Heuristic lipophilicity potential for computer-aided rational drug design: Optimizations of screening functions and parameters

Journal of Computer-Aided Molecular Design

Volumn 12, Issue 5, 1998, Pages 451-470

  Du, Qishi ^a   Mezey, Paul G ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

Combinatorial chemistry; Drug design; Electrostatic potential; Lipophilicity potential; Molecular modeling; Molecular shape

Indexed keywords

BIOCHIPS; RATIONAL FUNCTIONS;

COMBINATORIAL CHEMISTRY; DEPENDENT FUNCTIONS; DRUG DESIGN; ELECTROSTATIC POTENTIALS; EXPONENTIALS; LIPOPHILICITY; LIPOPHILICITY POTENTIAL; MOLECULAR SHAPES; POWER; SCREENING FUNCTIONS;

OPTIMIZATION;

LIPID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER AIDED DESIGN; DRUG DESIGN; HYDROGEN BOND;

COMPUTER-AIDED DESIGN; DRUG DESIGN; HYDROGEN BONDING; LIPIDS; MOLECULAR STRUCTURE;

EID: 0032151474     PISSN: 0920654X     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1008040309114     Document Type: Article

References (51)

1. Du, Q., Arteca, G.A. and Mezey, P.G., J. Comput.-Aided Mol. Design, 11 (1997) 503.
2. Du, Q. and Arteca, G.A., J. Comput.-Aided Mol. Design, 10 (1996) 133.
3. Ghose, A.K. and Crippen, G.M., J. Comput. Chem., 7 (1986) 565.
4. Furet, P., Sele, A. and Cohen, N.C., J. Mol. Graph., 6 (1988) 182.
5. Heiden, W., Moeckel, G. and Brickmann, J., J. Comput.-Aided Mol. Design, 7 (1993) 503.
6. Viswanadhan, V.N., Ghose, A.K., Revankar, G.R. and Robins, R.K., J. Chem. Inf. Comput. Sci., 29 (1989) 163.
7. Kantola, A., Villar, H.O. and Loew, G. H., J. Comput. Chem., 12 (1991) 681.
8. Alkorta, I. and Villar H.O., Int. J. Quantum Chem., 44 (1992) 203.
9. Eisenberg, D., Weiss, R.M. and Terwilliger, T.C., Nature, 299 (1982) 371.
10. von Heijne, G. and Blomberg, C., Eur. J. Biochem., 97 (1979) 175
11. Ooi, T., Oobatake, M., Némethy, G. and Scheraga, H.A., Proc. Natl. Acad. Sci. USA, 84 (1987) 3086.
12. Cabani, S., Conti, G. and Lepori, L., Trans. Faraday Soc., 67 (1971) 1933.
13. Pleiss, M.A. and Grunewald, G.L., J. Med. Chem., 26 (1983) 1760.
14. Klopman, G., Namboodiri, K. and Schochet, M., J. Comput. Chem., 6 (1985) 28.
15. Israelachvili, J.N., Intermolecular and Surface Forces, Academic Press, London, 1992.
16. Politzer, P., In: Politzer, P. and Truhlar, D.G. (Eds.), Chemical Applications of Atomic and Molecular Electrostatic Potentials, Use of the Electrostatic Potential as a Guide to Understanding Molecular Properties, Plenum Press, New York, NY, 1981.
17. Murray, J.S., Ranganathan, S. and Politzer, P., J. Org. Chem., 56 (1991) 3734.
18. Murray, J.S., Brinck, T., Lane, P., Paulsen, K. and Politzer, P., J. Mol. Struct. (Theochem), 307 (1994) 55.
