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Keywords:

  • DNA alkylation;
  • nucleobases;
  • nucleophilic addition;
  • quinone methide;
  • retro reactions
Thumbnail image of graphical abstract

Who wants to live forever? Compounds that act as strong nucleophiles and good leaving groups repeatedly capture and release a transient quinone methide to extend its effective lifetime under aqueous conditions and promote DNA cross-linking (see scheme). This finding may expand the biological and therapeutic activity of quinone methides.