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Journal of Liquid Chromatography Volume 18, 1995 - Issue 9
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Original Articles

Structural Properties Governing Retention Mechanisms on RP-HPLC Stationary Phases Used for Lipophilicity Measurements

Alessandra Pagliara Institut de Chimie Thérapeutique Section de Pharmacie, Université de Lausanne, CH-1015, Lausanne, Switzerland
,
Essam Khamis Institut de Chimie Thérapeutique Section de Pharmacie, Université de Lausanne, CH-1015, Lausanne, Switzerland
,
An Trinh Institut de Chimie Thérapeutique Section de Pharmacie, Université de Lausanne, CH-1015, Lausanne, Switzerland
,
Pierre-Alain Carrupt Institut de Chimie Thérapeutique Section de Pharmacie, Université de Lausanne, CH-1015, Lausanne, Switzerland
,
Ruey-Shiuan Tsai Institut de Chimie Thérapeutique Section de Pharmacie, Université de Lausanne, CH-1015, Lausanne, Switzerland
&
Bernard Testa Institut de Chimie Thérapeutique Section de Pharmacie, Université de Lausanne, CH-1015, Lausanne, Switzerland
Pages 1721-1745 | Received 10 Dec 1994, Accepted 27 Dec 1994, Published online: 23 Sep 2006

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Ana Mornar, Miranda Damić & Biljana Nigović. (2011) Pharmacokinetic Parameters of Statin Drugs Characterized by Reversed Phase High-Performance Liquid Chromatography. Analytical Letters 44:6, pages 1009-1020.
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Deborah Benhaim & Eli Grushka. (2008) Characterization of the GEMINI C18™ Column: Lipophilicity Measurement and LSER. Journal of Liquid Chromatography & Related Technologies 31:15, pages 2198-2218.
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Costas Giaginis & Anna Tsantili‐Kakoulidou. (2007) Current State of the Art in HPLC Methodology for Lipophilicity Assessment of Basic Drugs. A Review. Journal of Liquid Chromatography & Related Technologies 31:1, pages 79-96.
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Chau My Du, Klara Valko, Chris Bevan, Derek Reynolds & Michael H. Abraham. (2001) RAPID METHOD FOR ESTIMATING OCTANOL-WATER PARTITION COEFFICIENT (LOG POCT) FROM ISOCRATIC RP-HPLC AND A HYDROGEN BOND ACIDITY TERM (A). Journal of Liquid Chromatography & Related Technologies 24:5, pages 635-649.
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J. Debord, P. N'diaye, J- C. Bollinger, K. Fikri, B. Penicaut, J M. Robert, S. Robert-piessard & G. Le Baut. (1997) Cholinesterase Inhibition by Derivatives of 2-Amino-4,6-Dimethylpyridine. Journal of Enzyme Inhibition 12:1, pages 13-26.
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Articles from other publishers (54)

José X. Soares, Álvaro Santos, Carla Fernandes & Madalena M. M. Pinto. (2022) Liquid Chromatography on the Different Methods for the Determination of Lipophilicity: An Essential Analytical Tool in Medicinal Chemistry. Chemosensors 10:8, pages 340.
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Daniel Katz, Kate Fike, Justin Longenberger, Steve Placko, Laurence Philippe-Venec & Andrew Chervenak. (2022) AlphaLogD determination: An optimized Reversed-Phase Liquid Chromatography method to measure lipophilicity on neutral and basic small and Beyond-Rule-of-Five compounds. Journal of Chromatography A 1674, pages 463146.
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S. Amézqueta, X. Subirats, E. Fuguet, M. Rosés & C. Ràfols. 2020. Liquid-Phase Extraction. Liquid-Phase Extraction 183 208 .
Darija Obradović, Slavica Oljačić, Katarina Nikolić & Danica Agbaba. (2019) Investigation and prediction of retention characteristics of imidazoline and serotonin receptor ligands and their related compounds on mixed-mode stationary phase. Journal of Chromatography A 1585, pages 92-104.
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Li Di & Edward H. Kerns. 2016. Drug-Like Properties. Drug-Like Properties 299 306 .
