In silico prediction of drug solubility: 1. Free energy of hydration

Journal of Physical Chemistry B

Volumn 111, Issue 7, 2007, Pages 1872-1882

  Westergren, Jan ^a   Lindfors, Lennart ^a   Höglund, Tobias ^a   Lüder, Kai ^b   Nordholm, Sture ^b   Kjellander, Roland ^b  

^a ASTRAZENECA R AND D   (Sweden)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTER SIMULATION; COULOMB BLOCKADE; FREE ENERGY; HYDRATION; SOLUBILITY;

DRUG SOLUBILITY; PREDICTIVE MODELS;

DRUG PRODUCTS;

EID: 33847705703     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp064220w     Document Type: Article

References (52)

1. Jain, N; Yalkowsky S. J. Pharm. Sci. 2001, 90, 234.
2. Jorgensen, W. L.; Duffy, E. M. Adv. Drug Delivery Rev. 2002, 54, 355.
3. Pearlman, D. A.; Rao, B. G. In The Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; John Wiley: New York, 1998; Vol. 2, p 1036.
4. Åquist, J.; Medina, C.; Samuelsson, J. E. Protein Eng. 1994, 7, 385.
5. Westergren, J.; Nordholm, S. Chem. Phys. 2003, 290, 189.
6. Hildebrand, J. J. Am. Chem. Soc. 1916, 38, 1452.
7. Gallicchio, E.; Kubo, M.; Levy, R. J. Phys. Chem. B 2000, 104, 6271.
8. Graziano, G. Phys. Chem. Chem. Phys. 1999, 1, 3567.
9. Huang, D.; Chandler, D. J. Phys. Chem. B 2002, 106, 2047.
10. Guillot, B.; Guissani, Y. J. Chem. Phys. 1993, 99, 8075.
11. Carlson, H. A.; Jorgensen, W. L. J. Phys. Chem. 1995, 99, 10667.
12. Tanford, C. The Hydrophobic Effect; Wiley: New York, 1973.
13. Southall, N. T.; Dill, K. A.; Haymet, A. D. J. J. Phys. Chem. B 2002, 106, 521.
14. Frank, F. S.; Evans, M. W. J. Chem. Phys. 1945, 13, 507.
15. Gavezotti, A. CrystEngComm 2002, 4, 343.
16. Day, G. M.; Motherwell, W. D. S.; Amon, H. L.; Boerrigter, S. X. M.; Della Valle, R. G.; Vinuti, E.; Dzyabchenko, A.; Dunitz, J. D.; Schweitzer, B.; van Eijck, B. P.; Erk, P.; Vacelli, J. C.; Bazterra, V. E.; Ferraro, M. B.; Hofmann, D. W. M.; Leusen, F. J. J.; Liang, C.; Pantelides, C. C.; Karamertzanis, P. G.; Price, S. L.; Lewis, T. C.; Nowell, H.; Torrisi, A.; Scheraga, H. A.; Arnautova, Y. A.; Schmidt, M. U.; Verwe, P. Acta Crystallogr., Sect. B: Struct. Sci. 2005, 61, 511.
17. Neau, S. H.; Bhandarkar, S. V.; Hellmuth, E. H. Pharm. Res. 1997, 14, 601.
18. Lindfors, L.; Forssén, S.; Skantze, P.; Skantze, U.; Zackrisson, A.; Olsson, U. Langmuir 2006, 22, 911.
19. McDonanld, N. A.; Carlson, H. A.; Jorgensen, W. L. J. Phys. Org. Chem. 1997, 10, 563.
20. Sandberg, L.; Casemyr, R.; Edholm, O. J. Phys. Chem. B 2002, 106, 7889.
21. Jorgensen, W. L. Biochemical and Organic Simulation System, version 4.6; Yale University: New Haven, CT, 2004.