19. Tomasi, J., In: Politzer, P. and Truhlar, D.G. (Eds.), Chemical Applications of Atomic and Molecular Electrostatic Potentials, Use of the Electrostatic Potential as a Guide to Understanding Molecular Properties, Plenum Press, New York, NY, 1981.
20. Náray-Szabó, G., J. Mol. Struct. (Theochem), 138 (1986) 197.
21. Náray-Szabó, G., J. Mol. Graph., 7 (1989) 76.
22. Náray-Szabó, G., Int. J. Quantum. Chem.: Quant. Biol. Symp., 16 (1989) 87.
23. Náray-Szabó, G. and Nagy, P., Int. J. Quantum. Chem., 35 (1989) 215.
24. Murray, J.S., Brinck, T., Lane, P., Paulsen, K. and Politzer, P., J. Mol. Struct. (Theochem), 307 (1993) 55.
25. Murray, J.S., Brinck, T. and Politzer, P., J. Phys. Chem., 97 (1993) 13807.
26. Hansch, C. and Leo, A., Substituent Constants for Correlation Analysis in Chemistry and Biology, Wiley, New York, NY (1979).
27. Rekker, R.F., The Hydrophobic Fragmental Constants, Eisevier, New York, NY (1977).
28. Eisenberg, D. and McLachlan, A.D., Nature, 319 (1986) 199.
29. Dughan, L., Burt, C. and Richards, W.G., J. Mol. Struct. (Theochem), 481 (1991) 235.
30. Mishra, P.C. and Kumar, A., In: Sen, K. (Ed.), 'Topics in Current Chemistry (174), Molecular similarity II', Springer-Verlag, New York, NY
31. Platt, D.E. and Silverman, B.D., J. Comput. Chem., 17 (1996) 358.
32. Israelachvili, J.N. and Pashley, R.M., Nature, 300 (1982) 341.
33. Marcelja, S., Mitchell, D.J., Ninham, B.W. and Sculley, M.J., J. Chem. Soc. Faraday Trans, 73 (1977) 630.
34. Audry, E., Dubost, J.P., Colleter, J.C. and Dallet, P., Eur. J. Med. Chem. Chim. Thér., 21 (1986) 71.
35. Audry, E., Dubost, J.P., Dallet, P., Langlois, M.H. and Colleter, J.C., Eur. J. Med. Chem. Chim. Thér., 24 (1989) 155.
36. Audry, E., Dubost, J.P., Dallet, P., Langlois, M.H. and Colleter, J.C., Eur. J. Med. Chem., 24 (1989) 155.
37. Croizet, F., Langlois, M.H., Dubost, J.P., Braquet, P., Audry, E., Dallet, Ph. and Colleter, J.C., J. Mol. Graph., 8 (1990) 153.
38. Fauchére, J.L., Quarendon, P. and Kaetterer, L., J. Mol. Graph., 6 (1988) 203.
39. Stillinger, F.H. and Rahman, A., J. Chem. Phys., 60 (1974) 1545.
40. Du, Q. and Arteca, G.A., J. Comput. Chem., 17 (1996) 1258.
41. Connolly, M.L., Science, 221 (1983) 709.
42. Connolly, M.L., J. Appl. Crystallog., 16 (1983) 548.
43. Connolly, M.L., J. Am. Chem. Soc., 107 (1985) 1118.
44. Leo, A., Hansch, C. and Elkins, D., Chem. Rev., 71 (1971) 525.
45. Cabani, S. and Gianni, P., J. Chem. Soc., Faraday Trans. I, 75 (1979) 1184.
46. Cabani, S., Gianni, P., Mollica, V. and Lepori, L., J. Sol. Chem., 10 (1981) 563.
47. Lee, S.H. and Rossky, P.J., J. Chem. Phys., 100 (1994) 3334.
48. Piculell, L., J. Chem. Soc., Faraday Trans., 82 (1986) 387.
49. Piculell, L. and Halle, B., J. Chem. Soc., Faraday Trans., 82 (1986) 401.
50. Halle, B. and Piculell, L., J. Chem. Soc., Faraday Trans., 82 (1986) 415.
51. Halle, B., Andersson, T., Forsén, S. and Lindman B., J. Am. Chem. Soc., 103 (1981) 500.