QSAR in Chromatography: Quantitative Structure–Retention Relationships (QSRRs)

Challenges and Advances in Computational Chemistry and Physics

Volumn 8, Issue , 2010, Pages 223-259

  Kaliszan, Roman ^a   Bączek, Tomasz ^a  

^a MEDICAL UNIVERSITY OF GDANSK   (Poland)

Author keywords

Characterization of stationary phases; QSRR; Retention predictions

Indexed keywords

EID: 85073161589     PISSN: 25424491     EISSN: 25424483     Source Type: Book Series    
DOI: 10.1007/978-1-4020-9783-6_8     Document Type: Chapter

References (158)

1. Kaliszan R (1992) Quantitative structure–retention relationships. Anal Chem 64:619A–631A
2. Kaliszan R, Foks H (1977) The relationship between the Rm values and the connectivity indices for pyrazine carbothioamide derivatives. Chromatographia 10:346–349
3. Kaliszan R (1977) Correlation between the retention indices and the connectivity indices of alcohols and methyl esters with complex cyclic structure. Chromatographia 10:529–531
4. Michotte Z, Massart DL (1977) Molecular connectivity and retention indexes. J Pharm Sci 66:1630–1632
5. Kaliszan R (1987) Quantitative structure–chromatographic retention relationships. Wiley, New York
6. Karelson M, Lobanov VS, Katritzky AR (1996) Quantum-chemical descriptors in QSAR/QSPR studies. Chem Rev 96:1027–1043
7. Kaliszan R (2000) Recent advances in quantitative structure–retention relationships. In: Valko K (ed) Separation methods in drug synthesis and purification. Elsevier, Amsterdam
8. Kaliszan R (2007) QSRR: Quantitative structure–(chromatographic) retention relationships. Chem Rev 107:3212–3246.
9. Smith RM (1995) Retention and selectivity in liquid chromatography. Elsevier, Amsterdam
10. Jurs PC (1996) Computer software applications in chemistry. Wiley, New York
11. Forgacs E, Cserhati T (1997) Molecular bases of chromatographic separations. CRC Press, Boca Raton
12. Kaliszan R (1997) Structure and retention in chromatography. A chemometric approach. Harwood, Amsterdam
13. Jinno K (ed) (1997) Chromatographic separations based on molecular recognition. Wiley, New York
14. Hansch C, Fujita T (1964) ρ-σ-π analysis. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86:1616–1626
15. Albert A (1965) Selective toxicity. Wiley, New York
16. Seydel JK, Schaper K-J (1979) Chemische struktur und biologische aktivität von wirkstoffen. Verlag Chemie, Weinheim
17. Iwasa J, Fuijta T, Hansch CJ (1965) Substituent constants for aliphatic functions obtained from partition coefficients. J Med Chem 8:150–153
18. Wang QS, Zhang L (1999) Review of research on quantitative structure–retention relationships in thin-layer chromatography. J Liq Chrom Rel Techn 22:1–14
19. Sadek PC, Carr PW, Doherty RM et al. (1985) Study of retention processes in reversed-phase high-performance liquid chromatography by the use of the solvatochromic comparison method. Anal Chem 57:2971–2978
20. Carr PW, Doherty RM, Kamlet MJ et al. (1986) Study of temperature and mobile-phase effects in reversed-phase high-performance liquid chromatography by the use of the solvatochromic comparison method. Anal Chem 58:2674–2680
21. Snyder LR, Carr PW, Rutan SC (1993) Solvatochromically based solvent-selectivity triangle. J Chromatogr A 656:537–547
22. Hasan MN, Jurs PC (1990) Prediction of gas and liquid chromatographic retention indices of polyhalogenated biphenyls. Anal Chem 62:2318–2323
23. Katritzky AR, Karelson M, Lobanov VS (1997) QSPR as a means of predicting and understanding chemical and physical properties in terms of structure. Pure Appl Chem 69:245–248
24. Lucic B, Trinajstic N, Sild S et al. (1999) A new efficient approach for variable selection based on multiregression: Prediction of gas chromatographic retention times and response factors. J Chem Inf Comput Sci 39:610–621
25. Katritzky AR, Chen K, Maran U et al. (2000) QSPR correlation and predictions of GC retention indexes for methyl-branched hydrocarbons produced by insects. Anal Chem 72:101–109
26. Ignatz-Hoover F, Petrukhin R, Karelson M et al. (2001) QSRR correlation of free-radical polymerization chain-transfer constants for styrene. J Chem Inf Comput Sci 41:295–299
