Lipophilicity in drug action and toxicology /edited by Vladimir Pliška, Bernard Testa, and Han van de Waterbeemd

Swiss Federal Institute of Technology, Zurich, Switzerland. Research on the role of lipophilicity in toxicology and drug action, for investigators involved in drug design or the drug action research. 40 contributors, 7 U.S. Cover Page......Page 1 Title: Lipophilicity in Drug Action and Toxicology......Page 4 ISBN 3527293833......Page 5 Preface......Page 6 Methods and Principles in Medicinal Chemistry......Page 7 A Personal Foreword......Page 8 List of Contributors......Page 9 2 Lipophilicity: A History......Page 13 4 Intramolecular Interactions Encoded in Lipophilicity: Their Nature and Significance......Page 14 5 Lipophilicity Measurement by Reversed- Phase High Performance Liquid Chromatography (RP-HPLC)......Page 15 6 Centrifugal Partition Chromatography for Lipophilicity Measurements......Page 16 8 Estimation of Lipophilicity by Reversed- Phase Thin-Layer Chromatography......Page 17 11 Cellular Automata Model of Partitioning Between Liquid Phases......Page 18 12 The Molecular Lipophilicity Potential (MLP): A New Tool for log P Calculations and Docking, and in Comparative Molecular Field Analysis (CoMFA)......Page 19 14 Physico-Chemical and Biological Factors that Influence a Drug's Cellular Permeability by Passive Diffusion......Page 20 16 The Role of Lipophilicity in Biological Response to Drugs and Endogenous Ligands......Page 21 18 Applications of a Solvation Equation to Drug Transport Properties......Page 22 20 Lipophilicity in Peptide Chemistry and Peptide Drug Design......Page 23 23 Lipophilicity Descriptors for Structure- Property Correlation Studies: Overview of Experimental and Theoretical Methods and A Benchmark of log P Calculations......Page 24 1 Lipophilicity: The Empirical Tool and the Fundamental Objective. An Introduction......Page 26 2 Lipophilicity: A History......Page 32 3 Thermodynamics of van der Waals and Hydrophobic Interactions......Page 52 4 Intramolecular Interactions Encoded in Lipophilicity: Their Nature and Significance......Page 74 5 Lipophilicity Measurement by Reversed- Phase High Performance Liquid Chromatography (RP-HPLC)......Page 98 6 Centrifugal Partition Chromatography for Lipophilicity Measurements......Page 114 7 Assessment of Distribution-pH Profiles......Page 134 8 Estimation of Lipophilicity by Reversed- Phase Thin-Layer Chromatography......Page 166 9 The Future of log P Calculation......Page 182 10 Theoretical Calculation of Partition Coefficients......Page 198 11 Cellular Automata Model of Partitioning Between Liquid Phases......Page 206 12 The Molecular Lipophilicity Potential (MLP): A New Tool for log P Calculations and Docking, and in Comparative Molecular Field Analysis (CoMFA)......Page 220 13 Hydrophobic Fields in Quantitative Structure-Activity Relationships......Page 244 14 Physico-Chemical and Biological Factors that Influence a Drug's Cellular Permeability by Passive Diffusion......Page 258 15 Lipophilicity of Metabolites and Its Role in Biotransformation......Page 278 16 The Role of Lipophilicity in Biological Response to Drugs and Endogenous Ligands......Page 288 17 Membrane Transport and Cellular Distribution......Page 320 18 Applications of a Solvation Equation to Drug Transport Properties......Page 336 19 Environmental Hazard Assessment Using Lipophilicity Data......Page 364 20 Lipophilicity in Peptide Chemistry and Peptide Drug Design......Page 380 21 Side Chain Lipophilicity of Noncoded α-Amino Acids: π-Values......Page 400 22 The Application of The Intermolecular Force Model to Bioactivity. Peptide and Protein Quantitative Structure-Activity Relationships......Page 412 23 Lipophilicity Descriptors for Structure- Property Correlation Studies: Overview of Experimental and Theoretical Methods and A Benchmark of log P Calculations......Page 426 A......Page 444 B......Page 445 C......Page 446 D......Page 448 F......Page 449 H......Page 450 I......Page 452 L......Page 453 M......Page 454 O......Page 456 P......Page 457 R......Page 459 S......Page 460 T......Page 461 U,V......Page 462 W,X,Y,Z......Page 463 "In keeping with the outstanding importance of lipophilicity in biosciences, this volume examines all its facets in more than twenty contributions from leading experts. It offers a thorough and highly topical survey of this rapidly developing field of research. Color plates demonstrating structural aspects, a vast number of references, and the straightforward presentation of the material make this volume a invaluable tool for all researchers involved in drug design or in the investigation of drug action."--Provided by publisher