Lipophilicity and biomimetic properties measured by HPLC to support drug discovery

Journal of Pharmaceutical and Biomedical Analysis

Volumn 130, Issue , 2016, Pages 35-54

  Valkó, Klára L ^a,b  

^a UNIVERSITY OF LONDON   (United Kingdom)

^b Bio Mimetic Chromatography Consultancy   (United Kingdom)

Author keywords

Biomimetic HPLC; Drug efficiency; HSA binding; IAM binding; Lipophilicity; Volume of distribution

Indexed keywords

ALPHA 1 ACIDGLYCOPROTEIN; GLYCOPROTEIN; HUMAN SERUM ALBUMIN; LIPID; PHOSPHOLIPID; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; ARTIFICIAL MEMBRANE; BIOLOGICAL MODEL; BIOMIMETICS; CHEMICAL STRUCTURE; COMPARATIVE STUDY; DRUG DEVELOPMENT; DRUG DISTRIBUTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIPOPHILICITY; MATHEMATICAL ANALYSIS; PH; PHASE SEPARATION; PRIORITY JOURNAL; PROTEIN BINDING; REVERSED PHASE LIQUID CHROMATOGRAPHY; SOLVATION; VOLUME OF DISTRIBUTION; PROCEDURES;

BIOMIMETICS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG DISCOVERY; LIPIDS; PHOSPHOLIPIDS;

EID: 84964330274     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2016.04.009     Document Type: Article

References (154)

1. [1] Valkó, K., Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. J. Chromatogr. A. 1037 (2004), 299–310, 10.1016/j.chroma.2003.10.084.
2. [2] Valko, K., Physicochemical and Biomimetic Properties in Drug Discovery: Chromatographic Techniques for Lead Optimization. 2014, Wiley, Hoboken, NJ.
3. [3] Hansch, C., Fujita, T., p-σ-π analysis. A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc. 86 (1964), 1616–1626, 10.1021/ja01062a035.
4. [4] Horváth, C., Melander, W., Molnár, I., Solvophobic interactions in liquid chromatography with nonpolar stationary phases. J. Chromatogr. A 125 (1976), 129–156, 10.1016/S0021-9673(00)93816-0.
5. [5] Vailaya, A., Horváth, C., Solvophobic theory and normalized free energies of nonpolar substances in reversed phase chromatography. J. Phys. Chem. B 101 (1997), 5875–5888, 10.1021/jp9708658.
6. [6] Dorsey, J.G., Khaledi, M.G., Hydrophobicity estimations by reversed-phase liquid chromatography. Implications for biological partitioning processes. J. Chromatogr. 656 (1993), 485–499.
7. [7] Ayouni, L., Cazorla, G., Chaillou, D., Herbreteau, B., Rudaz, S., Lantéri, P., et al. Fast determination of lipophilicity by HPLC. Chromatographia 62 (2005), 251–255, 10.1365/s10337-005-0608-6.
8. [8] Gocan, S., Cimpan, G., Comer, J., Lipophilicity measurements by liquid chromatography. Adv. Chromatogr. 44 (2006), 79–176.
9. [9] Giaginis, C., Tsantili-Kakoulidou, A., Current state of the art in HPLC methodology for lipophilicity assessment of basic drugs. A review. J. Liq. Chromatogr. Relat. Technol. 31 (2007), 79–96, 10.1080/10826070701665626.
10. [10] Henchoz, Y., Guillarme, D., Rudaz, S., Veuthey, J.-L.L., Carrupt, P.-A.A., High-throughput log P determination by ultraperformance liquid chromatography: a convenient tool for medicinal chemists. J. Med. Chem. 51 (2008), 396–399, 10.1021/jm7014809.
11. [11] Liang, C., Lian, H., Recent advances in lipophilicity measurement by reversed-phase high-performance liquid chromatography. TrAC Trends Anal. Chem. 68 (2015), 28–36, 10.1016/j.trac.2015.02.009.
12. [12] Valkó, K., Snyder, L.R., Glajch, J.L., Retention in reversed-phase liquid chromatography as a function of mobile-phase composition. J. Chromatogr. A 656 (1993), 501–520, 10.1016/0021-9673(93)80816-Q.
13. [13] Harnisch, M., Möckel, H.J., Schulze, G., Relationship between log Pow, shake-flask values and capacity factors derived from reversed-phase high-performance liquid chromatography for n-alkylbenzenes and some OECD reference substances. J. Chromatogr. A 282 (1983), 315–332, 10.1016/S0021-9673(00)91610-8.
14. [14] Janicka, M., Kwietniewski, L., Perišić-Janjić, N.U., Determination of retention factors of s-Triazines homologous series in water using a numerical method basing on Ościk's equation. Chromatographia 63 (2006), S87–S93, 10.1365/s10337-006-0817-7.
15. [15] Janicka, M., Application of Ościk's equation for description of solute retention in RP HPLC and calculation of retention factor in water. J. Liq. Chromatogr. Relat. Technol. 32 (2009), 2779–2794, 10.1080/10826070903288060.
16. [16] Valkó, K., General approach for the estimation of octanol/water partition coefficient by reversed-phase high-performance liquid chromatography. J. Liq. Chromatogr. Relat. Technol., 1984, 1405–1424.
17. [17] Jandera, P., Comparison of various modes and phase systems for analytical HPLC. Valkó, K., (eds.) Separation Methods in Drug Synthesis and Purification, 2000, Elsevier, 10.1016/S1567-7192(00)80004-2.
