen J. Studies of the affinity of human serum albumin for binding of bilirubin at different temperatures and ionic strength. Int. J. Pept. Protein Res. 9:1977;235-239.
75. Brodersen R.B. Bilirubin. Solubility and interaction with albumin and phospholipid. J. Biol. Chem. 254:1979;2364-2369.
76. Khan M.M., Muzammil S., Tayyab S. Role of salt bridges(s) in the binding and photoconversion of bilirubin bound to high affinity site on human serum albumin. Biochim. Biophys. Acta. 1479:2000;103-113.
77. Brodersen R. Binding of bilirubin to albumin. Crit. Rev. Clin. Lab. Sci. 11:1980;305-399.
78. Ichimura F., Matsushita R., Tsuji A., Deguchi Y. Mutual interaction between bilirubin and cefazolin in binding to human serum albumin. J. Pharm. Sci. 79:1990;1041-1042.
79. Zini R. Les modes de fixation des médicaments sur les proteines plasmatiques humaines et leurs conséquences pharmacologiques. UER de Sciences de l'Université Paris XII, France, Dissertation, 1984.
80. Fleury F., Ianoul A., Berjot M., Feofanov A., Alix A.J.P., Nabiev I. Camptothecin-binding site in human serum albumin and protein transformations induced by drug binding. FEBS Lett. 411:1997;215-220.
81. Mi Z., Burke T.G. Marked interspecies variations concerning the interactions of camptothecin with serum albumins: a frequency-domain fluorescence spectroscopic study. Biochemistry. 33:1994;12540-12545.
82. Mi Z., Burke T.G. Differential interactions of camptothecin lactone and carboxylate forms with human blood components. Biochemistry. 33:1994;10325-10336.
83. Kragh-Hansen U. Molecular aspects of ligand binding to serum albumin. Pharmacol. Rev. 33:1981;17-53.
84. Chignell C.F. Recent advances in methodology: spectroscopic techniques. Ann. NY Acad. Sci. 226:1973;44-59.
85. Rahman M.H., Maruyama T., Okada T., Yamasaki K., Otagiri M. Study of interaction of caprofen and its enantiomers with human serum albumin-I. Mechanism of binding studied by dialysis and spectroscopic methods. Biochem. Pharmacol. 46:1993;1721-1731.
86. Rahman M.H., Maruyama T., Okada T., Imai T., Otagiri M. Study of interaction of carprofen and its enantiomers with human serum albumin-II. Stereoselective site-to-site displacement of carprofen by ibuprofen. Biochem. Pharmacol. 46:1993;1733-1740.
87. Rahman M.H., Yamasaki K., Shin Y.-H., Lin C.C., Otagiri M. Characterization of high affinity binding sites of non-steroidal anti-inflammatory drugs with respect to site-specific probes on human serum albumin. Biol. Pharm. Bull. 16:1993;1169-1174.
88. Kohita H., Matsushita Y., Moriguchi I. Binding of carprofen to human and bovine serum albumins. Chem. Pharm. Bull. 42:1994;937-940.
89. Nerli B., Romanini D., Pico G. Structural specificity requirements in the binding of beta lactam antibiotics to human serum albumin. Chem. Biol. Interact. 104:1997;179-202.
90. Briand C., Sarrazin M., Peyrot V., Gilli R., Bourdeaux M., Sari J.C. Study of the interaction between human serum albumin and some cephalosporins. Mol. Pharmacol. 21:1982;92-99.
91. Decroix M.O., Zini R., Chaumeil J.C., Tillement J.-P. Cefazolin serum protein binding and its inhibition by bilirubin fatty acids and other drugs. Biochem. Pharmacol. 37:1988;2807-2814.
92. Tawara S., Matsumoto S., Matsumoto Y., Kamimura T., Goto S. Structure-binding relationship and binding sites of cephalosporins in human serum albumin. J. Antibiot. 45:1992;1346-1357.
93. McNamara P.J., Trueb V., Stoeckel K. Ceftriaxone binding to human serum albumin indirect displacement by probenecid and diazepam. Biochem. Pharmacol. 40:1990;1247-1253.
94. Brodersen R., Robertson A. Ceftriaxone binding to human serum albumin: competition with bilirubin. Mol. Pharmacol. 36:1989;478-483.
