Synthesis of DNA-sequence-selective hairpin polyamide platinum complexes

Robin I. Taleb, David Jaramillo, Nial J. Wheate, Janice R. Aldrich-Wright

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16 Citations (Scopus)

Abstract

Two DNA-sequence-selective hairpin polyamide platinum(II) complexes, containing pyrrole and imidazole heterocyclic rings, have been synthesised by different methods. A six-ring complex, selective for (A/T)GGG(A/T) DNA sequences, was made by using solid-phase synthesis, whilst an eight-ring complex, selective for (A/T)CCTG(A/T) DNA sequences, was made by utilising standard wet chemistry. Solid-phase synthesis resulted in a significantly higher yield, required less purification and is more efficient than the wet synthesis; as such, it is the preferred method for further work. The metal complexes were characterised by 1H and 195Pt NMR spectroscopy and ESI mass spectrometry. The two compounds provide a foundation for the synthesis of more complex molecules containing multiple hairpins and/or platinum groups.
Original languageEnglish
Pages (from-to)3177-3186
Number of pages10
JournalChemistry - A European Journal
Volume13
Issue number11
DOIs
Publication statusPublished - 5 Apr 2007
Externally publishedYes

Keywords

  • DNA recognition
  • Antitumor agents
  • Platinum
  • Polyamides
  • Synthesis design

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