Skip to main content
SpringerLink
Log in

Quantitative Structure–Retention Relationships as Useful Tool to Characterize Chromatographic Systems and Their Potential to Simulate Biological Processes

  • Review
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

Quantitative structure–retention relationships (QSRR) date back to the 1970s and are associated with the evolution of modern Chromatography, while in conjunction with quantitative structure–property relationships (QSPR), they make part of the QSAR discipline. The present review offers a survey of QSRR from a medicinal chemistry point of view, highlighting the merits of this approach in exploiting the friendly chromatographic techniques for the establishment of the physico chemical profiling of drug and drug candidates. It starts with a short overview on QSRR methodology concerning molecular representation, statistical tools and model validation. It continues focusing on the major recent achievements of QSRR with regard to the characterization of chromatographic systems and thereupon to the improvement of stationary phases and to experimental design, while emphasizing their application in drug design. The inter-relation of retention with lipophilicity, a property of paramount interest in drug action and the merit of biomimetic chromatography and of MEEKC systems to simulate essential pharmacokinetic properties are commented under the insights offered by QSRR, in conjunction with QSPR. Characteristic examples are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Kaliszan R, Foks H (1977) Chromatographia 10:346

    CAS  Google Scholar 

  2. Kaliszan R (1977) Chromatographia 10:529

    CAS  Google Scholar 

  3. Kaliszan R (1987) Quantitative structure–chromatographic relationships, vol 93, Chemical Analysis. Wiley, New York

  4. Kaliszan R (1997) Structure and retention in chromatography: a chemometric approach. Harwood Academic Publishers, Amsterdam

    Google Scholar 

  5. Heberger K (2007) J Chromatogr A 1158:273

    CAS  Google Scholar 

  6. Hansch C, Fujita T (1964) J Am Chem Soc 86:1616

    CAS  Google Scholar 

  7. Van de Waterbeemd H, Kansy M, Wagner B, Fischer H (1996) Lipophilicity measurement by high performance liquid chromatography (RP-HPLC). In: Pilska V, Testa B, van de Waterbeemd H (eds) Lipophilicity in drug action and toxicology. VCH Publishers, Weinheim, pp 73–87

    Google Scholar 

  8. Dorsey JG, Khaledi MG (1993) J Chromatogr A 656:485

    CAS  Google Scholar 

  9. Lombardo F, Shalaeva MY, Tupper KA, Gao F (2001) J Med Chem 44:2490

    CAS  Google Scholar 

  10. Liu X, Tanaka H, Yamauchi A, Testa B, Chuman H (2005) J Chromatogr A 1091:51

    CAS  Google Scholar 

  11. Kaliszan R (1990) Quant Struct Act Relat 9:83

    CAS  Google Scholar 

  12. Giaginis C, Tsantili-Kakoulidou A (2008) J Liq Chrom Relat Tech 31:79

    CAS  Google Scholar 

  13. Buciński A, Wnuk M, Goryński K, Giza A, Kochańczyk J, Nowaczyk A, Baczek T, Nasal A (2009) J Pharm Biomed Anal 50:591