18. [18] Shoenmakers, P.J., Billiet, H.A.H., De Galan, L., Influence of organic modifiers on the rentention behaviour in reversed-phase liquid chromatography and its consequences for gradient elution. J. Chromatogr. A 185 (1979), 179–195, 10.1016/S0021-9673(00)85604-6.
19. [19] Kerns, E.H., Di, L., Petusky, S., Kleintop, T., Huryn, D., McConnell, O., et al. Pharmaceutical profiling method for lipophilicity and integrity using liquid chromatography-mass spectrometry. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 791 (2003), 381–388.
20. [20] Lombardo, F., Shalaeva, M.Y., Tupper, K.A., Gao, F., E log Doct: a tool for lipophilicity determination in drug discovery. 2. Basic and neutral compounds. J. Med. Chem. 44 (2001), 2490–2497, 10.1021/jm0100990.
21. [21] Lombardo, F., Obach, R.S., Shalaeva, M.Y., Gao, F., Prediction of human volume of distribution values for neutral and basic drugs. 2. Extended data set and leave-class-out statistics. J. Med. Chem. 47 (2004), 1242–1250, 10.1021/jm030408h.
22. [22] Liu, X., Tanaka, H., Yamauchi, A., Testa, B., Chuman, H., Determination of lipophilicity by reversed-phase high-performance liquid chromatography. J. Chromatogr. A 1091 (2005), 51–59, 10.1016/j.chroma.2005.07.029.
23. [23] Valkó, K., Bevan, C., Reynolds, D., Chromatographic hydrophobicity index by fast-gradient RP-HPLC: a high-throughput alternative to log P/log D. Anal. Chem. 69 (1997), 2022–2029, 10.1021/ac961242d.
24. [24] Valkó, K., Slégel, P., New chromatographic hydrophobicity index (0) based on the slope and the intercept of the log k′ versus organic phase concentration plot. J. Chromatogr. A 631 (1993), 49–61, 10.1016/0021-9673(93)80506-4.
25. [25] Valko, K., Du, C.M., Bevan, C.D., Reynolds, D.P., Abraham, M.H., Rapid-gradient HPLC method for measuring drug interactions with immobilized artificial membrane: comparison with other lipophilicity measures. J. Pharm. Sci. 89 (2000), 1085–1096, 10.1002/1520-6017(200008)89:8<1085::AID-JPS13>3.0.CO;2-N.
26. [26] Mutton, I., Fast generic HPLC methods. Valkó, K., (eds.) Separation Methods in Drug Synthesis and Purification, 2000, Elsevier.
27. [27] Rudraraju, A.V., Amoyaw, P.N.A., Hubin, T.J., Khan, M.O.F., Determination of log P values of new cyclen based antimalarial drug leads using RP-HPLC. Pharmazie 69 (2014), 655–662.
28. [28] Valko, K., Measurements of lipophilicity and acid/base character using HPLC methods. Borchardt, R., Kerns, E., Lipinky, C., (eds.) Pharmaceutical Profiling in Drug Discovery for Lead Selection, 2004, AAPE, Arlington, VA, 127–182.
29. [29] Young, R.J., Green, D.V.S.S., Luscombe, C.N., Hill, A.P., Getting physical in drug discovery II: the impact of chromatographic hydrophobicity measurements and aromaticity. Drug Discov. Today 16 (2011), 822–830, 10.1016/j.drudis.2011.06.001.
30. [30] Valko, K., Du, C.M.M., Bevan, C., Reynolds, D.P.P., Abraham, M.H.H., Rapid method for the estimation of octanol/water partition coefficient (log Poct) from gradient RP-HPLC retention and a hydrogen bond acidity term (∑α2H). Curr. Med. Chem. 8 (2001), 1137–1146.
31. [31] Horvath, C., Melander, W., Molnar, I., Liquid chromatography of ionogenic substances with nonpolar stationary phases. Anal. Chem. 49 (1977), 142–154, 10.1021/ac50009a044.
32. [32] Lopez Marques, R.M., Schoenmakers, P.J., Modelling retention in reversed-phase liquid chromatography as a function of pH and solvent composition. J. Chromatogr. A 592 (1992), 157–182, 10.1016/0021-9673(92)85084-7.
33. [33] Seydel, J.K., Wiese, M., Mannhold, R., et al. Drug-Membrane Interactions: Analysis, Drug Distribution, Modeling, vol. 15, 2009, Wiley, Hoboken, NJ.
34. [34] Canals, I., Valkó, K., Bosch, E., Hill, A.P.P., Rosés, M., Retention of ionizable compounds on HPLC. 8. Influence of mobile-phase pH change on the chromatographic retention of acids and bases during gradient elution. Anal. Chem. 73 (2001), 4937–4945, 10.1021/ac0101454.
35. [35] Espinosa, S., Bosch, E., Rosés, M., Retention of ionizable compounds in high-performance liquid chromatography. 14. Acid–base pK values in acetonitrile-water mobile phases. J. Chromatogr. A 964 (2002), 55–66, 10.1016/S0021-9673(02)00558-7.
36. a of analytes. Sep. Purif. Rev. 36 (2007), 231–255, 10.1080/15422110701539129.
37. [37] Fuguet, E., Ràfols, C., Bosch, E., Rosés, M., Determination of the chromatographic hydrophobicity index for ionisable solutes. J. Chromatogr. A 1173 (2007), 110–119, 10.1016/j.chroma.2007.10.012.
38. a estimates from gradient high-performance liquid chromatography. J. Chromatogr. A 965 (2002), 117–127, 10.1016/S0021-9673(02)00114-0.
