TLC Determination of Drug Lipophilicity

Thin Layer Chromatography in Drug Analysis

Volumn , Issue , 2013, Pages 225-246

  Tešić, Živoslav Lj ^a   Milojković Opsenica, Dušanka M ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85033206355     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/b15637-17     Document Type: Chapter

References (127)

1. Abraham, M.H., H.S. Chandha, and A. Leo. 1994. Hydrogen-bonding. 35. Relationship between high-perfor-mance liquid chromatography capacity factors and water-octanol partition-coefficients. J. Chromatogr. A 685: 203-211.
2. Aleksić, M., J. Odović, D. M. Milojković-Opsenica, and Ž. Lj. Tešić. 2003. Salting-out thin-layer chromatog-raphy of several myorelaxants. J. Planar Chromatogr. Mod. TLC 16: 144-146.
3. Andrić, F.Lj., J.D. Trifković, A.D. Radoičić, S.B. Šegan, Ž.Lj. Tešić, and D.M. Milojković-Opsenica. 2010. Determination of the soil-water partition coefficients (log KOC) of some mono- and poly-substituted phenols by reversed-phase thin-layer chromatography. Chemosphere 81: 299-305.
4. Ares, A.M. and J. Bernal. 2012. Hydrophilic interaction chromatography in drug analysis. Cent. Eur. J. Chem. 10: 534-553.
5. Avdeef, A. 1996. Assessment of distribution-pH profiles. In Methods and Principles in Medicinal Chemistry, eds., V. Pliška, B. Testa, and H. Van de Waterbeemd, pp. 109-139. Weinheim, Germany: VCH.
6. Avdeef, A. 2001. Physico-chemical profiling (solubility, permeability and charge state). Curr. Top. Med. Chem. 1: 277-351.
7. Avdeef, A. 2008. Drug ionization and physicochemical profiling. In Molecular Drug Properties Measurement and Prediction, ed. R. Mannhold, pp. 55-83. Weinheim, Germany: Wiley-VCH.
8. Bard, B., P.-A. Carrupt, and S. Martel. 2009. Lipophilicity of basic drugs measured by hydrophilic interaction chromatography. J. Med. Chem. 52: 3416-3419.
9. Bate-Smith, E.C. and R.G. Westall. 1950. Chromatographic behavior and chemical structure.1. Some naturally occurring phenolic substances. Biochim. Biophys. Acta 4: 427-440.
10. Berthelot, M. and E. Jungfleisch. 1872. On the laws that operate for the partition of a substance between two solvents. Ann. Chim. Phys. 4: 26.
11. Berthod, A. and S. Carda-Broch. 2004. Determination of liquid-liquid partition coefficients by separation methods. J. Chromatogr. A 1037: 3-14.
12. Berthod, A., S. Carda-Broch, and M.C. Garcia-Alvarez-Coque. 1999. Hydrophobicity of ionizable compounds. A theoretical study and measurements of diuretic octanol-water partition coefficients by countercurrent chromatography. Anal. Chem. 71: 879-888.
13. Biagi, G.L., A.M. Barbaro, and A. Sapone. 1994a. Determination of lipophilicity by means of reversed-phase thin-layer chromatography. I: Basic aspects and relationship between slope and intercept of TLC equa-tions. J. Chromatogr. A 662: 341-361.
14. Biagi, G.L., A.M. Barbaro, A. Sapone, and M. Recanatini. 1994b. Determination of lipophilicity by means of reversed-phase thin-layer chromatography. II. Influence of the organic modifier on the slope of the thin-layer chromatographic equation. J. Chromatogr. A 669: 246-253.
15. Bieganowska, M.L., A. Doraczynska-Szopa, and A. Petruczynik. 1995. The retention behavior of some sulfon-amides on different TLC plates. 2. Comparison of the selectivity of the systems and quantitative determi-nation of hydrophobicity parameters. J. Planar Chromatogr. Mod. TLC 8: 122-128.
16. Bouchard, G., P.-A. Carrupt, B. Testa, V. Gobry, and H.H. Girault. 2002. Lipophilicity and solvation of anionic drugs. Chem. Eur. J. 8(15): 3478-3484.
