Potentiometric determination of octanol-water and liposome-water partition coefficients (log P) of ionizable organic compounds

Claire Barzanti; Rebecca Evans; Jeremey Fouquet; Leonard Gouzin; Nicola M. Howarth; Gary Kean; Emilie Levet; Daniel Wang; Estelle Wayemberg; Agnes A Yeboah; Arno Kraft

doi:10.1016/j.tetlet.2007.03.085

Potentiometric determination of octanol-water and liposome-water partition coefficients (log P) of ionizable organic compounds

Claire Barzanti, Rebecca Evans, Jeremey Fouquet, Leonard Gouzin, Nicola M. Howarth, Gary Kean, Emilie Levet, Daniel Wang, Estelle Wayemberg, Agnes A Yeboah, Arno Kraft

School of Engineering & Physical Sciences

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

Abstract

The logarithm of the octanol-water partition coefficient, log P, is a key physicochemical property for both pharmaceutical drugs and agrochemicals. It is also required by legislation as part of the physicochemical properties profile for high volume production chemicals. This Letter describes a simple method for determining log P values (over a wide range from -0.8 to 5.3) for 12 organic weak acids and bases using potentiometric titrations, with octanol or phosphatidyl choline liposomes as the partitioning medium. Such titrations take comparatively little time (about 30-45 min per titration), are easy to implement, and can be carried out with an inexpensive laboratory titrator. © 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3337-3341
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2007.03.085
Publication status	Published - 7 May 2007

Keywords

Ionization constant
Liposomes
Octanol
Partition coefficient
Potentiometric titration

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10.1016/j.tetlet.2007.03.085

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title = "Potentiometric determination of octanol-water and liposome-water partition coefficients (log P) of ionizable organic compounds",

abstract = "The logarithm of the octanol-water partition coefficient, log P, is a key physicochemical property for both pharmaceutical drugs and agrochemicals. It is also required by legislation as part of the physicochemical properties profile for high volume production chemicals. This Letter describes a simple method for determining log P values (over a wide range from -0.8 to 5.3) for 12 organic weak acids and bases using potentiometric titrations, with octanol or phosphatidyl choline liposomes as the partitioning medium. Such titrations take comparatively little time (about 30-45 min per titration), are easy to implement, and can be carried out with an inexpensive laboratory titrator. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

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AU - Barzanti, Claire

AU - Evans, Rebecca

AU - Fouquet, Jeremey

AU - Gouzin, Leonard

AU - Howarth, Nicola M.

AU - Kean, Gary

AU - Levet, Emilie

AU - Wang, Daniel

AU - Wayemberg, Estelle

AU - Yeboah, Agnes A

AU - Kraft, Arno

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AB - The logarithm of the octanol-water partition coefficient, log P, is a key physicochemical property for both pharmaceutical drugs and agrochemicals. It is also required by legislation as part of the physicochemical properties profile for high volume production chemicals. This Letter describes a simple method for determining log P values (over a wide range from -0.8 to 5.3) for 12 organic weak acids and bases using potentiometric titrations, with octanol or phosphatidyl choline liposomes as the partitioning medium. Such titrations take comparatively little time (about 30-45 min per titration), are easy to implement, and can be carried out with an inexpensive laboratory titrator. © 2007 Elsevier Ltd. All rights reserved.

KW - Ionization constant

KW - Liposomes

KW - Octanol

KW - Partition coefficient

KW - Potentiometric titration

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JO - Tetrahedron Letters

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Potentiometric determination of octanol-water and liposome-water partition coefficients (log P) of ionizable organic compounds

Abstract

Keywords

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