Structure-retention correlation in liquid chromatography for pharmaceutical applications

Journal of Liquid Chromatography and Related Technologies

Volumn 30, Issue 5-7, 2007, Pages 761-789

  David, Victor ^a   Medvedovici, Andrei ^a  

^a UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

Dissociation constants; Hydrophobicity; LC retention; LSER; Molecular descriptors; Pharmaceutical compounds; QSRR; Review

Indexed keywords

ACIDITY; ALKALINITY; CHROMATOGRAPHIC ANALYSIS; DISSOCIATION; DRUG PRODUCTS; HYDROPHOBICITY; INDUSTRIAL APPLICATIONS; RATE CONSTANTS;

DISSOCIATION CONSTANTS; LC RETENTION; MOLECULAR DESCRIPTORS; PHARMACEUTICAL COMPOUNDS; QSRR;

LIQUID CHROMATOGRAPHY;

ACIDITY; ALKALINITY; CORRELATION ANALYSIS; ENERGY; HYDROPHOBICITY; LIQUID CHROMATOGRAPHY; PARTITION COEFFICIENT; REVIEW; SOLUBILITY; SOLVATION;

EID: 33947122617     PISSN: 10826076     EISSN: 1520572X     Source Type: Journal    
DOI: 10.1080/10826070701191052     Document Type: Review

References (105)

