Partition coefficient vs. binding constant: How best to assess molecular lipophilicity

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 92, Issue , 2015, Pages 204-215

  Cevc, Gregor ^a  

^a Advanced Treatments Institute   (Germany)

Author keywords

Analytical procedure; Concentration effects; Drug partitioning; Mathematical modelling; Solute binding

Indexed keywords

SOLVENT; DRUG; DRUG CARRIER; WATER;

ARTICLE; BINDING AFFINITY; LIPOPHILICITY; LIQUID; PARTITION COEFFICIENT; PREDICTION; SOLUTE; STATISTICAL MODEL; STOICHIOMETRY; CHEMICAL PHENOMENA; CHEMISTRY; COMPARATIVE STUDY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MEDICINAL CHEMISTRY; PROCEDURES; THEORETICAL MODEL;

CHEMISTRY, PHARMACEUTICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG CARRIERS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LINEAR MODELS; MODELS, THEORETICAL; PHARMACEUTICAL PREPARATIONS; SOLVENTS; WATER;

EID: 84925439266     PISSN: 09396411     EISSN: 18733441     Source Type: Journal    
DOI: 10.1016/j.ejpb.2015.03.008     Document Type: Article

References (28)

1. C. Hansch, D. Hoekman, A. Leo, D. Weininger, and C.D. Selassie Chem-bioinformatics: comparative QSAR at the interface between chemistry and biology Chem. Rev. 102 2002 783 812
2. C.D. Selassie History of quantitative structure-activity relationships D.J. Abraham, Burgers Medicinal Chemistry and Drug Discovery 6th ed. Drug Discovery vol. 1 2003 John Wiley& Sons New York 1 48
3. A. Mälkiä, L. Murtomäki, A. Urtti, and K. Kontturi Drug permeation in biomembranes. In vitro and in silico prediction and influence of physicochemical properties Eur. J. Pharm. Sci. 23 2004 13 47
4. J. Siepmann, F. Lecomte, and R. Bodmeier Diffusion-controlled drug delivery systems: calculation of the required composition to achieve desired release profiles J. Control. Rel. 60 1999 379 389
5. D. Lichtenberg Characterization of the solubilization of lipid bilayers by surfactants BBA Biomembranes 821 1985 470 478
6. U. Kragh-Hansen, M. le Maire, and J.V. Moller The mechanism of detergent solubilization of liposomes and protein-containing membranes Biophys. J. 75 1998 2932 2946
7. V.P. Torchilin Structure and design of polymeric surfactant-based drug delivery systems J. Contr. Rel. 73 2001 137 172
8. Y.C. Barenholz Doxilthe first FDA-approved nano-drug: lessons learned J. Contr. Rel. 160 2012 117 134
9. M. Elsayed, and G. Cevc The vesicle-to-micelle transformation of phospholipid-cholate mixed aggregates: a state of the art analysis including membrane curvature effects BBA Biomembranes 1808 2011 140 153
10. Partition Coefficient. < http://en.wikipedia.org/wiki/Partition-coefficient > (accessed November 2014).
11. Octanol-Water Partition Coefficient (KOW). < http://toxics.usgs.gov/definitions/kow.html > (accessed November 2014).
12. A. Avdeef Absorption and Drug Development: Solubility, Permeability, and Charge State 2012 John Wiley & Sons New York
13. OECD Test No. 117: Partition Coefficient (n-octanol/water), HPLC Method. < http://www.oecd-ilibrary.org/environment/test-no-117-partition-coefficient-n-octanol-water-hplc-method-9789264069824-en > (accessed December 2014).
14. OECD Test No. 107: Partition Coefficient (n-octanol/water): Shake Flask Method. < http://www.oecd-ilibrary.org/content/book/9789264069626-en > (accessed November 2014).
15. S. Ben-Dror, I. Bronshtein, A. Wiehe, B. Röder, M.O. Senge, and B. Ehrenberg On the correlation between hydrophobicity, liposome binding and cellular uptake of porphyrin sensitizers Photochem. Photobiol. 82 2000 695 701
16. M.M. Elsayed, U. Vierl, and G. Cevc Accurate potentiometric determination of lipid membrane-water partition coefficients and apparent dissociation constants of ionizable drugs: electrostatic corrections Pharm. Res. 26 2009 1332 1343
17. G.M. Pauletti, and H. Wunderli-Allenspach Partition coefficients in vitro: artificial membranes as a standardized distribution model Eur. J. Pharm. Sci. 1 1994 273 282
18. N.C. Santos, M. Prieto, and M.A. Castanho Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods BBA Biomembranes 1612 2003 123 135
19. C. Giaginis, and A. Tsantili-Kakoulidou Alternative measures of lipophilicity: from octanol-water partitioning to IAM retention J. Pharm. Sci. 97 2008 2984 3004
20. J. Sangster Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry 1997 John Wiley & Sons New York
21. CFR 799.6755 TSCA partition coefficient (n-octanol/water), shake flask method. < http://www.law.cornell.edu/cfr/text/40/799.6755 > (accessed 28.11.2014).
22. R. Mannhold, G.I. Poda, C. Ostermann, and I.V. Tetko Calculation of molecular lipophilicity: state-of-the-art and comparison of logP methods on more than 96,000 compounds J. Pharm. Sci. 98 2009 861 893
23. A. Paschke, and G. Schüürmann Concentration dependence of the octanol/water partition coefficients of the hexachlorocyclohexane isomers at 25 C Chem. Eng. Technol. 23 2000 666 670
24. P. Beltrame, P.L. Beltrame, P. Carniti, D. Guardione, and C. Lanzetta Inhibiting action of chlorophenols on biodegradation of phenol and its correlation with structural properties of inhibitors Biotechnol. Bioengin. 31 1988 821 828
25. L. Bernazzani, S. Cabani, G. Conti, and V. Mollica Thermodynamic study of the partitioning of organic compounds between water and octan-1-ol. Effects of water as cosolvent in the organic phase J. Chem. Soc., Faraday Trans. 91 1995 649 655
26. V. Lukacova, M. Peng, R. Tandlich, A. Hinderliter, and S. Balaz Partitioning of organic compounds in phases imitating the headgroup and core regions of phospholipids bilayers Langmuir 22 2006 1869 1874
27. G. Cevc Molecular force theory of solvation of the polar solutes. The mean-field solvation model, its implications and examples from lipid/water mixtures Chem. Scripta 25 1985 97 107
28. G. Cevc Lipid properties as a basis for membrane modeling and rational liposome design Lipos. Technol. 1 1993 1 36