Progress in the use of HPLC for evaluation of lipophilicity

Current Computer-Aided Drug Design

Volumn 2, Issue 4, 2006, Pages 327-340

  Nasal, Antoni ^a   Kaliszan, Roman ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Electrochromatographic methods; Gradient elution; Lipophilicity; Log P; RP HPLC

Indexed keywords

BIOCHEMISTRY; CHROMATOGRAPHY;

DRUG CANDIDATES; ELECTROCHROMATOGRAPHIC METHOD; EXPONENTIAL INCREASE; GRADIENT ELUTION; LIPOPHILICITY; LIPOPHILICITY PARAMETERS; LOG P; MULTICOMPONENT MIXTURE; ORGANIC SYNTHESIS; RP-HPLC;

MIXTURES;

2 (2,4 DIHYDROXYPHENYL)BENZOTHIAZOLE DERIVATIVE; 3,4 DICHLOROANILINE; ALPRENOLOL; ANTIARRHYTHMIC AGENT; ANTIFUNGAL AGENT; ANXIOLYTIC AGENT; ATENOLOL; AZAPIRONE DERIVATIVE; BETAXOLOL; FLUPHENAZINE; FUROCOUMARIN DERIVATIVE; METOPROLOL; NONSTEROID ANTIINFLAMMATORY AGENT; NUCLEOSIDE DERIVATIVE; OCTANOL; OXPRENOLOL; PESTICIDE; PHENOTHIAZINE; PINDOLOL; PROPRANOLOL; QUINIDINE; QUININE; RESORCINOL; SEROTONIN UPTAKE INHIBITOR; THIORIDAZINE; TIMOLOL; UNCLASSIFIED DRUG; UNINDEXED DRUG; VERAPAMIL; WATER; XENOBIOTIC AGENT;

ANALYTICAL PARAMETERS; CAPILLARY ELECTROCHROMATOGRAPHY; CHEMICAL ANALYSIS; COMPUTER MODEL; CORRELATION ANALYSIS; DRUG DESIGN; DRUG INFORMATION; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; HUMAN; HYDROPHOBICITY; LIPOPHILICITY; MICELLAR ELECTROKINETIC CHROMATOGRAPHY; MICELLAR LIQUID CHROMATOGRAPHY; MICROEMULSION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PARTITION COEFFICIENT; PLANAR CHROMATOGRAPHY; RELIABILITY; REVIEW; SEPARATION TECHNIQUE; STRUCTURE ACTIVITY RELATION;

EID: 33845938738     PISSN: 15734099     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340906778992328     Document Type: Review

References (135)