95. Coassolo P., Briand C., Bourdeaux M., Sari J.C. Microcalorimetric method to determine competitive binding Action of a psychotropic drug (dipotassium chlorazepate) on L-tryptophan human serum albumin complex. Biochim. Biophys. Acta. 538:1978;512-520.
96. Breckenridge A., Rosen A. The binding of chlorothiazide to plasma proteins. Biochim. Biophys. Acta. 229:1971;610-617.
97. Takamura N., Rahman M.H., Yamasaki K., Tsuruoka M., Otagiri M. Interaction of benzothiadiazides with human serum albumin studied by dialysis and spectroscopic methods. Pharm. Res. 11:1994;1452-1457.
98. Walji F., Rosen A., Hilder R.C. The existence of conformationally labile(preformed) drug binding sites in human serum albumin as evidenced by optical rotation measurements. J. Pharm. Pharmacol. 45:1993;551-558.
99. Huang P.C., Gabay S. Examination of phenothiazine-albumin interaction by ultraviolet difference spectrophotometry. Biochem. Pharmacol. 23:1974;957-972.
100. Gabay S., Huang P.C. The binding behavior of phenothiazines and structurally related compounds to albumin from several species. Adv. Biochem. Psychopharmacol. 9:1974;175-189.
101. Sharples D. The binding of chlorpromazine to human serum albumin. J. Pharm. Pharmacol. 26:1974;640-641.
102. Sharples D. Competition for plasma protein binding sites between phenothiazine tranquillizers and iminodibenzyl antidepressants. J. Pharm. Pharmacol. 27:1975;379-381.
103. Crooks M.J., Brown K.F. Binding of sulfonylureas to serum albumin. J. Pharm. Pharmacol. 26:1974;304-311.
104. Zini R., Morin D., Jouenne P., Tillement J.-P. Cicletanine binding to human plasma proteins and erythrocytes a particular HSA-Drug interaction. Life Sci. 43:1988;2103-2115.
105. Twine S.M., Lee A.G., Gore M.G., Fish B.C., Turner A., East M.J. Characterisation of domain fragments of recombinant human albumin. Biochem. Soc. Trans. 26:1998;S279.
106. Kragh-Hansen U. Relations between high-affinity binding sites of markers for binding regions on human serum albumin. Biochem. J. 225:1985;629-638.
107. Vestberg K., Galliano M., Minchiotti L., Kragh-Hansen U. High affinity binding of warfarin salicylate and diazepam to natural mutants of human serum albumin modified in the C-terminal end. Biochem. Pharmacol. 44:1992;1515-1521.
108. Viani A., Cappiello M., Pacifici G.M. Binding of diazepam salicylic acid and digitoxin to albumin isolated from fetal and adult serum. Dev. Pharmacol. Ther. 17:1991;100-108.
109. Wilting J., Hart B.J.T., De Gier J.J. A study on the allosteric interaction between the major binding sites of human serum albumin using microcalorimetry. Biochim. Biophys. Acta. 626:1980;291-298.
110. Brodersen R., Sjodin T., Sjoholm I. Independent binding of ligands to human serum albumin. J. Biol. Chem. 252:1977;5067-5072.
111. Lucas D., Menez J.F., Daniel J.Y., Bardou L.G., Floch H.H. Acetaldehyde adducts with serum proteins: effect on diazepam and phenytoin binding. Pharmacology. 32:1986;134-140.
112. Kober A., Ekman B., Sjoholm I. Direct and indirect determination of binding constants of drug-protein complexes with microparticles. J. Pharm. Sci. 67:1978;107-109.
113. Muller W., Wollert U. Characterization of the binding of benzodiazepines to human serum albumin. Naunyn-Schmiedeberg's Arch. Pharmacol. 280:1973;229-237.
114. Chamouard J.-M., Barre J., Urien S., Houin G., Tillement J.-P. Dicolfenac binding to albumin and lipoproteins in human serum. Biochem. Pharmacol. 34:1985;1695-1700.
115. van Boekel M.A.M., van den Bergh J.P.C., Hoenders H.J. Glycation of human serum albumin: inhibition by diclofenac. Biochim. Biophys. Acta. 1120:1992;201-204.
116. Perrin J.H., Vallner J.J., Nelson D.A. Some quantitative investigations of the binding to and the displacement of bishydroxycoumarin from human serum albumin. Biochem. Pharmacol. 24:1975;769-774.
