Lipophilicity Measurement by Reversed-Phase High Performance Liquid Chromatography (RP-HPLC)

Lipophilicity in Drug Action and Toxicology

Volumn 4, Issue , 2008, Pages 73-87

  van de Waterbeemd, Han ^a   Kansy, Manfred ^a   Wagner, Björn ^a   Fischer, Holger ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

Hydrogen bond; Hydrophobic interaction chromatography; Logarithm of the isocratic capacity factor; Octadecylsilane; Structure property correlations

Indexed keywords

HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGEN BONDS; HYDROPHOBICITY;

CAPACITY FACTORS; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; LIPOPHILICITY MEASUREMENT; OCTADECYLSILANE; REVERSED-PHASE HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY; STRUCTURE-PROPERTY CORRELATION;

HYDROPHOBIC CHROMATOGRAPHY;

EID: 84958623621     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527614998.ch5     Document Type: Chapter

References (64)

1. Haggerty, W. J., and Murrill, E. A., Res. Dev. 25, 30 (1974)
2. Henry, D., Block, J. H., Anderson, J. L., and Carlson, G. R., J. Med. Chem. 19, 619-626 (1976)
3. Mirrlees, M. S., Moulton, S. J., Murphy, C. T., and Taylor, P. J., J. Med. Chem. 19, 615-619 (1976)
4. Unger, S. H., Cook, J. R., and Hollenberg, J. S, J. Pharm. Sci. 67, 1364-1366 (1978)
5. Kaliszan, R., J. Chromatogr. 220, 71-83 (1981)
6. Lambert, W. J., J. Chromatogr. A 656, 469-484 (1993)
7. Braumann, Th., Weber, G., and Grimme, L. H., J. Chromatogr. 261, 329-343 (1983)
8. El Tayar, N., Van de Waterbeemd, H., and Testa, B., J. Chromatogr. 320, 293-304 (1985)
9. El Tayar, N., Van de Waterbeemd, H., and Testa, B., J. Chromatogr. 320, 305-312 (1985)
10. Reymond, D., Chung, G. N., Mayer, J. M., and Testa, B., J. Chromatogr. 391, 97-109 (1987)
11. Valko, K., Snyder, L. R., and Glajch, J. L., J. Chromatogr. A 656, 501-520 (1993)
12. Schoenmakers, P. J., Billiet, H. A. H., and De Galan, L., J. Chromatogr. 185, 179-195 (1979)
13. Hsieh, M.-M., and Dorsey, J. G., J. Chromatogr. 631, 63-78 (1993)
14. Horvath, C., Melander, W., and Molnar, I., J. Chromatogr. 125, 129-156 (1976)
15. Wells, M. J. M., and Clark, R., J. Chromatogr. 284, 319-355 (1984)
16. Valko, K., and Slégel, P., J. Chromatogr. 631, 49-61 (1993)
17. El Tayar, N., Van de Waterbeemd, H., and Testa, B., Quant. Struct.-Act. Relat. 4, 69-77 (1985)
18. Yamagami, C., Yokota, M., and Takao, N., J. Chroamtogr. A 662, 49-60 (1994)
19. Yamagami, C., Yokota, M. and Takao, N., Chem. Pharm. Bull. 42, 907-912 (1994)
20. Tan, L. C., and Carr, P. W., J. Chromatogr. A 656, 521-535 (1993)
21. Kalizan, R., Quant. Struct-Act. Relat. 9, 83-87 (1990)
22. Rippel, G., Alattyani, E., and Szepésy, L., J. Chromatogr. A 668, 301-312 (1994)
23. Miyake, K., and Terade, H., J. Chromatogr. 157, 386-390 (1978)
24. Taylor, P. J. Hydrophobic properties of drugs. In: Comprehensive Medicinal Chemistry, Vol. 4 Hansch, C., Sammes, P. G. and Taylor, J. B. (Eds.). Pergamon Press: Oxford; 241-294 (1990)
25. El Tayar, N., Tsantili-Kakoulidou, Röthlisberger, T., Testa, B., and Gal, J., J. Chromatogr. 439, 237-244 (1988)
26. Pagliara, A., Khamis, E., Trinh, A., Carrupt, P.-A., Tsai, R.-S. and Testa, B., J. Liq. Chromatogr. 18, 1721-1745 (1995)
27. w values: effect of charge and conformation. In: Trends in QSAR and Molecular Modeling 94. Sanz, F. (Ed.). Prouse: Barcelona 1995
28. Van de Waterbeemd, H., Karajiannis, H., Kansy, M., Obrecht, D., Müller, K., and Lehmann, Chr., Conformation-lipophilicity relationships of peptides and peptide mimetics. In: Trends in QSAR and Molecular Modeling 94. Sanz, F. (Ed.). Prouse: Barcelona 1995
