Contribution of ionization and lipophilicity to drug binding to albumin: A preliminary step toward biodistribution prediction

Journal of Medicinal Chemistry

Volumn 47, Issue 16, 2004, Pages 3949-3961

  Ermondi, Giuseppe ^a   Lorenti, Miriam ^a   Caron, Giulia ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACEBUTOLOL; ALBUMIN; AMLODIPINE; AMLODIPINE BESYLATE; BOVINE SERUM ALBUMIN; CHLOROQUINE; FUROSEMIDE; HYDROCHLOROTHIAZIDE; INDOMETACIN; METHOTREXATE; NAPROXEN; NICARDIPINE; PRAZOSIN; QUINIDINE; RANITIDINE; TENOXICAM; TETRACYCLINE;

ARTICLE; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG EXCRETION; DRUG METABOLISM; DRUG PROTEIN BINDING; FRACTIONATION; IONIZATION; LIGAND BINDING; LIPOPHILICITY; MATHEMATICAL ANALYSIS; MOLECULAR MECHANICS; PREDICTION; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION; ULTRACENTRIFUGATION;

CHROMATOGRAPHY, AFFINITY; HYDROGEN-ION CONCENTRATION; IONS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHARMACEUTICAL PREPARATIONS; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SERUM ALBUMIN, BOVINE; ULTRACENTRIFUGATION;

EID: 3242757468     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm040760a     Document Type: Article

References (75)

