In silico prediction of aqueous solubility: The solubility challenge

Journal of Chemical Information and Modeling

Volumn 49, Issue 11, 2009, Pages 2572-2587

  Hewitt, M ^a   Cronin, M T D ^a   Enoch, S J ^a   Madden, J C ^a   Roberts, D W ^a   Dearden, J C ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FORECASTING;

AQUEOUS SOLUBILITY; EXPERIMENTAL DETERMINATION; IN-SILICO MODELS; PREDICTIVE METHODS; PROCESS FUNDAMENTALS; SIMPLE LINEAR REGRESSION; SOLUBILITY MODELS; SOLUBILITY PREDICTION;

SOLUBILITY;

WATER;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; SOLUBILITY;

MODELS, CHEMICAL; SOLUBILITY; WATER;

EID: 72949117724     PISSN: 15499596     EISSN: 1549960X     Source Type: Journal    
DOI: 10.1021/ci900286s     Document Type: Article

References (59)

1. Musha, A. Body water in man. I. Total body water in normal subjects and edematous patients. Tohoku J. Exp. Med. 1956, 63, 309-317.
2. 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 Delivery Rev. 1997, 23, 3-25.
3. Di, L.; Kerns, E. H. Biological assay challenges from compound solubility: strategies for bioassay optimization. Drug Discovery Today 2006, 11, 446-451.
4. Barker, S. A.; Khossravi, D. Drug delivery strategies for the new millennium. Drug Discovery Today 2001, 6, 75-77.
5. Borchardt, R. T., Kerns, E. H., Hageman, M., Thakker, D. R. Stevens, J. L., Eds. Optimizing the "Drug-Like" Properties of Leads in DrugDiscovery; Springer: New York, 2006.
6. Ekins, S.; Rose, J. In silico ADME/Tox: The state of the art. J. Mol. Graph. Model. 2002, 20, 305-309.
7. Stegemann, S.; Leveiller, F.; Franchi, D.; de Jong, H.; Lindèn, H. When poor solubility becomes an issue: From early stage to proof of concept. Eur. J. Pharm. Sci. 2007, 31, 249-261.
8. Kennedy, T. Managing the drug discovery/development interface. Drug Discovery Today 1997, 2, 436-444.
9. Palmer, A. M. New horizons in drug metabolism, pharmacokinetics and drug discovery. Drug News Perspect. 2003, 16, 57-62.
10. Kerns, E. H.; Li, D. Drug-like Properties: Concepts, Structure Design and Methods: from ADME to Toxicity Optimization; Academic Press: Boston, 2008.
11. Bhattachar, S. N.; Deschenes, L. A.; Wesley, J. A. Solubility: It's not just for physical chemists. Drug Discovery Today 2006, 11, 1012-1018.
12. Dai, W.; Pollock-Dove, C.; Dong, L. C.; Li, S. Advanced screening assays to rapidly identify solubility-enhancing formulations: Highthroughput, miniaturization and automation. Adv. Drug Delivery Rev. 2008, 60, 657-672.
13. Alsenz, J.; Kansy, M. High throughput solubility measurement in drug discovery and development. Adv. Drug Delivery Rev. 2007, 59, 546-567.
14. Fühner, H. The aqueous solubility of homologous series. Ber. Dtsch. Chem. Ges. 1924, 57B, 510-515.
15. Dearden, J. C. In silico prediction of aqueous solubility. Expert. Opin. Drug Discovery 2006, 1, 31-52.
16. Reynolds, J. A.; Gilbert, D. B.; Tanford, C. Empirical correlation between hydrophobic free energy and aqueous cavity surface area. Proc. Natl. Acad. Sci. 1974, 71, 2925-2927.
17. Hansch, C.; Quinlan, J. E.; Lawrence, G. L. The linear free-energy relationship between partition coefficients and aqueous solubility of organic liquids. J. Org. Chem. 1968, 33, 347-350.
