Targeting loop adenines in G-quadruplex by a selective oxirane

Chemistry. 2013 Jan 2;19(1):78-81. doi: 10.1002/chem.201203097. Epub 2012 Dec 4.

Abstract

Caught in the oxirane: Naphthalene diimides conjugated to a quinone methide and an oxirane have been synthesized and investigated as selective DNA G-quadruplex alkylating agents. The oxirane derivative generates a stable adduct with a G-quadruplex and shows selective alkylation of the loop adenines, as illustrated.

Publication types

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

MeSH terms

  • Adenine / analogs & derivatives*
  • Adenine / chemistry*
  • Alkylation
  • Base Sequence
  • DNA / chemistry*
  • Ethylene Oxide / chemical synthesis
  • Ethylene Oxide / chemistry*
  • G-Quadruplexes
  • Tandem Mass Spectrometry

Substances

  • DNA
  • Adenine
  • Ethylene Oxide