39. a and lipophilicity by gradient RP HPLC. Anal. Chem. 78 (2006), 239–249, 10.1021/ac0512103.
40. [40] Trainor, G.L., The importance of plasma protein binding in drug discovery. Expert Opin. Drug Discov. 2 (2007), 51–64, 10.1517/17460441.2.1.51.
41. [41] Rolan, P.E., Plasma protein binding displacement interactions – why are they still regarded as clinically important?. Br. J. Clin. Pharmacol. 37 (1994), 125–128, 10.1111/j.1365-2125.1994.tb04251.x.
42. [42] Banker, M.J., Clark, T.H., Williams, J.A., Development and validation of a 96-well equilibrium dialysis apparatus for measuring plasma protein binding. J. Pharm. Sci. 92 (2003), 967–974, 10.1002/jps.10332.
43. [43] Barré, J., Chamouard, J.M., Houin, G., Tillement, J.P., Equilibrium dialysis, ultrafiltration, and ultracentrifugation compared for determining the plasma-protein-binding characteristics of valproic acid. Clin. Chem. 31 (1985), 60–64.
44. [44] Vuignier, K., Schappler, J., Veuthey, J.-L., Carrupt, P.-A., Martel, S., Drug–protein binding: a critical review of analytical tools. Anal. Bioanal. Chem. 398 (2010), 53–66, 10.1007/s00216-010-3737-1.
45. [45] Kaliszan, R., Noctor, T.A., Wainer, I.W., Stereochemical aspects of benzodiazepine binding to human serum albumin. II. Quantitative relationships between structure and enantioselective retention in high performance liquid affinity chromatography. Mol. Pharmacol. 42 (1992), 512–517.
46. [46] Noctor, T.A.G., Diaz-Perez, M.J., Wainer, I.W., Use of a human serum albumin-based stationary phase for high-performance liquid chromatography as a tool for the rapid determination of drug-plasma protein binding. J. Pharm. Sci. 82 (1993), 675–676, 10.1002/jps.2600820629.
47. [47] Buchholz, L., Cai, C.-H., Andress, L., Cleton, A., Brodfuehrer, J., Cohen, L., Evaluation of the human serum albumin column as a discovery screening tool for plasma protein binding. Eur. J. Pharm. Sci. 15 (2002), 209–215, 10.1016/S0928-0987(01)00219-6.
48. [48] Beaudry, F., Coutu, M., Brown, N.K., Determination of drug-plasma protein binding using human serum albumin chromatographic column and multiple linear regression model. Biomed. Chromatogr. 13 (1999), 401–406, 10.1002/(SICI)1099-0801(199910)13:6<401::AID-BMC899>3.0.CO;2-C.
49. [49] Cevc, G., Partition coefficient vs. binding constant: how best to assess molecular lipophilicity. Eur. J. Pharm. Biopharm.[nl]J. Arbeitsgemeinschaft Für Pharm. Verfahrenstechnik e.V. 92 (2015), 204–215, 10.1016/j.ejpb.2015.03.008.
50. [50] Vuignier, K., Guillarme, D., Veuthey, J.-L., Carrupt, P.-A., Schappler, J., High performance affinity chromatography (HPAC) as a high-throughput screening tool in drug discovery to study drug-plasma protein interactions. J. Pharm. Biomed. Anal. 74 (2013), 205–212, 10.1016/j.jpba.2012.10.030.
51. [51] Ascoli, G.A., Bertucci, C., Salvadori, P., Ligand binding to a human serum albumin stationary phase: use of same-drug competition to discriminate pharmacologically relevant interactions. Biomed. Chromatogr. 12 (1998), 248–254, 10.1002/(SICI)1099-0801(199910)13:6<401::AID-BMC899>3.0.CO;2-C.
52. [52] Ashton, D.S., Beddell, C.R., Cockerill, G.S., Gohil, K., Gowrie, C., Robinson, J.E., et al. Binding measurements of indolocarbazole derivatives to immobilised human serum albumin by high-performance liquid chromatography. J. Chromatogr. B: Biomed. Appl. 677 (1996), 194–198, 10.1016/0378-4347(95)00458-0.
53. [53] Valko, K., Nunhuck, S., Bevan, C., Abraham, M.H., Reynolds, D.P., Fast gradient HPLC method to determine compounds binding to human serum albumin. Relationships with octanol/water and immobilized artificial membrane lipophilicity. J. Pharm. Sci. 92 (2003), 2236–2248, 10.1002/jps.10494.
54. [54] Kratochwil, N.A., Huber, W., Müller, F., Kansy, M., Gerber, P.R., Predicting plasma protein binding of drugs: a new approach. Biochem. Pharmacol. 64 (2002), 1355–1374, 10.1016/S0006-2952(02)01074-2.
55. [55] Colmenarejo, G., Alvarez-Pedraglio, A., Lavandera, J.L., Cheminformatic models to predict binding affinities to human serum albumin. J. Med. Chem. 44 (2001), 4370–4378, 10.1021/jm010960b.
56. [56] Chrysanthakopoulos, M., Giaginis, C., Tsantili-Kakoulidou, A., Retention of structurally diverse drugs in human serum albumin chromatography and its potential to simulate plasma protein binding. J. Chromatogr. A 1217 (2010), 5761–5768, 10.1016/j.chroma.2010.07.023.
57. [57] Yang, J., Hage, D.S., Effect of mobile phase composition on the binding kinetics of chiral solutes on a protein-based high-performance liquid chromatography column: interactions of D- and L-tryptophan with immobilized human serum albumin. J. Chromatogr. A 766 (1997), 15–25.