27. Todeschini R, Consonni V (2000) Handbook of molecular descriptors. Wiley-VCH, Weinheim
28. Todeschini R, Consonni V, Pavan M (http://www.disat.unimib.it/chm/dragon.htm) Dragon software version 5.0, 2004
29. Ivanciuc O, Ivanciuc T, Cabrol-Bass D et al. (2000) Comparison of weighting schemes for molecular graph descriptors: Application in quantitative structure–retention relationship models for alkylphenols in gas-liquid chromatography. J Chem Inf Comput Sci 40:723–743
30. Junkes BS, Amboni RDMC, Yunes RA et al. (2003) Prediction of the chromatographic retention of saturated alcohols on stationary phases of different polarity applying the novel semi-empirical topological index. Anal Chim Acta 477:29–39
31. Ośmiałowski K, Halkiewicz J, Kaliszan R (1986) Quantum chemical parameters in correlation analysis of gas–liquid chromatographic retention indices of amines. J Chromatogr 361:63–69
32. Randić M (1975) On characterization of molecular branching. J Am Chem Soc 97:6609–6615
33. Hanai T (2005) Chromatography in silico, basic concept in reversed-phase liquid chromatography. Anal Bioanal Chem 382:708–717
34. Salo M, Sirén H, Volin P et al. (1996) Structure–retention relationships of steroid hormones in reversed-phase liquid chromatography and micellar electrokinetic capillary chromatography. J Chromatogr A 728:83–88
35. Makino M (1999) An analysis of the chromatographic behavior of the environmental contaminants polychlorinated naphthalenes using electrical and topological descriptors. Toxicol Environ Chem 73:117–128
36. Dimov N, Stoev S (1999) A new approach to structure–retention relationships. Acta Chromatogr 9:17–18
37. Zhang L, Zhang M, Tang GZ et al. (2000) Retention prediction system of O-aryl,O-(1-methylthioethylidene-amino)phosphates on RP-HPLC. HRC J High Resol Chromatogr 23:445– 448
38. Ledesma EB, Wornat MJ (2000) QSRR prediction of chromatographic retention of ethynyl-substituted PAH from semiempirically computed solute descriptors. Anal Chem 72:5437–5443
39. Kaliszan R, Ośmiałowski K, Tomellini SA et al. (1986) Quantitative retention relationships as a function of mobile and C18 stationary phase composition for non-cogeneric solutes. J Chromatogr 352:141–155
40. Kaliszan R, Lamparczyk H, Radecki A (1979) A relationship between regression of dimethylnitrosamine-demethylase by polycyclic aromatic hydrocarbons and their shape. Biochem Pharmacol 28:123–125
41. Wise SA, Bonnett WJ, Guenther FR et al. (1981) A relationship between reversed-phase C18 liquid chromatographic retention and the shape of polycyclic aromatic hydrocarbons. J Chromatogr Sci 19:457–465
42. Lippa KA, Sander LC, Mountain RD (2005) Molecular dynamics simulations of alkylsilane stationary-phase order and disorder. 1. Effects of surface coverage and bonding chemistry. Anal Chem 77:7852–7861
43. Montaña MP, Pappao B, Debattista NB et al. (2000) High-performance liquid chromatography of chalcones: Quantitative structure–retention relationships using partial least-squares (PLS) modeling. Chromatographia 51:727–735
44. Silva MF, Chipre LF, Raba J et al. (2001) Amino acids characterization by reversed-phase liquid chromatography. Partial least-squares modeling of their transport properties. Chromatographia 53:392–400
45. Csiktusnádi-Kiss GA, Forgács E, Markuszewski M (1998) Application of multivariate mathematical–statistical methods to compare reversed-phase thin-layer and liquid chromatographic behaviour of tetrazolium salts in Quantitative Structure–Retention Relationships (QSRR) studies. Analusis 26:400–406
46. Åberg MK, Jacobsson SP (2001) Pre-processing of three-way data by pulse-coupled neural networks – An imaging approach. Chemom Intell Lab Sys 57:25–36
47. Tham SY, Agatonovic-Kustrin S (2000) Application of the artificial neural network in quantitative structure-gradient elution retention relationship of phenylthiocarbamyl amino acids derivatives. J Pharm Biomed Anal 28:581–590
48. Ruggieri F, D’Archivio AA, Carlucci G et al. (2005) Application of artificial neural networks for prediction of retention factors of triazine herbicides in reversed-phase liquid chromatography. J Chromatogr A 1076:163–169