117. Garten S., Wosilait W.D. Analysis of the binding of coumarin anticoagulants by human serum albumin. Comp. Gen. Pharmacol. 3:1972;83-88.
118. Chignell C.F. Optical studies of drug-protein complexes IV. The interaction of warfarin and dicoumarol with human serum albumin. Mol. Pharmacol. 6:1970;1-12.
119. Cho M.J., Mitchell A.G., Pernarowski M. Interaction of bishydroxycoumarin with human serum albumin. J. Pharm. Sci. 60:1971;196-200.
120. Larsen C.G., Larsen F.G., Jakobsen P., Brodersen R. Multiple cobinding of two ligands to serum albumin: a stoichiometric description of binding equilibria. Arch. Biochem. Biophys. 239:1985;74-86.
121. Hage D.S., Sengupta A. Characterisation of the binding of digitoxin and acetyldigitoxin to human serum albumin by high-performance affinity chromatography. J. Chromatogr. 724:1999;91-100.
122. Brock A. Binding of digitoxin to human serum proteins: influence of pH on the binding of digitoxin to human albumin. Acta Pharmacol. Toxicol. 36:1975;13-24.
123. Lukas D.S., De Martino A.G. Binding of digitoxin and some related cardenolides to human plasma proteins. J. Clin. Invest. 48:1969;1041-1053.
124. Sengupta A., Hage D.S. Characterization of minor site probe for human serum albumin by high-performance affinity chromatography. Anal. Chem. 71:1999;3821-3827.
125. Sjoeholm I., Ekman B., Kober A., Ljungstedt-Pahlman I., Seiving B., Sjoedin T. Binding of drugs to human serum albumin: XI. The specifity of three binding sites as studied with albumin immobilized in microparticles. Mol. Pharmacol. 16:1979;767-777.
126. Muller N., Lapique F., Monot C., Payan E., Dropsy R., Netter P. Stereoselective binding of etodolac to human serum albumin. Chirality. 4:1992;240-246.
127. Mignot I., Presle N., Lapique F., Monot C., Dropsy R., Netter P. Albumin binding sites for etodolac enantiomers. Chirality. 8:1996;271-280.
128. Urien S., D'Athis P., Tillement J.-P. The binding of aryl carboxylic acid derivatives to human serum albumin-A structure-activity study. Biochem. Pharmacol. 33:1984;2283-2289.
129. Vallner J.J., Perrin J.H., Wold S. Comparison of graphical and computerized methods for calculating binding parameters for two strongly bound drugs to human serum albumin. J. Pharm. Sci. 65:1976;1182-1187.
130. Wang H., Zou H., Zhang Y. Multi-site binding of fenoprofen to human serum albumin studied by a combined technique of microdialysis with high performance liquid chromatography. Biomed. Chromatogr. 12:1998;4-7.
131. Sun P., Hoops A., Hartwick R.A. Enhanced albumin protein separations and protein-drug binding constant measurements using anti-inflammatory drugs as run buffer additives in affinity capillary electrophoresis. J. Chromatogr. 661:1994;335-340.
132. Aarons L., Khan A.Z., Grennan D.M., Siddiqi M.A. The binding of flurbiprofen to plasma proteins. J. Pharm. Pharmacol. 37:1985;644-646.
133. Takamura N., Haruta A., Kodama H., Tsuruoka M., Yamasaki K.T., Suenaga A., Otagiri M. Mode of interaction of loops diuretics with human serum albumin and characterization of binding site. Pharm. Res. 13:1996;1015-1019.
134. Takamura N., Shinozawa S., Maryuyama T., Suenaga A., Otagiri M. Effects of fatty acids on serum binding between furosemide and valproic acid. Biol. Pharm. Bull. 21:1998;174-176.
135. Sebille B., Thuaud N., Tillement J.-P. Study of binding of low-molecular-weight ligand to biological macromolecules by high-performance liquid chromatography. Evaluation of binding parameters for two drugs bound to human serum albumin. J. Chromatogr. 167:1978;159-170.
136. Koizumi K., Ikeda C., Ito M., Suzuki J., Kinoshita T., Yasukawa K., Hanai T. Influence of glycosylation on the drug binding of human serum albumin. Biomed. Chromatogr. 12:1998;203-210.
137. Spector A.A., Santos E.C., Ashbrook J.D., Fletcher J.E. Influence of free fatty acid concentration on drug binding to plasma albumin. Ann. NY Acad. Sci. 226:1973;247-258.