1. Seydel, J. K. Quantitative structure-pharmacokinetics relationships and their importance in drug design, possibilities and limitations. Methods Find. Exp. Clin. Pharmacol. 1984, 6, 571-581.
2. Urien, S.; Tillement, J. P.; Barré, J. The significance of plasma-protein binding in drug research. In Pharmacokinetic Optimization in Drug Research; Testa, B., van de Waterbeemd, H., Folkers, G., Guy, R. H., Eds.; Wiley-VCH: Zürich, 2001; pp 189-197.
3. van de Waterbeemd, H.; Smith, D. A.; Beaumont, K.; Walker, D. K. Property-based design: Optimization of drug absorption and pharmacokinetics. J. Med. Chem. 2001, 44, 1313-1333.
4. Bhattacharya, A. A.; Grüne, T.; Curry, S. Chrystallographic analysis reveals common modes of binding of medium and long-chain fatty acids to human serum albumin. J. Mol. Biol. 2000, 303, 721-732.
5. Petitpas, I.; Grüne, T.; Bhattacharya, A. A.; Curry, S. Crystal structures of human serum albumin complexed with monounsaturated and polyunsatured fatty acid. J. Mol. Biol. 2001, 314, 955-960.
6. Petitpas, I.; Bhattacharya, A. A.; Twine, S.; East, M.; Curry, S. Crystal structure analysis ofwarfarin binding to human serum albumin. J. Biol. Chem. 2001, 276, 22804-22809.
7. Bhattacharya, A. A.; Curry, S.; Franks, P. Binding of the general anesthetic propofol and halothane to human serum albumin. J. Biol. Chem. 2000, 275, 38731-38738.
8. Colmenarejo, G.; Alvarez-Pedraglio, A.; Lavandera, J.-L. Chem-informatic models to predict binding affinities to human serum albumin. J. Med. Chem. 2001, 44, 4370-4378.
9. Kratochwil, N. A.; Huber, W.; Müller, F.; Kansy, M.; Gerber, P. R. Predicting plasma protein binding of drugs: a new approach. Biochem. Pharmacol. 2002, 64, 1355-1374.
10. Vallner, J. J. Binding of drugs by albumin and plasma protein. J. Pharm. Sci. 1977, 66, 447-465.
11. Cserhati, T.; Forgacs, E.; Deyl, Z.; Miksik, I. Effect of molecular parameters on the binding of phenoxyacetic acid derivatives to albumin. J. Chromatogr. B 2001, 753, 87-92.
12. Sowell, J.; Christian Mason, J.; Strekowski, L.; Patonay, G. Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis. Electrophoresis 2001, 22, 2512-2517.
13. Seydel, J. K.; Butte, W. p-Aminobenzoic acid derivatives. Mode of action and structure-activity relationships in cell-free system (Escherichia coli). J. Med. Chem. 1977, 20, 439-447.
14. Seydel, J. K.; Trettin, D.; Cordes, H. P.; Wassermann, O.; Malyusz, M. Quantitative structure-pharmacokinetic relationships derived on antibacterial sulfonamides in rats and its comparison to quantitative structure-activity relationships. J. Med. Chem. 1980, 23, 607-613.
15. Girard, I.; Ferry, S. Protein binding of methohexital. Study of parameters modulating factors using the equilibrium dialysis technique. J. Pharm. Biomed. Anal. 1996, 14, 583-591.
16. Urien, S.; Albengres, E.; Comte, A.; Kiechel, J.-R.; Tillement, J. P. Plasma protein binding and erythrocite partitioning of nicardipine in vitro. J. Cardiovasc. Pharmacol. 1985, 7, 891-898.
17. Silva, C.; Plazzi, P. V.; Bordi, F.; Rivara, S.; Vacondio, F.; Zuliani, V.; Caretta, A.; Mor, M. Structure-property relationships on histamine H3-antagonists: Binding of phenyl-substituted alkyl-thioimidazole derivatives to rat plasma proteins. Farmaco 2000, 55, 239-245.
18. Hervé, F.; Caron, G. Ligand specificity of the genetic variants of human α1-acid glycoprotein: generation of a three-dimensional quantitative structure-activity relationship model for drug binding to the A variant. Mol. Pharmacol. 1998, 54, 129-138.
19. Peters, T. P. All About Albumin. Biochemistry, Genetics, and Medical Applications; Academic Press: New York, 1995.
20. Matsushita, Y.; Moriguchi, I. Measurement of protein binding by ultracentrifugation. Chem. Pharm. Bull. 2003, 33, 2948-2955.
21. Testa, B.; Crivori, P.; Reist, M.; Carrupt, P. A. The Influence of Lipophilicity on the Pharmacokinetic Behavior of Drugs: Concepts and Examples; Kluwer Academic Publisher: Norwell, MA, 2000; pp 179-211.
22. Caron, G.; Reymond, F.; Carrupt, P. A.; Girault, H. H.; Testa, B. Combined molecular lipophilicity descriptors and their role in understanding intramolecular effects. PSST 1999, 2, 327-335.
23. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The protein data bank. Nucleic Acids Res. 2000, 28, 235.
24. MOE, 2002.03; Chemical Computing Group Inc: Montreal, Quebec Canada, 2002.