1. Hadjipavlou-Litina, D.; Garg, R.; Hansch, C. Comparative quantitative structure-activity relationship studies (QSAR) on non-benzodiazepine compounds binding to benzodiazepine receptor (BzR). Chem. Rev. 2004, 104, 3751-3793.
2. Dudek, A.Z.; Arodz, T.; Galvez, J. Computational methods in developing quantitative-activity relationships (QSAR): a review. Comb. Chem. & High Throughput Screening 2006, 9, 213-228.
3. Sutherland, J.J.; O'Brien, L.A.; Weaver, D.F. A comparison of methods for modeling quantitative structure-activity relationships. J. Med. Chem. 2004, 47, 5541-5554.
4. Hanai, T. Structure-retention correlation in liquid chromatography. J. Chromatogr. A 1991, 550, 313-324.
5. Xia, Y.; Guo, Y.; Wang, H.; Wang, Q.; Zuo, Y. Quantitative structure-retention relationships of benzoylphenylureas on polystyrene- octadecene-encapsulated zirconia stationary phase in reversed-phase high performance liquid chromatography. J. Sep. Sci. 2005, 28, 73-77.
6. Wang, Q.S.; Zhang, L. Review of research on quantitative structure-retention relationships in thin-layer chromatography. J. Liq. Chromatogr. Rel. Technol. 1999, 22, 1-14.
7. Dimov, N. Quantitative structure-retention relationship by TLC. In Encyclopedia of Chromatography; Cazes, J., (ed).; Taylor & Francis: New York, 2005; 1408-1411.
8. w in reversed-phase liquid chromatography. Implications for quantitative structure-retention relationship. J. Chromatogr. A 1993, 631, 63-78.
9. Rimmer, C.A.; Simmons, C.R.; Dorsey, J.G. The measurement and meaning of void volumes in reversed-phase liquid chromatography. J. Chromatogr. A 2002, 965, 219-232.
10. Guha, R.; Jurs, P.C. Determining the validity of a QSAR model-a classification approach. J. Chem. Inf. Model. 2005, 45, 65-73.
11. Al-Haj, M.A.; Kaliszan, R.; Buszewski, B. QSRR with model analytes as a means of an objective evaluation of chromatographic columns. J. Chromatogr. Sci. 2001, 39, 29-38.
12. Waterbeemd, H.; Van de Carter, R.E.; Grassy, G.; Kubinskyi, H.; Martin, Y.C.; Tute, M.S.; Willett, P. Glossary of terms used in computational drug design. Pure & Appl. Chem. 1997, 69, 1137-1152.
13. Xue, L.; Bajorath, J. Molecular descriptors in chemoinformatics, computational combinatorial chemistry and virtual screening. Comb. Chem. & High Throughput Screenining 2000, 3, 363-372.
14. Jinno, K. Study on retention in liquid chromatography. Chromatography 2001, 22, 1-9.
15. Kerelson, M. Molecular Descriptors in QSAR/QSPR; John Wiley & Sons Inc.: New York, 2000.
16. Fujita, T.; Iwasa, J.; Hanch, C. A new substituent constant π derived from partition coefficients. J. Am. Chem. Soc. 1964, 86, 5176-5180.
17. Medvedovici, A.; Sandra, P.; Kot, A.; David, F. Supercritical Fluid Chromatography with Packed Columns; Anton, K., Berger, C., Eds.; Marcel Dekker Inc.: New York, 1997; Vol. 75, Chapter 6, 161-194.
18. Sandra, P.; Medvedovici, A.; David, F. Comprehensive pSFC x pSFC - MS for the characterization of triglycerides in vegetable oils. LC-GC Europe 2003, 12, 2-4.
19. Hansch, C.; Leo, A.; Taft, R.W. A surwey of Hammet substituent constants and resonance and field parameters. Chem. Rev. 1991, 91, 165-195.
20. Carrasco Velar, R.; Padron, J.A.; Galvez, J. Definition of a novel atomic index in QSAR: the refractopological state. J. Pharm. Pharmaceut. Sci. 2004, 7, 19-26.
21. Wise, S.A.; Bonnet, W.J.; Guenther, F.R.; May, W.E. A relationship between RP chromatography and elution of PAHs. J. Chromatogr. Sci. 1981, 18, 457-465.
22. Kier, L.B.; Hall, L.H. The meaning of molecular connectivity: a bimolecular accessibility model. Croat. Chem. Acta 2002, 75, 371-382.
23. Radecki, A.; Lamparczyk, H.; Kaliszan, R. A relationship between the retention indices on nematic and isotropic phases and the shape of PAHs. Chromatographia 1979, 12, 595-600.
24. Franczkiewicz, R.; Braun, W. Exact and efficient analytical calculation of the accessible surface areas and their gradients for macromolecules. J. Comp. Chem. 1998, 19, 319-333.