29. Altomare, C., Cellamera, S., Carotti, A., and Ferappi, M., Quant. Struct.-Act. Relat. 12, 261-268 (1993)
30. Miyake, K., and Terada, H., J. Chromatogr. 240, 9-20 (1982)
31. Vallat, P., Fan, W., El Tayar, N., Carrupt, P.-A., and Testa, B., J. Liq. Chromatogr. 15, 2133-2151 (1992)
32. Altomare, C., Tsai, R.-S., El Tayar, N., Testa, B., Carotti, A., Cellamare, S., and De Benedetti, P. G., J. Pharm. Pharmacol. 43, 191-197 (1991)
33. Miyake, K., Kitaura, F., Mizuno, N., and Terada, H., Chem. Pharm. Bull. 35, 377-388 (1987)
34. Rothemund, S., Krause, E., Ehrlich, A., Bienert, M., Glusa, E. and Verhallen, P., J. Chromatogr. A. 661, 77-82 (1994)
35. Haky, J. E. and Vemulapalli, S., J. Liq. Chromatogr. 13, 3111-3131 (1990)
36. Miyake, K., Kitaura, F., Mizuno, N. and Terada, H., J. Chromatogr. 389, 47-56 (1987)
37. Ong, S., Cai, S.-J., Bernai, C., Rhee, D., Qui, X., and Pidgeon, C., Anal. Chem. 66, 782-792 (1994)
38. Kaliszan, R., Nasal, A., and Bucinski, A., Eur. J. Med. Chem. 29, 163-170 (1994)
39. Pidgeon, C., Ong, S., Liu, H., Qui, X., Pidgeon, M., Dantzig, A. H., Munroe, J., Hornback W. J., Kasher, J. S., Glunz, L., and Szczerba, T., J. Med. Chem. 38, 590-594 (1995)
40. Ong, S., Liu, H., Qiu, X., Bhat, G., and Pidgeon, C., Anal. Chem. 67, 755-762 (1995)
41. Kaibara, A., Hohda, C., Hirata, N., Hirose, M., and Nakagawa, T., Chromatographia 29, 275-288 (1990)
42. Tanaka, A., Nakamura, K., Nakanishi, I., and Fujiwara, H., J. Med. Chem. 37, 4563-4566 (1994)
43. Van de Waterbeemd, H., and Testa, B., Adv. Drug Res. 16, 85-225 (1987)
44. Horvath, C., Melander, W. and Molnar, I., J. Anal. Chem. 49, 142-154 (1977)
45. Hanai, T., J. Chromatogr. 550, 313-324 (1991)
46. Belsner, K., Pfeifer, M., and Wilfert, B., J. Chromatogr. 629, 123-134 (1993)
47. Rodgers, A. H., and Khaledi, M. G., Anal. Chem. 66, 327-334 (1994)
48. Zou, H., Zhang, Y., Hong, M., and Lu, P., J. Chromatogr. 625, 169-175 (1992)
49. Martorell, C., Calpena, A. C., Escribano, E., and Poblet, J. M., J. Chromatogr. A. 655, 177-184 (1993)
50. Carr, P. W., Martire, D. E., and Snyder, L. R., Special issue on the retention process inreversed-phase liquid chromatography, J. Chromatogr. 656A, 1-616 (1993)
51. Hanai, T., J. Liq. Chromatogr. 16, 1453-1462 (1993)
52. Carr, P., Microchem. Rev. 48, 4-28 (1993)
53. Cheong, W. J., and Carr, P. W., Anal. Chem. 61, 1524-1529 (1989)
54. Rosés, M., and Bosch, E., Anal. Chim. Acta 274, 147-162
55. Hellai, F., Phan-Tan-Luu, R., and Siouffi, A. M., J. Liq. Chromatogr. 17, 2845-2869 (1994)
56. Park, J. H., Chae, J. J., Nah, T. H., and Jang, M. D., J. Chromatogr. A 664, 149-158 (1994)
57. Helburn, R. S., Rufan, S. C., Pompano, J., Mitchem, D., and Patterson, W. T., Anal. Chem. 66, 610-618 (1994)
58. Tan, L. C., Carr, P. W., Fréchet, J. M. J., and Smigol, V., Anal. Chem. 66, 450-457 (1994)
59. Minick, D. J., Brent, D. A., and Frenz, J., J. Chromatogr. 461, 177-191 (1989)
60. Chen, N., Zhang, Y., and Lu, P., J. Chromatogr. 633, 31-41 (1993)
61. El Tayar, N., Karajiannis, H., and Van de Waterbeemd, H., Amino Acids 8, 125-139 (1995)
62. Büttner, K., Ostresh, J. M., and Houghten, R. A., Induced conformational effects during RPHPLC: Prediction of immunodominant TH-cell antigenic sites. In: Peptides. Chemistry, Structure and Biology. Rivier, J. E., and Marshall, G. R. (Eds.). Escom: Leiden; 423-425 (1990)
63. Lee, D. W., and Cho, B. Y., J. Liq. Chromatogr. 17, 2541-2558 (1994)
64. Harnisch, M., Mockel, H. J. , and Schulze, G., J. Chromatogr. 282, 315-332 (1983)