Fractional description of free energies of solvation

Journal of Computer-Aided Molecular Design

Volumn 13, Issue 2, 1999, Pages 139-152

  Javier Luque, F ^a   Barril, Xavier ^a   Orozco, Modesto ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Continuum models; Hydrophilicity; Hydrophobicity; Partition coefficient; Solvation free energy; Transfer free energy

Indexed keywords

CONTINUUM MECHANICS; ENERGY TRANSFER; FREE ENERGY; SOLVATION;

CONTINUUM MODEL; DRUG DESIGN; ENERGY OF SOLVATION; FIELD METHODS; MOLECULAR MODELING STUDIES; PARTITION COEFFICIENT; SELF-CONSISTENT REACTION FIELDS; SOLVATION FREE ENERGIES; SURFACE ELEMENTS; TRANSFER FREE ENERGY;

HYDROPHOBICITY;

ARTICLE; DRUG DESIGN; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PARTITION COEFFICIENT; PRIORITY JOURNAL;

EID: 84962349045     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1008036526741     Document Type: Article

References (78)

1. Hansch, C., Maloney, P.P., Fujita, T. and Mui, R., Nature, 194 (1963) 178.
2. Hansch, C., Acc. Chem. Res., 2 (1969) 232.
3. Leo, A., Hansch, C. and Elkins, D., Chem Rev., 71 (1971) 525.
4. Martin, Y.C., Quantitative Drug Design. A Critical Introduction, Marcel Dekker, New York, NY, 1978.
5. Hansch, C. and Leo, A., Exploring QSAR: Fundaments and Applications in Chemistry and Biology, ACS, Washington, DC, 1995.
6. Mansch, C. and Fujita, T., J. Am. Chem. Soc., 86 (1964) 1616.
7. Eisenberg, D. and McLachlan, A.D., Nature, 319 (1986) 199.
8. Audry, E., Dubost, J.P., Colleter, J.C. and Dallet, P., Eur. J. Med. Chem.-Chim. Ther., 21 (1986) 71.
9. Fauchère, J.L., Quarendon, P. and Kaetterer, L., J. Mol. Graphics, 6 (1988) 202.
10. Furet, P., Sele, A. and Cohen, N.C., J. Mol. Graphics, 6 (1988) 182.
11. Hansch, C. and Leo, A., Substituent Constants for Correlation Analysis in Chemistry and Biology, John Wiley and Sons, New York, NY, 1979.
12. Nys, G.G. and Rekker, R.F., Chim. Ther., 8 (1973) 521.
13. Rekker, R.F., The Hydrophobic Fragmental Constant. Elsevier, Amsterdam, 1977.
14. Suzuki, Y. and Kudo, Y., J. Comput.-Aided Mol. Design, 4 (1990) 155.
15. Bodor, N., Gabany, Z. and Wong, C.K., J. Am. Chem. Soc., 111 (1989) 3783.
16. Ghose, A.K. and Crippen, G.M., J. Comput. Chem., 7 (1986) 565.
17. Viswanadhan, V.N., Ghose, A.K., Revenkar, G.R. and Robins, R., J. Chem. Inf. Comput. Sci., 29 (1989) 163.
18. Klopman, G. and Wang, S., J. Comput. Chem., 12 (1991) 1025.
19. Meylan, W.M. and Howard, P.H., J. Pharm. Sci., 84 (1995) 83.
20. Mannhold, R. and Dross, K., Quant. Struct.-Act. Relat., 15 (1996) 403, and references therein.
21. Wang, R., Fu, Y. and Lai, L., J. Chem. Inf. Comput. Sci., 37 (1997) 615.
22. Gombar, V. and Enslein, K., J. Chem. Inf. Comput. Sci., 36 (1996) 1127, and references therein.
23. Bask, S.C., Gute, B.D. and Grunwald, G.D., J. Chem. Inf. Comput. Sci., 36 (1996) 1054.
