Introduction of a nitroxide group on position 2 of 9-phenoxyacridine: easy access to spin labelled DNA-binding conjugates

Bioorg Med Chem Lett. 1998 Mar 17;8(6):669-74. doi: 10.1016/s0960-894x(98)00089-4.

Abstract

In the search for spin labelled intercalators of general use to construct DNA-binding conjugates, 6-chloro-2-[(1-oxyl-2,2,5,5-tetramethyl- pyrrolin-3-yl)methyloxy]-9-phenoxy-acridine 5, has been prepared. This key-intermediate reacts with amines to give the corresponding labelled 9-amino substituted acridines. Comparative EPR and fluorescence measurements show that the label causes only little modification of the binding properties of acridine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acridines / metabolism*
  • Antioxidants / metabolism*
  • DNA / metabolism*
  • DNA-Binding Proteins / metabolism*
  • Electron Spin Resonance Spectroscopy
  • Free Radicals
  • Models, Chemical
  • Nitrogen Oxides / metabolism*
  • Spectrometry, Fluorescence
  • Spin Labels*

Substances

  • Acridines
  • Antioxidants
  • DNA-Binding Proteins
  • Free Radicals
  • Nitrogen Oxides
  • Spin Labels
  • DNA
  • nitroxyl