Oxazole-based peptide macrocycles: a new class of G-quadruplex binding ligands

J Am Chem Soc. 2006 Oct 25;128(42):13662-3. doi: 10.1021/ja064713e.

Abstract

Herein we report on the synthesis and DNA binding properties of a new class of water soluble oxazole-based peptide macrocycles that bind selectively to quadruplex DNA, with no detectable binding to duplex DNA. We have recently identified one quadruplex in the proto-oncogene c-kit that is suspected to act as a regulatory element for the expression of the c-kit gene. Here we provide the first example of a ligand binding to and stabilizing the c-kit quadruplex. Moreover, we show that these macrocycles show a preference for the c-kit quadruplex as compared to the human telomeric quadruplex.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Binding Sites
  • Circular Dichroism
  • DNA / chemistry*
  • G-Quadruplexes
  • Ligands
  • Macrocyclic Compounds / chemistry*
  • Molecular Structure
  • Oxazoles / chemistry*
  • Peptides / chemistry*
  • Proto-Oncogene Mas
  • Stereoisomerism

Substances

  • Ligands
  • MAS1 protein, human
  • Macrocyclic Compounds
  • Oxazoles
  • Peptides
  • Proto-Oncogene Mas
  • DNA