    Google Scholar 

  14. Liu H, Ong S, Glunz L, Pidgeon C (1995) Anal Chem 67:3550

    CAS  Google Scholar 

  15. Barbato F, di Martino G, Grunetto G, La Rotonda MI (2004) Eur J Pharm Sci 22:261

    CAS  Google Scholar 

  16. Noctor TAG, Diaz-Perez MJ, Wainer IW (1993) J Pharm Sci 82:675

    CAS  Google Scholar 

  17. Domenici E, Bertucci C, Salvadori P, Felix G, Cahagne I, Motellier S, Wainer IW (1990) Chromatographia 29:170

    CAS  Google Scholar 

  18. Payares P, Diaz D, Olivero J, Vivas R, Gomez I (1997) J Chromatogr A 771:213

    CAS  Google Scholar 

  19. Heberger K, Kowalska T (1999) J Chromatogr A 845:13

    CAS  Google Scholar 

  20. Hinckley DA, Bidleman TF, Foreman WT, Tuschall JR (1990) J Chem Eng Data 35:232

    CAS  Google Scholar 

  21. Heberger K, Kowalska T (1997) Chromatographia 44:179

    CAS  Google Scholar 

  22. Heberger K, Kowalska T, Gorgenyi M (1999) Acta Chromatogr 9:25

    CAS  Google Scholar 

  23. Szaleniec M, Dudzik A, Pawul M, Kozik B (2009) J Chromatogr A 1216:6224

    CAS  Google Scholar 

  24. Suzuki T, Timofei S, Iuoras BE, Uray G, Verdino P, Fabian WM (2001) J Chromatogr A 922:13

    CAS  Google Scholar 

  25. Karimi H, Farmany A, Noorizadeh H (2012) Environ Monit Assess [Epub ahead of print]

  26. Ghavami R, Mohammad Sajadi S (2010) Chromatographia 72:523–533

    CAS  Google Scholar 

  27. Drosos JC, Viola-Rhenals M, Vivas-Reyes R (2010) J Chromatogr A 1217:4411

    CAS  Google Scholar 

  28. Lin Z, Liu S, Li Z (2002) J Chromatogr Sci 40:7

    CAS  Google Scholar 

  29. Fragkaki AG, Tsantili-Kakoulidou A, Angelis YS, Koupparis M, Georgakopoulos C (2009) J Chromatogr A 1216:8404

    CAS  Google Scholar 

  30. Liu T, Nicholls IA, Öberg T (2011) Anal Chim Acta 702:37

    CAS  Google Scholar 

  31. Vervoort RJ, Debets AJ, Claessens HA, Cramers CA, de Jong GJ (2000) J Chromatogr A 897:1

    CAS  Google Scholar 

  32. Perisic-Janjic NA, Kaliszan RBC, Wiczling PB, Milosevic ND, Uscumlic GE, Banjac N (2011) Mol Pharm 8:555

    CAS  Google Scholar 

  33. Creek DJ, Jankevics A, Breitling R, Watson DG, Barrett MP, Burgess KE (2011) Anal Chem 83:8703

    CAS  Google Scholar 

  34. Mihaleva VV, Verhoeven HA, de Vos RC, Hall RD, van Ham RC (2009) Bioinformatics 25:787

    CAS  Google Scholar 

  35. Schefzick S, Kibbey C, Bradley MP (2004) J Comb Chem 6:916

    CAS  Google Scholar 

  36. Kovats E (1965) In: Jennings W (ed) Gas chromatography with glass capillary columns, 2nd edn. Academic Press, New York

  37. Ghavami R, Faham S (2010) Chromatographia 72:893

    CAS  Google Scholar 

  38. Snyder LR, Dolan JW (1998) In: The linear solvent-strength model of gradient elution in advances in chromatography, vol 38. Marcel Dekker, New York, pp 115–187

  39. Dross K, Sonntag C, Mannhold R (1994) J Chromatogr A 673:113

    CAS  Google Scholar 

  40. Horvath C, Melander W, Molnar I (1976) J Chromatogr 125:129

    CAS  Google Scholar 

  41. Valko K, Slegel P (1993) J Chromatogr 631:69

    Google Scholar 

  42. Valko K, Bevan C, Reynolds D (1997) Anal Chem 69:2022

    CAS  Google Scholar 

  43. West C, Lesellier E (2006) J Chromatogr A 1110:181

    CAS  Google Scholar 

  44. Jiskra J, Claessens HA, Cramers CA, Kaliszan R (2002) J Chromatogr A 977:193

    CAS  Google Scholar 

  45. Cazenave-Gassiot A, Boughtflower R, Caldwell J, Coxhead R, Hitzel L, Lane S, Oakley P, Holyoak C, Pullen F, Langley GJ (2008) J Chromatogr A 1189:254