1. Ekins, S.; Waller, C.L.; Swaan, P.W.; Cruciani, G.; Wrighton, S.A.; Wikel, J.H.J. J. Pharm. Toxicol. Methods, 2000, 44, 251.
2. Williams G.P. Drug Discov. Today, 2004, 9, 515.
3. Kube, D.M. Drug Discov. Dev., 2003, 6, 50.
4. Kaliszan, R. In Advances in Chromatography; Brown, P.R.; Grushka, E., Eds.; Marcel Dekker: New York, 1993; pp. 147-176.
5. Kaliszan, R. Trends Anal. Chem., 1999, 18, 400.
6. Boyce, C.B.C.; Milborrow, B.V. Nature, 1965, 208, 537.
7. Kaliszan, R. Quantitative Structure-Chromatographic Retention Relationships, Wiley: New York, 1987.
8. Kuchar, M.; Rejholec, V. The Use of Quantitative Structure-Biological Activity Relationships (in Czech), Academia: Praha, 1987.
9. Pliška, V.; Testa, B.; van de Waterbeemd, H.; Eds.; Lipophilicity in Drug Action and Toxicology, VCH Weinheim: New York, 1994.
10. Kaliszan, R. Structure and Retention in Chromatography. A Chemometric Approach, Harwood Academic: Amsterdam, 1997.
11. Forgács, E.; Cserháti, T. Molecular Bases of Chromatographic Separations, CRC Press, Boca Raton, FL, 1997.
12. Valkó, K. In Separation Methods in Drug Synthesis and Purification; Valkó, K., Ed.; Elsevier: Amsterdam, 2000; pp. 535-583.
13. Braumann, T.; Weber, G.; Grimme, L.H. J. Chromatogr., 1983, 261, 329.
14. Kaliszan, R. Quant. Struct.-Act. Relat., 1990, 9, 83.
15. Kaliszan, R. Anal. Chem., 1992, 64, 619A.
16. Dorsey, J.G.; Khaledi, M.G. J. Chromatogr. A, 1993, 656, 485.
17. Lambert, W.J. J. Chromatogr. A, 1993, 656, 469.
18. Pagliara, A.; Khamis, E.; Trinh, A.; Carrupt, P.-A.; Tsai, R.-S.; Testa, B. J. Liq. Chromatogr., 1995, 18, 1721.
19. Nasal, A.; Siluk, D.; Kaliszan, R. Curr. Med. Chem., 2003, 10, 381.
20. Kaliszan, R.; Nasal, A.; Markuszewski, M.J. Anal. Bioanal. Chem., 2003, 377, 803.
21. Tchapla, A.; Colin, H.; Guiochon, G. Anal. Chem., 1984, 56, 621.
22. Sentell, K.B.; Dorsey, J.G. Anal. Chem., 1989, 61, 930.
23. Kaliszan, R. Adv. Chromatogr., 1993, 33, 147.
24. Novotny, L.; Abdel-Hamid, M.; Hamza, H.J. Pharm. Biomed. Anal., 2000, 24, 125.
25. Dai, J.; Jin, S.; Yao, S.; Wang, L.S. Chemosphere, 2001, 42, 899.
26. Vrakas, D.; Panderi, I.; Hadjipavlou-Litina, D.; Tsantili-Kakoulidou, A. QSAR Comb. Sci., 2005, 24, 254.
27. Caffieri, S. J. Pharm. Sci., 2001, 90, 732.
28. Pehourcq, F.; Matoga, M.; Jarry, C.; Bannwarth, B. J. Liq. Chromatogr. Rel. Technol., 2001, 24, 2177.
29. Jiskra, J.; Claessens, H.A.; Cramers, C.A.; Kaliszan, R. J. Chromatogr. A, 2002, 977, 193.
30. Kaliszan, R.; van Straten, M.A.; Markuszewski, M.; Cramers, C.A.; Claessens, H.A. J. Chromatogr. A, 1999, 855, 455.
31. Lombardo, F.; Shalayeva, M.Y.; Tupper, K.A.; Gao, F.; Abraham, M.H. J. Med. Chem., 2000, 43, 2922.
32. Lombardo, F.; Shalayeva, M.Y.; Tupper, K.A.; Gan, F.; Abraham, M.H. J. Med. Chem., 2001, 44, 2490.
33. Ayouni, L.; Cazorla, G.; Chaillou, D.; Herbreteau, B.; Rudaz, S.; Lantéri, P.; Carrupt, P.-A. Chromatographia, 2005, 62, 251.
34. Pehourcq, F.; Thomas, J.; Jarry, C. J. Liq. Chrom. Rel. Technol., 2000, 23, 443.
35. Pidgeon, C.; Venkatarum, U.V. Anal. Biochem., 1989, 176, 36.
