Synthesis of DNA-sequence-selective hairpin polyamide platinum complexes

R.I. Taleb, D. Jaramillo, N.J. Wheate, J.R. Aldrich-Wright

Research output: Contribution to journalArticle

14 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 pages9
JournalChemistry - A European Journal
Volume13
DOIs
Publication statusPublished - 2007

Keywords

  • antitumor agents
  • DNA recognition
  • platinum
  • polyamides
  • synthesis design
  • cancer

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