    CAS  Google Scholar 

  46. Milano Chemometrics and QSAR Research Group, Talete, Milano, Italy. http://www.disat.unimib.it/chm/Dragon.htm

  47. Todeschini R, Consonni V (2000) Handbook of molecular descriptors. Wiley, Weinheim

    Google Scholar 

  48. Dross KP, Rekker RF, de Vries G, Mannhold R (1998) Quant Struct Act Relat 17:549

    CAS  Google Scholar 

  49. Rykowska I, Bielecki P, Wasiak W (2010) J Chromatogr A 1217:1971

    CAS  Google Scholar 

  50. Kier LB, Hall LH (1999) Molecular structure description: the electrotopological state. Academic Press, San Diego

    Google Scholar 

  51. Kier LB, Hall LH (2002) Croat Chem Acta 75:371

    CAS  Google Scholar 

  52. Olivero J, Gracia T, Payares P, Vivas R, Díaz D, Daza E, Geerlings P (1997) J Pharm Sci 86:62

    Google Scholar 

  53. Dai J, Jin L, Yao S, Wang L (2001) Chemosphere 42:899

    CAS  Google Scholar 

  54. Abraham MH, Chandha HS, Leo A (1994) J Chromatogr A 685:203

    CAS  Google Scholar 

  55. Abraham MH, Ibrahim A, Zissimos AM, Zhao YH, Comer J, Reynolds DP (2002) Drug Discov Today 7:1056

    CAS  Google Scholar 

  56. Zissimos AM, Abraham MH, Du CM, Valko K, Bevan C, Reynolds D, Wood J, Tam K (2001) J Chem Soc 2

  57. Abraham MH, McGowan JC (1987) Chromatographia 23:243

    CAS  Google Scholar 

  58. Abraham MH, Ibrahim A, Zissimos AM (2004) J Chromatogr A 1037:29

    Google Scholar 

  59. Vitha M, Carr PW (2006) J Chromatogr A 1126:143

    CAS  Google Scholar 

  60. Benhaim D, Grushka E (2010) J Chromatogr A 1217:65

    CAS  Google Scholar 

  61. Al-Haj MA, Kaliszan R, Buszewski B (2001) J Chromatogr Sci 39:29

    CAS  Google Scholar 

  62. Janečková L, Kalíková K, Vozka J, Armstrong DW, Bosáková Z, Tesařová E (2011) J Sep Sci 34:2639

    Google Scholar 

  63. Abraham MH, Treiner C, Roses M, Rafols C, Ishihama Y (1996) J Chromatogr A 752:243

    CAS  Google Scholar 

  64. Bodzioch K, Dejaegher B, Baczek T, Kaliszan R, van der Heyden Y (2009) J Sep Sci 32:2075

    CAS  Google Scholar 

  65. Baczek T, Kaliszan R, Novotná K, Jandera P (2005) J Chromatogr A 1075:109

    CAS  Google Scholar 

  66. D’Archivio AA, Incani A, Ruggieri F (2011) Anal Bioanal Chem 399:903

    Google Scholar 

  67. Riahi S, Pourbasheer E, Ganjali MR, Norouzi P (2009) J Hazard Mater 166:853

    CAS  Google Scholar 

  68. Kempe H, Kempe M (2010) Anal Bioanal Chem 398:3087

    CAS  Google Scholar 

  69. Put R, van der Heyden Y (2007) Anal Chim Acta 602:164

    CAS  Google Scholar 

  70. Hidalgo-Rodriguez M, Fuguet E, Rafols C, Roses M (2010) Anal Chem 82:10236

    CAS  Google Scholar 

  71. Eriksson L, Johansson E, Kettaneh-Wold N, Wold S (2001) Multi-and megavariate data analysis, principles and applications. Umetrics AB, Umea