Christel A.S. Bergström, René Holm, Søren Astrup Jørgensen, Sara B.E. Andersson, Per Artursson, Stefania Beato, Anders Borde, Karl Box, Marcus Brewster, Jennifer Dressman, Kung-I. Feng, Gavin Halbert, Edmund Kostewicz, Mark McAllister, Uwe Muenster, Julian Thinnes, Robert Taylor & Anette Mullertz. (2014) Early pharmaceutical profiling to predict oral drug absorption: Current status and unmet needs. European Journal of Pharmaceutical Sciences 57, pages 173-199.
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Costas Giaginis, Stamatios Theocharis & Anna Tsantili-Kakoulidou. (2013) Octanol/water partitioning simulation by RP-HPLC for structurally diverse acidic drugs: Comparison of three columns in the presence and absence of n -octanol as the mobile phase additive . Journal of Separation Science 36:24, pages 3830-3836.
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Giulia Caron, Maura Vallaro & Giuseppe Ermondi. (2013) The Block Relevance (BR) analysis to aid medicinal chemists to determine and interpret lipophilicity. MedChemComm 4:10, pages 1376.
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Heiko Tietgen & Michael Walden. 2013. Drug Discovery and Evaluation: Safety and Pharmacokinetic Assays. Drug Discovery and Evaluation: Safety and Pharmacokinetic Assays 1125 1138 .
Melvin R Euerby, Matthew James, Bengt‐Olof Axelsson, Olof Rosén & Patrik Petersson. (2012) Validation of the extended T anaka column characterization protocol by multivariate analysis of chromatographic retention of low‐molecular‐weight analytes on reversed phase columns using methanol and acetonitrile as organic modifiers . Journal of Separation Science 35:19, pages 2592-2598.
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Costas Giaginis & Anna Tsantili-Kakoulidou. (2011) The performance of 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid as mobile phase additive in HPLC-based lipophilicity assessment. Biomedical Chromatography 25:5, pages 606-612.
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Giulia Caron, Mauro Ravera & Giuseppe Ermondi. (2010) Molecular Interaction Fields (MIFs) to Predict Lipophilicity and ADME Profile of Antitumor Pt(II) Complexes. Pharmaceutical Research 28:3, pages 640-646.
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Yveline Henchoz, Stéphanie Romand, Julie Schappler, Serge Rudaz, Jean-Luc Veuthey & Pierre-Alain Carrupt. (2010) High-throughput log P determination by MEEKC coupled with UV and MS detections. ELECTROPHORESIS 31:5, pages 952-964.
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Marios Chrysanthakopoulos, Ioannis Nicolaou, Vassilis J. Demopoulos & Anna Tsantili-Kakoulidou. (2010) HPLC-based lipophilicity of pyrrolyl-acetic acid ARIs: Relationships with biological activity. Journal of Chromatography B 878:1, pages 61-67.
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Deborah Benhaim & Eli Grushka. (2010) Characterization of Ascentis RP-Amide column: Lipophilicity measurement and linear solvation energy relationships. Journal of Chromatography A 1217:1, pages 65-74.
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Amandine Guillot, Yveline Henchoz, Cyril Moccand, Davy Guillarme, Jean‐Luc Veuthey, Pierre‐Alain Carrupt & Sophie Martel. (2009) Lipophilicity Determination of Highly Lipophilic Compounds by Liquid Chromatography. Chemistry & Biodiversity 6:11, pages 1828-1836.
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Sophie Martel, Vincent Gasparik & Pierre‐Alain Carrupt. 2009. Hit and Lead Profiling. Hit and Lead Profiling 91 116 .
Yveline Henchoz, Davy Guillarme, Sophie Martel, Serge Rudaz, Jean-Luc Veuthey & Pierre-Alain Carrupt. (2009) Fast log P determination by ultra-high-pressure liquid chromatography coupled with UV and mass spectrometry detections. Analytical and Bioanalytical Chemistry 394:7, pages 1919-1930.
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Roberto Todeschini & Viviana Consonni. 2009. Molecular Descriptors for Chemoinformatics. Molecular Descriptors for Chemoinformatics 1 241 .
Yveline Henchoz, Bruno Bard, Davy Guillarme, Pierre-Alain Carrupt, Jean-Luc Veuthey & Sophie Martel. (2009) Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution. Analytical and Bioanalytical Chemistry 394:3, pages 707-729.