138. Okabe N., Hashizume N. Drug binding properties of glycosylated human serum albumin as measured by fluorescence and circular dichroism. Biol. Pharm. Bull. 17:1994;16-21.
139. Whitlam J.B., Crooks M.J., Brown K.F., Pedersen P.V. Binding of nonsteroidal anti-inflammatory agents to proteins-I ibuprofen-serum albumin interaction. Biochem. Pharmacol. 28:1979;628-675.
140. Lookwood G.F., Albert K.S., Szpunar G.J., Wagner J.G. Pharmacokinetics of ibuprofen in man - III: plasma protein binding. J. Pharmacokinet. Biopharm. 11:1983;469-482.
141. Montero M.T., Estelrich J., Valls O. Binding of nonsteroidal anti-inflammatory drugs to human serum albumin. Int. J. Pharm. 62:1990;21-25.
142. Cheruvallath V.K., Riley C.M., Narayanan S.R., Lindenbaum S., Perrin J.H. The effect of octanoic acid on the binding of the enantiomers of ibuprofen and naproxen to human serum albumin: a chromatographic implication. Pharm. Res. 13:1996;173-178.
143. Cheruvallath V.K., Riley C.M., Narayanan S.R., Lindenbaum S., Perrin J.H. A quantitative circular dichroic investigation of the binding of the enantiomers of ibuprofen and naproxen to human serum albumin. Pharm. Biomed. Anal. 15:1997;1719-1724.
144. Itoh T., Saura Y., Tsuda Y., Yamada H. Stereoselectivity and enantiomer-enantiomer interactions in the binding of ibuprofen to human serum albumin. Chirality. 9:1997;643-649.
145. Paliwal J.K., Smith D.E., Cox S.R., Berardi R.R., DunnKurchaski V.A., Elta G.H. Stereoselective competitive and nonlinear plasma protein binding of ibuprofen enantiomers as determined in vivo in healthy subjects. J. Pharmacokinet. Biopharm. 21:1993;145-161.
146. Hage D.S., Noctor T.A.G., Wainer I.W. Characterization of the protein binding of chiral drugs by high-performance affinity chromatography Interactions of R- and S-ibuprofen with human serum albumin. J. Chromatogr. 693:1995;23-32.
147. Trivedi V.D., Vorum H., Honore B., Qasim M.A. Molecular basis of indomethacin-human serum albumin interaction. J. Pharm. Pharmacol. 51:1999;591-600.
148. Hultmark D., Borg K.O., Elofsson R., Palmer L. Interaction between salicylic acid and indomethacin in binding to human serum albumin. Acta Pharm. Suec. 12:1975;259-276.
149. Mason R.W., McQueen E.G. Protein binding of indomethacin binding of indomethacin to human plasma albumin and its displacement from binding by ibuprofen phenylbutazone and salicylate in vitro. Pharmacology. 12:1974;12-19.
150. Ekman B., Sjoedin T., Sjoeholm I. Binding of drugs to human serum albumin-characterisation and identification of the binding sites of indomethacin. Biochem. Pharmacol. 29:1980;1759-1765.
151. Juni K., Nieves E.A., Perrin J.H. Some novel observations of a drug (indoprofen)-albumin interaction. Biopharm. Drug Dispos. 4:1983;1-7.
152. Kamisaka K., Listowsky I., Betheil J.J., Arias I.M. Competitive binding of bilirubin sulfobromophthalein indocyanine green and other organic anions to human and bovine serum albumin. Biochim. Biophys. Acta. 365:1974;169-180.
153. Mudge G.H., Desbiens N., Stibitz G.R. Binding of iophenoxate and iopanoate to human serum albumin. Drug Metab. Dispos. 6:1978;432-439.
154. Dubois N., Lapicque F., Abiteboul M., Netter P. Stereoselective protein binding of ketoprofen: effect of albumin concentration and of the biological system. Chirality. 5:1993;126-134.
155. Noctor T.A.G., Wainer I.W. Allosteric and competitive displacement of drugs from human serum albumin by octanoic acid as revealed by high-performance liquid chromatography on a human serum albumin-based stationary phase. J. Chromatogr. 577:1992;305-315.
156. Rendic S., Sunjic V., Kajfez F., Blazevic N., AlebizKolbah T. Resolution of (+-)-(-(3-benzoylphenyl-)propionic acid (ketoprofen) and diastereometric interaction of its enantiomers with some biological systems. Chimia. 29:1975;170-172.