24. van de Waterbeemd, H. and Mannhold, R., Quant. Struct.-Act. Relat., 15 (1996) 410, and references therein.
25. Convard, T., Dubost, J.P., Le Solleu, H. and Kummer, E., Quant. Struct.-Act. Relat., 13 (1994) 34.
26. Haeberlein, M. and Brinck, T., J. Chem. Soc., Perkin Trans. 2, (1997) 289.
27. Bodor, N. and Buchwald, P., J. Phys. Chem. B., 101 (1997) 3404.
28. Du, Q. and Arteca, G.A., J. Comput.-Aided Mol. Design, 10 (1996) 13.
29. Lien, E.J., Gao, H., Wang, F. and Shinouda, H.G., Quant. Struct.-Act. Relat., 12 (1993) 158.
30. Orozco, M., Alhambra, C., Barril, X., Lopez, J.M., Busquets, M.A. and Luque, F.J., J. Mol. Model., 2 (1996) 1.
31. Jorgensen, W.L., In Van Gunsteren, W.F. and Weiner, P.K. (Eds.) Computer Simulation of Biomolecular Systems. Theoretical and Experimental Applications, ESCOM, Leiden, 1989, pp. 60-72.
32. Rivail, J.L. and Rinaldi, D., In Leszcynski, J. (Ed.) Computational Chemistry, Review of Current Trends, World Scientific Publishing, Singapore, 1996, pp. 139-169.
33. Tomasi, J. and Persico, M., Chem. Rev., 94 (1994) 2027.
34. Cramer, C.J. and Truhlar, D.G., In Tapia, O. and Bertraán, J. (Eds.) Solvent Effects and Chemical Reactivity, Kluwer Academic Publishers, Dordrecht, 1996, pp. 1-80.
35. Barone, V., Cossi, M. and Tomasi, J., J. Comput. Chem., 19 (1998) 404.
36. Sitkoff, D., Sharp, K.A. and Honig, B., J. Phys. Chem., 98 (1994) 1978.
37. Still, W.C., Tempczyk, A., Hawley, R.C. and Hendrickson, T., J. Am. Chem. Soc., 112 (1990) 6127.
38. Luty, B.A., Wasserman, Z.R., Stouten, P.F.W., Hodge, C.N., Zacharias, M. and McCammon, J.A., J. Comput. Chem., 16 (1995) 454.
39. DELPHI computer program, Biosym Technologies, San Diego, CA, 1992.
40. Giesen, D.J., Gu, M.Z., Cramer, C.J. and Truhlar, D.G., J. Org. Chem., 61 (1996) 8720.
41. Giesen, D.J., Hawkins, G.D., Liotard, D.A., Cramer, C.J. and Truhlar, D.G., Theor. Chem. Acc., 98 (1997) 85.
42. Luque, F.J., Bachs, M., Alemán, C. and Orozco, M., J. Comput. Chem., 17 (1996) 806.
43. Luque, F.J., Zhang, Y., Alemán, C., Bachs, M., Gao, J. and Orozco, M., J. Phys. Chem., 100 (1996) 4269.
44. Miertus, S., Scrocco, E. and Tomasi, J., Chem. Phys., 55 (1981) 117.
45. Miertus, S. and Tomasi, J., Chem. Phys., 65 (1982) 239.
46. Pierotti, R.A., Chem. Rev., 76 (1976) 717.
47. Claverie, P., In Pullman, B. (Ed.) Intermolecular Interactions: from Diatomics to Biomolecules, Wiley, Chichester, 1978, p. 71.
48. Bachs, M., Luque, F.J. and Orozco, M., J. Comput. Chem., 15 (1994) 446.
49. Hoshi, H., Sakurai, M., Inoue, Y. and Chûjô, R., J. Mol. Struct. (Theochem), 180 (1988) 267.
50. Coitiño, E.L., Tomasi, J. and Cammi, R., J. Comput. Chem., 16 (1995) 20.
51. Cammi, R. and Tomasi, J., J. Comput. Chem., 16 (1995) 1449.
52. Cammi, R. and Tomasi, J., J. Chem. Phys., 101 (1994) 3888.
