AlphaLogD determination: An optimized Reversed-Phase Liquid Chromatography method to measure lipophilicity on neutral and basic small and Beyond-Rule-of-Five compounds

J Chromatogr A. 2022 Jul 5:1674:463146. doi: 10.1016/j.chroma.2022.463146. Epub 2022 May 13.

Abstract

Lipophilicity can be measured with different methods, such as Shake-Flask or liquid chromatography. HPLC presents the advantage of overcoming solubility issues and therefore extending the range of lipophilicity to high values. A specific HPLC method, called ELogD, had been developed 20 years ago on a C16-amide stationary phase, enhancing hydrophobic and hydrogen bond interactions to mimic octanol-water partition. The emergence of novel stationary phases and the need for a less complex mobile phase have led to the development of a new HPLC assay called alphaLogD, applicable to neutral and basic compounds at pH 7.4, that combines superficially porous particles with a high number of equilibriums between solutes and stationary phase, leading to a lower number of isocratic methods to determine the logk'w at a higher throughput. Statistical studies have been run to successfully evaluate the alphaLogD method compared to the Shake-Flask method and to allow this lipophilicity measurement into the so-called Beyond-Rule-of-5-molecules space.

Keywords: Beyond-rule-of-5; High performance liquid chromatography; Lipophilicity; Shake-flask method; Superficially porous particle.

MeSH terms

  • Chromatography, High Pressure Liquid / methods
  • Chromatography, Reverse-Phase* / methods
  • Hydrophobic and Hydrophilic Interactions
  • Octanols / chemistry
  • Solubility
  • Water* / chemistry

Substances

  • Octanols
  • Water