    Google Scholar 

  72. Eriksson L, Johansson E (1996) Chemometr Intell Lab Syst 34:1

    CAS  Google Scholar 

  73. Wold S, Josefson M, Gottfries J, Linusson S (2004) J Chemometrics 18:156

    CAS  Google Scholar 

  74. Garkani-Nejad MA (2011) Chromatographia 73:733

    CAS  Google Scholar 

  75. Noorizadeh H, Farmany A (2010) Chromatographia 72:563

    CAS  Google Scholar 

  76. Zupan J, Gasteiger J (1999) Neural networks in chemistry and drug design. Wiley-VCH, Weinheim

  77. Hornik K, Stinchcombe M, White H (1989) Neural Networks 2:359

    Google Scholar 

  78. Krose B, Van der Smagt P (1996) An introduction to neural networks. The University of Amsterdam, Amsterdam

    Google Scholar 

  79. Hancock T, Put R, Coomans D, van der Heyden Y, Everingham Y (2005) Chemom Intell Lab Syst 76:185

    CAS  Google Scholar 

  80. Goodarzi M, Jensen R, Vander Heyden Y (2012) J Chromatogr B Analyt Technol Biomed Life Sci (in press)

  81. Fatemi MH, Baher E, Ghorbanzadeh M (2009) J Sep Sci 32:4133

    CAS  Google Scholar 

  82. Komsta Ł (2008) J Sep Sci 31:2899

    Google Scholar 

  83. Roy K, Mitra L, Kar S, Ojha P, Das RN, Kabir H (2012) J Chem Inf Model 52:396

    CAS  Google Scholar 

  84. Ojha PK, Mitra I, Das RN, Roy K (2011) Chemom Intell Lab Syst 107:194

    CAS  Google Scholar 

  85. Tropsha A, Gramatica P, Gombar VK (2003) QSAR Comb Sci 22:69

    CAS  Google Scholar 

  86. Ivanciuc O, Ivanciuc T, Filip PA, Cabrol-Bass D (1999) J Chem Inf Comput Sci 39:515

    CAS  Google Scholar 

  87. Chirico N, Gramatica P (2012) J Chem Inf Model 52:2044

    CAS  Google Scholar 

  88. Jackson PT, Schure MR, Weber TP, Carr PW (1997) Anal Chem 69:416

    CAS  Google Scholar 

  89. Park JH, Yoon MH, Ryu JW, Jang MD (1998) J Chromatogr A 796:249

    CAS  Google Scholar 

  90. Poole CF, Atapattu SN, Poole SK, Bell AK (2009) Anal Chim Acta 652:32

    CAS  Google Scholar 

  91. D’Archivio AA, Giannitto A, Maggi MA, Ruggieri F (2012) Anal Chim Acta 717:52

    Google Scholar 

  92. Wilson NS, Nelson MD, Dolan JW, Snyder LR, Wolcott RG, Carr PW (2002) J Chromatogr A 961:171

    CAS  Google Scholar 

  93. Reta M, Carr PW (1999) J Chromatogr A 855:121

    CAS  Google Scholar 

  94. Gilroy1 JJ, Dolan1 JW, Snyder LR (2003) J Chromatogr A 1000:757

    Google Scholar 

  95. Euerby MR, Petersson P (2003) J Chromatogr A 994:13

    CAS  Google Scholar 

  96. Kimata K, Iwaguchi K, Onishi S, Jinno K, Eksteen R, Hosoya K, Arki M, Tanaka N (1989) J Chromatogr Sci 27:721

    CAS  Google Scholar 

  97. Lopez Lawrence A, Rutan Sarah C (2002) J Chromatogr A 965:301

    CAS  Google Scholar 

  98. Claessens HA, van Straten MA, Cramers CA, Jezizrska M, Buszewski B (1998) J Chromatogr A 826:135

    CAS  Google Scholar 

  99. Claessens HA (2001) Trends Anal Chem 20:563

    CAS  Google Scholar 

  100. Neue UD, Serowik E, Iraneta P, Alde BA, Walter TH (1999) J Chromatogr A 849:87

    CAS  Google Scholar 

  101. Rogers SD, Dorsey JG (2000) J Chromatogr A 892:57

    CAS  Google Scholar 

  102. Wilson NS, Dolan JW, Snyder LR, Carr PW, Sander LC (2002) J Chromatogr A 961:217

    CAS  Google Scholar 

  103. Wilson NS, Nelson MD, Dolan JW, Snyder LR, Carr PW (2002) J Chromatogr A 961:195

    CAS  Google Scholar 

  104. Lesellier E, West C (2007) J Chromatogr A 1158:329

    CAS  Google Scholar 

  105. Lesellier E, West C, Tchapla A (2006) J Chromatogr A 1111:62

    CAS  Google Scholar 

  106. Gilroy JJ, Dolan JW, Snyder LR (2003) J Chromatogr A 1000:757

    CAS  Google Scholar 

  107. Neue UD (2007) J Sep Sci 30:1611

    CAS  Google Scholar 

  108. Yang M, Fazio S, Munch D, Drumm P (2005) J Chromatogr A 1097:124

    CAS  Google Scholar 

  109. Snyder LR, Dolan JW, Carr PW (2007) Anal Chem 79:3255–3262

    Google Scholar 

  110. Cruz E, Euerby M, Johnson CM, Hackett CA (1997) Chromatographia 44:151

    CAS  Google Scholar 

  111. Engelhardt H, Lobert T (1999) Anal Chem 71:1885

    CAS  Google Scholar 

  112. Slingsby RW, Bordanov A, Grimes M (2001) J Chromatogr A 913:159

    CAS  Google Scholar 

  113. Visky D, Heyden YV, Ivanyi T, Baten P, De Beer J, Kovacs Z, Noszal B, Roets E, Massart DL, Hoogmartens J (2002) J Chromatogr A 977:39