58. [58] Cheng, Y., Ho, E., Subramanyam, B., Tseng, J.-L., Measurements of drug-protein binding by using immobilized human serum albumin liquid chromatography-mass spectrometry. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 809 (2004), 67–73, 10.1016/j.jchromb.2004.06.006.
59. [59] Singh, S.S., Mehta, J., Measurement of drug-protein binding by immobilized human serum albumin-HPLC and comparison with ultrafiltration. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 834 (2006), 108–116, 10.1016/j.jchromb.2006.02.053.
60. [60] Endo, S., Goss, K.-U., Serum albumin binding of structurally diverse neutral organic compounds: data and models. Chem. Res. Toxicol. 24 (2011), 2293–2301, 10.1021/tx200431b.
61. [61] Reilly, J., Etheridge, D., Everatt, B., Jiang, Z., Aldcroft, C., Wright, P., et al. Studies in drug albumin binding using HSA and RSA affinity methods. J. Liq. Chromatogr. Relat. Technol. 34 (2011), 317–327, 10.1080/10826076.2011.548299.
62. [62] Israili, Z.H., Dayton, P.G., Human alpha-1-glycoprotein and its interactions with drugs. Drug Metab. Rev. 33 (2001), 161–235, 10.1081/DMR-100104402.
63. [63] Fuchs, H., Tillement, J.-P., Urien, S., Greischel, A., Roth, W., Concentration-dependent plasma protein binding of the novel dipeptidyl peptidase 4 inhibitor BI 1356 due to saturable binding to its target in plasma of mice, rats and humans. J. Pharm. Pharmacol. 61 (2009), 55–62, 10.1211/jpp.61.01.0008.
64. [64] Edeki, T., Dillon-Moore, B., He, N., Comparison of plasma protein binding of basic drugs in black and white individuals. Am. J. Ther. 3 (1996), 611–615.
65. [65] Fitos, I., Visy, J., Zsila, F., Bikádi, Z., Mády, G., Simonyi, M., Specific ligand binding on genetic variants of human α 1-acid glycoprotein studied by circular dichroism spectroscopy. Biochem. Pharmacol. 67 (2004), 679–688, 10.1016/j.bcp.2003.09.039.
66. [66] Jewell, R.C., Brouwer, K.L.R., McNamara, P.J., α1-Acid glycoprotein high-performance liquid chromatography column (EnantioPAC) as a screening tool for protein binding. J. Chromatogr. B: Biomed. Sci. Appl. 487 (1989), 257–264, 10.1016/S0378-4347(00)83035-2.
67. [67] Chrysanthakopoulos, M., Vallianatou, T., Giaginis, C., Tsantili-Kakoulidou, A., Investigation of the retention behavior of structurally diverse drugs on alpha1 acid glycoprotein column: insight on the molecular factors involved and correlation with protein binding data. Eur. J. Pharm. Sci. 60 (2014), 24–31, 10.1016/j.ejps.2014.04.015.
68. [68] McDonnell, P.A., Caldwell, G.W., Masucci, J.A., Using capillary electrophoresis/frontal analysis to screen drugs interacting with human serum proteins. Electrophoresis 19 (1998), 448–454, 10.1002/elps.1150190315.
69. [69] Pidgeon, C., Ong, S., Liu, H., Qiu, X., Pidgeon, M., Dantzig, A.H., et al. IAM chromatography: an in vitro screen for predicting drug membrane permeability. J. Med. Chem. 38 (1995), 590–594, 10.1021/jm00004a004.
70. [70] Barbato, F., The use of immobilised artificial membrane (IAM) chromatography for determination of lipophilicity. Curr. Comput. Aided. Drug Des. 2 (2006), 341–352, 10.2174/157340906778992319.
71. [71] Valko, K., Du, C.M., Bevan, C.D., Reynolds, D.P., Abraham, M.H., Rapid-gradient HPLC method for measuring drug interactions with immobilized artificial membrane: comparison with other lipophilicity measures. J. Pharm. Sci. 89 (2000), 1085–1096, 10.1002/1520–6017200008898<1085::AID-JPS13>3.0.CO;2-N.
72. [72] Taillardat-Bertschinger, A., Martinet, C.A.M., Carrupt, P., Reist, M., Caron, G., Fruttero, R., et al. Retention on immobilized artifical membranes (IAM) compared to partitioning in liposomes and n-octanol. Pharm. Res. 19 (2002), 729–737, 10.1023/A:1016156927420.
73. [73] Taillardat-Bertschinger, A., Carrupt, P.A., Barbato, F., Testa, B., Immobilized artificial membrane HPLC in drug research. J. Med. Chem. 46 (2003), 655–665, 10.1021/jm020265j.
74. [74] Wiedmer, S.K., Riekkola, M.L., Jussila, M.S., Phospholipids and liposomes in liquid chromatographic and capillary electromigration techniques. TrAC – Trends Anal. Chem. 23 (2004), 562–582, 10.1016/j.trac.2004.03.001.
75. [75] Barbato, F., di Martino, G., Grumetto, L., La Rotonda, M.I., Prediction of drug-membrane interactions by IAM-HPLC: effects of different phospholipid stationary phases on the partition of bases. Eur. J. Pharm. Sci. 22 (2004), 261–269, 10.1016/j.ejps.2004.03.019.
76. [76] Lepont, C., Poole, C.F., Retention characteristics of an immobilized artificial membrane column in reversed-phase liquid chromatography. J. Chromatogr. A 946 (2002), 107–124, 10.1016/S0021-9673(01)01579-5.