49. Baczek T, Kaliszan R (2002) Combination of linear solvent strength model and quantitative structure–retention relationships as a comprehensive procedure of approximate prediction of retention in gradient liquid chromatography. J Chromatogr A 962:41–55
50. Kaliszan R, Baczek T, Buciński A et al. (2003) Prediction of gradient retention from the linear solvent strength (LSS) model, quantitative structure–retention relationships (QSRR), and artificial neural networks (ANN). J Sep Sci 26:271–282
51. Snyder R, Dolan JW (1998) The linear-solvent-strength model of gradient elution. Adv Chromatogr 38:115–185
52. Haber P, Baczek, T, Kaliszan R et al. (2000) Computer simulation for the simultaneous optimization of any two variables and any chromatographic procedure. J Chromatogr Sci 38:386–392
53. Al-Haj MA, Kaliszan R, Nasal A (1999) Test analytes for studies of the molecular mechanism of chromatographic separations by quantitative structure–retention relationships. Anal Chem 71:2976–2985
54. Schefzick S, Kibbey C, Bradley MP (2004) Prediction of HPLC conditions using QSPR techniques: An effective tool to improve combinatorial library design. J Comb Chem 6:916–927
55. Cramer RD III, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959–5967
56. Luo H, Cheng Y-K (2005) Quantitative structure–retention relationship of nucleic-acid bases revisited. CoMFA on purine RPLC retention. QSAR Comb Sci 24:969–975
57. Sybyl (Linux) 6.9.1 (2003) Tripos, Inc. St. Louis, MO, USA
58. Sutter JM, Peterson TA, Jurs PC (1997) Prediction of gas chromatographic retention indices of alkylbenzenes. Anal Chim Acta 342:113–122
59. Massart DL, Vandeginste BGM, Buydens LMC et al. (1997) Handbook of chemometrics and qualimetrics: Part A. Elsevier, Amsterdam
60. Vandeginste BGM, Massart DL, Buydens LMC et al. (1998) Handbook of chemometrics and qualimetrics: Part B. Elsevier, Amsterdam
61. Ros F, Pintore M, Chrétien JR (2002) Molecular descriptor selection combining genetic algorithms and fuzzy logic: Application to database mining procedures. Chemometr Intell Lab Sys 63:15–26
62. Put R, Perrin C, Questier F et al. (2003) Classification and regression tree analysis for molecular descriptor selection and retention prediction in chromatographic quantitative structure–retention relationship studies. J Chromatogr A 988:261–276
63. Put R, Xu QS, Massart DL, Vander Heyden Y (2004) Multivariate adaptive regression splines (MARS) in chromatographic quantitative structure–retention relationship studies. J Chromatogr A 1055:11–19
64. Abraham MH, Chadha HS, Whiting GS et al. (1994) Hydrogen bonding. 32. An analysis of water– octanol and water–alkane partitioning and the Δlog P parameter of seiler. J Pharm Sci 83:1085– 1100
65. Abraham MH, Treiner C, Rosés M et al. (1996) Linear free energy relationship analysis of microemulsion electrokinetic chromatographic determination of liophilicity. J Chromatogr A 752:243–249
66. Abraham MH, Chadha HS, Leitao RAE et al. (1997) Determination of solute lipophilicity, as log P(octanol) and log P(alkane) using poly(styrene-divinylbenzene) and immobilised artificial membrane stationary phases in reversed-phase high-performance liquid chromatography. J Chromatogr A 766:35–47
67. Abraham MH (1997) On characterization of some GLC chiral stationary phases: LFER analysis. Anal Chem 69:613–617
68. Abraham MH (2004) The factors that influence permeation across the blood–brain barrier. Eur J Med Chem 39:235–240
69. Abraham MH, Poole CF, Poole SK (1999) Classification of stationary phases and other materials by gas chromatography. J Chromatogr A 842:79–114
70. Abraham MH, Ibrahim A, Zissimos AM (2004) Determination of sets of solute descriptors from chromatographic measurements. J Chromatogr A 1037:29–47
71. Wilson NS, Nelson MD, Dolan JW et al. (2002) Column selectivity in reversed-phase liquid chromatography: I. A general quantitative relationship. J Chromatogr A 961:171–193
72. Zhao J, Carr PW (2000) A comparative study of the chromatographic selectivity of polystyrene-coated zirconia and related reversed-phase materials. Anal Chem 72:302–309