    CAS  Google Scholar 

  114. Dabić D, Natić M, Džambaski Z, Marković R, Milojković-Opsenica D, Tešić Ž (2011) J Sep Sci 34:2397

    Google Scholar 

  115. Buszewski B, Michel M (2010) J AOAC Int 93:1703

    CAS  Google Scholar 

  116. Luo H, Cheng Y-K (2005) QSAR Comb Sci 24:968

    CAS  Google Scholar 

  117. Plenis A, Balakowska E, Baczek T (2011) J Sep Sci 34:3310

    CAS  Google Scholar 

  118. Stella C, Rudaz S, Gauvrit JY, Lantéri P, Huteau A, Tchapla A, Veuthey JL (2007) J Pharm Biomed Anal 43:89

    CAS  Google Scholar 

  119. Neue UD, van Tran K, Iraneta PC, Alden BA (2003) J Sep Sci 26:174

    CAS  Google Scholar 

  120. Winget P, Dolney DM, Giesen DJ, Cramer CJ, Truhla DG (2010) Minnesota solvent descriptor database. University of Minnesota, Minneapolis

    Google Scholar 

  121. Tan LC, Carr PW (1998) J Chromatogr A 799:1

    CAS  Google Scholar 

  122. Reta M, Carr PW, Sadek PC, Rutan SC (1999) Anal Chem 71:3484

    CAS  Google Scholar 

  123. Lazaro E, Rafols C, Roses M (2005) J Chromatogr A 1081:163

    CAS  Google Scholar 

  124. Lázaro E, Izquierdo P, Ràfols C, Rosés M, Bosch E (2009) J Chromatogr A 1216:5214

    Google Scholar 

  125. Katritzky AR, Fara DC, Kuanar M, Hur E, Karelson M (2005) J Phys Chem A 109:10323

    CAS  Google Scholar 

  126. Bird E, Marshall AC (1971) J Chromatogr 63:313

    CAS  Google Scholar 

  127. Hushoff A, Perrin JH (1973) J Med Chem 20:430

    Google Scholar 

  128. Braumann T (1986) J Chromatogr 373:191

    CAS  Google Scholar 

  129. Kakoulidou A, Rekker RF (1984) J Chromatogr 295:341

    CAS  Google Scholar 

  130. Bechalany A, Tsantili-Kakoulidou A, El Tayar N, Testa B (1991) J Chromatogr 541:221

    CAS  Google Scholar 

  131. Yamagami C, Yokota M, Takao N (1994) Chem Pharm Bull 42:907

    CAS  Google Scholar 

  132. Biagi GL, Barbaro MC, Sapone A, Recanatini M (1994) J Chromatogr A 662:341

    CAS  Google Scholar 

  133. Leo A, Hansch C, Elkins D (1971) Chem Rev 71:525

    CAS  Google Scholar 

  134. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (1997) Adv Drug Deliv Rev 23:3

    CAS  Google Scholar 

  135. van der Waterbeemd H, Smith DA, Beaumont K, Walker DK (2001) J Med Chem 44:1

    Google Scholar 

  136. Liu X, Testa B, Fahr A (2011) Pharm Res 28:962

    CAS  Google Scholar 

  137. Avdeef A (1996) In: Pliska V, Testa B, van de Waterbeemd H (eds) Methods and principles in medicinal chemistry, vol 4. VCH Publishers, Weinheim, pp 109–139

    Google Scholar 

  138. Avdeef A, Box KJ (1995) Sirius technical application notes (STAN), vol 2. Sirius Analytical Instruments Ltd., Forest Row

