Contribution of ionization and lipophilicity to drug binding to albumin: a preliminary step toward biodistribution prediction

J Med Chem. 2004 Jul 29;47(16):3949-61. doi: 10.1021/jm040760a.

Abstract

Understanding the molecular mechanisms governing albumin binding is a major challenge in absorption-distribution-metabolism-excretion prediction. To gain insight into this complex field, an ultracentrifugation method to measure the drug fraction bound to bovine serum albumin [%B(DAB)] is presented. The second part of the study shows the dependence of the experimental binding parameter on ionization and lipophilicity descriptors (pK(a) and log D(oct)(7.4) for a series of 14 structurally diverse drugs. Finally, a docking strategy is used to rationalize the findings; the results confirm the mostly nonspecific nature of the interaction of albumin with neutral ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Affinity
  • Hydrogen-Ion Concentration
  • Ions / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Pharmaceutical Preparations / chemistry*
  • Protein Binding
  • Quantitative Structure-Activity Relationship
  • Serum Albumin, Bovine / chemistry*
  • Ultracentrifugation

Substances

  • Ions
  • Pharmaceutical Preparations
  • Serum Albumin, Bovine