36. Pidgeon, C. Enz. Microb. Technol., 1990, 12, 149.
37. Thurnhofer, H.; Schnabel, J.; Betz, M.; Lipka, G.; Pidgeon, C.; Hauser, H. Biochim. Biophys. Acta, 1991, 1064, 275.
38. Pidgeon, C.; Marcus, C.; Alvarez, F. In Applications of Enzyme Biotechnology; Baldwin, T.D.; Kelly, J.W., Eds.; Plenum Press: New York, 1992, pp. 201-220.
39. Kaliszan R.; Kaliszan, A.; Wainer, I.W. J. Pharm. Biomed. Anal., 1993, 11, 505.
40. Kaliszan, R.; Nasal, A.; Buciński, A. Eur. J. Med. Chem., 1994, 29, 163.
41. Stewart, B.H.; Chung, F.Y.; Tait, B.; John, C.; Chan, O.H. Pharm. Res., 1998, 15, 1401.
42. Salminen, T.; Pulli, A.; Taskinen, J. J. Pharm. Biomed. Anal., 1997, 15, 469.
43. Ducarme, A.; Neuwels, M.; Goldstein, S.; Massingham, R. Eur. J. Med. Chem., 1998, 33, 215.
44. Taillardat-Bertschinger, A.; Barbato, F.; Quercia, M.T.; Carrupt, P.-A.; Reist, M.; La Rotonda, M.I.; Testa, B. Helv. Chim. Acta, 2002, 85, 519.
45. Barbato, F.; di Martino, G.; Grumetto, L.; La Rotonda, M.I. Eur. J. Pharm. Sci., 2004, 22, 261.
46. Nasal, A.; Sznitowska, M.; Buciński, A.; Kaliszan, R. J. Chromatogr A, 1995, 692, 83.
47. Barbato, F.; La Rotonda, M.I.; Quaglia, F. Pharm. Res., 1997, 14, 1699.
48. Vrakas, D.; Hadjipavlou-Litina, D.; Tsantili-Kakoulidou, A. J. Pharm. Biomed. Anal., 2005, 39, 908.
49. Barbato, F.; di Martino, G.; Grumetto, L.; La Rotonda, M.I.F. Eur. J. Pharm. Sci., 2005, 45, 379.
50. Barbato, F.; La Rotonda, M.I.; Quaglia, F. J. Pharm. Sci., 1997, 86, 225.
51. Sabatka, J.J.; Minick, D.K.; Shumaker, T.J.; Hodgson, Jr., G.L.; Brent, D.A. J. Chromatogr., 1987, 384, 349.
52. Braumann, T. J. Chromatogr., 1988, 373, 191.
53. Unger, S.H.; Chiang, G.H. J. Med. Chem., 1981, 24, 162.
54. Minnick, D.J.; Sabatka, J.J.; Brent, D.A. J. Liq. Chromatogr., 1987, 10, 2565.
55. Minnick, D.J.; Frenz, J.H.; Patrick, M.A.; Brent, D.A. J. Med. Chem., 1988, 31, 1923.
56. Kaliszan, R.; Marszałł, M.P.; Markuszewski, M.J.; Baczek, T.; Pernak, J. J. Chromatogr. A, 2004, 1030, 263.
57. McCalley, D.V. J. Sep. Sci., 2003, 26, 187.
58. Buszewski, B.; Welerowicz, T. Comb. Chem. High Throughput Screen., 2004, 7, 291.
59. Stella, C.; Seuret, P.; Rudaz, S.; Carrupt, P.-A.; Gauvrit, P.-A.; Lantéri, P.; Veuthey, J.-L. J. Sep. Sci., 2002, 25, 1351.
60. Stella, C.; Galland, A.; Liu, X.; Testa, B.; Rudaz, S.; Veuthey, J.-L.; Carrupt, P.-A. J. Sep. Sci., 2005, 28, 2350.
61. Tanaka, N.; Nagayama, H.; Kobayashi, H.; Ikegami, T.; Hosoya, K.; Ishizuka, N.; Minakuchi, H.; Nakanishi, K.; Cabrera, K.; Lubda, D. J. High Resolut. Chromatogr., 2000, 23, 111.
62. Cabrera, K.; Lubda, D.; Eggenweiler, H.-M.; Minakuchi, H.; Nakanishi, K. J. High Resolut. Chromatogr., 2000, 23, 93.
63. Ikegami, T.; Tanaka, N. Curr. Opinion Chem. Biol., 2004, 8, 527.
64. Rieux, L.; Niederländer, H.; Verpoorte, E.; Bischoff, R. J. Sep. Sci., 2005, 28, 1628.
65. Kato, M.; Sakai-Kato, K.; Toyo'oka, T. J. Sep. Sci., 2005, 28, 1893.
66. Zou, H.; Huang, X.; Ye, M.; Luo, Q. J. Chromatogr. A, 2002, 954, 5.
67. Li, Y.; Zhang, J.; Xiang, R.; Yang, Y.; Horvath, C. J. Sep. Sci., 2004, 27, 1467.