    Google Scholar 

  139. Giaginis C, Theocharis S, Tsantili-Kakoulidou A (2006) Anal Chim Acta 573:311

    Google Scholar 

  140. Liu X, Tanaka H, Yamauchi A, Testa B (2004) Helv Chim Act 87:2866

    CAS  Google Scholar 

  141. Valko K (2004) J Chromatogr A 1037:299

    CAS  Google Scholar 

  142. El Tayar N, van de Waterbeemd H, Testa B (1985) J Chromatogr 320:305

    Google Scholar 

  143. Tsantili-Kakoulidou A, Filippatos E, Todoulou O, Papadaki-Valiraki A (1993) J Chromatogr A 654:43

    CAS  Google Scholar 

  144. Panderi I, Angelopoulos Ch, Tsantili-Kakoulidou A, Kazanis M, Vavayannis A (1997) Farmaco 52:167

    CAS  Google Scholar 

  145. Moreno E, Gabano E, Torres E, Platts JA, Ravera M, Aldana I, Monge A, Pérez-Silanes S (2011) Molecules 16:7893

    CAS  Google Scholar 

  146. Pallicer JM, Sales J, Rosés M, Ràfols C, Bosch E (2011) J Chromatogr A 1218:6356

    CAS  Google Scholar 

  147. Onişor C, Poša M, Kevrešan S, Kuhajda K, Sârbu C (2010) J Sep Sci 33:3110

    Google Scholar 

  148. Sztanke K, Markowski W, Swieboda R, Polak B (2010) Eur J Med Chem 45:2644

    CAS  Google Scholar 

  149. Chrysanthakopoulos M, Nicolaou I, Demopoulos VJ, Tsantili-Kakoulidou A (2010) J Chromatogr B Analyt Technol Biomed Life Sci 878:61

    CAS  Google Scholar 

  150. Leo Α (1983) J Chem Soc Perkins Trans II 825

  151. Tsantili-Kakoulidou Α, El Tayar N, van de Waterbeemd H, Testa B (1987) J Chromatogr 389:33

    CAS  Google Scholar 

  152. Testa B, Carrupt P-A, Gaillard P, Tsai R-S (1996) In: Pliska V, Testa B, van de Waterbeemd H (eds) Lipophilicity in drug action and toxicology. VCH, Weinheim, pp 49–71

  153. Raevsky OA, Schaper K-J, Seydel JK (1995) Quant Struct Act Relat 14:433

    CAS  Google Scholar 

  154. Vrakas D, Panderi I, Hadjipavlou-Litina D, Tsantili-Kakoulidou A (2005) QSAR Comb Sci 24:254

    CAS  Google Scholar 

  155. Cimpan G, Hadaruga M, Miclaus V (2000) J Chromatogr A 869:49

    CAS  Google Scholar 

  156. Reiner GN, Labuckas DO, García DA (2009) J Pharm Biomed Anal 49:686

    CAS  Google Scholar 

  157. Janicka M, Stępnik K, Pachuta-Stec A (2012) Chromatographia 75:449

    CAS  Google Scholar 

  158. Giaginis C, Theocharis S, Tsantili-Kakoulidou A (2007) J Chromatogr A 1166:116

    CAS  Google Scholar 

  159. Pallicer JM, Calvet C, Port A, Rosés M, Ràfols C, Bosch E (2012) J Chromatogr A 1240:113

    CAS  Google Scholar 

  160. Layne J (2002) J Chromatogr A 957:149

    CAS  Google Scholar 

  161. Mendez A, Bosch E, Roses M, Neue UD (2003) J Chromatogr A 986:33

    CAS  Google Scholar 

  162. Tate PA, Dorsey JG (2004) J Chromatogr A 1042:37

    CAS  Google Scholar 

  163. Minick DJ, Brent DA, Frenz JH (1989) J Chromatogr 461:177

    CAS  Google Scholar 

  164. Dellis D, Giaginis C, Tsantili-Kakoulidou A (2007) J Pharm Biomed Anal 44:57

    CAS  Google Scholar 

  165. Kawczak P, Van der Heyden Y, Nasal A, Baczek T, Drabczyñska A, Kieć-Kononowicz K, Kaliszan R (2010) J Sep Sci 33:1546

    CAS  Google Scholar 

  166. Huie CW (2006) Electrphoresis 27:60

    CAS  Google Scholar 

  167. Abraham MH, Chadha HS, Whiting GS, Mitchell RC (1994) J Pharm Sci 83:1085

    CAS  Google Scholar 

  168. Ruggieri F, D’Archivio AA, Carlucci G, Mazzeo P (2005) J Chromatogr A 1076:163

    CAS  Google Scholar 

  169. Espinosa S, Bosch E, Roses M (2002) J Chromatogr A 945:83

    CAS  Google Scholar 

  170. Valko K, Plass M, Bevan C, Reynolds D, Abraham MH (1998) J Chromatogr A 797:41

    CAS  Google Scholar 

  171. Walters RR (1985) Anal Chem 57:1099

  172. Hage DS (1998) In: Katz E, Eksteen R, Miller N (eds) Handbook of HPLC, Chap. 13. Mercel Dekker, New York

  173. Hansch C, Leo A, Hoekman D (1995) Fundamentals and applications in chemistry and biology in exploring QSAR. American Chemical Society, Washington, DC

