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Functionalized Rhodium Intercalators for DNA Recognition.

Robert H. Terbrueggen1, Timothy W. Johann, Jacqueline K. Barton

  • 1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125.

Inorganic Chemistry
|October 24, 2001
PubMed
Summary

Rhodium complexes with guanidinium groups show high enantioselectivity and site-specificity for DNA binding and photo-induced strand breaks. These findings highlight the advantage of guanidinium functionalities in designing targeted DNA-interacting molecules.

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Area of Science:

  • Coordination Chemistry
  • Bioinorganic Chemistry
  • Chemical Biology

Background:

  • DNA-binding small molecules are crucial for targeted therapeutics and diagnostics.
  • Rhodium complexes with phenanthrenequinone diimine (phi) ligands can intercalate into DNA and induce strand breaks upon photoactivation.
  • Functionalization of ancillary ligands can impart sequence-specific DNA recognition.

Purpose of the Study:

  • To synthesize and characterize rhodium complexes with functionalized ligands for site-specific DNA binding.
  • To investigate the DNA binding affinity, enantioselectivity, and photocleavage activity of these complexes.
  • To determine the role of pendant functional groups (guanidinium, amido, amino) in DNA recognition and cleavage.

Main Methods:

  • Synthesis of rhodium complexes with phenanthrenequinone diimine and functionalized bipyridyl/phenanthroline ligands.

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  • DNA binding studies using techniques to determine affinity and sequence specificity (e.g., footprinting).
  • Photocleavage assays to evaluate DNA strand break induction upon photoactivation.

    • Main Results:

    • Rhodium complexes with guanidinium functionalities exhibited high enantioselectivity and site-specific binding to DNA sequences (e.g., 5'-CATATG-3' and 5'-CATCTG-3').
    • The stereochemistry and positioning of guanidinium groups significantly influenced DNA recognition and photocleavage efficiency.
    • Complexes with amido or amino groups showed less specific DNA interaction, resembling the parent compound.

    Conclusions:

    • Pendant guanidinium groups are highly advantageous for constructing small molecules with precise DNA site-specificity.
    • The stereochemical arrangement of functional groups on ancillary ligands dictates enantioselective DNA recognition.
    • These findings pave the way for developing novel rhodium-based agents for targeted DNA manipulation.