Synthesis of DNA-sequence-selective hairpin polyamide platinum complexes

Taleb, R.I. and Jaramillo, D. and Wheate, N.J. and Aldrich-Wright, J.R. (2007) Synthesis of DNA-sequence-selective hairpin polyamide platinum complexes. Chemistry - A European Journal, 13. pp. 3177-3186. ISSN 0947-6539

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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.