  174. van de Waterbeemd H, Testa B (1987) In: Testa B (ed) Advances in drug research, vol 16. Academic Press, New York, pp 85–227

    Google Scholar 

  175. Mason RP, Rhodes DG, Herbette LG (1991) J Med Chem 34:870

    Google Scholar 

  176. Balon K, Mueller BW, Riebesehl BU (1999) Pharm Res 16:882

    CAS  Google Scholar 

  177. Krämer S (2001) Liposomes/water partitioning: theory techniques and applications. In: Testa B, van de Waterbeemd H, Folkers G, Guy R (eds) Pharmacokinetic Optimization in Drug Research. Verlag Helvetica ChimicaActa/Wiley–VCH, Zürich/Weinheim

    Google Scholar 

  178. Markovich RJ, Qiu X, Nichols DE, Pidgeon C, Invergo B, Alvarez FM (1991) Anal Chem 63:1851

    CAS  Google Scholar 

  179. Taillardat-Bertschinger A, Carrupt PA, Barbato F, Testa B (2003) J Med Chem 46:655

    CAS  Google Scholar 

  180. Caldwell GW, Masucci JA, Evangelisto M, White R (1998) J Chromatogr A 800:161

    CAS  Google Scholar 

  181. Ong S, Pidgeon C (1995) Anal Chem 67:2119

    CAS  Google Scholar 

  182. Taillardat-Bertschinger A, Barbato F, Quercia MT, Carrupt P-A, Reist M, La Rotonda MI, Testa B (2002) Helv Chim Act 85:519

    CAS  Google Scholar 

  183. Vrakas D, Hadjipavlou-Litina D, Tsantili-Kakoulidou A (2005) J Pharm Biomed Anal 39:908

    CAS  Google Scholar 

  184. Abraham MH, Chandha HS, Leitao RAE, Mitchell RC, Lambert WJ, Kaliszan R, Nasal A, Haber P (1997) J Chromatogr A 766:35

    CAS  Google Scholar 

  185. Li J, Suna J, Cui S, He Z (2006) J Chromatogr A 1132:174

    CAS  Google Scholar 

  186. Vrakas D, Giaginis C, Tsantili-Kakoulidou A (2008) J Chromatogr A 1187:67

    CAS  Google Scholar 

  187. Barbato F, di Martino G, Grumetto L, La Rotonda MI (2005) Eur J Pharm Sci 25:379

    CAS  Google Scholar 

  188. Vrakas D, Giaginis C, Tsantili-Kakoulidou A (2006) J Chromatogr A 1116:158

    CAS  Google Scholar 

  189. Grumetto L, Carpentiero C, Barbato F (2012) Eur J Pharm Sci 45:685

    CAS  Google Scholar 

  190. Barbato F (2006) Curr Comput Aided Drug Des 2:341

    CAS  Google Scholar 

  191. Pidgeon C, Ong S, Liu H, Qiu X, Pidgeon M, Dantzig AH, Munroe J, Hornback WJ, Kasher JS, Glunz L, Szczerba T (1995) J Med Chem 38:590