73. Park JH, Yoon MH, Ryu YK et al. (1998) Characterization of some normal-phase liquid chromatographic stationary phases based on linear solvation energy relationships. J Chromatogr A 796:249–258
74. Rosés M, Bolliet D, Poole CF (1998) Comparison of solute descriptors for predicting retention of ionic compounds (phenols) in reversed-phase liquid chromatography using the solvation parameter model. J Chromatogr A 829:29–40
75. Li J, Cai B (2001) Evaluation of the retention dependence on the physicochemical properties of solutes in reversed-phase liquid chromatographic linear gradient elution based on linear solvation energy relationships. J Chromatogr A 905:35–46
76. Li J, Sun J, Cui Z et al. (2006) Quantitative structure–retention relationship studies using immobilized artificial membrane chromatography I: Amended linear solvation energy relationships with the introduction of a molecular electronic factor. J Chromatogr A 1132:174–182
77. Vonk EC, Lewandowska K, Claessens HA et al. (2003) Quantitative structure–retention relationships in reversed-phase liquid chromatography using several stationary and mobile phases. J Sep Sci 26:777–792
78. Poole CF, Poole SK (2002) Column selectivity from the perspective of the solvation parameter model. J Chromatogr A 965:263–299
79. Vitha M, Carr PC (2006) The chemical interpretation and practice of linear solvation energy relationships in chromatography. J Chromatogr A 1126:143–194
80. Jackson PT, Schure MR, Weber TP et al. (1997) Intermolecular interactions involved in solute retention on carbon media in reversed-phase high-performance liquid chromatography. Anal Chem 69:416–425
81. Sandi A, Bede A, Szepesy I et al. (1997) Characterization of different RP-HPLC columns by a gradient elution technique. Chromatographia 45:206–214
82. Tan LC, Carr PW (1998) Study of retention in reversed-phase liquid chromatography using linear solvation energy relationships II. The mobile phase. J Chromatogr A 799:1–19
83. Snyder LR, Dolan JW, Carr PW (2004) The hydrophobic-subtraction model of reversed-phase column selectivity. J Chromatogr A 1060:77–116
84. Baczek T, Kaliszan R, Novotná K et al. (2005) Comparative characteristics of HPLC columns based on quantitative structure–retention relationships (QSRR) and hydrophobic-subtraction model. J Chromatogr A 1075:109–115
85. Kaliszan R, van Straten MA, Markuszewski M et al. (1999) Molecular mechanism of retention in reversed-phase high-performance liquid chromatography and classification of modern stationary phases by using quantitative structure–retention relationships. J Chromatogr A 855:455–486
86. Al-Haj MA, Kaliszan R, Buszewski B (2001) Quantitative structure–retention relationships with model analytes as a means of an objective evaluation of chromatographic columns. J Chromatogr Sci 39:29–38
87. Baczek T, Kaliszan R (2003) Predictive approaches to gradient retention based on analyte structural descriptors from calculation chemistry. J Chromatogr A 987:29–37
88. Kaliszan R, Wiczling P, Markuszewski MJ (2004) pH gradient reversed-phase HPLC. Anal Chem 76:749–760
89. Meek JL (1980) Prediction of peptide retention times in high-pressure liquid chromatography on the basis of amino acid composition. Proc Natl Acad Sci USA 77:1632–1636
90. Palmblad M, Ramström M, Markides KE et al. (2002) Prediction of chromatographic retention and protein identification in liquid chromatography/mass spectrometry. Anal Chem 74:5826–5830
91. Petritis K, Kangas LJ, Ferguson PL et al. (2003) Use of artificial neural networks for the accurate prediction of peptide liquid chromatography elution times in proteome analyses. Anal Chem 75:1039–1048
92. Kaliszan R, Baczek T, Cimochowska A et al. (2005) Prediction of high-performance liquid chromatography retention of peptides with the use of quantitative structure–retention relationships. Proteomics 5:409–415
93. Baczek T, Wiczling P, Marszałł M et al. (2005) Prediction of peptide retention at different HPLC conditions from multiple linear regression models. J Proteome Res 4:555–563
94. Baczek T (2006) Chemometric evaluation of relationships between retention and physicochemical parameters in terms of multidimensional liquid chromatography of peptides. J Sep Sci 29:547–554