18. Faller, B.; Ertl, P. Computational approaches to determine drug solubility. Adv. Drug Delivery Rev. 2007, 59, 533-545.
19. Yalkowsky, S. H.; Valvani, S. C. Solubility and partitioning I: solubility of nonelectrolytes in water. J. Pharm. Sci. 1980, 69, 912-922.
20. Kamlet, M. J.; Doherty, R. M.; Abboud, J.-L. M.; Abraham, M. H.; Taft, R. W. Linear salvation energy relationships: 36. Molecular properties governing solubilities of organic nonelectrolytes in water. J. Pharm. Sci. 1986, 75, 338-348.
21. Irmann, F. A simple correlation of water solubility and structure of hydrocarbons and hydrocarbon halides. Chem.-Ing.-Tech. 1965, 37, 789-798.
22. Wakita, K.; Yoshimoto, M.; Miyamoto, S.; Watanabe, H. A method for calculation of the aqueous solubility of organic compounds by using new fragment solubility constants. Chem. Pharm. Bull. 1986, 34, 4663-4681.
23. Randic, M. Characterization of molecular branching. J. Am. Chem. Soc. 1975, 97, 6609-6615.
24. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry and Drug Design; Academic Press: New York, 1976.
25. Kier, L. B.; Hall, L. H. Molecular Connectivity in Structure-Activity Analysis; John Wiley & Sons: New York, 1986.
26. Mitchell, B. E.; Jurs, P. C. Prediction of aqueous solubility of organic compounds from molecular structure. J. Chem. Inf. Comput. Sci. 1998, 38, 489-496.
27. Liu, R.; So, S.-S. Development of quantitative structure-property relationship models for early ADME evaluation in drug discovery. 1. Aqueous solubility. J. Chem. Inf. Comput. Sci. 2001, 41, 1633-1639.
28. Wegner, J. K.; Zell, A. Prediction of aqueous solubility and partition coefficient optimized by a genetic algorithm based descriptor selection method. J. Chem. Inf. Comput. Sci. 2003, 43, 1077-1084.
29. Delaney, J. S. Predicting aqueous solubility from structure. Drug Discovery Today 2005, 10, 289-295.
30. Costa, M. F.; Pádua. A. A. H. In Developments and Applications in Solubility; Letcher, T. M., Ed.; Royal Society of Chemistry: London, 2007; Chapter 10, pp 153-170.
31. Llinàs, A.; Glen, R. C.; Goodman, J. M. Solubility challenge: Can you predict solubilities of 32 molecules using a database of 100 reliable measurements. J. Chem. Inf. Model. 2008, 48, 1289-1303.
32. Hopfinger, A. J.; Esposito, E. X.; Llinàs, A.; Glen, R. C.; Goodman, J. M. Finding of the Challenge to predict aqueous solubility. J. Chem. Inf. Model. 2009, 49, 1-5.
33. Stuart, M.; Box, K. Chasing equilibrium: Measuring the intrinsic solubility of weak acids and bases. Anal. Chem. 2005, 77, 983-990.
34. ChemIDPlus Advanced. http://chem.sis.nlm.nih.gov/chemidplus/ (accessed April 22, 2009).
35. ChemBioFinder. http://chembiofinder.cambridgesoft.com/chembiofinder/ SimpleSearch.aspx (accessed April 22, 2009).
36. ChemAxon. http://www.chemaxon.com/ (accessed April 22, 2009).
37. US EPA Estimation Program Interface (EPI) Suite. http://www.epa.gov/oppt/ exposure/pubs/episuite.htm (accessed April 22, 2009).
38. Raevsky, O. A., Grigor'ev, V. Ju. Trepalin, S. V. HYBOT (Hydrogen Bond Thermodynamics) Program Package (Version 2.1.0.706). Reg-istration by Russian State Patent Agency N 990090 of 26.02.99 (Raevsky, O. A., Skvortsov, V. S., Grigor'ev, V. Ju. Trepalin, S. V.).
39. Dragon Professional Software Package, Version 5.3 for Windows; Milano Chemometrics and QSAR Research Group; Milano, Italy, 2009.
