Synthesis of DNA-Sequence-Selective Hairpin Polyamide Platinum Complexes

Authors

  • Robin I. Taleb,

    1. School of Biomedical and Health Sciences, University of Western Sydney, Locked Bag 1797, Penrith South DC, NSW, Australia, Fax: (+61) 2-4620-3025
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  • David Jaramillo Dr.,

    1. School of Biomedical and Health Sciences, University of Western Sydney, Locked Bag 1797, Penrith South DC, NSW, Australia, Fax: (+61) 2-4620-3025
    2. Current address: Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, CA 92093, USA
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  • Nial J. Wheate Dr.,

    1. School of Biomedical and Health Sciences, University of Western Sydney, Locked Bag 1797, Penrith South DC, NSW, Australia, Fax: (+61) 2-4620-3025
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  • Janice R. Aldrich-Wright Assoc. Prof.

    1. School of Biomedical and Health Sciences, University of Western Sydney, Locked Bag 1797, Penrith South DC, NSW, Australia, Fax: (+61) 2-4620-3025
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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.

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