A Nitroxide-Tagged Platinum(II) Complex Enables the Identification of DNA G-Quadruplex Binding Mode

Chemistry. 2016 Mar 1;22(10):3405-3413. doi: 10.1002/chem.201504960. Epub 2016 Feb 4.

Abstract

We reported a novel strategy for investigating small molecule binding to G-quadruplexes (GQs). A newly synthesized dinuclear platinum(II) complex (Pt2L) containing a nitroxide radical was shown to selectively bind a GQ-forming sequence derived from human telomere (hTel). Using the nitroxide moiety as a spin label, electron paramagnetic resonance (EPR) spectroscopy was carried out to investigate binding between Pt2L and hTel GQ. Measurements indicated that two molecules of Pt2L bind with one molecule of hTel GQ. The inter-spin distance measured between the two bound Pt2L, together with molecular docking analyses, revealed that Pt2L predominately binds to the neighboring narrow and wide grooves of the G-tetrads as hTel adopts the antiparallel conformation. The design and synthesis of nitroxide tagged GQ binders, and the use of spin-labeling/EPR to investigate their interactions with GQs, will aid the development of small molecules for manipulating GQs involved in crucial biological processes.

Keywords: EPR spectroscopy; G-quadruplexes; molecular docking; nitroxide; platinum(II) complexes.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Binding Sites
  • Circular Dichroism
  • Coordination Complexes / chemistry*
  • Coordination Complexes / metabolism
  • Coordination Complexes / pharmacology
  • DNA / chemistry
  • DNA / metabolism
  • Electron Spin Resonance Spectroscopy
  • G-Quadruplexes / drug effects*
  • Humans
  • Molecular Docking Simulation
  • Nitrogen Oxides / chemistry*
  • Nucleic Acid Conformation
  • Platinum / chemistry*
  • Telomerase / antagonists & inhibitors
  • Telomerase / metabolism
  • Telomere / chemistry
  • Transition Temperature

Substances

  • Coordination Complexes
  • Nitrogen Oxides
  • Platinum
  • DNA
  • Telomerase
  • nitroxyl