77. [77] Lázaro, E., Ràfols, C., Abraham, M.H., Rosés, M., Chromatographic estimation of drug disposition properties by means of immobilized artificial membranes (IAM) and C18 columns. J. Med. Chem. 49 (2006), 4861–4870, 10.1021/jm0602108.
78. [78] Caldwell, G.W., Masucci, J.A., Evangelisto, M., White, R., Evaluation of the immobilized artificial membrane phosphatidylcholine. J. Chromatogr. A 800 (1998), 161–169, 10.1016/S0021-9673(97)01143-6.
79. [79] Giaginis, C., Tsantili-Kakoulidou, A., Alternative measures of lipophilicity: from octanol–water partitioning to IAM retention. J. Pharm. Sci. 97 (2008), 2984–3004, 10.1002/jps.21244.
80. [80] Godard, T., Grushka, E., The use of phospholipid modified column for the determination of lipophilic properties in high performance liquid chromatography. J. Chromatogr. A 1218 (2011), 1211–1218, 10.1016/j.chroma.2010.12.105.
81. [81] Bin Luo, H., Zheng, C., Cheng, Y.K., Is phospholipid-saturated alkyl column a convenient replacement for immobilized-artificial-membrane?. J. Chromatogr. A 1176 (2007), 100–106, 10.1016/j.chroma.2007.10.093.
82. [82] Abraham, M.H., Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes. Chem. Soc. Rev., 22, 1993, 73, 10.1039/cs9932200073.
83. [83] Barbato, F., Cirocco, V., Grumetto, L., Immacolata La Rotonda, M., Comparison between immobilized artificial membrane (IAM) HPLC data and lipophilicity in n-octanol for quinolone antibacterial agents. Eur. J. Pharm. Sci. 31 (2007), 288–297, 10.1016/j.ejps.2007.04.003.
84. [84] Kotecha, J., Shah, S., Rathod, I., Subbaiah, G., Relationship between immobilized artificial membrane chromatographic retention and human oral absorption of structurally diverse drugs. Int. J. Pharm. 333 (2007), 127–135, 10.1016/j.ijpharm.2006.10.010.
85. [85] Luo, H., Zheng, C., Cheng, Y., The retention properties of nucleobases in alkyl C 8-/C 18- and IAM-chromatographic systems in relation to log Pow. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 847 (2007), 245–261, 10.1016/j.jchromb.2006.10.009.
86. [86] Abraham, M.H., Acree, W.E., Equations for the transfer of neutral molecules and ionic species from water to organic phases. J. Org. Chem. 75 (2010), 1006–1015, 10.1021/jo902388n.
87. [87] Abraham, M.H., Chadha, H.S., Martins, F., Mitchell, R.C., Bradbury, M.W., Gratton, J.A., Hydrogen bonding part 46: a review of the correlation and prediction of transport properties by an LFER method: physicochemical properties, brain penetration and skin permeability. Pestic. Sci. 55 (1999), 78–88, 10.1002/(SICI)1096-9063(199901)55:1<78::AID-PS853>3.0.CO;2-7.
88. [88] Abraham, M.H., Chadha, H.S., Whiting, G.S., Mitchell, R.C., Hydrogen bonding. 32. An analysis of water-octanol and water-alkane partitioning and the Δlog P parameter of seiler. J. Pharm. Sci. 83 (1994), 1085–1100, 10.1002/jps.2600830806.
89. [89] Du, C.M., Valko, K., Bevan, C., Reynolds, D., Abraham, M.H., Rapid gradient RP-HPLC method for lipophilicity determination: a solvation equation based comparison with isocratic methods. Anal. Chem. 70 (1998), 4228–4234.
90. [90] Abraham, M.H., Chadha, H.S., Mitchell, R.C., The factors that influence skin penetration of solutes*. J. Pharm. Pharmacol. 47 (1995), 8–16, 10.1111/j.2042-7158.1995.tb05725.x.
91. [91] Platts, J.A., Abraham, M.H., Zhao, Y.H., Hersey, A., Ijaz, L., Butina, D., Correlation and prediction of a large blood-brain distribution data set – an LFER study. Eur. J. Med. Chem. 36 (2001), 719–730, 10.1016/S0223–52340101269–7.
92. [92] Valkó, K., Plass, M., Bevan, C., Reynolds, D., Abraham, M.H., 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 (1998), 41–55, 10.1016/S0021-9673(97)00961-8.
93. [93] Zhao, Y.H., Le, J., Abraham, M.H., Hersey, A., Eddershaw, P.J., Luscombe, C.N., et al. Evaluation of human intestinal absorption data and subsequent derivation of a quantitative structure – activity relationship (QSAR) with the Abraham descriptors. J. Pharm. Sci. 90 (2001), 749–784, 10.1002/jps.1031.
94. [94] Du, C.M., Valko, K., Bevan, C., Reynolds, D., Abraham, M.H., Characterizing the selectivity of stationary phases and organic modifiers in reversed-phase high-performance liquid chromatographic systems by a general solvation equation using gradient elution. J. Chromatogr. Sci. 38 (2000), 503–511.
95. [95] Cimpean, D.M., Poole, C.F., Systematic search for surrogate chromatographic models of biopartitioning processes. Analyst 127 (2002), 724–729, 10.1039/b202010f.
96. [96] Hidalgo-Rodriguez, M., Fuguet, E., Ra, C., Estimation of biological properties by means of chromatographic systems: evaluation of the factors that contribute to the variance of biological – chromatographic correlations. Anal. Chem. 82 (2010), 10236–10245.