25. Lewis, D.F.V. Frontier orbitals in chemical and biological activity: quantitative relationships and mechanistic implications. Drug Metab. Rev. 1999, 31, 755-816.
26. Pompe, M.; Randic, M. Anticonnectivity": a challenge for structure-property-activity studies. J. Chem. Inf. Mod. 2006, 46, 2-8.
27. Katritzky, A.R.; Gordeeva, E.R. Traditional topological indexes vs electronic, geometrical and combined molecular descriptors in QSAR/QSPR research. J. Chem. Inf. Comput. Sci. 1993, 33, 835-857.
28. Karelson, M.; Lobanov, V.S.; Katritzky, A.R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev. 1996, 96, 1027-1043.
29. Devillers, J.; Balaban, A.T. Topological Indices and Related Descriptors in QSAR and QSPR; Gordon and Breach: Amsterdam, 1999.
30. Todeschini, R.; Consonni, V. The Handbook of Molecular Descriptors; Mannhold, R., Kubinyi, H., Timmerman, H., (eds).; Series of Methods and Principles in Medicinal Chemistry; Wiley-VCH: New York, 2000; Vol. 11.
31. Hanai, T. Chromatography in silico, basic concept in reversed-phase liquid chromatography. Anal. Bioanal. Chem. 2005, 382, 708-717.
32. Sander, L.C.; Lippa, K.A.; Wise, S.A. Order and disorder in alkyl stationary phase. Anal. Bioanal. Chem. 2005, 383, 646-668.
33. Croes, K.; Steffens, A.; Marchand, D.H.; Snyder, L.R. Relevance of π-π and dipole-dipole interactions for retention on cyano and phenyl columns in reversed-phase liquid chromatography. J. Chromatogr. A 2005, 1098, 123-130.
34. Marchand, D.H.; Croes, K.; Dolan, J.W.; Snyder, L.R. Column selectivity in reversed-phase liquid chromatography. VII. Cyanopropyl columns. J. Chromatogr. A 2005, 1062, 57-64.
35. Clark, M. Generalized fragment-substructure based property prediction method. J. Chem. Inf. Model. 2005, 45, 30-38.
36. Turowski, M.; Yamakawa, N.; Meller, J.; Kimata, K.; Ikegami, T.; Hosoya, K.; Tanaka, N.; Thornton, E.R. Deuterium isotope effects on hydrophobic interactions: the importance of dispersion interactions in the hydrophobic phase. J. Am. Chem. Soc. 2003, 125, 13836-13849.
37. Avdeef, A. Absorption and Drug Development: Solubility, Permeability and Charge State; Wiley-Interscience: Hoboken, 2003; 67-90.
38. Katritzky, A.R.; Tamm, K.; Kuanar, M.; Fara, D.C.; Oliferenko, A.; Oliferenco, P.; Huddleston, J.G.; Rogers, R.D. Aqueous biphasic systems. Partitioning of organic molecules: a QSPR treatment. J. Chem. Inf. Comput. Sci. 2004, 44, 136-142.
39. Caron, G.; Steyaert, G.; Pagliara, A.; Reymond, F.; Crivori, P.; Gaillard, P.; Carrupt, P.; Avdeef, A.; Comer, J.; Box, K.J.; Girault, H.H.; Testa, B. Structure-lipophilicity relationships of neutral and protonated β-blockers. I. Intra- and intermolecular effects in isotropic solvent systems. Helv. Chim. Acta 1999, 82, 1211-1222.
40. Escuder-Gilabert, L.; Bermudez-Saldana, J.M.; Villanueva-Camanas, R.M.; Medina-Hernadez, M.J.; Sagrado, S. Reliability of the retention factor estimations in liquid chromatography. J. Chromatogr. A 2004, 1033, 247-255.
41. Renner, R. The Ko,w controversy. Environ. Sci. Technol. 2002, 413A.
42. Poole, S.K.; Poole, C.F. Separation methods for estimating octanol-water partition coefficients. J. Chromatogr. B 2003, 797, 3-19.
43. Leo, A. Calculating log Poct from structures. Chem. Rev. 1993, 93, 1281-1306.
44. Meylan, W.M.; Howard, P.H. Atom/fragment contribution method for estimating octanol-water partition coefficients. J. Pharm. Sci. 1995, 84, 83-92.
45. Nikitas, P.; Pappa-Louisi, A.; Agrafiotou, P. Effects of the organic modifier concentration on the retention in reversed-phase liquid chromatography. I. General semi-thermodynamic treatment for adsorption and partition mechanisms. J. Chromatogr. A 2002, 946, 9-32.
46. Nikitas, P.; Pappa-Louisi, A.; Agrafiotou, P. Effects of the organic modifier concentration on the retention in reversed-phase liquid chromatography. II. Tests using various simplified models. J. Chromatogr. A 2002, 946, 33-45.
