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

被引：32

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

[31] Determination and estimation of aqueous solubilities and n-octanol/water partition coefficients for phenylacrylates [J].

Wei D.B. ;

Wu C.D. ;

Zhang A.Q. ;

Liu X.H. ;

Wei Z.B. ;

Wang L.S. .

Bulletin of Environmental Contamination and Toxicology, 2001, 67 (3) :392-398

[32] PARTITION-COEFFICIENTS IN A LIPOSOME WATER-SYSTEM - METHODS FOR DETERMINATION AND ERROR ANALYSIS [J].

TAKAGI, T ;

KIMURA, A ;

DA, YZ ;

NAKAI, H ;

FUJIWARA, H .

ANALYTICAL SCIENCES, 1992, 8 (06) :761-765

[33] New magnetic nano-absorbent for the determination of n-octanol/water partition coefficients [J].

Gao, X ;

Yu, CH ;

Tam, KY ;

Tsang, SC .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2005, 38 (02) :197-203

[34] Partition coefficients in octanol-water and liquid chromatographic behavior of eight oxygenated triterpenes which are paired stereo- and positional isomers [J].

Lin, LJ ;

Lee, KR ;

Shiao, MS .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1995, 42 (06) :981-985

[35] Determination of Octanol-Water Partition Coefficient by Normal Phase TLC: A New Simple Method to Adopt for Graduate Laboratory Practical [J].

Jatan, Shah, V ;

Dipen, Purohit A. ;

Nishit, Basera A. ;

Dhaval, Sojitra ;

Sathish, N. K. ;

Gowramma, B. ;

Kumar, Prashantha B. R. .

INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH, 2009, 43 (04) :365-369

[36] A blind SAMPL6 challenge: insight into the octanol-water partition coefficients of drug-like molecules via a DFT approach [J].

Arslan, Evrim ;

Findik, Basak K. ;

Aviyente, Viktorya .

JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN, 2020, 34 (04) :463-470

[37] Micellar electrokinetic capillary chromatography as a method for the determination of n-octanol/water partition coefficients of pesticides [J].

Dinelli, G ;

Mallegni, R ;

Vicari, A .

ELECTROPHORESIS, 1997, 18 (02) :214-219

[38] Computational prediction of octanol-water partition coefficient based on the extended solvent-contact model [J].

Kim, Taeho ;

Park, Hwangseo .

JOURNAL OF MOLECULAR GRAPHICS & MODELLING, 2015, 60 :108-117

[39] Estimating the octanol-water partition coefficients of NPAHs and PAHs by solid-phase microextraction and gas chromatography-ion trap detector [J].

Wang, Yiru ;

Wang, Yonghong .

ANALYTICAL LETTERS, 2007, 40 (02) :307-319

[40] pH-Metric logP 10. Determination of Liposomal Membrane-Water Partition Coefficients of lonizable Drugs [J].

A. Avdeef ;

K. J. Box ;

J. E. A. Comer ;

C. Hibbert ;

K. Y. Tam .

Pharmaceutical Research, 1998, 15 :209-215

← 1 2 3 4 5 →