17. Braumann, T. 1986. Determination of hydrophobic parameters by reversed-phase liquid chromatography: Theory, experimental techniques, and application in studies on quantitative structure-activity relation-ships. J. Chromatogr. 373: 191-225.
18. Brooke, D.N., A.J. Dobbs, and N. Williams. 1986. Octanol:water partition coefficient (P). Measurement, estimation, and interpretation, particularly for chemicals with P > 105. Ecotoxicol. Environ. Safe. 11: 251-260.
19. Carlsson, K. and B. Karlberg. 2000. Determination of octanol-water partition coefficients using a micro-vol-ume liquid-liquid flow extraction system. Anal. Chim. Acta 423: 137-144.
20. Casoni, D. and C. Sârbu. 2012. Comprehensive evaluation of lipophilicity of biogenic amines and related compounds using different chemically bonded phases and various descriptors. J. Sep. Sci. 35(8): 915-921.
21. Cichna, M., P. Markl, and J.F.K. Huber. 1995. Determination of true octanol-water partition coefficients by means of solvent generated liquid-liquid chromatography. J. Pharm. Biomed. Anal. 13: 339-351.
22. Cserháti, T., Y.M. Darwish, and G. Matolcsy. 1983. Effect of support characteristics on the determination of the lipophilicity of some neutral, acidic and alkaline compounds by reversed-phase thin-layer chromatogra-phy. J. Chromatogr. 270: 97-104.
23. Dabić, D., M. Natić, Z. Džambaski et al. 2011. Estimation of lipophilicity of N-substituted 2-alkylidene-4-oxothiazolidines by means of reversed-phase thin-layer chromatography. J. Liq. Chromatogr. Relat. Technol. 34: 791-804.
24. Dabić, D., M. Natić, Z. Džambaski, R. Marković, D. Milojković-Opsenica, and Ž. Tešić. 2011. Quantitative structure-retention relationship of new N-substituted 2-alkylidene-4 oxothiazolidines. J. Sep. Sci. 34(18): 2397-2404.
25. Danielsson, L.-G. and Y.-H. Zhang. 1994. Mechanized determination of n-octanol/water partition constants using liquid-liquid segmented flow extraction. J. Pharm. Biomed. Anal. 12: 1475-1481.
26. Danielsson, L.-G. and Y.-H. Zhang. 1996. Methods for determining n-octanol-water partition constants. Trends Anal. Chem. 15: 188-196.
27. De Bruijn, J., F. Busser, W. Seinen, and J. Hermens. 1989. Determination of octanol/water partition coefficients for hydrophobic organic chemicals with the '‘slow stirring” method. Environ. Toxicol. Chem. 8: 499-512.
28. Dorsey, J. and M. Khaledi. 1993. Hydrophobicity estimations by reversed-phase liquid chromatography. Implications for biological partitioning processes. J. Chromatogr. A 656: 485-499.
29. Du, C.M., K. Valko, C. Bevan, D. Reynolds, and M.H. Abraham. 1998. Rapid gradient RP-HPLC method for lipophilicity determination: A solvation equation based comparison with isocratic methods. Anal. Chem. 70: 4228-4234.
30. Dzimiri, N., U. Fricke, and W. Klaus. 1987. Influence of derivatization on the lipophilicity and inhibitory actions of cardiac glycosides on myocardial sodium-potassium ATPase. J. Pharmacol. 91: 31-38.
31. Eadsforth, C.V. 1986. Application of reverse H.P.L.C. for the determination of partition coefficient. Pestic. Sci. 17: 311-325.
32. Eadsforth, C.V. and P. Moser. 1983. Assessment of reverse phase chromatographic methods for determining partition coefficients. Chemosphere 12: 1459-1475.
33. Eros, D., I. Kovesdi, L. Orfi, K. Takacs-Novak, G. Acsady, and G. Keri. 2002. Reliability of logP predictions based on calculated molecular descriptors: A critical review. Curr. Med. Chem. 9(20): 1819-1829.
34. Ettre, L.S. 1993. Nomenclature for chromatography. IUPAC Recommendations. Pure Appl. Chem. 65(4): 819-872.
35. Forgács, E. and T. Cserháti. 1995. Effect of various organic modifier on the determination of the hydrophobicity parameters of non-homologous series of anticancer drugs. J. Chromatogr. A 697: 59-69.