22. Jorgensen, W. L. In The Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; John Wiley: New York, 1998; Vol. 5, p 3281.
23. Jorgensen, W. L.; Tirado-Rives, J. J. Comput. Chem. 2005, 26, 1689.
24. Hooper, M.; Nordholm, S. J. Chem. Phys. 1984, 81, 2432.
25. Pierotti, R. A. Chem. Rev. 1976, 76, 717.
26. Åquist, J.; Hansson, T. J. Phys. Chem. 1996, 100, 9512.
27. (a) Ben-Nairn, A. Salvation Thermodynamics, 1st ed.; Plenum Press: New York, 1987.
28. (b) Ben-Nairn, A; Marcus, Y. J. Chem. Phys. 1984, 81, 2016.
29. Jorgensen, W. L.; Chandrasekhar, J.; Madura, J.; Impey, R.; Klein, M.; Tirado-Rives, J. J. Chem. Phys. 1983, 79, 926.
30. Connolly, M. L. J. Mol. Graphics 1993, 77, 139.
31. Jorgensen, W. L.; Maxwell, D. S.; Tirado-Rives, J. J Am. Chem. Soc. 1996, 118, 11225.
32. Jamshed, A.; Heyes, D. M. J. Chem. Phys. 2005, 122, 224117.
33. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
34. Storer, J. W.; Giesen, D. J.; Cramer C. J.; Truhlar, D. G. J. Comput.-Aided Mol. Des. 1995, 9, 87.
35. Udier-Blagović, M.; De Tirado, P. M.; Pearlman, S. A.; Jorgensen, W. L. J. Comp. Chem. 2004, 25, 1322.
36. Jorgensen, W. L.; Ravimohan, C. J. Chem. Phys. 1985, 83, 3050.
37. Floris, F.; Selmi, M.; Tani, A.; Tomasi, J. J. Chem. Phys. 1997, 107, 6353.
38. Pohorille, A.; Wilson, M. J. Mol. Struct. (THEOCHEM) 1993, 284, 271.
39. Abraham, M.; Nasehzadeh, A. J. Chem. Soc., Faraday Trans. 1 1981, 77, 321.
40. McAuliffe, C. J. Phys. Chem. 1966, 70, 1267.
41. (a) Perlovich, G. L.; Bauer-Brandl, A. Curr. Drug Delivery 2004, 1, 213.
42. (b) Perlovich, G. L.; Rodionov, S. V.; Bauer-Brandl, A. Eur. J. Pharm. Sci. 2005, 24, 25.
43. (c) Perlovich, G. L.; Bauer-Brandl, A. Eur. J. Pharm. Sci. 2003, 19, 423.
44. (d) Perlovich, G. L.; Kurkov, S. V.; Hansen, L. K.; Bauer-Brandl, A. J. Pharm. Sci. 2004, 93, 654.
45. (e) Perlovich, G. L.; Kurkov, S. V.; Kinchin, A. N.; Bauer-Brandl, A. J. Pharm. Sci. 2003, 92, 2502.
46. (f) Perlovich, G. L.; Kurkov, S. V.; Kinchin, A. N.; Bauer-Brandl, A. Eur. J. Pharm. Biopharm. 2004, 57, 411.
47. (g) Stephenson, R. M.; Malanowski, S. Handbook of the Thermodynamics of Organic Compounds; Elsevier: New York, 1987.
48. Graziano, G. Biophys. Chem. 1999, 82, 69.
49. (a) Bergström, C. A. S; Norinder, U.; Luthman, K.; Artursson, P. Pharm. Res. 2002, 19, 182.
50. (b) Chen, X.-Q.; Cho, J. S.; Li, Y.; Venkatesh, S. J. Pharm. Sci. 2002, 91, 1938.
51. (c) Jorgensen, W. L.; Duffy, E. M. Bioorg. Med. Chem. Lett. 2000, 10, 1155.
52. (d) James, W. McFarland, J. W.; Avdeef, A; Berger, C. M.; Raevsky, O. A. J. Chem. Inf. Comput. Sci. 2001, 41, 1355.