68. Svec, F. J. Sep. Sci., 2004, 27, 1419.
69. Baczek, T.; Wiczling, P.; Marszałł, M.P.; Vander Heyden, Y.; Kaliszan, R. J. Proteome Res., 2005, 4, 555.
70. Valkó, K.; Slegel, P. J. Chromatogr., 1993, 631, 49.
71. Kuchar, M.; Jelinkova, M. In QSAR in Design of Bioactive Compounds; Kuchar, M., Ed.; J.R. Prous Science Publishers: Barcelona, 1992; pp. 67.
72. Du, C.M.; Valkó, K.; Bevan, C.; Reynolds, D.; Abraham, M.H. Anal. Chem., 1998, 70, 4228.
73. Valkó, K.; Plass, M.; Bevan, C.; Reynolds, D.; Abraham, M.H. J. Chromatogr. A, 1998, 797, 41.
74. Krass, J.D.; Jastorff, B.; Genieser, H.G. Anal. Chem., 1997, 69, 2575.
75. Snyder, L.R.; Dolan, J.W.; Gant, J.R. J. Chromatogr., 1979, 165, 3.
76. Dolan, J.W.; Gant, J.R.; Snyder, L.J. J. Chromatogr., 1979, 165, 31.
77. Snyder, L.J.; Dolan, J.W. Adv. Chromatogr., 1998, 38, 115.
78. Soczewiński, E.; Wachtmeister, C.A. J. Chromatogr., 1962, 7, 311.
79. Snyder, L.J.; Dolan, J.W. J. Chromatogr. A, 1996, 721, 3.
80. Kaliszan, R.; Wiczling, P., Markuszewski, M.J. Anal. Chem., 2004, 76, 749.
81. Kaliszan, R.; Haber, P.; Baczek, T.; Siluk, D. Pure Appl. Chem., 2001, 73, 1465.
82. Kaliszan R.; Haber, P.; Baczek, T.; Siluk, D.; Valkó, K. J. Chromatogr. A, 2002, 965, 117.
83. Kaliszan, R.; Blain, R.W.; Hartwick, R.A. Chromatographia, 1988, 25, 5.
84. Donovan, S.F.; Pescatore, M.C. J. Chromatogr. A, 2002, 952, 47.
85. Gulyaeva, N.; Zaslavsky, A.; Lechner, P., Chlenov, M.; McConnell, O.; Chait, A.; Kipnis, V.; Zaslavsky, B. Eur. J. Med. Chem., 2003, 38, 391.
86. Hansch, C.; Leo, A. Exploring QSAR: Fundamentals and Application in Chemistry and Biology, American Chemical Society: Washington, 1995.
87. Gulyaeva, N.; Zaslavsky, A.; Lechner, P.; Chait, A.; Zaslavsky, B. J. Pharm. Sci., 2001, 90, 1366.
88. Gulyaeva, N.; Zaslavsky, A.; Lechner, P.; Chlenov, M.; Chait, A.; Zaslavsky, B. Eur. J. Pharm. Sci., 2002, 17, 81.
89. Welerowicz, T.; Buszewski, B. Biomed. Chromatogr., 2005, 19, 725.
90. Wiczling, P.; Markuszewski, M.J.; Kaliszan, R. Anal. Chem., 2004, 76, 3069.
91. Wiczling, P.; Markuszewski, M.J.; Kaliszan, M.; Kaliszan, R. Anal. Chem., 2005, 77, 449.
92. Kaliszan, R.; Wiczling, P. Anal. Bioanal. Chem., 2005, 382, 718.
93. Wiczling, P.; Kawczak, P.; Nasal, A.; Kaliszan, R. Anal. Chem., 2006, 78, 239.
94. De Marco, A.; de Candia, M.; Carotti, A.; Cellamare, S.; De Candia, E.; Altomare, C. Eur. J. Pharm. Sci., 2004, 22, 153.
95. Matysiak, J.; Niewiadomy, A.; Senczyna, B.; Zabinska, A.; Rózylo, J.K. J. AOAC Int., 2004, 87, 579.
96. Nasal, A.; Buciński, A.; Baczek, T.; Wojdełko, A. Comb. Chem. High Throughput Screen., 2004, 7, 313.
97. Bartalis, J.; Halaweish, F.T. J. Chromatogr. B, 2005, 818, 159.
98. Taillardat-Bertschinger, A.; Carrupt, P.-A.; Barbato, F.; Testa, B. J. Med. Chem., 2003, 46, 655.
99. Pehourcq, F.; Matoga, M.; Bannwarth, B. Fundam. Clin. Pharmacol., 2004, 18, 65.
100. Yen, T.E.; Agatonovic-Kustrin, S.; Evans, A.M.; Nation, R.L.; Ryand, J. J. Pharm. Biomed. Anal., 2005, 38, 472.
