Modeling Drug Albumin Binding Affinity with E-State Topological Structure Representation

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 6, 2003, Pages 2120-2128

  Hall, L Mark ^a   Hall, Lowell H ^b   Kier, Lemont B ^c  

^a Hall Associates Consulting ^*  (United States)

^b EASTERN NAZARENE COLLEGE   (United States)

^c VIRGINIA COMMONWEALTH UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING AFFINITY; ELECTROTOPOLOGICAL STATE (E-STATE); RANDOMIZATIONS;

CARBOXYLIC ACIDS; COMPUTER SOFTWARE; DATABASE SYSTEMS; DRUG PRODUCTS; ELECTRONS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTEINS;

MOLECULAR STRUCTURE;

ALBUMINOID; PLASMA PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NOMENCLATURE; PROTEIN BINDING; PROTEIN CONFORMATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ALBUMINS; BLOOD PROTEINS; MODELS, MOLECULAR; PROTEIN BINDING; PROTEIN CONFORMATION; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TERMINOLOGY;

EID: 0345548608     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci030019w     Document Type: Article

References (41)

1. Prentis, R. A.; Lis Y.; Walker, S. R. Pharmaceutical innovation by the seven UK-owned pharmaceutical companies (1964-1985) Br. J. Clin. Pharmacol. 1988, 25, 387-396.
2. Kennedy, T. Managing the Drug Discovery/development Interface. Drug Discovery Today 1997, 2(10), 436-444.
3. Hall, L. M.; Hall, L. H.; Kier, L. B. QSAR Modeling of Beta-Lactam Binding to Serum Proteins. J. Comput.-Aided Mol. Des. 2003, 17, 103-118.
4. Bird, A. E.; Marshall, A. C. Correlation of Serum Binding of Penicillins with Partition Coefficients. Biochem. Pharmacol. 1967, 16, 2275-2290.
5. Pacifici, G. M.; Viani, A. Methods of Determining Plasma and Tissue Binding of Drugs. Clin. Pharmacokinet. 1992, 23, 449-459.
6. Frostell-Karlsson, A.; Ramaeus, A.; Roos, H.; Andersson, K.; Borg, P.; Hamalainen, M.; Karlsson, R. Biosensor Analysis of the Interaction between Immobilized Human Serum Albumin Binding Levels. J. Med. Chem. 2000, 43, 1986-1992.
7. Domenici, E.; Bortucci, C.; Salvadori, P.; Motellier, S.; Wainer, I. W. Immobilized Serum Albumin: Rapid HPLC Probe of Stereo-selective Protein Binding Interactions. Chirality 1990, 2, 263-268.
8. Domenici, E.; Bortucci, C.; Salvadori, P.; Wainer, I. W. Use of a Human Serum Albumin-Based Chiral Stationary Phase for High-Performance Liquid Chromatography for the Investigation of Protein Binding: Detection of the Allosteric Interaction Between Warfarin and Benzodiazopine Binding Sites. J. Pharm Sci. 1991, 80, 164-169.
9. Colmenarejo, G.; Alvarez-Pedraglio, A.; Lavandera, J.-L. Chemin-formatic Models to Predict Binding Affinities to Human Serum Albumin. J. Med. Chem. 2001, 44, 4370-4378.
10. CS ChemDraw PRO, ver 4.5, CambridgeSoft, 875 Massachusetts Avenue, Cambridge, MA 02139.
11. MDL QSAR, MDL Information Systems, 14600 Catalina Street, San Leandro, CA 94577.
12. Kier, L. B.; Hall, L. H. Molecular Structure Description: The Electrotopological State; Academic Press: San Diego, 1999.
13. (a) Kier, L. B.; Hall, L. H. Molecular Connectivity In Chemistry and Drug Research; Academic Press: New York, 1976.
14. (b) Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis; John Wiley Publications: London, 1986.
15. Hall, L. H.; Kier, L. B. The Molecular Connectivity Chi Indexes and Kappa Shape Indexes in Structure-Property Relations. In Reviews of Computational Chemistry; Boyd, D., Lipkowitz, K., Eds.; VCH Publishers: 1991; Chapter 9, pp 367-422.
16. Kier, L. B.; Hall, L. H. The Kappa Indices for Modeling Molecular Shape and Flexibility. In Topological Indices and Related Descriptors in QSAR and QSPR; Devillers, J., Balaban, A. T., Eds.; Gordon and Breach: Reading, U.K., 1999; pp 455-490.
17. Kier, L. B.; Hall, L. H. Inhibition of Salicylamide Binding: An Electrotopological State Analysis. Med. Chem. Res. 1992, 2, 497-502.
18. Gough, J. D.; Hall, L. H. QSAR Models of the Antileukemic Potency of Carboquinones: Electrotopological State and Chi Indices. J. Chem. Inf. Comput. Sci. 1999, 39, 356-361.