157. Russeva V., Rakovska R., Stavreva N., Mihailova D., Berova N. Binding of ketoprofen to human serum albumin studied by circular dichroism. Pharmazie. 49:1994;519-522.
158. Sawinski V.J., Rapp G.W. Interaction of human serum proteins with local anesthetic agents. J. Dent. Res. 42:1963;1429-1438.
159. Krauss E., Polnaszek C.F., Scheller D.A., Halsall H.B., Eckfeldt J.H., Holtzman J.L. Interaction between human serum albumin and alpha1-acidglycoprotein in the binding of lidocaine to purified fractions and sera. J. Pharm. Exp. Ther. 239:1986;754-759.
160. Mortensen A., Jensen E.B., Petersen P.B., Husted S., Andreasen F. The determination of naproxen by spectrofluorometry and its binding to serum proteins. Acta Pharmacol. Toxicol. 44:1979;277-283.
161. Li K.L., Thakur K., Kapoor A.L. Structural requirements for binding of nonsteroidal anti-inflammatory drugs to human serum albumin. J. Pharm. Sci. 77:1988;251-254.
162. Urien S., Nguyen P., Berlioz S., Bree F., Vacherot F., Tillement J.-P. Characterization of discrete classes of binding sites of human serum albumin by application of thermodynamic principles. Biochem. J. 302:1994;69-72.
163. Brand J.G., Toribara T.Y. Equilibrium dialysis and circular dichroic analysis of the novobiocin-human serum albumin complex. Arch. Biochem. Biophys. 167:1975;91-98.
164. Epps D.E., Raub T.J., Kezdy F.J. A general wide-range spectrofluorometric method for measuring the site-specific affinities of drugs toward human serum albumin. Anal. Biochem. 227:1995;343-350.
165. Mueller W., Wollert U. High stereospecifity of the benzodiazepine binding site on human serum albumin. Mol. Pharmacol. 11:1975;52-60.
166. Elbary A.A., Vallner J.J., Whitworth C.W. Effect of albumin conformation on the binding of phenylbutazone and oxyphenbutazone to human serum albumin. J. Pharm. Sci. 71:1982;241-244.
167. Chignell C.F. Optical studies of drug-protein complexes II. Interaction of phenylbutazone and its analogues with human serum albumin. Mol. Pharmacol. 5:1969;244-252.
168. Rosen A. The measurement of binding constants using circular dichroism Binding of phenylbutazone and oxyphenbutazone. Biochem. Pharmacol. 19:1970;2075-2081.
169. Droege J.H.M., Janssen L.H.M., Wilting J. A study on the allosteric interaction between the major binding sites of human serum albumin using microcalorimetry. Biochim. Biophys. Acta. 827:1985;396-402.
170. Solomon H.M., Schrogie J.J., Williams D. The displacement of phenylbutazone-14C and warfarin-14C from human albumin by various drugs and fatty acids. Biochem. Pharmacol. 17:1968;143-151.
171. Brown K.F., Crooks M.J. Displacement of tolbutamide glibencalmide and chlorpropamide from serum albumin by anionic drugs. Biochem. Pharmacol. 25:1976;1175-1178.
172. Kober A., Olsson Y., Sjoeholm I. Binding of drugs to human serum albumin: the theoretical basis for the interaction between phenytoin and valproate. Mol. Pharmacol. 18:1980;237-242.
173. Dale O. The interaction of enflurane halothane and the halothane metabolite trifluoroacetic acid with the binding of acidic drugs to human serum albumin-an in vitro study. Biochem. Pharmacol. 35:1986;557-561.
174. Otagiri M., Masuda K., Imai T., Imamura Y., Yamasaki M. Binding of pirprofen to human serum albumin studied by dialysis and spectroscopy techniques. Biochem. Pharmacol. 38:1989;1-7.
175. Oravcova J, Mlynaril V, Bystricky S, Soltes L, Szalay P, Bohacik L, Trnovec T. Interaction of pirprofen enantiomers with human serum albumin. Chirality 1991;3412-7.
176. Fischer M.J.E., Bos O.J.M., Van der Linden R.F., Wilting J., Janssen L.H.M. Steroid binding to human serum albumin and fragments thereof: role of protein conformation and fatty acid contents. Biochem. Pharmacol. 45:1993;2411-2416.