47. Neue, U.D. Nonlinear retention relationships in reversed-phase chromatography. Chromatographia 2006, 63, S45-S53.
48. Medvedovici, A.; Albu, F.; David, V. Selection of the retention mechanism for separation of amitryptiline and the main related impurities by liquid chromatography. Rev. Roum. Chim. 2005, 50, 225-234.
49. David, V.; Bala, C.; Rotariu, L. Thermodynamic parameters of the reversed-phase liquid chromatography retention for some lipid-soluble vitamins. Chem. Anal. (Warsaw) 2004, 49, 191-199.
50. Howkins, D.M. The problem of overfitting. J. Chem. Inf. Comput. Sci. 2004, 44, 1-12.
51. Dai, J.; Yao, S.; Ding, Y.; Wang, L. Retention of substituted indole compounds on RP-HPLC: correlation with molecular connectivity indices and quantum chemical descriptors. J. Liq. Chromatogr. Rel. Technol. 1999, 22, 2271-2282.
52. Jakab, A.; Schubert, G.; Prodan, M.; Forgacs, E. Determination of the retention behavior of barbituric acid derivatives in reversed-phase HPLC by using quantitative structure-retention relationships. J. Chromatogr. B 2002, 770, 227-236.
53. Jakab, A.; Schubert, G.; Prodan, M.; Forgacs, E. PCA, followed by two-dimensional nonlinear mapping and cluster analysis, versus multilinear regression in QSRR. J. Liq. Chromatogr. Rel. Technol. 2002, 25, 1-16.
54. Agatonovic-Kustrin, A.; Zecevic, M.; Zivanovic, LJ. Use of modeling in structure-retention relationships of diuretics in RP-HPLC. J. Pharm. Biomed. Anal. 1999, 21, 95-103.
55. Tham, S.Y.; Agatonovic-Kustrin, A. Application of the artificial neural network in quantitative structure-gradient elution retention relationship of phenylcarbamyl amino acids derivatives. J. Pharm. Biomed. Anal. 2002, 28, 581-590.
56. Loukas, Y. Radial basis function networks in LC: improved structure-retention relationships compared to principal components regression (PCR) and nonlinear partial least squares regression (PLS). J. Liq. Chromatogr. Rel. Technol. 2001, 24, 2239-2256.
57. Xiang, Y.H.; Liu, M.C.; Zhang, X.Y.; Zhang, R.S.; Hu, Z.D.; Fan, B.T.; Doucet, J.P.; Panaye, A. Quantitative prediction of LC retention of N-benzylideneanilines based on quantum chemical parameters and radial basis function neural network. J. Chem. Inf. Comput. Sci. 2002, 42, 592-597.
58. Song, M.; Breneman, C.M.; Bi, J.; Sukumar, N.; Bennett, K.P.; Cramer, S.; Tugcus, N. Prediction of protein retention times in anion-exchange chromatography systems using support vector regression. J. Chem. Inf. Comput. Sci. 2002, 42, 1347-1357.
59. Liu, H.X.; Xue, C.X.; Zhang, R.S.; Yao, X.J.; Liu, M.C.; Hu, Z.D.; Fan, B.T. Quantitative prediction of log k of peptides in HPLC based on molecular descriptors by using the heuristic method and support vector machine. J. Chem. Inf. Comput. Sci. 2004, 44, 1979-1986.
60. Luco, J.M.; Salinas, A.P.; Ferriero, A.A.J.; Vazquez, R.N.; Raba, J.; Marchevsky, E. Immobilized artificial membrane chromatography: quantitative structure-retention relationships of structurally diverse drugs. J. Chem. Inf. Comput. Sci. 2003, 43, 2129-2136.
61. Detroyer, A.; Stokbroekx, S.; Bohets, H.; Lorreyne, W.; Timmerman, P.; Verboven, P.; Massart, D.L.; Vander-Heyden, Y. Fast monolithic micellar LC: an alternative drug permeability assessing method for high-throughput screening. Anal. Chem. 2004, 76, 7304-7309.
62. Varga-Defterdarovic, L.; Horvat, S.; Skuric, M.; Horvat, J. Correlation of structure and retention behavior in reversed-phase HPLC. II. Methionine-enkephalin-related glycoconjugates. J. Chromatogr. A 1994, 687, 107-112.
63. Yang, S.; Bumgarner, J.G.; Kruk, L.F.R.; Khaledi, M.G. Quantitative structure-activity relationships studies with micellar electrokinetic chromatography influence of surfactant type and mixed micelles on estimation of hydrophobicity and bioavailability. J. Chromatogr. A 1996, 721, 323-335.
64. Momose, T.; Yamaguchi, Y.; Iida, T.; Goto, J.; Nambara, T. Structure-retention correlation of isomeric bile acids in inclusion HPLC with methyl beta-cyclodextrin. Lipids 1998, 33, 101-108.
