Synthesis, DNA binding and cleavage activity of macrocyclic polyamines bearing mono- or bis-acridine moieties

Eur J Med Chem. 2010 Nov;45(11):5302-8. doi: 10.1016/j.ejmech.2010.08.051. Epub 2010 Sep 17.

Abstract

Two acridine-pendant cyclen (1,4,7,10-tetraazacyclododecane) derivatives 1 and 2 were synthesized, and their DNA interactions have been systematically investigated by UV absorption, fluorescence titration, viscosity measurement, DNA melting and gel electrophoresis experiments. The results showed that acridine-cyclen derivatives could bind to DNA in intercalative mode, and bis-acridine 2 has higher DNA binding ability than that of mono-acridine 1. Moreover, both compounds exhibited preferential interactions with G-rich DNA sequences. Their copper(II) complexes could cleave DNA without the existence of other additives under physiological conditions through an oxidative pathway.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / chemistry*
  • DNA / chemistry*
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Polyamines / chemical synthesis*
  • Polyamines / chemistry
  • Spectrometry, Fluorescence
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Ultraviolet

Substances

  • Acridines
  • Polyamines
  • DNA