177. Paubel J.P., Niviere P. Bonding of therapeutic organic molecules with proteins quinine. Eur. J. Med. Chem. 9:1974;508-512.
178. Zaroslinski J.F., Keresztes-Nagy S., Mais R.F., Oester Y.T. Effect of temperature on the binding of salicylate by human serum albumin. Biochem. Pharmacol. 23:1974;1767-1776.
179. Keresztes-Nagy S., Mais R.F., Oester Y.T., Zarolinski J.F. Protein binding methodology: comparison of equilibrium dialysis and frontal analysis chromatography in the study of salicylate binding. Anal. Biochem. 48:1972;80-89.
180. Janssen L.H.M., Nelen T.H.A. Influence of hydrogen and chloride ions on the interaction between sulfaethidole and bovine serum albumin studied by microcalorimetric and acid-base titrimetric methods. J. Biol. Chem. 254:1979;5300-5303.
181. Otagiri M., Nakamura H., Imamura Y., Matsumoto U., Fleitman J., Perrin J.H. Effect of pH and small inorganic ions on binding of sulfadimethoxine and sulfaphenazole to human serum albumin. Chem. Pharm. Bull. 37:1989;1401-1403.
182. Baker K.J., Bradley S.E. Binding of sulfobromophthalein (BSP) sodium by plasma albumin. Its role in hepatic BSP extraction. J. Clin. Invest. 45:1966;281-287.
183. Mudge G.H., Stibitz G.R., Robinson M.S., Gemborys M.W. Competition for binding to multiple sites of human serum albumin for cholecystographic agents and sulfobromophthalein. Drug Metab. Disp. 6:1978;440-451.
184. Russeva V., Stavreva N., Rakovska R., Michailova D. Binding of sulindac to human serum albumin studied by circular dichroism. Arzneim-Forsch/Drug Res. 44:1994;159-162.
185. ShamsEldeen M.A., Vallner J.J., Needham T.E. Interaction of sulindac and metabolite with human serum albumin. J. Pharm. Sci. 67:1978;1077-1080.
186. Maruyama T., Lin C.C., Yamasaki K., Miyoshi T., Imai T., Yamasaki M., Otagiri M. Binding of suprofen to human serum albumin: role of suprofen carboxyl group. Biochem. Pharmacol. 45:1993;1017-1026.
187. Pearlman W.H., Crepy O. Steroid-protein interaction with particular reference to testosterone binding by human serum. J. Biol. Chem. 242:1967;182-189.
188. Kragh-Hansen U., Minchiotti L., Brennan S.O., Sugita O. Hormone binding to natural mutants of human serum albumin. Eur. J. Biochem. 193:1990;169-174.
189. Watanbe S., Sato T. Effects of free fatty acids on the binding of bovine and human serum albumin with steroid hormones. Biochim. Biophys. Acta. 1289:1996;385-396.
190. Petersen C.E., Ha C.-E., Harohalli K., Park D., Bhagavan N.V. Mutagenesis studies of thyroxine binding to human serum albumin define an important structural characteristic of subdomain 2A. Biochemistry. 36:1997;7012-7017.
191. Steiner R.F., Roth J., Robbins J. The binding of thyroxine by serum albumin as measured by fluorescence quenching. J. Biol. Chem. 241:1966;560-567.
192. Petersen C.E., Ha C.E., Jameson D.M., Bhagavan N.V. Mutations in a specific human serum albumin thyroxine binding site define the structural basis of familial dysalbuminemic hyperthyroxinemia. J. Biol. Chem. 271:1996;19110-19117.
193. Sterling K., Tabachnick M. J. Biol. Chem. 236:1961;2241-2243.
194. Sterling K., Rosen P., Tabachnick M. Equilibrium dialysis studies of the binding of thyroxine by human serum albumin. J. Clin. Invest. 41:1962;1021-1030.
195. Sterling K. Molecular structure of thyroxine in relation to its binding by human serum albumin. J. Clin. Invest. 43:1964;1721-1729.
196. Tabachnick M., Giorgio N.A. Jr. Thyroxine-protein interactions II. The binding of thyroxine and its analogues to human serum albumin. Arch. Biochem. Biophys. 105:1964;563-569.
197. Tabachnick M. Thyroxine-protein interactions I. Binding of thyroxine to human serum albumin and modified albumins. J. Biol. Chem. 239:1964;1242-1249.