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Ivano Marchi, Serge Rudaz & Jean-Luc Veuthey. (2009) Sample preparation development and matrix effects evaluation for multianalyte determination in urine. Journal of Pharmaceutical and Biomedical Analysis 49:2, pages 459-467.
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Spyros Gikas, Fotios Tsopelas, Costas Giaginis, John Dimitrakopoulos, Theodora Livadara, Helen Archontaki & Anna Tsantili-Kakoulidou. (2008) Chromatographic behavior of zwitterionic enalapril—Exploring the conditions for lipophilicity assessment. Journal of Pharmaceutical and Biomedical Analysis 48:3, pages 739-743.
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Deborah Benhaim & Eli Grushka. (2008) Effect of n-octanol in the mobile phase on lipophilicity determination by reversed-phase high-performance liquid chromatography on a modified silica column. Journal of Chromatography A 1209:1-2, pages 111-119.
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Costas Giaginis & Anna Tsantili-Kakoulidou. (2008) Alternative Measures of Lipophilicity: From Octanol–Water Partitioning to IAM Retention. Journal of Pharmaceutical Sciences 97:8, pages 2984-3004.
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Yveline Henchoz, Davy Guillarme, Serge Rudaz, Jean-Luc Veuthey & Pierre-Alain Carrupt. (2008) High-Throughput log  P Determination by Ultraperformance Liquid Chromatography: A Convenient Tool for Medicinal Chemists . Journal of Medicinal Chemistry 51:3, pages 396-399.
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Edward H. Kerns & Li Di. 2008. Drug-like Properties: Concepts, Structure Design and Methods. Drug-like Properties: Concepts, Structure Design and Methods 260 270 .
Costas Giaginis, Stamatios Theocharis & Anna Tsantili-Kakoulidou. (2007) Octanol/water partitioning simulation by reversed-phase high performance liquid chromatography for structurally diverse acidic drugs: Effect of n-octanol as mobile phase additive. Journal of Chromatography A 1166:1-2, pages 116-125.
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G. Caron, G. Ermondi & R.A. Scherrer. 2007. Comprehensive Medicinal Chemistry II. Comprehensive Medicinal Chemistry II 425 452 .
Costas Giaginis, Stamatios Theocharis & Anna Tsantili-Kakoulidou. (2006) Contribution to the standardization of the chromatographic conditions for the lipophilicity assessment of neutral and basic drugs. Analytica Chimica Acta 573-574, pages 311-318.
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Heiko Tietgen. 2006. Drug Discovery and Evaluation. Drug Discovery and Evaluation 399 408 .
Cinzia Stella, Alexandra Galland, Xiangli Liu, Bernard Testa, Serge Rudaz, Jean‐Luc Veuthey & Pierre‐Alain Carrupt. (2005) Novel RPLC stationary phases for lipophilicity measurement: Solvatochromic analysis of retention mechanisms for neutral and basic compounds. Journal of Separation Science 28:17, pages 2350-2362.
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L. Ayouni, G. Cazorla, D. Chaillou, B. Herbreteau, S. Rudaz, P. Lantéri & P.-A. Carrupt. (2005) Fast Determination of Lipophilicity by HPLC. Chromatographia 62:5-6, pages 251-255.
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Annika Mälkiä, Lasse Murtomäki, Arto Urtti & Kyösti Kontturi. (2004) Drug permeation in biomembranes. European Journal of Pharmaceutical Sciences 23:1, pages 13-47.
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Klára Valkó. (2004) Application of high-performance liquid chromatography based measurements of lipophilicity to model biological distribution. Journal of Chromatography A 1037:1-2, pages 299-310.
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Edward H. Kerns & Li Di. 2004. Cellular Drug Delivery. Cellular Drug Delivery 345 365 .
Salwa K Poole & Colin F Poole. (2003) Separation methods for estimating octanol–water partition coefficients. Journal of Chromatography B 797:1-2, pages 3-19.
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Xiangli Liu, Géraldine Bouchard, Nathalie Müller, Alexandra Galland, Hubert Girault, Bernard Testa & Pierre‐Alain Carrupt. (2003) Solvatochromic Analysis of Partition Coefficients in the o ‐Nitrophenyl Octyl Ether ( o ‐NPOE)/Water System . Helvetica Chimica Acta 86:11, pages 3533-3547.