97. [97] Hidalgo-Rodríguez, M., Soriano-Meseguer, S., Fuguet, E., Ràfols, C., Rosés, M., Evaluation of the suitability of chromatographic systems to predict human skin permeation of neutral compounds. Eur. J. Pharm. Sci. 50 (2013), 557–568, 10.1016/j.ejps.2013.04.005.
98. [98] Hollósy, F., Valkó, K., Hersey, A., Nunhuck, S., Kéri, G., Bevan, C., Estimation of volume of distribution in humans from high throughput HPLC-based measurements of human serum albumin binding and immobilized artificial membrane partitioning. J. Med. Chem. 49 (2006), 6958–6971, 10.1021/jm050957i.
99. [99] Abraham, M.H., The permeation of neutral molecules, ions, and ionic species through membranes: brain permeation as an example. J. Pharm. Sci. 100 (2011), 1690–1701, 10.1002/jps.22404.
100. [100] Zhang, K., Chen, M., Scriba, G.K.E., Abraham, M.H., Fahr, A., Liu, X., Human skin permeation of neutral species and ionic species: extended linear free-energy relationship analyses. J. Pharm. Sci. 101 (2012), 2034–2044, 10.1002/jps.23086.
101. [101] Cho, C.-W., Stolte, S., Yun, Y.-S., Krossing, I., Thöming, J., In silico prediction of linear free energy relationship descriptors of neutral and ionic compounds. RSC Adv. 5 (2015), 80634–80642, 10.1039/C5RA13595H.
102. [102] Zissimos, A.M., Abraham, M.H., Barker, M.C., Box, K.J., Tam, K.Y., Calculation of Abraham descriptors from solvent-water partition coefficients in four different systems; evaluation of different methods of calculation. J. Chem. Soc. Perkin Trans. 2 (2002), 470–477, 10.1039/b110143a.
103. [103] Zissimos, A.M., Abraham, M.H., Du, C.M., Valko, K., Bevan, C., Reynolds, D., et al. Calculation of Abraham descriptors from experimental data from seven HPLC systems; evaluation of five different methods of calculation. J. Chem. Soc. Perkin Trans. 2 (2002), 2001–2010, 10.1039/b206927j.
104. [104] Barbato, F., di Martino, G., Grumetto, L., La Rotonda, M.I., Can protonated beta-blockers interact with biomembranes stronger than neutral isolipophilic compounds? A chromatographic study on three different phospholipid stationary phases (IAM-HPLC). Eur. J. Pharm. Sci. 25 (2005), 379–386, 10.1016/j.ejps.2005.03.011.
105. [105] Li, J., Sun, J., Cui, S., He, Z., 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 (2006), 174–182, 10.1016/j.chroma.2006.07.073.
106. [106] Vrakas, D., Giaginis, C., Tsantili-Kakoulidou, A., Different retention behavior of structurally diverse basic and neutral drugs in immobilized artificial membrane and reversed-phase high performance liquid chromatography: comparison with octanol–water partitioning. J. Chromatogr. A 1116 (2006), 158–164, 10.1016/j.chroma.2006.03.058.
107. [107] Ottiger, C., Wunderli-Allenspach, H., Immobilized artificial membrane (lAM)-HPLC for partition studies of neutral and ionized acids and bases in comparison with the liposomal partition system. Pharm. Res. 16 (1999), 643–650, 10.1023/A:1018808104653.
108. [108] Li, J., Sun, J., He, Z., Quantitative structure-retention relationship studies with immobilized artificial membrane chromatography. II: partial least squares regression. J. Chromatogr. A 1140 (2007), 174–179, 10.1016/j.chroma.2006.11.091.
109. [109] Barbato, L.R.F., Interactions of nonsteroidal antiinflammatory drugs with phospholipids: comparison between octanol/buffer partition coefficients and chromatographic indexes on immobilized artificial membranes. J. Pharm. Sci. 86 (1997), 225–229, 10.1021/js960233h.
110. [110] Hansch, C., The physicochemical approach to drug design and discovery (QSAR). Drug Dev. Res. 1 (1981), 267–309, 10.1002/ddr.430010403.
111. [111] Lombardo, F., Obach, R.S., Shalaeva, M.Y., Gao, F., Prediction of volume of distribution values in humans for neutral and basic drugs using physicochemical measurements and plasma protein binding data. J. Med. Chem. 45 (2002), 2867–2876, 10.1021/jm0200409.
112. [112] Hollosy, F., Valko, K., Hersey, A., Nunhuck, S., Keri, G., Bevan, C., et al. Estimation of volume of distribution in humans from HPLC measurements of human serum albumin binding and immobilized artificial membrane partitioning. J. Med. Chem. 49 (2006), 6958–6971, 10.1021/jm050957i.
113. [113] Theil, F.-P., Guentert, T.W., Haddad, S., Poulin, P., Utility of physiologically based pharmacokinetic models to drug development and rational drug discovery candidate selection. Toxicol. Lett. 138 (2003), 29–49, 10.1016/S0378-4274(02)00374-0.
114. [114] Kell, D., Dobson, P., The cellular uptake of pharmaceutical drugs is mainly carrier-mediated and is thus an issue not so much of biophysics but of systems biology. Syst. Chem., 2009, 149–168.
115. [115] Brodie, B.B., Kurz, H., Schanker, L.S., The importance of dissociation constant and lipid-solubility in influencing the passage of drugs into the cerebrospinal fluid. J. Pharmacol. Exp. Ther. 130 (1960), 20–25.
