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

被引：31

作者：

Barzanti, Claire ^{[1
]}

Evans, Rebecca ^{[1
]}

Fouquet, Jeremy ^{[1
]}

Gouzin, Leonard ^{[1
]}

Howarth, Nicola M. ^{[1
]}

Kean, Gary ^{[1
]}

Levet, Emilie ^{[1
]}

Wang, Daniel ^{[1
]}

Wayemberg, Estelle ^{[1
]}

Yeboah, Agnes A. ^{[1
]}

Kraft, Arno ^{[1
]}

机构：

[1] Heriot Watt Univ, Sch Engn & Phys Sci, Edinburgh EH14 4AS, Midlothian, Scotland

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 19期

关键词：

ionization constant; liposomes; octanol; partition coefficient; potentiometric titration;

D O I：

10.1016/j.tetlet.2007.03.085

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3337 / 3341

页数：5

共 50 条

[21] Simple method to calculate octanol-water partition coefficient of organic compounds
Tehrany, EA
Fournier, F
Desobry, S
JOURNAL OF FOOD ENGINEERING, 2004, 64 (03) : 315 - 320
[22] Computational Approaches to Estimating Octanol-Water Partition Coefficient and Water Solubility of Organic Compounds
Wang Yan-Ling
Li Jie
Wang Ren-Xiao
ACTA PHYSICO-CHIMICA SINICA, 2010, 26 (07) : 1742 - 1754
[23] H-bond contribution to octanol-water partition coefficients of polar compounds
Raevsky, OA
Schaper, KJ
Seydel, JK
QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS, 1995, 14 (05): : 433 - 436
[24] Calculation of octanol-water partition coefficients of organic solutes from their molecular volumes
Edward, JT
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1998, 76 (09): : 1294 - 1303
[25] Prediction of pH Effect on the Octanol-Water Partition Coefficient of Ionizable Pharmaceuticals
Chen, Chao-Shou
Lin, Shiang-Tai
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2016, 55 (34) : 9284 - 9294
[26] Calculation of octanol-water partition coefficients of organic solutes from their molecular volumes
Can J Chem, 9 (1294-1303):
[27] DETERMINATION OF OCTANOL-WATER PARTITION-COEFFICIENTS FOR THE MAJOR COMPONENTS OF TECHNICAL CHLORDANE
SIMPSON, CD
WILCOCK, RJ
SMITH, TJ
WILKINS, AL
LANGDON, AG
BULLETIN OF ENVIRONMENTAL CONTAMINATION AND TOXICOLOGY, 1995, 55 (01) : 149 - 153
[28] Determination of liposome-water partition coefficients of pharmaceutical drugs using a simple laboratory titrator
Kraft, A
Howarth, NM
Evans, R
Yeboah, AA
Gouzin, L
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U2743 - U2744
[29] Prediction of octanol-water partition coefficients, Henry coefficients and water solubilities using UNIFAC
Wienke, G.
Gmehling, J.
Toxicological and Environmental Chemistry, 1998, 65 (1-4): : 57 - 86
[30] Aqueous solubilities and octanol-water partition coefficients of cymenes and chlorocymenes
Lun, R
Varhanickova, D
Shiu, WY
Mackay, D
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1997, 42 (05): : 951 - 953

← 1 2 3 4 5 →