Synthesis and biological evaluation of cycloalkylidene carboxylic acids as novel effectors of Ras/Raf interaction

J Med Chem. 2002 Mar 28;45(7):1535-42. doi: 10.1021/jm011101q.

Abstract

The protooncogenes Ras and Raf play important roles in signal transduction pathways regulated by mitogen-activated protein kinases. Mutations of Ras that arrest the protein in its active state are frequently implicated in tumor formation. We used Ras and Raf proteins in the yeast two-hybrid system to search for natural or synthesized substances capable of modulating Ras/Raf interaction by specifically binding to one of the interacting partners. We found that cycloalkylidene carboxylic acids enhanced Ras/Raf interaction by acting on the cysteine-rich domain of Raf. Several analogues of the active substance 2-cyclohexylidene propanoic acid were synthesized and the importance of the semicyclic double bond in the stabilization of Ras/Raf interaction was demonstrated. Variation of the size and the substituents of the cyclic system as well as the length of the carboxylic acid resulted in enhanced Ras/Raf interaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Motifs
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / pharmacology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Mutagenesis, Site-Directed
  • Mutation
  • Plasmids / metabolism
  • Protein Binding / drug effects
  • Protein Structure, Tertiary
  • Proto-Oncogene Proteins c-raf / metabolism*
  • Two-Hybrid System Techniques
  • ras Proteins / metabolism*

Substances

  • Carboxylic Acids
  • Proto-Oncogene Proteins c-raf
  • ras Proteins