116. [116] Smith, D.A., Di, L., Kerns, E.H., The effect of plasma protein binding on in vivo efficacy: misconceptions in drug discovery. Nat. Rev. Drug Discov. 9 (2010), 929–939, 10.1038/nrd3287.
117. [117] Øie, S., Tozer, T.N., Effect of altered plasma protein binding on apparent volume of distribution. J. Pharm. Sci. 68 (1979), 1203–1205, 10.1002/jps.2600680948.
118. [118] Valkó, K.L., Nunhuck, S.B., Hill, A.P., Estimating unbound volume of distribution and tissue binding by in vitro HPLC-based human serum albumin and immobilised artificial membrane-binding measurements. J. Pharm. Sci. 100 (2011), 849–862, 10.1002/jps.22323.
119. [119] Braggio, S., Montanari, D., Rossi, T., Ratti, E., Drug efficiency: a new concept to guide lead optimization programs towards the selection of better clinical candidates. Expert Opin. Drug Discov. 5 (2010), 609–618, 10.1517/17460441.2010.490553.
120. [120] Valko, K., Chiarparin, E., Nunhuck, S., Montanari, D., In vitro measurement of drug efficiency index to aid early lead optimization. J. Pharm. Sci. 101 (2012), 4155–4169, 10.1002/jps.23305.
121. [121] Wasan, K.M., Brocks, D.R., Lee, S.D., Sachs-Barrable, K., Thornton, S.J., Impact of lipoproteins on the biological activity and disposition of hydrophobic drugs: implications for drug discovery. Nat. Rev. Drug Discov. 7 (2008), 84–99, 10.1038/nrd2353.
122. [122] Hughes, J.D., Blagg, J., Price, D.A., Bailey, S., DeCrescenzo, G.A., Devraj, R.V., et al. Physiochemical drug properties associated with in vivo toxicological outcomes. Bioorg. Med. Chem. Lett. 18 (2008), 4872–4875, 10.1016/j.bmcl.2008.07.071.
123. [123] Wager, T.T., Kormos, B.L., Brady, J.T., Will, Y., Aleo, M.D., Stedman, D.B., et al. Improving the odds of success in drug discovery: choosing the best compounds for in vivo toxicology studies. J. Med. Chem. 56 (2013), 9771–9779, 10.1021/jm401485p.
124. [124] Montanari, D., Chiarparin, E., Gleeson, M.P.M.P., Braggio, S., Longhi, R., Valko, K., et al. Application of drug efficiency index in drug discovery: a strategy towards low therapeutic dose. Expert Opin. Drug Discov. 6 (2011), 913–920, 10.1517/17460441.2011.602968.
125. [125] Leeson, P.D., Springthorpe, B., The influence of drug-like concepts on decision-making in medicinal chemistry. Nat. Rev. Drug Discov. 6 (2007), 881–890, 10.1038/nrd2445.
126. [126] Lipinski, C.A., Lombardo, F., Dominy, B.W., Feeney, P.J., Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46 (2001), 3–26, 10.1016/j.addr.2012.09.019.
127. [127] Kerns, E.H., Di, L., Petusky, S., Kleintop, T., Huryn, D., Mcconnell, O., et al. Pharmaceutical profiling method for lipophilicity and integrity using liquid chromatography–mass spectrometry. J. Chrom. B. 791 (2003), 381–388.
128. [128] Kerns, E.H., Di, L., Pharmaceutical profiling in drug discovery. Drug Discov. Today 8 (2003), 316–323.
129. [129] Young, R.J., Green, D.V.S., Luscombe, C.N., Hill, A.P., Getting physical in drug discovery II: the impact of chromatographic hydrophobicity measurements and aromaticity. Drug Discov. Today 16 (2011), 822–830, 10.1016/j.drudis.2011.06.001.
130. [130] Lovering, F., Bikker, J., Humblet, C., Escape from flatland: increasing saturation as an approach to improving clinical success. J. Med. Chem. 52 (2009), 6752–6756, 10.1021/jm901241e.
131. [131] Ritchie, T.J., Macdonald, S.J.F., The impact of aromatic ring count on compound developability – are too many aromatic rings a liability in drug design?. Drug Discov. Today 14 (2009), 1011–1020, 10.1016/j.drudis.2009.07.014.
132. [132] Kenny, P.W., Leitão, A., Montanari, C.A., Ligand efficiency metrics considered harmful. J. Comput. Aided Mater. Des. 28 (2014), 699–710, 10.1007/s10822-014-9757-8.
133. [133] Valko, K., Butler, J., Eddershaw, P., Predictive approaches to increase absorption of compounds during lead optimisation. Expert Opin. Drug Discov. 8 (2013), 1225–1238, 10.1517/17460441.2013.815613.
134. [134] Borthwick, A.D., Davies, D.E., Exall, A.M., Hatley, R.J.D., Hughes, J.A., Irving, W.R., et al. 2,5-Diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists. 3. Synthesis, pharmacokinetics, and in vivo potency. J. Med. Chem. 49 (2006), 4159–4170, 10.1021/jm060073e.
135. [135] Johnson, T.W., Dress, K.R., Edwards, M., Using the Golden Triangle to optimize clearance and oral absorption. Bioorg. Med. Chem. Lett. 19 (2009), 5560–5564, 10.1016/j.bmcl.2009.08.045.