36. Forgács, E., T. Cserháti, R. Kaliszan, P. Haber, and A. Nasal. 1998. Reversed-phase thin-layer chromatographic determination of the hydrophobicity parameters of nonsteroidal anti-inflammatory drugs. J. Planar Chromatogr. 11: 383-387.
37. Fujita, T., J. Iwasa, and C. Hansch. 1964. A new substituent constant, π, derived from partition coefficients. J. Am. Chem. Soc. 86: 5175-5180.
38. Gaica, S.B., D.M. Opsenica, B.A. Šolaja, Ž.Lj. Tešić, and D.M. Milojković-Opsenica. 2002. The retention behavior of some cholic acid derivatives on different adsorbents. J. Planar Chromatogr. Mod. TLC 15: 299-305.
39. Gaudette, L.E. and B.B. Brodie. 1959. Relationship between lipid solubility of drugs and their oxidation by liver microsomes. Biochem. Pharmacol. 2: 89-96.
40. Giaginis, C., D. Dellis, and A. Tsantili-Kakoulidou. 2006. Effect of the aqueous component of the mobile phase on RP-TLC retention and its implication in the determination of lipophilicity for a series of structurally diverse drugs. J. Planar Chromatogr. Mod. TLC 19: 151-156.
41. Giaginis, C. and A. Tsantili-Kakoulidou. 2008a. Alternative measures of lipophilicity: From octanol-water partitioning to IAM retention. J. Pharm. Sci. 97: 2984-3004.
42. Giaginis, C. and A. Tsantili-Kakoulidou. 2008b. Current state of the art in HPLC methodology for lipophilicity assessment of basic drugs. A review. J. Liq. Chromatogr. Relat. Technol. 31: 79-96.
43. Gilpin, R.K. and C.S. Gilpin. 2011. Pharmaceuticals and related drugs. Anal. Chem. 83(12): 4489-4507.
44. Gleeson, M.P. 2008. Generation of a set of simple, interpretable ADMET rules of thumb. J. Med. Chem. 51: 817-834.
45. Gocan, S., G. Cimpan, and J. Comer. 2005. Lipophilicity measurements by liquid chromatography. In Advances in Chromatography, ed., E. Grushka and N. Grinberg, pp. 79-176. Boca Raton, FL: CRC Press.
46. Gupta, S., K. Shanker, and S.K. Srivastava. 2012. HPTLC method for the simultaneous determination of four indole alkaloids in Rauwolfia tetraphylla: A study of organic/green solvent and continuous/pulse sonica-tion. J. Pharm. Biomed. Anal. 66: 33-39.
47. Han, S.-Y., J.-Q. Qiao, Y.-Y. Zhang et al. 2011. Determination of n-octanol/water partition coefficient for DDT-related compounds by RP-HPLC with a novel dual-point retention time correction. Chemosphere 83: 131-136.
48. Hansch, C. and T. Fujita. 1964. ρ-σ-π analysis. A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc. 86: 1616-1626.
49. Hansch, C. and A.J. Leo. 1979. Substituent Constants for Correlation Analysis in Chemistry and Biology. New York: John Wiley.
50. Hawryl, A., D. Cichocki, and M. Waksmundzka-Hajnos. 2008. Determination of the lipophilicity of some psy-chotropic drugs by RP-TLC. J. Planar Chromatogr. 21: 343-348.
51. Héberger, K. 2007. Quantitative structure-(chromatographic) retention relationships. J. Chromatogr. A 1158: 273-305.
52. Henchoz, Y., B. Bard, D. Guillarme, P.A. Carrupt, J.L. Veuthey, and S. Martel. 2009. Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution. Anal. Bioanal. Chem. 394: 707-729.
53. Hill, A.P. and R.J. Young. 2010. Getting physical in drug discovery: A contemporary perspective on solubility and hydrophobicity. Drug Discov. Today 15(15/16): 648-655.
54. Hitzel, L., A.P. Watt, and K.L. Locker. 2000. An increased throughput method for the determination of partition coefficients. Pharm. Res. 17: 1389-1395.
55. Horváth, C., W. Melander, and I. Molnar. 1976. Solvophobic interactions in liquid chromatography with non-polar stationary phases. J. Chromatogr. 125: 129-156.
