Lipophilicity profiles of ampholytes

Chemical Reviews

Volumn 97, Issue 8, 1997, Pages 3385-3400

  Pagliara, Alessandra ^a   Carrupt, Pierre Alain ^a   Caron, Giulia ^a   Gaillard, Patrick ^a   Testa, Bernard ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001651580     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9601019     Document Type: Article

References (69)

1. Manners, C. N.; Payling, D. W.; Smith, D. A. Xenobiotica 1988, 18, 331.
2. van de Waterbeemd, H.; Testa, B. In Advances in Drug Research; Testa, B., Ed.; Academic Press: London, 1987; Vol. 16, p 87.
3. Kubinyi, H. QSAR: Hansch Analysis and Related Approaches; VCH Publishers: Weinheim, 1993.
4. Martin, Y. C.; Bush, E. N.; Kyncl, J. J. Comprehensive Medicinal Chemistry. The Rational Design, Mechanistic Study & Therapeutic Applications of Chemical Compounds; Ramsden, C. A., Hansch, C., Sammer, P. G., Taylor, J. B., Eds.; Pergamon: Oxford, 1990; Vol. 4, p 349.
5. Jiang, X. K. Acc. Chem. Res. 1988, 21, 362.
6. Kier, L. B.; Cheng, C. K.; Testa, B.; Carrupt, P. A. Pharm. Res. 1995, 12, 615.
7. Testa, B.; Kier, L. B.; Carrupt, P. A. Med. Res. Rev. 1997, 17, 303.
8. Albert, A., Serjeant, E. P. The Determination of Ionization Constants. A Laboratory Manual; Chapman and Hall: London, 1984.
9. Takacs-Novak, K.; Jozan, M.; Szasz, G. Int. J. Pharm. 1995, 113, 47.
10. Polster, J., Lachmann, H. Spectrometric Titrations. Analysis of Chemical Equilibria; VCH Publishers: Weinheim, 1989.
11. Edsall, J. T.; Martin, R. B.; Hollingworth, B. R. Proc. Natl. Acad. Sci. U.S.A. 1958, 44, 505.
12. Polster, J.; Lachmann, H. Spectrometric Titrations. Analysis of Chemical Equilibria Anonymous VCH Publishers: Weinheim, 1989; p 223.
13. Tsai, R. S.; Carrupt, P. A.; El Tayar, N.; Testa, B.; Giroud, Y.; Andrade, P.; Brée, F.; Tillement, J. P. Helv. Chim. Acta 1993, 76, 842.
14. Rabenstein, D. L. J. Am. Chem. Soc. 1973, 95, 2797.
15. Nagy, P. I.; Takacs-Novak, K. J. Am. Chem. Soc. 1997, 119, 4999.
16. Murthy, K. S.; Zografi, G. J. Pharm. Sci. 1970, 59, 1281.
17. Caron, G.; Gaillard, P.; Carrupt, P. A.; Testa, B. Helv. Chim. Acta 1997, 80, 449.
18. Reymond, F.; Steyaert, G.; Carrupt, P. A.; Testa, B.; Girault, H. H. Helv. Chim. Acta 1996, 79, 101.
19. The detailed experimental procedure used to obtain unpublished results reported here can be obtained directly from the authors.
20. Takacs-Novak, K.; Kökösi, J.; Podanyi, B.; Noszal, B.; Tsai, R. S.; Lisa, G.; Carrupt, P. A.; Testa, B. Helv. Chim. Acta 1995, 78, 553.
21. a of the parent zwitterion (Scheme 4).
22. Metzler, D. E.; Snell, E. E. J. Am. Chem. Soc. 1955, 77, 2431.
23. Takacs-Novak, K.; Avdeef, A.; Box, K. J.; Podanyi, B.; Szasz, G. J. Pharm. Biomed. Anal. 1994, 12, 1369.
24. Z by linear extrapolation to 0% of dioxane.
25. Dearden, J. C.; Bresnen, G. M. Quant. Struct.-Act. Relat. 1988, 7, 133.
26. Tsai, R. S.; Lisa, G.; Carrupt, P. A.; Testa, B. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Publishers: Weinheim, 1996; p 89.
27. Avdeef, A. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Publishers: Weinheim, 1996; p 109.
28. Leo, A. J. Chem. Reu. 1993, 93, 1281.
29. Rekker, R. F., Mannhold, R. Calculation of Drug Lipophilicity; VCH Publishers: Weinheim, 1992.
30. Hansch, C., Leo, A. Substituent Constants for Correlation Analysis in Chemistry and Biology; John Wiley and Sons: New York, 1979.
31. Medchem95 database, Daylight Chemical Information System, Inc., Irvine, CA, 1995.
32. CLIP1.0, Institute of Medicinal Chemistry, University of Lausanne, 1996.
33. Gaillard, P.; Carrupt, P. A.; Testa, B.; Boudon, A. J. Comput.-Aided Mol. Design 1994, 8, 83.