136. [136] Cuenca-Benito, M., Sagrado, S., Villanueva-Camañas, R., Medina-Hernández, M., Quantitative retention–structure and retention–activity relationships of barbiturates by micellar liquid chromatography. J. Chromatogr. A 814 (1998), 121–132, 10.1016/S0021-9673(98)00375-6.
137. [137] Belena-Pozo, I., Villanueva-Camanas, R.M., Sagrado, S., Medina-Hernandez, M.J., Development and validation of a procedure for estimating the hydrophobicity of structurally unrelated compounds by micellar liquid chromatography. J. Chromatogr. Sci. 37 (1999), 375–382, 10.1093/chrsci/37.10.375.
138. [138] Molero-Monfort, M., Escuder-Gilabert, L., Villanueva-Camañas, R.M., Sagrado, S., Medina-Hernández, M.J., Biopartitioning micellar chromatography: an in vitro technique for predicting human drug absorption. J. Chromatogr. B: Biomed. Sci. Appl. 753 (2001), 225–236.
139. [139] Èudina, O., Markoviæ, B., Karljikoviæ-Rajiæ, K., Vladimirov, S., Biopartitioning micellar chromatography-partition coefficient micelle/water as a potential descriptor for hydrophobicity in prediction of oral drug absorption. Anal. Lett. 45 (2012), 677–688, 10.1080/00032719.2011.653904.
140. [140] Escuder-Gilabert, L., Martínez-Pla, J.J., Sagrado, S., Villanueva-Camañas, R.M., Medina-Hernández, M.J., Biopartitioning micellar separation methods: modelling drug absorption. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 797 (2003), 21–35, 10.1016/S1570-0232(03)00606-8.
141. [141] Martín-Biosca, Y., Torres-Cartas, S., Villanueva-Camañas, R.M., Sagrado, S., Medina-Hernández, M.J., Biopartitioning micellar chromatography to predict blood to lung, blood to liver, blood to fat and blood to skin partition coefficients of drugs. Anal. Chim. Acta 632 (2009), 296–303, 10.1016/j.aca.2008.11.004.
142. [142] Salary, M., Hadjmohammadi, M., Human serum albumin-mimetic chromatography based hexadecyltrimethylammonium bromide as a novel direct probe for protein binding of acidic drugs. J. Pharm. Biomed. Anal. 114 (2015), 1–7, 10.1016/j.jpba.2015.04.040.
143. [143] Grumetto, L., Russo, G., Barbato, F., Relationships between human intestinal absorption and polar interactions drug/phospholipids estimated by IAM-HPLC. Int. J. Pharm. 489 (2015), 186–194, 10.1016/j.ijpharm.2015.04.062.
144. [144] Harrell, A.W., Sychterz, C., Ho, M.Y., Weber, A., Valko, K., Negash, K., Interrogating the relationship between rat in vivo tissue distribution and drug property data for >200 structurally unrelated molecules. Pharmacol. Res. Perspect., 3, 2015, 10.1002/prp2.173 n/a–n/a.
145. [145] Mälkiä, A., Murtomäki, L., Urtti, A., Kontturi, K., Drug permeation in biomembranes: in vitro and in silico prediction and influence of physicochemical properties. Eur. J. Pharm. Sci. 23 (2004), 13–47, 10.1016/j.ejps.2004.05.009.
146. [146] Subirats, X., Rosés, M., Bosch, E., High-throughput log Po/w determination from UHPLC measurements: revisiting the chromatographic hydrophobicity index. J. Pharm. Biomed. Anal., 2015, 10.1016/j.jpba.2015.12.015.
147. [147] Kouskoura, M.G., Kachrimanis, K.G., Markopoulou, C.K., Modeling the drugs’ passive transfer in the body based on their chromatographic behavior. J. Pharm. Biomed. Anal. 100 (2014), 94–102, 10.1016/j.jpba.2014.07.031.
148. [148] Héberger, K., Quantitative structure-(chromatographic) retention relationships. J. Chromatogr. A 1158 (2007), 273–305, 10.1016/j.chroma.2007.03.108.
149. [149] Luttringer, O., Theil, F.-P., Poulin, P., Schmitt-Hoffmann, A.H., Guentert, T.W., Lavé, T., Physiologically based pharmacokinetic (PBPK) modeling of disposition of epiroprim in humans. J. Pharm. Sci. 92 (2003), 1990–2007, 10.1002/jps.10461.
150. [150] Jones, H.M., Parrott, N., Jorga, K., Lavé, T., A novel strategy for physiologically based predictions of human pharmacokinetics. Clin. Pharmacokinet. 45 (2006), 511–542, 10.2165/00003088-200645050-00006.
151. [151] Geetha, T., Singh, S., Applications of immobilized stationary-phase liquid chromatography: a potential in vitro technique. Pharm. Sci. Technol. Today. 3 (2000), 406–416, 10.1016/S1461-5347(00)00315-1.
152. [152] Temporini, C., Ceruti, S., Calleri, E., Ferrario, S., Moaddel, R., Abbracchio, M.P., et al. Development of an immobilized GPR17 receptor stationary phase for binding determination using frontal affinity chromatography coupled to mass spectrometry. Anal. Biochem. 384 (2009), 123–129, 10.1016/j.ab.2008.09.010.
153. [153] Moaddel, R., Wainer, I.W., The preparation and development of cellular membrane affinity chromatography columns. Nat. Protoc. 4 (2009), 197–205, 10.1038/nprot.2008.225.
154. [154] Meng, Q.C., Johansson, J.S., Eckenhoff, R.G., Chromatographic approach for determining the relative membrane permeability of drugs. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 774 (2002), 89–95.