65. Luo, H.; Cheng, Y.K. Quantitative structure-retention relationship of nucleic-acid bases revisited. CoMFA on purine RPLC retention. QSAR & Comb. Sci. 2005, 24, 968-975.
66. Welerowicz, T.; Buszewski, B. The effect of stationary phase on lipophilicity determination of β-blockers using reversed-phase chromatographic systems. Biomed. Chromatogr. 2005, 19, 725-736.
67. Sarbu, C.; Todor, S. Determination of lipophilicity of some non-steroidal anti-inflamatory agents and their relationships by using principal component analysis based on thin-layer chromatographic retention data. J. Chromatogr. A 1998, 822, 263-269.
68. Espinoza, S.; Bosch, E.; Roses, M. Retention of ionizable compounds on HPLC. 5. pH scales and the retention of acids and bases with acetonitrile-water mobile phases. Anal. Chem. 2000, 72, 5193-5200.
69. Espinoza, S.; Bosch, E.; Roses, M. Retention of ionizable compounds in HPLC. IX. Modeling retention in reversed-phase LC as a function of pH and solvent composition with acetonitrile-water mobile phase. J. Chromatogr. A 2002, 947, 47-58.
70. David, V.; Albu, F.; Medvedovici, A. Retention behavior of metformin and related impurities in ion-pairing liquid chromatography. J. Liq. Chromatogr. Rel. Technol. 2005, 28, 83-98.
71. David, V.; Medvedovici, A. Partition model applied to the retention process of basic analytes in reversed-phase and ion-pairing liquid chromatography. Rev. Roum. Chim. 2005, 50, 837-843.
72. Neue, U.D.; Phoebe, C.H.; Tran, K.; Cheng, Y.F.; Lu, Z. Dependence of reversed-phase retention of ionizable analytes on pH, concentration of organic solvent and silanol activity. J. Chromatogr. A 2001, 925, 49-67.
73. a by pH gradient reversed-phase HPLC. Anal. Chem. 2004, 76, 3069-3077.
74. a predicting. Curr. Drug Disc. Technol. 2005, 2, 221-229.
75. Espinoza, S.; Bosch, E.; Roses, M. Acid-base constants of neutral bases in acetonitrile mixtures. Anal. Chim. Acta 2002, 454, 157-166.
76. Vervoort, R.J.M.; Ruyter, E.; Debets, A.J.J.; Claessens, H.A.; Cramers, C.A.; de Jong, G.J. Characterisation of reversed phase LC stationary phases for the analytes of basic pharmaceuticals: eluent properties and comparison of empirical test methods. J. Chromatogr. A 2001, 931, 67-79.
77. Bartolini, M.; Bertucci, C.; Gotti, R.; Tumiatti, V.; Covalli, A.; Recanatini, M.; Andrisana, V. Determination of the dissociation constants (pKa) of basic acetylcholinesterase inhibitors by RP-LC. J. Chromatogr. A 2002, 958, 59-67.
78. Wilson, D.M.; Wang, X.; Walsh, E.; Rourick, R.A. High throughput log D using liquid chromatography-mass spectrometry. Comb. Chem. & High Throughput Screening 2001, 4, 511-519.
79. Ruiz-Angel, M.J.; Carda-Broch, S.; Garcia-Alvarez-Coque, M.C.; Berthod, A. Effect of ionization and the nature of the mobile phase in QSRR studies. J. Chromatogr. A 2005, 1063, 25-34.
80. David, V.; Albu, F.; Medvedovici, A. Structure-retention correlation of some oxicam drugs in reversed-phase liquid chromatography. J. Liq. Chromatogr. Rel. Technol. 2004, 27, 965-984.
81. Torres-Lapasio, J.R.; Garcia-Alvarez-Coque, M.C.; Roses, M.; Bosch, E. Prediction of the retention in reverse-phase liquid chromatography using solute-mobile phase-stationary phase polarity parameters. J. Chromatogr. A 2002, 955, 19-34.
82. Bosque, R.; Sales, J.; Bosch, E.; Roses, M.; Garcia-Alvarez-Coque, M.C.; Torres-Lapasio, J.R. A QSPR study of the p solute polarity parameter to estimate retention in HPLC. J. Chem. Inf. Comput. Sci. 2003, 43, 1240-1247.
83. Pyka, A.; Sliwiok, J. Use of traditional structural descriptors in QSRR analysis of nicotinic acid esters. J. Liq. Chromatogr. Rel. Technol. 2004, 27, 785-798.
84. Bacsek, T.; Kaliszan, R. Combination of linear solvent strength model and QSRRs as a comprehensive procedure of approximate prediction of retention in gradient liquid chromatography. J. Chromatogr. A 2002, 962, 41-55.