101. Terabe, S.; Otsuka, K.; Ichikawa, K.; Tsuchiya, A.; Ando, T. Anal. Chem., 1984, 56, 111.
102. Terabe, S.; Otsuka, K.; Ando, T. Anal. Chem., 1985, 57, 834.
103. Takeda, S.; Wakida, S.; Yamane, M.; Kawahara, A.; Higashi, K. Anal. Chem., 1993, 65, 2489.
104. Muijselaar, P.G.H.M.; Claessens, H.A.; Cramers, C.A. Anal. Chem., 1994, 66, 635.
105. Abraham, M.H.; Treiner, C.; Rosés, M.; Ràfols, C.; Ishihama, Y. J. Chromatogr. A, 1996, 752, 243.
106. Fuguet, E.; Ràfols, C.; Bosch, E.; Abraham, M.H.; Rosés, M. J. Chromatogr. A, 2002, 942, 237.
107. Khaledi, M.G., Ed. High Performance Liquid Electrophoresis, Wiley: New York, 1998.
108. Berthod, A.; Carda-Broch, S. J. Chromatogr. A, 2004, 1037, 3.
109. Mrestani, Y.; Marestani, Z.; Neubert, R.H.H. Electrophoresis, 2001, 22, 3573.
110. Müller, L.; Bednár, P.; Barták, P.; Lemr, K.; Ševcik, J. J. Sep. Sci., 2005, 28, 1285.
111. Mrestani, Y.; Marestani, Z.; Neubert, R.H.H. J. Pharm. Biomed. Anal., 2001, 26, 883.
112. Rogachev, I.; Serra, C.; Farran, A.; Cortina, J.L.; Gressel, J.; Warshawsky, A. React. Funct. Polymers, 2003, 54, 17.
113. Rappel, C.; Galanski, M.; Yasemi, A.; Habala, L.; Keppler, B.K. Electrophoresis, 2005, 26, 878.
114. Haung, X.C.; Quesada, M.A.; Mathies, R.A. Anal. Chem., 1992, 64, 967.
115. Taylor, J.A.; Yeung, E.S. Anal. Chem., 1993, 65, 956.
116. Ueno, K.; Yeung, E.S. Anal. Chem., 1994, 66, 1424.
117. Kambara, H.; Takahashi, S. Nature, 1993, 361, 565.
118. Ma, L.; Gong, X.; Yeung, E. Anal. Chem., 2000, 72, 3383.
119. Gong, X.; Yeung, E. Anal. Chem., 1999, 71, 4989.
120. Zhang, Y.; Gong, X.; Zhang, H.; Larock, R.C.; Yeung, E.S. J. Combin. Chem., 2000, 2, 450.
121. Kang, S.H.; Gong, X.; Yeung, E.S. Anal. Chem., 2000, 72, 3014.
122. Dai, J.; Tu, J.; Anderson, L.N.; Bao, J.J.; Liu, C.; Quay, B.; Wehmeyer, K.R. LCGC North America, 2002, 20, 606.
123. Britz-McKibbin, P.; Nishioka, T.; Terabe, S. Anal. Sci., 2003, 19, 99.
124. Wehmeyer, K.R.; Tu, J.; Jin Y.; King, S.; Stella, M.; Stanton, D.T.; Strasburg, R.; Kenseth, J.; Wong, K.-S. LCGC North America, 2003, 21, 1078.
125. Wong, K.-S.; Kenseth, J.; Strasburg, R. J. Pharm. Sci., 2004, 93, 916.
126. Tu, J.; Halsall, H.B.; Seliskar, C.J.; Limbach, P.A.; Arias, F.; Wehmeyer, K.R.; Heineman, W.R. J. Pharm. Biomed. Anal., 2005, 38, 1.
127. Hansen, S.H. Electrophoresis, 2003, 24, 3900.
128. Armstrong, D.W.; Nome, F. Anal. Chem., 1981, 53, 1662.
129. Berthod, A.; Gerard, I.; Gonnet, C. Anal. Chem., 1986, 58, 1356.
130. Medina-Hernandez, M.J.; Garcia Alvarez-Coque, M.C. Analyst, 1992, 117, 831.
131. Khaledi, M.G.; Breyer, E.D. Anal. Chem., 1989, 61, 1040.
132. Detroyer, A.; Vander Heyden Y.; Cambre, I.; Massart, D.L. J. Chromatogr. A, 2003, 986, 227.
133. Woodrow, B.N.; Dorsey, J.G. Environ. Sci. Technol., 1997, 31, 2812.
134. Bermúdez-Saldaña, J.M.; Escuder-Gilabert, L.; Medina-Hernández, M.J.; Villanueva-Camañas, R.M.; Sagrado, S. J. Chromatogr. B, 2005, 814, 115.
135. Quiñones-Torrelo, C.; Sagrado, S.; Villanueva-Camañas, R.M.; Medina-Hernández, M.J. Biomed. Chromatogr., 2004, 18, 427.