    CAS  Google Scholar 

  192. Ong S, Liu H, Pidgeon C (1996) J Chromatogr A 728:113

    CAS  Google Scholar 

  193. Chan ECY, Tan WL, Fang LJ (2005) J Chromatogr A 1072:159

    CAS  Google Scholar 

  194. Genty M, Gonzalez G, Clere C, Desangle-Gouty V, Legendre JY (2001) Eur J Pharm Sci 12:223

    CAS  Google Scholar 

  195. Nasal A, Sznitowska M, Bucinski A, Kaliszan R (1995) J Chromatogr A 692:83

    CAS  Google Scholar 

  196. Kotecha J, Shah S, Rathod I, Subbaiah G (2008) Int J Pharm 360:96

    CAS  Google Scholar 

  197. Reichel A, Begley DJ (1998) Pharm Res 15:1270

    CAS  Google Scholar 

  198. Salminen T, Pulli A, Taskinen J (1997) J Pharm Biomed Anal 15:469

    CAS  Google Scholar 

  199. Lazaro E, Rafols C, Abraham MH, Roses M (2006) J Med Chem 49:4861

    Google Scholar 

  200. Hanumegowda UM, Wenke G, Regueiro-Ren A, Yordanova R, Corradi S, Adams P (2010) Chem Res Toxicol 23:749

    CAS  Google Scholar 

  201. Casartelli A, Bonato M, Cristofori P, Crivellente F, Dal Negro G, Masotto I, Mutinelli C, Valko K, Bonfante V (2003) Cell Biol Toxicol 19:161

    CAS  Google Scholar 

  202. Stewart KK, Doherty RF (1973) Proc Natl Acad Sci USA 70:2850

    CAS  Google Scholar 

  203. Haginaka J (2001) J Chromatogr A 906:253

    CAS  Google Scholar 

  204. Lammers N, De Bree H, Groen CP, Ruijten HM, Jong BJ (1989) J Chromatogr Biomed Appl 496:291

    CAS  Google Scholar 

  205. Kaliszan R, Nasal A, Turowski M (1996) J Chromatogr A 722:25

    CAS  Google Scholar 

  206. Ashton DS, Beddell CR, Cockerill GS, Gohil K, Gowrie C, Robinson JE, Slater MJ, Valko K (1996) J Chromatogr B 677:194

    Google Scholar 

  207. Noctor TA, Pham CD, Kaliszan R, Wainer IW (1992) Mol Pharmacol 42:506

    CAS  Google Scholar 

  208. Beaudry F, Coutu M, Brown NK (1999) Biomed Chromatogr 13:401

    CAS  Google Scholar 

  209. Reilly J, Etheridge D, Everatt B, Jiang Z, Springer C, Fairhurst RA (2011) J Liq Chromatogr Relat Technol 34:317

    CAS  Google Scholar 

  210. Valko K, Nunhuck S, Bevan C, Abraham MH, Reynolds DP (2003) J Pharm Sci 92:2236

    CAS  Google Scholar 

  211. Barbato F, di Martino G, Grumetto L, La Rotonda MI (2007) Eur J Pharm Sci 30:211

    CAS  Google Scholar 

  212. Chrysanthakopoulos M, Giaginis C, Tsantili-Kakoulidou A (2010) J Chromatogr A 1217:5761

    CAS  Google Scholar 

  213. Schmid K (1975) In: Putnam FW (ed) Plasma proteins, vol 1. Academic Press, New York, p 184

    Google Scholar 

  214. Tsopelas F, Tsantili-Kakoulidou A, Ochsenkühn-Petropoulou M (2010) Anal Bioanal Chem 397:2171

    CAS  Google Scholar 

  215. Tsopelas F, Ochsenkühn-Petropoulou M, Tsantili-Kakoulidou A (2011) J Sep Sci 34:376

    CAS  Google Scholar 

  216. Hollosy F, Valko K, Hersey A, Nunhuck S, Keri G, Bevan C (2006) J Med Chem 49:6958

    CAS  Google Scholar 

  217. Valko K, Nunhuck SB, Hill AP (2011) J Pharm Sci 100:849

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, School of Pharmacy, University of Athens, Panepistimiopolis, Zografou, 157 71, Athens, Greece

    Costas Giaginis & Anna Tsantili-Kakoulidou

  2. Department of Food Science and Nutrition, University of the Aegean, 81400, Myrina, Lemnos, Greece

    Costas Giaginis

Authors
  1. Costas Giaginis
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anna Tsantili-Kakoulidou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Anna Tsantili-Kakoulidou.

Additional information

Published in the topical collection Chemometrics in Chromatography with guest editors B. Jančić-Stojanović and Y. Dotsikas.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Giaginis, C., Tsantili-Kakoulidou, A. Quantitative Structure–Retention Relationships as Useful Tool to Characterize Chromatographic Systems and Their Potential to Simulate Biological Processes. Chromatographia 76, 211–226 (2013). https://doi.org/10.1007/s10337-012-2374-6

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10337-012-2374-6

Keywords

Search

Navigation