9-N-Substituted berberine derivatives: stabilization of G-quadruplex DNA and down-regulation of oncogene c-myc

Bioorg Med Chem. 2008 Aug 15;16(16):7582-91. doi: 10.1016/j.bmc.2008.07.029. Epub 2008 Jul 18.

Abstract

A series of 9-N-substituted berberine derivatives (2a-j) were synthesized and evaluated as a new class of G-quadruplex binding ligands. G-quadruplex of DNA had been proven to be the transcription controller of human c-myc gene. The interaction of 9-N-substituted berberine derivatives with G-quadruplex DNA in c-myc was examined via EMSA, CD spectroscopy, FRET-melting method, PCR-stop assay, competitive dialysis, cell proliferation assay, and RT-PCR assay. The experiment results indicated that these derivatives could selectively induce and stabilize the formation of intramolecular parallel G-quadruplex in c-myc, which led to down-regulation of transcription of the c-myc in the HL60 lymphomas cell line. The related structure-activity relationships were also discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Berberine / analogs & derivatives*
  • Berberine / chemical synthesis
  • Berberine / pharmacology
  • Cell Growth Processes / drug effects
  • Circular Dichroism
  • DNA / chemistry*
  • DNA / drug effects
  • DNA / metabolism
  • Down-Regulation / drug effects
  • Electrophoretic Mobility Shift Assay
  • Fluorescence Resonance Energy Transfer
  • G-Quadruplexes / drug effects*
  • Genes, myc / drug effects*
  • HL-60 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Sequence Data
  • Promoter Regions, Genetic / drug effects
  • Reverse Transcriptase Polymerase Chain Reaction
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Berberine
  • DNA