40. Jorgensen, W. L.; Duffy, E. M. Prediction of drug solubility from structure. Adv. Drug Delivery Rev. 2002, 355-366.
41. MobydigssSoftware for Multilinear Regression Analysis and Variable Selection by Genetic Algorithm, Version 1.0 for Windows; Milano Chemometrics and QSAR Research Group, Milano, Italy, 2006.
42. Topliss, J. G.; Edwards, R. P. Chance factors in studies of quantitative structure-activity relationships. J. Med. Chem. 1979, 22, 1238-1244.
43. Butina, D.; Segall, M. D.; Frankcombe, K. Predicting ADME properties in silico: Methods and models. Drug Discovery Today 2002, 7, S83-S88.
44. Statistica Statistical Software for Windows (Version 6.1); StatSoft, Inc., Tulsa, OK, 2004.
45. Enoch, S. J.; Cronin, M. T. D.; Schultz, T. W.; Madden, J. C. An evaluation of global QSAR models for the prediction of the toxicity of phenols to Tetrahymena pyriformis. Chemosphere 2008, 71, 1225-1232.
46. Ghasemi, J.; Saaidpour, S. Quantitative structure-property relationship study of n-octanol-water partition coefficients of some of diverse drugs using multiple linear regression. Anal. Chim. Acta 2007, 604, 99-106.
47. Hilal, S. H. Karickhoff, S. W. Verification and validation of the SPARC model. U.S. Environmental Protection Agency Report EPA/600/R-03/033. (Available via the Internet at http://www.epa.gov/athens/publications/reports/EPA-600-R-03- 033.pdf, accessed September 23, 2009.)
48. Minitab for Windows Statistical Software, Version 15; Minitab, Inc., State College, PA, 2007.
49. Toxmatch, Version 1.06; IdeaConsult, Ltd., Sofia, Bulgaria, 2008.
50. Enoch, S. J.; Cronin, M. T. D.; Madden, J. C.; Hewitt, M. Formation of structural categories to allow for read-across for teratogencity. QSAR Comb. Sci. 2009, 28, 696-708.
51. Shacham, M.; Brauner, N.; Cholakov, G.; Stateva, R. P. Identifying applicability domains for quantitative structure property relationships. Report from the 17th European Symposium on Computer Aided Process Engineering, 2007. (Available via the Internet at ftp://ftp.bgu.ac.il/shacham/publ-papers/Escape17- 327-07.pdf, accessed April 22, 2009.)
52. Massart, D. L. Chemometrics: A Textbook, 5th Edition; Elsevier: Amsterdam, 1988.
53. Consonni, V.; Todeschini, R.; Pavan, M. Structure/response correlations and similarity/diversity analysis by GETAWAY descriptors. 1. Theory of the novel 3D molecular descriptors. J. Chem. Inf. Comput. Sci. 2002, 42, 682-692. (Pubitemid 35355277)
54. TSAR for Windows Version 3.3; Accelrys, Inc.: Oxford, England, 2009.
55. Ebbing, D. D.; Gammon, S. D. General Chemistry, 9th Edition; Houghton Mifflin: Boston, 2009; Chapter 6, pp 223-262.
56. Taylor, J. B. Triggle, D. J. In ADME-Tox Approaches; Testa, B. van de Waterbeemd, H., Eds.; Comprehensive Medicinal Chemistry II, Vol.5; Elsevier: Oxford, 2007; pp 627-648.
57. O'Neil, M. J. The Merck Index, 13th Edition; Merck & Co., Inc.: Whitehouse Station, NJ, 2001.
58. Avdeef, A. Physicochemical profiling (solubility, permeability and charge state). Curr. Top. Med. Chem. 2001, 1, 277-351.
59. Nokhodchi, A. The effect of type and concentration of vehicles on the dissolution of a poorly soluble drug (indomethacin) from liquisolid compacts. J. Pharm. Pharmaceut. Sci. 2005, 8, 18-25.