56. Hulshoff, A. and J.H. Perrin. 1976. Chromatographic characterization of phenothiazine drugs by a reversed-phase thin-layer technique. J. Chromatogr. 129: 249-262.
57. Jafvert, C.T., J.C. Westall, E. Grieder, and R.P. Schwarzenbach. 1990. Distribution of hydrophobic ionogenic organic compounds between octanol and water: Organic acids. Environ. Sci. Technol. 24: 1795-1803.
58. Janjić, T.J., V.M. Živković-Radovanović, and M.B. Ćelap. 1997. Planar salting-out chromatography. J. Serb. Chem. Soc. 62: 1-17.
59. Kah, M. and C.D. Brown. 2008. LogD: Lipophilicity for ionizable compounds. Chemosphere 72: 1401-1408.
60. Kaliszan, R. 2007. QSRR: Quantitative structure-(chromatographic) retention relationships. Chem. Rev. 107: 3212-3246.
61. Kaliszan, R., A. Nasal, and M.J. Markuszewski. 2003. New approaches to chromatographic determination of lipophilicity of xenobiotics. Anal. Bioanal. Chem. 377: 803-811.
62. Karelson, M., V.S. Lobanov, and A.R. Katritzky. 1996. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 96: 1027-1043.
63. Komsta, Ł., R. Skibiński, A. Berecka, A. Gumieniczek, B. Radkiewicz, and M. Radon. 2010. Revisiting thin-layer chromatography as a lipophilicity determination tool-A comparative study on several techniques with a model solute set. J. Pharm. Biomed. Anal. 53: 911-918.
64. Kowalska, T. and W. Prus. 2003. Theory and mechanism of thin-layer chromatography. In Encyclopedia of Chromatography, pp. 821-825. New York: Marcel Dekker.
65. Lederer, M. 1980. Simple and fast separation of the iodotyrosines by thin-layer chromatography. J. Chromatogr. 194: 270-272.
66. Leo, A., C, Hansch, and D. Elkins. 1971. Partition coefficients and their uses. Chem. Rev. 71: 525-616.
67. Leo, J. 1993. Calculating logPoct from structure. Chem. Rev. 93(4): 1281-1306.
68. Mannhold, R. and C. Ostermann. 2008. Prediction of log P with substructure-based methods. In Molecular Drug Properties Measurement and Prediction, ed., R. Mannhold, pp. 357-379. Weinheim, Germany: Wiley-VCH.
69. Martel, S., D. Guillarme, Y. Henchoz et al. 2008. Chromatographic approaches for measuring log P. In Molecular Drug Properties-Measurement and Prediction, ed., R. Mannhold, pp. 331-357. Weinheim, Germany: Wiley-VCH.
70. Meyer, H. 1899. Zur Theorie der Alkoholnarkose I. Welche Eigenschaft der Anaesthetika bedingt ihre nar-kotische Wirkung? Archiv f. Experimentelle Pathologie und Pharmakologie. 42: 109-118.
71. Murakami, F. 1979. Retention behavior of benzene derivatives on bonded reversed-phase columns. J. Chromatogr. 178: 393-399.
72. Nasal, A., D. Siluk, and R. Kaliszan. 2003. Chromatographic retention parameters in medicinal chemistry and molecular pharmacology. Curr. Med. Chem. 10: 381-426.
73. Nernst, W. 1891. Verteilung eines Stoffes zwischen zwei Lösungsmitteln und zwischen Lösungsmitteln und Dampfraum. Z. Phys. Chem. 8: 110-139.
74. Nikitas, P. and A. Pappa-Louisi. 2009. Retention models for isocratic and gradient elution in reversed-phase liquid chromatography. J. Chromatogr. A 1216: 1737-1755.
75. Nowosielski, B.E. and J.B. Fein. 1998. Experimental study of octanol-water partition coefficients for 2, 4, 6-trichlorophenol and pentachlorophenol: Derivation of an empirical model of chlorophenol parti-tioning behaviour. Appl. Geochem. 13: 893-904.
76. Odović, J., M. Aleksić, B. Stojimirović, D. Milojković-Opsenica, and Ž. Tešić. 2009. Normal-phase thin-layer chromatography of some angiotensin converting enzyme (ACE) inhibitors and their metabolites. J. Serb. Chem. Soc. 74(6): 677-688.