95. Baczek T (2005) Improvement of peptides identification in proteomics with the use of new analytical and bioinformatic strategies. Curr Pharm Anal 1:31–40
96. Put R, Daszykowski M, Baczek T et al. (2006) Retention prediction of peptides based on uninformative variable elimination by partial least squares. J Proteome Res 5:1618–1625
97. Mazza CB, Sukumar N, Breneman CM et al. (2001) Prediction of protein retention in ion-exchange systems using molecular descriptors obtained from crystal structure. Anal Chem 73:5457–5461
98. Ladiwala A, Rege K, Breneman CM et al. (2003) Investigation of mobile phase salt type effects on protein retention and selectivity in cation-exchange systems using quantitative structure–retention relationship models. Langmuir 19:8443–8454
99. Tugcu N, Song M, Breneman CM et al. (2003) Prediction of the effect of mobile-phase salt type on protein retention and selectivity in anion-exchange systems. Anal Chem 75:3563–3572
100. Ladiwala A, Xia F, Luo Q et al. (2006) Investigation of protein retention and selectivity in HIC systems using quantitative structure–retention relationship models. Biotechnol Bioeng 93:836– 850
101. Chen J, Luo Q, Breneman CM et al. (2007) Classification of protein adsorption and recovery at low salt conditions in hydrophobic interaction chromatographic systems. J Chromatogr A 1139:236– 246
102. Song MH, Breneman CM, Bi JB et al. (2002) Prediction of protein retention times in anion-exchange chromatography systems using support vector regression. J Chem Inf Comput Sci 42:1347–1357
103. Heberger K (1999) Evaluation of polarity indicators and stationary phases by principal component analysis in gas–liquid chromatography. Chemom Intell Lab Sys 47:41–49
104. Markuszewski M, Krass JD, Hippe T et al. (1998) Separation of nitroaromatics and their transformation products in soil around ammunition plants: New high performance liquid chromatographic charge transfer stationary phases. Chemosphere 37:559–575
105. Jiskra J, Claessens HA, Cramers CA et al. (2002) Quantitative structure–retention relationships in comparative studies of behavior of stationary phases under high-performance liquid chromatography and capillary electrochromatography conditions. J Chromatogr A 977:193–206
106. Cserháti T, Forgacs E, Payer K et al. (1998) Quantitative structure–retention relationships in separation mechanism studies on polyethylene-coated silica and alumina stationary phases. LCGC Int 4:240–252
107. Abraham MH, Rosés M, Poole CF et al. (1997) Hydrogen bonding. 42. Characterization of reversed-phase high-performance liquid chromatographic C18 stationary phases. J Phys Org Chem 10:358–368
108. Sandi A, Szepesy L (1998) Characterization of various reversed-phase columns using the linear free energy relationship. I. Evaluation based on retention factors. J Chromatogr A 818:1–17
109. Valko K, Plass M, Bevan C et al. (1998) Relationships between the chromatographic hydrophobicity indices and solute descriptors obtained by using several reversed-phase, diol, nitrile, cyclodextrin and immobilised artificial membrane-bonded high-performance liquid chromatography columns. J Chromatogr A 797:41–55
110. Baranowska I, Zydroń, M (2002) Quantitative structure–retention relationships of xanthines in RP HPLC systems with the new Chromolith RP-18e stationary phases. Anal Bioanal Chem 373:889– 892
111. Topliss JG, Edwards RP (1979) Chance factors in studies of quantitative structure–activity relationships. J Med Chem 22:1238–1244
112. Jiskra J, Claessens HA, Cramers CA et al. (2002) Quantitative structure–retention relationships in comparative studies of behavior of stationary phases under high-performance liquid chromatography and capillary electrochromatography conditions. J Chromatogr A 977:193–206
113. Rohrschneider L (1999) Prototypical test substances for a reversed phase in a retention parameter model. HRC J High Resol Chromatogr 22:454–458
114. Kaliszan R (2000) Quantitative structure–retention relationships (QSRR) in chromatography. In: Wilson ID, Adlard ER, Cooke M (eds) et al. Encyclopedia of separation science, vol 9. Academic Press, San Diego
