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Separation methods for estimating octanol-water partition coefficients.

Salwa K Poole1, Colin F Poole

  • 1Discovery Technologies, Pfizer Global Research and Development, Ann Arbor Laboratories, 2800 Plymouth Road, Ann Arbor, MI 48105USA. salwa.poole@pfizer.com

Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
|November 25, 2003
PubMed
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This review explores efficient methods for estimating the octanol-water partition coefficient (logP). Micellar electrokinetic chromatography shows promise for high-throughput logP determination, outperforming traditional chromatography for diverse compounds.

Area of Science:

  • Analytical Chemistry
  • Physical Chemistry
  • Computational Chemistry

Background:

  • The octanol-water partition coefficient (logP) is a crucial parameter in drug discovery and environmental science.
  • Accurate and efficient logP estimation methods are vital for high-throughput screening.
  • Traditional methods often face limitations with diverse chemical structures.

Purpose of the Study:

  • To review separation methods for indirect logP estimation, focusing on high-throughput and wide applicability.
  • To identify suitable separation systems using the solvation parameter model.
  • To evaluate the suitability of different chromatographic and electrokinetic techniques for logP determination.

Main Methods:

  • Review of separation techniques including reversed-phase chromatography, micellar electrokinetic chromatography (MEKC), and microemulsion electrokinetic chromatography (MEKC).

Related Experiment Videos

  • Application of the solvation parameter model to analyze chromatographic retention and partitioning behavior.
  • Comparison of retention mechanisms with partitioning principles, particularly hydrogen bonding effects.

    • Main Results:

    • Reversed-phase chromatography is generally unsuitable for diverse structures due to differing retention and partitioning drivers.
    • MEKC and microemulsion systems demonstrate high correlation with logP for neutral, weakly acidic, and weakly basic compounds.
    • Charged compounds yield inaccurate logP estimations due to electrophoretic migration and electrostatic interactions.

    Conclusions:

    • Micellar and microemulsion electrokinetic chromatography offer efficient, high-throughput solutions for logP estimation of many compound types.
    • Experimental determination of solute descriptors provides a versatile alternative for estimating logP and other biopartitioning properties.
    • The solvation parameter model is key to selecting appropriate separation systems and predicting solute behavior across various distribution systems.