77. Odović, J., B. Stojimirović, M. Aleksić, D. Milojković-Opsenica, and Ž. Tešić. 2006. Reversed-phase thin-layer chromatography of some angiotensin converting enzyme (ACE) inhibitors and their active metabolites. J. Serb. Chem. Soc. 71(6): 621-628.
78. Odović, J.V., B.B. Stojimirović, M.B. Aleksić, D.M. Milojković-Opsenica, and Ž.Lj. Tešić. 2005. Examination of the hydrophobicity of ACE inhibitors and their active metabolites by salting-out thin-layer chromatog-raphy. J. Planar Chromatogr. Mod. TLC 18: 102-107.
79. OECD Guidelines for the Testing of Chemicals, OECD Organization for Economic Cooperation and Development, www.oecd.org (accessed July 3, 2013).
80. OECD Guideline for the testing of chemicals, Test No. 107. 1995. Partition coefficient (n-octanol/water): Shake flask method. OECD, Paris. www.oecd.org (accessed July 2, 2013).
81. OECD Guideline for the testing of chemicals, Proposal for Test No. 122. 2000. Partition coefficient (n-octanol/water), pH-Metric method for ionisable substances. OECD, Paris. www.oecd.org (accessed July 2, 2013).
82. OECD Guideline for the testing of chemicals, Test No. 117. 2004. Partition coefficient (n-octanol/water), HPLC method. OECD, Paris. www.oecd.org (accessed July 2, 2013).
83. OECD Guideline for the testing of chemicals, Test No. 123. 2006. Partition coefficient (n-octanol/water): Slow-stirring method. OECD, Paris. www.oecd.org (accessed July 2, 2013).
84. Onisor, C., M. Poša, S. Kevrešan, K. Kuhajda, and C. Sârbu. 2010. Estimation of chromatographic lipophilicity of bile acids and their derivatives by reversed-phase thin layer chromatography. J. Sep. Sci. 33: 3110-3118.
85. Overton, E. 1901. Studien über die Narkose, zugleich ein Beitrag zur allgemeinen Pharmakologie. Jena, Switzerland: Gustav Fischer.
86. Perišić Janjić, N.U., T.Lj. Ðaković-Sekulić, S.Z. Stojanović, and K.M. Penov-Gaši. 2005a. HPTLC chromatog-raphy of androstene derivates. Application of normal phase thin-layer chromatographic retention data in QSAR studies. Steroids 70: 137-144.
87. Perišić Janjić, N.U., G.S. Usčumlić, and N. Valentić. 2005b. The retention behavior of some uracil derivatives in normal and reversed-phase chromatography. Lipophilicity of the compounds. J. Planar Chromatogr. 18: 92-97.
88. Pliška, V., B. Testa, and H. van de Waterbeemd. 1996. Lipophilicity: The empirical tool and the fundamental objective. An introduction. In Lipophilicity in Drug Action and Toxicology, eds., V. Pliška, B. Testa, and H. van de Waterbeemd, pp. 1-6. Weinheim, Germany: VCH Publishers.
89. Poole, S.K. and C.F. Poole. 2003. Separation methods for estimating octanol-water partition coefficients. J. Chromatogr. B 797: 3-19.
90. Poša, M., M. Rašeta, and K. Kuhajda. 2011. A contribution to the study of hydrophobicity (lipophilicity) of bile acids with an emphasis on oxo derivatives of 5β-cholanoic acid. Hem. Ind. 65(2): 115-121.
91. Rabtti, El.H.M.A., M.M. Natić, D.M. Milojković-Opsenica et al. 2012. RP TLC-based lipophilicity assessment of some natural and synthetic coumarins. J. Braz. Chem. Soc. 23(3): 522-530.
92. Radoičić, A., H. Majstorović, T. Sabo, Ž. Tešić, and D. Milojković-Opsenica. 2009. Hydrophilic-interaction planar chromatography of some water-soluble Co(III) complexes on different adsorbents. J. Planar Chromatogr. 22(4): 249-253.