115. Pliška V, Testa B, van de Waaterbemd H (1996) Lipophilicity in drug action and toxicology. VCH, Weinheim
116. Berthelot M, Jungfleisch E (1872) Sur les lois qui pre ´sident au partage d’un corps entre deux dissolvants (expe ŕiences). Ann Chim Phys 26:396–407
117. Martin AJP (1941) A new form of chromatogram employing two liquid phases. Biochem J 35:1358–1368
118. Cserháti T, Valko K (1994) Chromatographic determination of molecular interactions. Applications in biochemistry, chemistry and biophysics. CRC Press, Boca Raton
119. Poole SK, Poole CF (2003) Separation methods for estimating octanol–water partition coefficients. J Chromatogr B 797:3–19
120. Wang QS, Zhang L, Yang HZ (1999) Lipophilicity determination of some potential photosystem ii inhibitors on reversed-phase high-performance thin-layer chromatography. J Chromatogr Sci 37:41–44
121. Nasal A, Siluk D, Kaliszan R (2003) Chromatographic retention parameters in medicinal chemistry and molecular pharmacology. Curr Med Chem 10:381–426
122. Kaliszan R, Nasal A, Markuszewski MJ (2003) New approaches to chromatographic determination of lipophilicity of xenobiotics. Anal Bioanal Chem 377:803–811
123. Nasal, A, Kaliszan R (2006) Progress in the use of HPLC for evaluation of lipophilicity. Curr Comp-Aided Drug Design 2:327–340
124. Baczek T, Markuszewski M, Kaliszan R, van Straten, MA, Claessens HA (2000) Linear and quadratic relationships between retention and organic modifier content in eluent in reversed phase high-performance liquid chromatography: A systematic comparative statistical study. HRC J High Resol Chromatogr 23:667–676
125. Poole CF, Gunatilleka AD, Poole SK (2000) In search of a chromatographic model for biopartitioning. Adv Chromatogr 40:159–230
126. Kaliszan R (1986) Quantitative relationships between molecular structure and chromatographic retention. Implications in physical, analytical, and medicinal chemistry. CRC Crit Rev Anal Chem 16:323–383
127. Braumann T (1986) Determination of hydrophobic parameters by reversed-phase liquid chromatography: Theory, experimental techniques, and application in studies on quantitative structure– activity relationships. J Chromatogr 373:191–225
128. Kaliszan R, Haber P, Baczek T et al. (2001) Gradient HPLC in the determination of drug lipophilicity and acidity. Pure Appl Chem 73:1465–1475
129. a estimates from gradient high-performance liquid chromatography. J Chromatogr A 965:117–127
130. Wiczling P, Markuszewski MJ, Kaliszan R (2004) Determination of pKa by pH gradient reversed-phase HPLC. Anal Chem 76:3069–3077
131. Wiczling P, Markuszewski MJ, Kaliszan M et al. (2005) pH/organic solvent double-gradient reversed-phase HPLC. Anal Chem 77:449–458
132. Kaliszan R, Wiczling P (2005) Theoretical opportunities and actual limitations of pH gradient HPLC. Anal Bioanal Chem 382:718–727
133. Wiczling P, Kawczak P, Nasal A et al. (2006) Simultaneous determination of pKa and lipophilicity by gradient RP HPLC. Anal Chem 78:239–249
134. Subirats X, Bosch E, Rosés M (2007) Retention of ionisable compounds on high-performance liquid chromatography XVII. Estimation of the pH variation of aqueous buffers with the change of the methanol fraction of the mobile phase. J Chromatogr A 1138:203–215
135. ′-deoxyinosine and their synthetic analogues: Lipophilicity in the relation to their retention in reversed-phase liquid chromatography and the stability characteristics. J Pharm Biomed Anal 24:125–132
136. Dai J, Jin S, Yao S, Wang LS (2001) Prediction of partition coefficient and toxicity for ben-zaldehyde compounds by their capacity factors and various molecular descriptors. Chemosphere 42:899–907
137. Donovan SF, Pescatore MC (2002) Method for measuring the logarithm of the octanol–water partition coefficient by using short octadecyl-poly(vinyl alcohol) high-performance liquid chromatography columns. J Chromatogr A 952:47–61
138. Gulyaeva N, Zaslavsky A, Lechner P et al. (2003) Relative hydrophobicity and lipophilicity of drugs measured by aqueous two-phase partitioning, octanol-buffer partitioning and HPLC. A simple model for predicting blood–brain distribution. Eur J Med Chem 38:391–396