53. Cammi, R. and Tomasi, J., J. Chem. Phys., 101 (1994) 7495.
54. Luque, F.J., Bofill, J.M. and Orozco, M., J. Chem. Phys., 103 (1995) 10183.
55. Ángyán, J.G., J. Chem. Phys., 107 (1997) 1291.
56. Luque, F.J., Bofill, J.M. and Orozco, M., J. Chem. Phys., 107 (1997) 1293.
57. Luque, F.J. and Orozco, M., J. Phys. Chem., 101 (1997) 5573.
58. Orozco, M., Roca, R., Alemán, C., Busquets, M.A., López, J.M. and Luque, F.J., J. Mol. Struct. (Theochem), 371 (1996) 269.
59. Colominas, C., Orozco, M., Luque, F.J., Borrell, J.I. and Teixidó, J., J. Org. Chem., 63 (1998) 4947.
60. Tomasi, J., Bonaccorsi, R., Cammi, R. and Olivares del Valle, F.J., J. Mol. Struct. (Theochem), 234 (1991) 401.
61. Olivares del Valle, F.J. and Aguilar, M.A., J. Comput. Chem., 13 (1992) 115.
62. Luque, F.J., Negre, M.J. and Orozco, M., J. Phys. Chem., 97 (1993) 4386.
63. Orozco, M. and Luque, F.J., Chem.Phys., 182 (1994) 237.
64. Luque, F.J., Bachs, M. and Orozco, M., J. Comput. Chem., 15 (1994) 847.
65. Orozco, M., Bachs, M. and Luque, F.J., J. Comput. Chem., 16 (1995) 563.
66. Giesen, D.J., Chambers, C.C., Cramer, C.J. and Truhlar, D.G., J. Phys. Chem. B., 101 (1997) 5084.
67. Giesen, D.J., Chambers, C.C., Hawkins, G.D., Cramer, C.J. and Truhlar, D.G., In Irikura, K. and Frurip, D.J. (Eds.), Computational Thermochemistry: Prediction and Estimation of Molecular Thermodynamics, ACS Symposium Series, American Chemical Society, Washington, DC, 1998, p. 285.
68. Hawkins, G.D., Liotard, D.A., Cramer, C.J. and Truhlar, D.G., J. Org. Chem., 63 (1998) 4305.
69. Chambers, C.C., Giesen, D.J., Hawkins, G.D., Vaes, W.H., Cramer, C.J. and Truhlar, D.G., In Truhlar, D.G., Howe, W.J., Blaney, J.M., Hopfinger, A.J. and Dammkoehler, R.A (Eds.) Computer-Assisted Drug Design, Springer, New York, NY, 1998.
70. Peterson, M. and Poirier, R., MONSTERGAUSS; Dept. of Chemistry, Univ. of Toronto, Canada; version modified by Cammi, R., Bonaccorsi, R. and Tomasi, J., University of Pisa, Pisa 1987. Modified by Luque, F.J. and Orozco, M., University of Barcelona, Barcelona 1997.
71. Stewart, J.J.P., MOPAC 93 Rev 2. Fujitsu Limited, 1993. Modified by Luque, F.J. and Orozco, M., University of Barcelona, Barcelona 1997.
72. Luque, F.J. and Orozco, M., MOPETE/MOPFIT, University of Barcelona, Barcelona 1998.
73. INSIGHT-II computer program, Biosym Technologies, San Diego, CA, 1994.
74. Alhambra, C., Luque, F.J. and Orozco, M., J. Comput. Chem., 15 (1994) 12.
75. Dewar, M.J.S., Zoebisch, E.G., Horsley, E.F. and Stewart, J.J.P., J. Am. Chem. Soc., 107 (1985) 3902.
76. Stewart, J.J.P., J. Comput. Chem., 10 (1989) 209.
77. Backbro, K., Lowgren, S., Osterlund, K., Atepo, J., Unge, T., Hulten, J., Bonham, N.M., Schaal, W., Karlen, A. and Hallberg, A., J. Med. Chem., 40 (1997) 898.
78. Lide, D.R. (Ed.) Handbook of Organic Solvents, CRC Press, Boca Raton, FL, 1995.