The binding of synthetic retinoids to lipocalin beta-lactoglobulins

J Med Chem. 2010 Jan 14;53(1):514-8. doi: 10.1021/jm901309r.

Abstract

The binding of therapeutically relevant synthetic retinoid derivatives to bovine and reindeer beta-lactoglobulin (betaLG) is demonstrated using fluorescence quenching and ultrafiltration/HPLC methods. Furthermore, synthesis of methyl (E)-3-[4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)vinyl]phenyl]-acrylate 4 and (E)-3-[4-[(E)-2-(2,6,6-trimethylcyclohex-1-enyl)vinyl]phenyl]acrylic acid 5 is described. All studied compounds bind to both betaLG homologues with nanomolar K(d) values, and the interaction diminishes the pH-dependent aggregation of retinoids. Thus, betaLG may show benefits in improving the bioavailability of retinoid derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Binding Sites
  • Biological Availability
  • Cattle
  • Crystallography, X-Ray
  • Drug Design
  • Hydrogen-Ion Concentration
  • Lactoglobulins / chemistry*
  • Lipocalins / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Reindeer
  • Retinoids / chemical synthesis
  • Retinoids / chemistry*
  • Retinoids / pharmacology
  • Structure-Activity Relationship

Substances

  • Lactoglobulins
  • Lipocalins
  • Retinoids