139. Welerowicz T, Buszewski B (2005) The effect of stationary phase on lipophilicity determination of β-blockers using reverse-phase chromatographic systems. Biomed Chromatogr 19:725–736
140. Vervoort RJM, Debets AJJ, Claessens HA et al. (2000) Optimisation and characterisation of silica-based reversed-phase liquid chromatographic systems for the analysis of basic pharmaceuticals. J Chromatogr A 897:1–22
141. Buszewski B, Gadzała-Kopciuch RM, Kaliszan R et al. (1998) Polyfunctional chemically bonded stationary phase for reversed phase high-performance liquid chromatography. Chromatographia 48:615–622
142. Lombardo F, Shalaeva MY, Tupper KA et al. (2001) ElogDoct: A tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds. J Med Chem 44:2490–2497
143. Kaliszan R, Marszałł MP, Markuszewski MJ et al. (2004) Suppression of deleterious effects of free silanols in liquid chromatography by imidazolium tetrafluoroborate ionic liquids. J Chromatogr A 1030:263–271
144. Marszałł MP, BA˛czek T, Kaliszan R (2006) Evaluation of the silanol-suppressing potency of ionic liquids. J Sep Sci 29:1138–1145
145. Pidgeon C, Venkataram UV (1989) Immobilized artificial membrane chromatography: Supports composed of membrane lipids. Anal Biochem 176:36–47
146. Thurnhofer H, Schnabel J, Betz M et al. (1991) Cholesterol-transfer protein located in the intestinal brush-border membrane. Partial purification and characterization. Biochim Biophys Acta 1064:275–286
147. Kaliszan R, Kaliszan A, Wainer IW (1993) Deactivated hydrocarbonaceous silica and immobilized artificial membrane stationary phases in high-performance liquid chromatographic determination of hydrophobicities of organic bases: Relationship to log P and CLOGP. J Pharm Biomed Anal 11:505–511
148. Ducarme A, Neuwels M, Goldstein S et al. (1998) IAM retention and blood–brain barrier penetration. Eur J Med Chem 33:215–223
149. Kępczyńska E, Bojarski J, Haber P et al. (2000) Retention of barbituric acid derivatives on immobilized artificial membrane stationary phase and its correlation with biological activity. Biomed Chromatogr 14:256–260
150. Vrakas D, Hadjipavlou-Litina D, Tsantili-Kakoulidou A (2005) Retention of substituted coumarins using immobilized artificial membrane (IAM) chromatography: A comparative study with n-octanol partitioning and reversed-phase HPLC and TLC. J Pharm Biomed Anal 39:908–913
151. Kaliszan R (1998) Retention data from affinity high-performance liquid chromatography in view of chemometrics. J Chromatogr B 715:229–244
152. Bertucci C, Bartolini M, Gotti R et al. (2003) Drug affinity to immobilized target bio-polymers by high-performance liquid chromatography and capillary electrophoresis. J Chromatogr B 797:111–129
153. Domenici E, Bertucci C, Salvadori P et al. (1990) Synthesis and chromatographic properties of an HPLC chiral stationary phase based upon human serum albumin. Chromatographia 29:170–176
154. Domenici E, Bertucci C, Salvadori P et al. (1991) Use of a human serum albumin-based high-performance liquid chromatography chiral stationary phase for the investigation of protein binding: Detection of the allosteric interaction between warfarin and benzodiazepine binding sites. J Pharm Sci 80:164–166
155. Noctor TAG, Pham CD, Kaliszan R et al. (1992) Stereochemical aspects of benzodiazepine binding to human serum albumin. I. Enantioselective high performance liquid affinity chromatographic examination of chiral and achiral binding interactions between 1,4-benzodiazepines and human serum albumin. Mol Pharmacol 42:506–511
156. Kaliszan R, Nasal A, Turowski M (1995) Binding site for basic drugs on α1-acid glycoprotein as revealed by chemometric analysis of biochromatographic data. Biomed Chromatogr 9:211–215
157. Kaliszan R, Nasal A, Turowski M (1996) Quantitative structure–retention relationships in the examination of the topography of the binding site of antihistamine drugs on α1-acid glycoprotein. J Chromatogr A 722:25–32
158. Goolkasian DL, Slaughter RL, Edwards DJ et al. (1983) Displacement of lidocaine from serum α1-acid glycoprotein binding sites by basic drugs. Eur J Clin Pharmacol 25:413–417