85. Kaliszan, R.; Baczek, T.; Bucinski, A.; Buszewski, B.; Sztupecka, M. Prediction of gradient retention from the linear solvent strength (LSS) model, quantitative structure-retention relationships (QSRR) and artificial neural networks (ANN). J. Sep. Sci. 2003, 26, 271-282.
86. Deanda, F.; Smith, K.M.; Liu, J.; Pearlman, R.S. GSSI, a general model for solute-solvent interactions. I. Description of the model. Molec. Pharm. 2004, 1, 23-39.
87. Wagoner, J.A.; Baker, N.A. Assessing implicit models for nonpolar mean solvation forces: the importance of dispersion and volume terms. Proc. Natl. Acad. Sci. USA 2006, 103, 8331-8336.
88. Okur, A.; Wickstrom, L.; Layten, M.; Geney, R.; Song, K.; Hornak, V.; Simmerling, C. Improved efficiency of replica exchange simulations through use of a hybrid explicit/implicit solvation model. J. Chem. Theory Comput. 2006, 2, 420-433.
89. Bordner, A.J.; Cavasotto, C.N.; Abagyan, R.A. Accurate transferable model for water, n-octanol, and n-hexadecane solvation free energies. J. Phys. Chem. B 2002, 106, 11009-11015.
90. Ranatunga, R.P.J.; Carr, P.W. A study of the enthalpy and entropy contributions of the stationary phase in RP-LC. Anal. Chem. 2000, 72, 5679-5692.
91. Szepesy, L. Effect of molecular interactions on retention and selectivity in reversed-phase LC. J. Chromatogr., A 2002, 960, 69-83.
92. Vonk, E.C.; Lewandowska, K.; Claessens, H.A.; Kaliszan, R.; Cramers, C.A. Quantitative structure-retention relationships in reversed-phase LC using several stationary and mobile phase. J. Sep. Sci. 2003, 26, 777-792.
93. Wilson, N.S.; Nelson, M.D.; Dolan, J.W.; Snyder, L.R.; Wolcott, R.G.; Carr, P.W. Column selectivity in reversed-phase LC. I. A general quantitative relationship. J. Chromatogr. A 2002, 961, 171-193.
94. Wilson, N.S.; Nelson, M.D.; Dolan, J.W.; Snyder, L.R.; Carr, P.W. Column selectivity in reversed-phase LC. II. Effects of a change in conditions. J. Chromatogr. A 2002, 961, 195-215.
95. Wilson, N.S.; Dolan, J.W.; Snyder, L.R.; Carr, P.W.; Sander, L.C. Column selectivity in reversed-phase LC. III. The physico-chemical basis of selectivity. J. Chromatogr. A 2002, 961, 217-236.
96. Jover, J.; Bosque, R.; Sales, J. Determination of Abraham solute parameters from molecular structure. J. Chem. Inf. Comput. Sci. 2004, 44, 1098-1106.
97. Oliferenko, A.A.; Oliferenko, P.V.; Huddleston, J.G.; Rogers, R.D.; Palyulin, V.A.; Zefirov, N.S.; Katritzky, A.R. Theoretical scales of hydrogen bond acidity and basicity for application in QSAR/QSPR studies and drug design. Partitioning of aliphatic compounds. J. Chem. Inf. Comput. Sci. 2004, 44, 1042-1055.
98. Li, J. Prediction of internal standards in RP-LC. IV. Correlation and prediction of retention in reversed-phase ion-pair chromatography based on linear solvation energy relationships. Anal. Chim. Acta 2004, 522, 113-126.
99. Suzuki, T.; Timofei, S.; Iuroas, B.E.; Uray, G.; Verdino, P.; Fabian, W.M.F. QSERR for chromatographic separation of arylalkylcarbinols on Pirkle type stationary phases. J. Chromatogr. A 2001, 922, 13-23.
100. Lipkowitz, K.B. Theoretical studies of brush-type chiral stationary phases. J. Chromatogr. A 1994, 666, 493-503.
101. Booth, T.D.; Azzaoui, K.; Wainer, I.W. Prediction of chiral chromatographic separations using combined multivariate regression and neural networks. Anal. Chem. 1997, 69, 3879-3883.
102. Del Rio, A.; Piras, P.; Roussel, C. Enantiophore modeling in 3D-QSAR. A data mining application on Whelk-O1 chiral stationary phase. Chirality 2006, 7, 498-508.
103. SYBYL Molecular Modeling Software; Tripos Associated: St. Louis, MO, 1999.
104. Clark, T. VAMP 4.4, Erlangen Vectorized Molecular Orbital Package; Computer-Chemie-Centrum, Univ. Erlangen: Nurnberg, Germany, 1992.
105. Gedeck, P.; Rohde, B.; Bartels, C. QSAR - How good is it in practice? Comparison of descriptor sets on an unbiased cross section of corporate data sets. J. Chem. Inf. Model. 2006, on-line 3 Aug 2006.