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Redox-active daunomycin-spin-labeled nucleic acid complexes.

J C Ireland, G T Pauly, E V Bobst

    Biochemistry
    |November 4, 1986
    PubMed
    Summary
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    Daunomycin (DM) interacts with nucleic acids via intercalation at low concentrations, and at higher concentrations, it destabilizes the helix, forming redox-active stacks. This interaction leads to irreversible oxidation of nitroxides in spin-labeled nucleic acids.

    Area of Science:

    • Biochemistry
    • Molecular Biology
    • Biophysics

    Background:

    • Daunomycin (DM) is an anthracycline antibiotic with known DNA-binding properties.
    • Understanding the precise mechanisms of drug-nucleic acid interactions is crucial for drug development and molecular biology.
    • Electron spin resonance (ESR) spectroscopy is a powerful tool for studying molecular dynamics and interactions.

    Purpose of the Study:

    • To investigate the binding modes of daunomycin (DM) to nucleic acids using ESR spectroscopy.
    • To elucidate the effect of DM on nucleic acid structure and dynamics.
    • To characterize the redox interactions between DM and spin-labeled nucleic acids.

    Main Methods:

    • Electron spin resonance (ESR) spectroscopy was employed to study the interaction between daunomycin (DM) and enzymatically spin-labeled nucleic acid duplexes and single strands.

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  • Varying drug/nucleotide (D/N) ratios were used to observe different binding stoichiometries.
  • The mobility and oxidation state of nitroxide spin labels covalently attached to nucleic acids were monitored.

    • Main Results:

    • Two distinct binding modes of DM to nucleic acid duplexes were identified: intercalation at low D/N ratios and helix destabilization at higher ratios.
    • Intercalation saturation occurred at lower D/N ratios for B' DNA compared to B DNA.
    • At higher D/N ratios, DM formed redox-active stacks that irreversibly oxidized nitroxides in spin-labeled nucleic acids.
    • DM interacted directly with single-stranded nucleic acids to form redox-active complexes, but not with free building blocks.

    Conclusions:

    • Daunomycin exhibits complex binding behavior with nucleic acids, involving both intercalation and helix destabilization.
    • The formation of redox-active daunomycin stacks is a key mechanism for the observed oxidation of spin labels.
    • ESR spectroscopy provides valuable insights into the dynamic and redox interactions between small molecules and nucleic acids.