34. Carrupt, P. A.; Testa, B.; Gaillard, P. In Reviews in Computational Chemistry; Boyd, D. B., Lipkowitz, K. B., Eds.; VCH Publishers: Weinheim, 1997; Vol. 11, p 241.
35. Takacs-Novak, K.; Jozan, M.; Hermecz, I.; Szasz, G. Int. J. Pharm. 1992, 79, 89.
36. Takacs-Novak, K.; Noszal, B.; Hermecz, I.; Kereszturi, G.; Podanyi, B.; Szasz, G. J. Pharm. Sci. 1990, 79, 1023.
37. Abraham, M. H.; Takacs-Novak, K.; Mitchell, R. C. J. Pharm. Sci. 1997, 86, 310.
38. Jolliet, P.; Simon, N.; Brée, F.; Urien, S.; Pagliara, A.; Carrupt, P. A.; Testa, B.; Tillement, J. P. Pharm. Res. 1997, 14, 650.
39. Luger, P.; Daneck, K.; Engel, W.; Trummlitz, G.; Wagner, K. Eur. J. Pharm. Sci. 1996, 4, 175.
40. Barbato, F.; Caliendo, G.; La Rotonda, M. I.; Morrica, P.; Silipo, C.; Vittoria, A. Farmaco 1990, 45, 647.
41. Tsuji, A.; Tamai, I. Pharm. Res. 1996, 13, 963.
42. Fauchère, J. L. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Publishers: Weinheim, 1996; p 355.
43. Akamatsu, M.; Yoshida, Y.; Nakamura, H.; Asao, M.; Iwamura, H.; Fujita, T. Quant. Struct.-Act. Relat. 1989, 8, 195.
44. Davis, M. G.; Manners, C. N.; Payling, D. W.; Smith, D. A.; Wilson, C. A. J. Pharm. Sci. 1984, 73, 949.
45. Manners, C. N.; Payling, D. W.; Smith, D. A. Xenobiotica 1989, 19, 1387.
46. Pagliara, A.; Testa, B.; Carrupt, P. A.; Jolliet, P.; Morin, C.; Morin, D.; Urien, S.; Tillement, J. P.; Rihoux, J. P. Submitted for publication.
47. Recanatini, M. J. Pharm. Pharmacol. 1992, 44, 68.
48. Gaillard, P.; Carrupt, P. A.; Testa, B. Bioorg. Med. Chem. Lett. 1994, 4, 737.
49. Altomare, C.; Cellamare, S.; Carotti, A.; Casini, G.; Ferappi, M.; Gavuzzo, E.; Mazza, F.; Carrupt, P. A.; Gaillard, P.; Testa, B. J. Med. Chem. 1995, 38, 170.
50. Caron, G.; Pagliara, A.; Carrupt, P. A.; Gaillard, P.; Testa, B. Helv. Chim. Acta 1996, 79, 1683.
51. Punch, E. D.; Colaizzi, J. L.; Poust, R. I. J. Pharm. Sci. 1973, 62, 545.
52. Hatanaka, T.; Morigaki, S.; Aiba, T.; Katayama, K.; Koizumi, T. Int. J. Pharm. 1995, 125, 195.
53. Jonkman, J. H. G.; Hunt, C. A. Pharmac. Weekblad Sci. Ed. 1983, 5, 41.
54. Testa, B.; Carrupt, P. A.; Gaillard, P.; Tsai, R. S. In Lipophilicity in Drug Action and Toxicology; Pliska, V., Testa, B., van de Waterbeemd, H., Eds.; VCH Publishers: Weinheim, 1996; p 49.
55. Smith, D. A.; Jones, B. C.; Walker, D. K. Med. Res. Rev. 1996, 16, 243.
56. Bernards, C. M.; Hill, H. F. Anesthesiology 1993, 77, 750.
57. Young, R. C.; Ganellin, C. R.; Griffiths, R.; Mitchell, R. C.; Parsons, M. E.; Saunders, D.; Sore, N. E. Eur. J. Med. Chem 1993, 28, 201.
58. Abraham, M. H.; Chadha, H. S.; Mitchell, R. C. J. Pharm. Pharmacol. 1995, 47, 8.
59. Hansch, C.; Björkroth, J. P.; Leo, A. J. Pharm. Sci. 1987, 76, 663.
60. Fujita, T. In Comprehensive Medicinal Chemistry. The Rational Design, Mechanistic Study & Therapeutic Applications of Chemical Compounds; Ramsden, C. A., Hansch, C., Sammer, P. G., Taylor, J. B., Eds.; Pergamon: Oxford, 1990; Vol. 4, p 497.
61. Xiang, T. X.; Anderson, B. D. Pharm. Res. 1993, 10, 1654.
62. Cherni, V. V.; Simonova, M. V.; Sokolov, V. S.; Markin, V. S. Bioelectrochem. Bioenerg. 1990, 23, 17.
63. Chakrabarti, A. C.; Clark-Lewis, I.; Cullis, P. R. Biochemistry 1994, 33, 8479.
64. Beal, M. F.; Hyman, B. T.; Koroshetz, W. Trends Neurosci. 1993, 16, 125.
65. Simon, S.; Roy, D.; Schindler, M. Proc. Natl. Acad. Sci. U.S.A. 1993, 91, 1128.
66. Treuhaft, P. S.; McCarty, D. J. Arthritis Rheum. 1971, 24, 701.
67. Fox, R. I.; Hang, H. I. Lupus 1993, 2, S9.
68. Simchowitz, L.; Crago, E. J. Mol. Pharmacol. 1986, 30, 112.
69. McNiff, P.; Robinson, R. P.; Gabel, C. A. Biochem. Pharmacol. 1995, 50, 1421.