Synthesis, DNA binding and photocleavage study of novel anthracene-appended macrocyclic polyamines

Org Biomol Chem. 2009 Jun 7;7(11):2278-85. doi: 10.1039/b823416g. Epub 2009 Apr 17.

Abstract

Two anthracene derivatives appended on cyclen (1,4,7,10-tetraazacyclododecane) moieties were synthesized and characterized. In these new compounds, the anthryl is used as a substitute for the nucleobases of classical PNA backbone, and the cyclen moiety appends on the terminal amino group. The interaction of the compounds with DNA was systematically investigated by absorption, fluorescence, and viscometric titration, DNA melting and gel electrophoresis experiments. From the absorption titration data, bis-anthryl compound can bind to CT DNA with K(b) = 1.21 x 10(5) M(-1) that is 121 times larger than that of mono-anthryl compound (K(b) = 1.00 x 10(3) M(-1)). Through the fluorescence titration data, compound shows distinct CG-selective DNA binding activity. DNA melting and viscometric titration experiments indicate that the binding mode of is a multiple binding mode that involves groove binding and partial intercalation. Compound also shows excellent DNA photocleavage ability, which is much more efficient than the mono-anthryl compound .

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemical synthesis*
  • Anthracenes / chemistry
  • Anthracenes / metabolism*
  • Binding Sites
  • Cyclams
  • DNA / chemistry
  • DNA / metabolism*
  • DNA / radiation effects
  • Fluorescence
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Heterocyclic Compounds / metabolism
  • Light
  • Nucleic Acid Denaturation
  • Photochemical Processes
  • Polyamines / chemical synthesis
  • Polyamines / chemistry*
  • Polyamines / metabolism
  • Spectrophotometry
  • Titrimetry
  • Viscosity

Substances

  • Anthracenes
  • Cyclams
  • Heterocyclic Compounds
  • Polyamines
  • DNA
  • cyclen
  • anthracene