Add time:07/20/2019         Source:sciencedirect.com

A high-throughput method for determining the octanol/water partition coefficient (Po/w) of a large variety of compounds exhibiting a wide range in hydrophobicity was established. The method combines a simple shake-flask method with a novel two-phase solvent system comprising an acetonitrile–phosphate buffer (0.1 M, pH 7.4)—1-octanol (25:25:4, v/v/v; AN system). The AN system partition coefficients (KAN) of 51 standard compounds for which log Po/w (at pH 7.4; log D) values had been reported were determined by single two-phase partitioning in test tubes, followed by measurement of the solute concentration in both phases using an automatic flow injection-ultraviolet detection system. The log KAN values were closely related to reported log D values, and the relationship could be expressed by the following linear regression equation: log D = 2.8630 log KAN –0.1497(n = 51). The relationship reveals that log D values (+8 to –8) for a large variety of highly hydrophobic and/or hydrophilic compounds can be estimated indirectly from the narrow range of log KAN values (+3 to –3) determined using the present method. Furthermore, log KAN values for highly polar compounds for which no log D values have been reported, such as amino acids, peptides, proteins, nucleosides, and nucleotides, can be estimated using the present method. The wide-ranging log D values (+5.9 to –7.5) of these molecules were estimated for the first time from their log KAN values and the above regression equation.

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