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Edward H. Kerns, Li Di, Susan Petusky, Teresa Kleintop, Donna Huryn, Oliver McConnell & Guy Carter. (2003) Pharmaceutical profiling method for lipophilicity and integrity using liquid chromatography–mass spectrometry. Journal of Chromatography B 791:1-2, pages 381-388.
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Agnes Taillardat-Bertschinger, Pierre-Alain Carrupt & Bernard Testa. (2002) The relative partitioning of neutral and ionised compounds in sodium dodecyl sulfate micelles measured by micellar electrokinetic capillary chromatography. European Journal of Pharmaceutical Sciences 15:2, pages 225-234.
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Agnes Taillardat-Bertschinger, Francesco Barbato, Maria Tiziana Quercia, Pierre-Alain Carrupt, Marianne Reist, Maria I. La Rotonda & Bernard Testa. (2002) Structural Properties Governing Retention Mechanisms on Immobilized Artificial Membrane (IAM) HPLC Columns. Helvetica Chimica Acta 85:2, pages 519-532.
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Edward H. Kerns. (2001) High throughput physicochemical profiling for drug discovery. Journal of Pharmaceutical Sciences 90:11, pages 1838-1858.
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Franco Lombardo, Marina Y. Shalaeva, Karl A. Tupper & Feng Gao. (2001) ElogD o ct :  A Tool for Lipophilicity Determination in Drug Discovery. 2. Basic and Neutral Compounds . Journal of Medicinal Chemistry 44:15, pages 2490-2497.
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Roberto Todeschini & Viviana Consonni. 2000. Handbook of Molecular Descriptors. Handbook of Molecular Descriptors 524 667 .
Franco Lombardo, Marina Y. Shalaeva, Karl A. Tupper, Feng Gao & Michael H. Abraham. (2000) ElogP oct :  A Tool for Lipophilicity Determination in Drug Discovery . Journal of Medicinal Chemistry 43:15, pages 2922-2928.
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V. John Jasys, Franco Lombardo, Troy A. Appleton, Jon Bordner, Martine Ziliox & Robert A. Volkmann. (2000) Preparation of Fluoroadamantane Acids and Amines:  Impact of Bridgehead Fluorine Substitution on the Solution- and Solid-State Properties of Functionalized Adamantanes. Journal of the American Chemical Society 122:3, pages 466-473.
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H. Stephan, R. Berger, H. Spies, B. Johannsen & F. P. Schmidtchen. (1999) Efficient phase transfer of pertechnetate with bicyclic guanidinium compounds. Journal of Radioanalytical and Nuclear Chemistry 242:2, pages 399-403.
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Roman Kaliszan, Marion A. van Straten, Michal Markuszewski, Carel A. Cramers & Henk A. Claessens. (1999) Molecular mechanism of retention in reversed-phase high-performance liquid chromatography and classification of modern stationary phases by using quantitative structure–retention relationships. Journal of Chromatography A 855:2, pages 455-486.
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Giulia Caron, Frédéric Reymond, Pierre-Alain Carrupt, Hubert H. Girault & Bernard Testa. (1999) Combined molecular lipophilicity descriptors and their role in understanding intramolecular effects. Pharmaceutical Science & Technology Today 2:8, pages 327-335.
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Yvan Giroud, Pierre‐Alain Carrupt, Alessandra Pagliara, Bernard Testa & Ronald G. Dickinson. (2005) Intrinsic and Intramolecular Lipophilicity Effects in O ‐Glucuronides . Helvetica Chimica Acta 81:2, pages 330-341.
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Michael H Abraham, Harpreet S Chadha, Ruben A.E Leitao, Robert C Mitchell, William J Lambert, Roman Kaliszan, Antoni Nasal & Piotr Haber. (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. Journal of Chromatography A 766:1-2, pages 35-47.
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Pierre-Alain Carrupt, Bernard Testa & Patrick Gaillard. 1997. Reviews in Computational Chemistry. Reviews in Computational Chemistry 241 315 .
H. van de Waterbeemd, M. Kansy, B. Wagner & H. Fischer. 1996. Lipophilicity in Drug Action and Toxicology. Lipophilicity in Drug Action and Toxicology 73 87 .
John G. Dorsey, William T. Cooper, Barbara A. Siles, Joe P. Foley & Howard G. Barth. (1996) Liquid Chromatography:  Theory and Methodology. Analytical Chemistry 68:12, pages 515-568.
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