25. Bergström, C. A. S.; Strafford, M.; Lazorova, L.; Avdeef, A.; Luthman, K.; Artursson, P. Absorption classification of oral drugs based on molecular surface properties. J. Med. Chem. 2003, 46, 558-570.
26. Taira, Z.; Terada, H. Specific and nonspecific ligand binding to serum albumin. Biochem. Pharmacol. 1985, 34, 1999-2005.
27. Joseph-McCarthy, D. Computational approaches to structure-based ligand design. Pharmacol. Ther. 1999, 84, 179-191.
28. Tsai, R. S.; Carrupt, P. A.; El Tayar, N.; Testa, B.; Giroud, Y.; Andrade, P.; Brée, F.; Tillement, J. P. Physicochemical and structural properties of nonsteroidal antiinflammatory oxicams. Helv. Chim. Acta 1993, 76, 842-854.
29. Pagliara, A.; Carrupt, P. A.; Caron, G.; Gaillard, P.; Testa, B. Lipophilicity profiles of ampholytes. Chem. Rev. 1997, 97, 3385-3400.
30. Colaizzi, J. L.; Klink, P. R. pH-Partition Behavior of Tetracyclines. J. Pharm. Sci. 1969, 58, 1184-1189.
31. Abraham, M. H. Hydrogen bonding. 27. Solvation parameters for functionally substituted aromatic compounds and heterocyclic compounds, from gas-liquid chromatography data. J. Chromatogr. 1993, 644, 95-139.
32. ADME Boxes; Advanced Pharma Algorithms: Toronto, Canada, 2003.
33. a values of medicinal compounds in pharmacy practice. Drug Intell. Clin. Pharm. 1978, 12, 546-554.
34. Reymond, F.; Gobry, V.; Bouchard, G.; Girault, H. H. Electrochemical aspects of drug partitioning. In Pharmacokinetic Optimization in Drug Research; Testa, B., van de Waterbeemd, H., Folkers, G., Guy, R. H., Eds.; VHCA: Zürich, 2001; pp 327-349.
35. Comer, J. E.; Tam, K. Y. Lipophilicity profiles: Theory and measurement. In Pharmacokinetic Optimization in Drug Research; Testa, B., van de Waterbeemd, H., Folkers, G., Guy, R. H., Eds.; Wiley-VCH: Zürich, 2001; pp 275-304.
36. Bouchard, G.; Carrupt, P. A.; Testa, B.; Gobry, V.; Girault, H. H. Lipophilicity and solvation of anionic drugs. Chem. Eur. J. 2002, 8, 3478-3484.
37. Plempler van Balen, G.; a Marca Martinet, C.; Caron, G.; Bouchard, G.; Reist, M.; Carrupt, P. A.; Fruttero, R.; Gasco, A.; Testa, B. Liposomes/water lipophilicity: Methods, information content, and pharmaceutical applications. Med. Res. Rev. 2004, 24, 299-324.
38. Tetko, I. V.; Tanchuk, V. Y.; Kasheva, T. N.; Villa, A. E. P. Internet software for the calculation of the lipophilicity and aqueous solubility of chemical compounds. J. Chem. Inf. Comput. Sci. 2001, 41, 246-252.
39. Tillement, J. P.; Houin, G.; Zini, R.; Urien, S.; Albengres, E.; Barré, J.; Lecomte, M.; d'Athis, P.; Sebille, B. The binding of drugs to blood plasma macromolecules: Recent advances and therapeutic significance. Academic Press: London, 1984; Vol. 13, pp 59-94.
40. Saiakhov, R. D.; Stefan, L. R.; Klopman, G. Multiple computer-automated structure evaluation model of the plasma protein binding affinity of diverse drugs. Perspect. Drug Discovery Des. 2000, 19, 133-155.
41. Testa, B.; Caron, G.; Crivori, P.; Rey, S.; Reist, M.; Carrupt, P. A. Lipophilicity and related molecular properties as determinants of pharmacokinetic behaviour. Chimia 2000, 54, 672-677.
42. 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. Biochem. Pharmacol. 1993, 45, 2411-2416.
43. Melten, J. W.; Witterbrood, A. J.; Wemer, J.; Faber, D. B. On the modulating effects of temperature, albumin, pH and calcium on the free fractions of phenobarbitone and phenytoin. J. Pharm. Pharmacol. 1986, 38, 643-646.
44. Weder, H. J.; Bickel, M. H. Interactions of drugs with proteins I: Binding of tricyclic thymoleptics to human and bovine plasma proteins. J. Pharm. Sci. 1970, 59, 1505-1507.
45. Arrowsmith, J. E.; Campbell, S. F.; Cross, P. E.; Stubbs, J. K.; Burges, R. A.; Gardiner, D. G.; Blackburn, K. J. Long-acting dihydripyridine calcium antagonists. 1. 2-Alkoxymethyl derivatives incorporating basic substituents. J. Med. Chem. 1986, 29, 1696-1702.
46. Taillardat-Bertschinger, A.; a Marca Martinet, C.; Carrupt, P. A.; Reist, M.; Caron, G.; Fruttero, R.; Testa, B. Molecular factors influencing retention on immobilised artificial membranes (IAM) compared to partitioning in liposomes and n-octanol. Pharm. Res. 2001, 19, 729-737.
47. Absolv; Sirius Analytical Instruments Ltd.: Forest Row, United Kingdom, 1.4.05.63, 2000.
48. Abraham, M. H.; Ibrahim, A.; Zissimos, A. M.; Zhao, Y. H.; Comer, J. E.; Reynolds, D. Application of hydrogen bonding calculations in property based drug design. DDT 2002, 7, 1056-1063.
