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A New Straightforward Method for Lipophilicity logP Measurement using 19F NMR Spectroscopy
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Optimised method to estimate octanol water distribution coefficient (logD) in a high throughput format.

Ying Wei Ivan Low1, Francesca Blasco1, Prakash Vachaspati1

  • 1Novartis Institute for Tropical Diseases, Singapore.

European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences
|July 5, 2016
PubMed
Summary

This study optimized a shake flask method for measuring lipophilicity (logD) in drug discovery. The new high-throughput assay minimizes matrix effects and DMSO interference for accurate results.

Keywords:
DMSO concentrationDistribution coefficientLipophilicityMiniaturised shake flaskOctanol-water

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Area of Science:

  • Medicinal Chemistry
  • Analytical Chemistry
  • Drug Discovery

Background:

  • Lipophilicity, measured as the octanol-water distribution coefficient (logD), is crucial in early drug discovery.
  • Traditional logD assays face challenges including wide concentration ranges, matrix effects from different phases, and interference from DMSO stock solutions.

Purpose of the Study:

  • To develop an optimized, high-throughput shake flask method for accurate logD determination.
  • To address and mitigate matrix effects, DMSO interference, and optimize incubation conditions.

Main Methods:

  • Development of a deepwell 96-well plate shake flask method for logD measurement.
  • Utilized the matched matrix concept to minimize liquid chromatography-mass spectrometry (LC-MS) errors between buffer and octanol phases.
  • Optimized incubation conditions, including plate orientation, for rapid equilibrium achievement.

Main Results:

  • Equilibrium for logD measurement was achieved within 30 minutes by orienting the plate on its side.
  • Even 0.5% Dimethyl sulfoxide (DMSO) significantly underestimated analyte lipophilicity, highlighting its detrimental effect.
  • The optimized method successfully minimized matrix effects and DMSO interference for accurate logD values.

Conclusions:

  • The developed shake flask method is efficient, high-throughput, and accurate for determining logD values.
  • This method overcomes key limitations of traditional logD assays, improving reliability in early drug discovery.
  • Careful control of assay conditions, particularly DMSO concentration, is essential for reliable lipophilicity measurements.