19. Huuskonen, J. Estimation of Aqueous Solubility for a Diverse Set of Organic Compounds Based on Molecular Topology. J. Chem. Inf. Comput. Sci. 2000, 40, 773-777.
20. Huuskonen, J. QSAR Modeling with the Electrotopological State: TIBO Derivatives. J. Chem. Inf. Comput. Sci. 2001, 41, 425-429.
21. 50 Values for ACAT Inhibitors from Molecular Structure. J. Chem. Inf. Comput. Sci. 2000, 40, 706-723.
22. Gozalbes, R.; Galvez, J.; Garcia-Domenech, R.; Derouin, F. Molecular Search of New Active Drugs Against Toxoplasma Gondii. SAR QSAR Environ. Res. 1999, 10, 47-60.
23. Hall, L. H.; Mohney, B. K.; Kier, L. B. Comparison of Electrotopological State Indexes with Molecular Orbital Parameters: Inhibition of MAO by Hydrarides. Quant. Struct.-Act. Relat. 1993, 12, 44-48.
24. Hall, L. H.; Kier, L. B. Electrotopological State Indices for Atom Types: A Novel Combination of Electronic, Topological and Valence State Information. J. Chem. Inf. Comput. Sci. 1995, 35, 1039-1045.
25. (a) Maw, H. H.; Hall, L. H. E-State Modeling of Dopamine Transporter Binding. Validation of Model for a Small Data Set. J. Chem. Inf. Comput. Sci. 2000, 40, 1270-1275.
26. (b) Maw, H. H.; Hall, L. H. E-State Modeling of Corticosteroid Binding Affinity. Validation of Model for a Small Data Set. J. Chem. Inf. Comput. Sci. 2001, 41, 1248-1254.
27. Maw, H. H.; Hall, L. H. E-State Modeling of HIV-1 Protease Inhibitor Binding Independent of 3D Information. J. Chem. Inf. Comput. Sci. 2002, 42, 290-298.
28. (a) Rose, K.; Hall, L. H.; Kier, L. B. Modeling Blood-Brain Barrier Penetration Using the Electrotopological State. J. Chem. Inf. Comput. Sci. 2002, 42, 651-666.
29. (b) Rose, K.; Hall, L. H. E-State Modeling of Fish Toxicity Independent of 3D Structure Information. SAR QSAR Environ. Sci. 2003, 14, 113-129.
30. Hall, L. H.; Kier, L. B. The Electrotopological State: Structure Modeling for QSAR and Database Analysis. In Topological Indices and Related Descriptors in QSAR and QSPR; Devillers, J., Balaban, A. T., Eds.; Gordon and Breach: Reading, U.K., 1999; pp 491-562.
31. (a) Kier, L. B.; Hall, L. H. Database Organization and Similarity Searching with E-State Indices. In Symposium on Computer Methods for Structure Representation; Kluwer Academic Publishing Co.: Amsterdam, The Netherlands, 2001; pp 33-49.
32. (b) Hall, L. H.; Kier, L. B. The E-State as the Basis for Molecular Structure Space Definition and Structure Similarity. J. Chem. Inf. Comput. Sci. 2000, 40, 784-791.
33. (a) Kier, L. B.; Hall, L. H. Database Organization and Searching with E-State Indices, SAR QSAR Environ. Sci. 2001, 12, 55-74.
34. (b) Hall, L. H.; Kier, L. B. Molecular Similarity Based on Novel Atom Type Electrotopological State Indices. J. Chem. Inf. Comput. Sci. 1995, 35, 1074-1080.
35. Kier, L. B.; Hall, L. H. Intermolecular Accessibility: The Meaning of Molecular Connectivity. J. Chem. Inf. Comput. Sci. 2000, 40, 792-795.
36. Kier, L. B.; Hall, L. H. Molecular Connectivity: Intermolecular Accessibility and Encounter Simulation. J. Mol. Graph. Model. 2001, 20, 76-83.
37. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis; Research Studies Press: John Wiley and Sons: Chichester, U.K., 1986.
38. Hall, L. H.; Kier, L. B. Molecular connectivity chi Indices for database analysis and structure-property modeling. In Topological Indices and Related Descriptors in QSAR and QSPR; Devillers, J., Balaban, A. T., Eds.; Gordon and Breach: Reading, U.K., 1999; pp 307-360.
39. Hall, L. H.; Kier, L. B. Molecular Connectivity and Substructure Analysis. J. Pharm. Sci. 1978, 67, 1743-1747.
40. Hall, L. H.; Kier, L. B. A Molecular Connectivity Study of the Muscarinic Receptor Affinity of Acetylcholine Antagonists. J. Pharm. Sci. 1978, 67, 1408-1412.
41. Kier, L. B.; Hall, L. H. Structure-Activity Studies on Hallucinogenic Amphetamines Using Molecular Connectivity. J. Med. Chem. 1977, 20, 1631-1636.