49. Dragon, v. 3.1; Talete Srl: Milano, Italy, 2003.
50. Reidenberg, M. M., Erill, S., Eds. Drug-Protein Binding; Praeger Publishers: New York, 1986.
51. Avdeef, A. High-throughput measurement of permeability profiles. In Drug Bioavailability; van de Waterbeend, H., Lennernas, H., Artursson, P., Eds.; Wiley-VCH: Weinheim, 2003; pp 46-71.
52. Kurz, H.; Trunk, H.; Weitz, B. Evaluation of methods to determine protein-binding of drugs. Arzneim.-Forsch. 1977, 27, 1373-1380.
53. Chapuis, N.; Brühlmann, C.; Reist, M.; Carrupt, P. A.; Mayer, J. M.; Testa, B. The esterase-like activity of serum albumin may be due to cholinesterase contamination. Pharm. Res. 2001, 18, 1435-1439.
54. Caron, G.; Gaillard, P.; Carrupt, P. A.; Testa, B. Lipophilicity behavior of model and medicinal compounds containing a sulfide, sulfoxide, or sulfone moiety. Helv. Chim. Acta 1997, 80, 449-462.
55. Avdeef, A. pH-Metric log P. Part 1. Difference plots for determining ion-pair octanol-water partition coefficients of multiprotic substances. Quant. Struct.-Act. Relat. 1992, 11, 510-517.
56. Avdeef, A. pH-Metric log P. II. Refinement of partition coefficients and ionization constants of multiprotic substances. J. Pharm. Sci. 1993, 82, 183-190.
57. Avdeef, A. Assessment of distribution-pH profiles. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Publishers: Weinheim, 1996; pp 109-139.
58. a determination of water-insoluble substances. Anal. Chem. 1993, 65, 42-49.
59. Ermondi, G.; Caron, G.; Bouchard, G.; Plemper van Balen, G.; Pagliara, A.; Grandi, T.; Carrupt, P. A.; Fruttero, R.; Testa, B. Molecular dynamics and NMR exploration of the property space of the zwitterionic antihistamine cetirizine. Helv. Chim. Acta 1999, 84, 360-374.
60. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J.; Meyer, E. E., Jr.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, M. The protein data bank: A computer-based archival file for macromolecular structures. J. Mol. Biol. 1977, 112, 535-542.
61. Halgren, T. A. Merck molecular force field. 1. Basis, form, scope, parametrization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519.
62. Christensen, I. T.; Jorgensen, F. S. Molecular mechanics calculations of proteins. Comparison of different energy minimization strategies. J. Biomol. Struct. Dyn. 1997, 15, 473-488.
63. MOE 2003.02 User Guide; Chemical Computing Group, Inc.: Montreal, Quebec, Canada, 2003.
64. Muegge, I.; Martin, Y. C. A general and fast scoring function for protein-ligand interactions: A simplified potential approach. J. Med. Chem. 1999, 42, 791-804.
65. Bruno, I. J.; Cole, J. C.; Lommerse, J. P. M.; Rowland, R. S.; Taylor, R.; Verdonk, M. L. IsoStar: A library of information about nonbonded interactions. J. Comput.-Aided Mol. Des. 1997, 11, 525-537.
66. Labute, P. Probabilistic receptor potentials. J. Chem. Comput. Group 2003, http://www.chemcomp.com/Journal_of_CCG/Features/cstat.htm.
67. SIMCA-P, v. 10.0.2.0; Umetrics: Umea, Sweden, 2003.
68. XLSTAT, Data Analysis Solution for Microsoft Excel, v. 7.1; Addinsoft: Paris, France, 2004.
69. Medchem95 Database; Daylight Chemical Information System, Inc.: Irvine, California, 1995.
70. Plemper van Balen, G.; Carrupt, P. A.; Morin, D.; Tillement, J. P.; Le Ridant, A.; Testa, B. Recognition forces involved in mitochondrial binding to a low-affinity trimetazidine binding site related to anti-ischemic activity. Biochem. Pharmacol. 2002, 63, 1691-1697.
71. Avdeef, A. Absorption and Drug Development. Solubility, Permeability, and Charge State; John Wiley & Sons: New York, 2003.
72. Auffinger, P.; Wipff, G. High-temperature annealed molecular dynamics simulations as a tool for conformational sampling-Application to the bicyclic-222 cryptand. J. Comput. Chem. 1990, 11, 19-31.
73. Murdock, D.; Heel, R. C. Amlodipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in cardiovascular disease. Drugs 1991, 41, 478-505.
74. Sorkin, E. M.; Clissold, S. P. Nicardipine. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy, in the treatment of angina pectoris, hypertension and related cardiovascular disorders. Drugs 1987, 33, 296-345.
75. Jolliet, P.; Simon, N.; Brée, F.; Urien, S.; Pagliara, A.; Carrupt, P. A.; Testa, B.; Tillement, J. P. Blood-to-brain transfer of various oxicams: effects of plasma binding on their brain delivery. Pharm. Res. 1997, 14, 650-656.