93. Radoičić, A., J. Trifković, D.M. Milojković-Opsenica, Ž.Lj. Tešić, D. Vučović, and M. Aleksić. 2009. Hydrophilic interaction planar chromatography of some anesthetics. Proceedings of the XXXIInd Symposium on “Chromatographic Methods of Investigating the Organic Compounds”, Katowice-Szczyrk, Poland, p. 61.
94. Rekker, R.F. 1977. The Hydrophobic Fragmental Constant. Pharmacochemistry Library. New York: Elsevier.
95. Rice, N.M., H.M.N.H. Irving, and M.A. Leonard. 1993. Nomenclature for liquid-liquid distribution (solvent extraction). IUPAC Recommendations. Pure. Appl. Chem. 65(11): 2373-2396.
96. Sârbu, C. and R.D. Briciu. 2010. Lipophilicity of natural sweeteners estimated on various oils and fats impreg-nated thin-layer chromatography plates. J. Liq. Chromatogr. Relat. Technol. 33: 903-921.
97. Sârbu, C., K. Kuhajda, and S. Kevrešan. 2001. Evaluation of the lipophilicity of bile acids and their derivatives by thin-layer chromatography and principal component analysis. J. Chromatogr. A 917: 361-366.
98. Šegan, S., F. Andrić, A. Radoičić et al. 2011. Correlation between structure, retention and activity of cholic acid derived cis-trans isomeric bis-steroidal tetraoxanes. J. Sep. Sci. 34(19): 2659-2667.
99. Šegan, S.B., D.M. Opsenica, B.A. Šolaja, and D.M. Milojković-Opsenica. 2009. Planar chromatography of cholic acid-derived cis-trans isomeric bis-steroidal tetraoxanes. J. Planar Chromatogr. 22(3): 175-181.
100. Sherma, J. 2010. Planar chromatography. Anal. Chem. 82: 4895-4910.
101. Shewiyo, D.H., E. Kaale, P.G. Risha, B. Dejaegher, J. Smeyers-Verbeke, and Y. Vander Heyden. 2012. HPTLC methods to assay active ingredients in pharmaceutical formulations: A review of the method development and validation steps. J. Pharm. Biomed. Anal. 66: 11-23.
102. Soczewinski, E. and G. Matysik. 1968. Two types of RM-composition relationships in liquid-liquid partition chromatography. J. Chromatogr. 32: 458-471.
103. Takács-Novák, K., M. Józan, and G. Szász. 1995. Lipophilicity of amphoteric molecules expressed by the true partition coefficient. Int. J. Pharm. 113: 47-55.
104. Takács-Novak, K., P. Pal, and V. Jozsef. 2001. Determination of logP for biologically active chalcones and cyclic chalcone analogs by RPTLC. J. Planar Chromatogr. Mod. TLC 14(1): 42-46.
105. Tarcsay, Á., K. Nyíri, and Gy.M. Keserű. 2012. Impact of lipophilic efficiency on compound quality. J. Med. Chem. 55: 1252-1260.
106. Tetko, I.V. and G.I. Poda. 2008. Prediction of Log P with property-based methods. In Molecular Drug Properties-Measurement and Prediction, ed., R. Mannhold, pp. 381-406. Weinheim, Germany: Wiley-VCH.
107. Torres-Lapasió, J.R., M. Rosés, E. Bosch, and M.C. Garcia-Alvarez-Coque. 2000. Interpretive optimisation strategy applied to the isocratic separation of phenols by reversed-phase liquid chromatography with acetonitrile-water and methanol-water mobile phases. J. Chromatogr. A 886: 31-46.
108. Tosti, T.B., K. Drljević, D.M. Milojković-Opsenica, and Ž.Lj. Tešić. 2005. Salting-out thin-layer chromatogra-phy of some macrolide antibiotics. J. Planar Chromatogr. Mod. TLC 18: 415-418.
109. Trifković, J.Ð., F.Lj. Andrić, P. Ristivojević, D. Andrić, Ž.Lj. Tešić, and D.M. Milojković-Opsenica. 2010. Structure-retention relationship study of arylpiperazines by linear multivariate modeling. J. Sep. Sci. 33: 2619-2628.
110. Tsantili-Kakoulidou, A. 2010. Lipophilicity: Assessment by RP/TLC and HPLC. In Encyclopedia of Chromatography, pp. 1400-1407. Boca Raton, FL: CRC Press.