198. Tabachnick M., Downs F.J., Giorgio N.A. Thyroxine-protein interactions VI. Structural requirements for binding of benzene derivatives to thyroxine-binding sites on human serum albumin. Arch. Biochem. Biophys. 136:1970;467-479.
199. Jakoby M.G., Covey D.G., Cistola D.P. Localization of tolbutamide binding sites on human serum albumin using titration calorimetry and heteronuclear 2-D NMR. Biochemistry. 34:1995;8780-8787.
200. Judis J. Binding of sulfonylureas to serum proteins. J. Pharm. Sci. 61:1972;89-93.
201. Zini R., d'Athis P., Hoareau A., Tillement J.-P. Binding of four sulfonamides to human albumin. Eur. J. Clin. Pharmacol. 10:1976;139-145.
202. Tanaka M.A.Y., Masuda S., Minagawa K. Binding position of tolbutamide to human serum albumin. Chem. Pharm. Bull. 46:1998;817-821.
203. Bohney J.P., Feldhoff R.C. Effects of nonenzymatic glycosylation and fatty acids on tryptophan binding to human serum albumin. Biochem. Pharmacol. 43:1992;1829-1834.
204. Chattopadhyay A., Tian T., Kortum L., Hage D.S. Development of tryptophan-modified human serum albumin columns for site-specific studies of drug-protein interactions by high-performance affinity chromatography. J. Chromatogr. 715:1998;183-190.
205. Yang J., Hage D.S. Characterization of the binding and chiral separation of D- and L-tryptophan on a high performance immobilized human serum albumin column. J. Chromatogr. 645:1993;241-250.
206. Fehske K.J., Mueller W.E., Wollert U. A highly reactive tyrosine residue as part of the indole and benzodiazepine binding site of human serum albumin. Biochim. Biophys. Acta. 577:1979;346-359.
207. Storck J., Kirsten R. Binding of urapidil to human serum albumin: dependency on free fatty acid concentration. Int. J. Clin. Pharm. Ther. Tox. 29:1991;204-208.
208. Ding Y., Zhu X., Lin B. Study of interaction between drug enantiomers and serum albumin by capillary electrophoresis. Electrophoresis. 20:1999;1890-1894.
209. O'Reily R.A. J. Clin. Invest. 46:1967;829-837.
210. Oester Y.T., Keresztes-Nagy S., Mais R.F., Becktel J., Zaroslinski J.F. Effect of temperature on binding of warfarin by human serum albumin. J. Pharm. Sci. 65:1976;1673-1677.
211. Chakrabarti S.K. Influence of heavy metals on the in vitro interaction between human serum albumin and warfarin. Biochem. Pharmacol. 27:1978;2957-2959.
212. Chakrabarti S.K. Cooperativity of warfarin binding with human serum albumin induced by free fatty acid anion. Biochem. Pharmacol. 27:1978;739-743.
213. Vorum H., Bang D., Fisker K. New procedure for analysing drug binding data exemplified by warfarin binding to human serum albumin. Biochem. Pharmacol. 45:1993;1715-1720.
214. Vorum H., Fisker K., Brodersen R. High-affinity binding of two molecules of warfarin and phenprocoumon to human serum albumin. Biochim. Biophys. Acta. 1205:1994;178-182.
215. Vorum H., Honore B. Influence of fatty acids on the binding of warfarin and phenprocoumon to human serum albumin with realtion to anticoagulant therapy. J. Pharm. Pharmacol. 48:1996;870-875.
216. Sudlow G., Birkett D.J., Wade D.N. Spectroscopic techniques in the study of protein binding. Fluorescence technique for the evaluation of the albumin binding and displacement of warfarin and warfarin-alcohol. Clin. Exp. Pharmacol. Physiol. 2:1975;129-140.
217. Rietbrock N., Menke G., Reuter G., Lassmann A., Schmeidl R. Influence of palmitate and oleate on the binding of warfarin to human serum albumin: stopped-flow studies. J. Clin. Chem. Clin. Biochem. 23:1985;719-723.
218. Maes V., Engelborghs Y., Hoebeke J., Maras Y., Vercruysse A. Fluorimetric analysis of the binding of warfarin to human serum albumin. Mol. Pharmacol. 21:1982;100-107.
219. The MedChem Project and BioByte Corp in Claremont CA maintains the MedChem database http://www.Daylight.com/products/databases/Medchemhtml.