111. Vailaya, A. 2005. Fundamentals of reversed phase chromatography: Thermodynamic and exothermodynamic treatment. J. Liq. Chromatogr. Relat. Technol. 28: 965-1054.
112. Valkó, K. 1987. The role of chromatography in drug design. TrAC, Trends Anal. Chem. 6(8): 214-219.
113. Valkó, K. 2000. Separation methods in drug synthesis and purification. In Handbook of Analytical Separations, pp. 539-542. Amsterdam, the Netherlands: Elsevier.
114. Valkó, K. 2004. Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. J. Chromatogr. A 1037: 299-310.
115. Valkó, K., C. Bevan, and D. Reynolds. 1997. Chromatographic hydrophobicity index by fast-gradient RP-HPLC: A high-throughput alternative to log P/log D. Anal. Chem. 69: 2022-2029.
116. Valkó, K., C.M. Du, C. Bevan, D.P. Reynolds, and M.H. Abraham. 2001. Rapid method for the estimation of water/octanol partition coefficient (logPoct) from gradient RP-HPLC retention and a hydrogen bond acidity term (sigma alpha2H). Curr. Med. Chem. 8: 1137-1146.
117. Valkó, K. and P. Slegel. 1993. New chromatographic hydrophobicity index (φ0) based on the slope and the intercept of the logk’ versus organic phase concentration plot. J. Chromatogr. 631: 49-61.
118. van de Waterbeemd, H. 2003. Physico-chemical approaches to drug absorption. In Drug Bioavailability: Estimation of Solubility, Permeability, Absorption and Bioavailability, ed., H. van de Waterbeemd, H. Lennernäs, and P. Artursson, pp. 3-20. Weinheim, Germany: Wiley-VCH.
119. van de Waterbeemd, H., R.E. Carter, G. Grassy et al. 1997. Glossary of terms used in computational drug design. Pure Appl. Chem. 69: 1137-1152.
120. van de Waterbeemd, H., M. Kansy, B. Wagner, and H. Fischer. 1996. Lipophilicity measurement by high performance liquid chromatography (RPHPLC). In Lipophilicity in Drug Action and Toxicology, ed., V. Pilška, B. Testa, and H. van de Waterbeemd, pp. 73-87. Weinheim, Germany: VCH Publishers.
121. van de Waterbeemd, H. and R. Manhold. 1996. Lipophilicity descriptors for structure-property correlation studies: Overview of experimental and theoretical methods and a benchmark of logP calculations. In Lipophilicity in Drug Action and Toxicology, ed., V. Pilška, B. Testa, and H. van de Waterbeemd, pp. 401-418. Weinheim, Germany: VCH Publishers.
122. Van der Giesen, W.F. and L.H.M. Janssen. 1982. Adsorption behaviour of several supports in reversed-phase thin-layer chromatography as demonstrated by the determination of relative partition coefficients of some 4-hydroxycoumarin derivatives. J. Chromatogr. 237: 199-213.
123. Varmuza, K. and P. Filzmoser. 2009. Introduction to Multivariate Statistical Analysis in Chemometrics. Boca Raton, FL: CRC Press.
124. Völgyi, G., K. Deák, J. Vámos, K. Valkó, and K. Takacs-Novák. 2008. RPTLC determination of logP of struc-turally diverse neutral compounds. J. Planar Chromatogr. 21: 143-149.
125. Waring, M.J. 2009. Defining optimum lipophilicity and molecular weight ranges for drug candidates-Molecular weight dependent lower logD limits based on permeability. Bioorg. Med. Chem. Lett. 19: 2844-2851.
126. Wick, C.D., J.I. Siepmann, and M.R. Schure. 2004. Simulation studies on the effects of mobile-phase modifica-tion on partitioning in liquid chromatography. Anal. Chem. 76: 2886-2892.
127. Yamagami, C., K. Kawase, and T. Fujita. 1999. Hydrophobicity parameters determined by reversed-phase liquid chromatography. XIII A new hydrogen-accepting scale of monosubstituted (di)azines for the relationship between retention factor and octanol-water partition coefficient. Quant. Struct. Act. Relat. 18: 26-34.