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Related Experiment Videos

9-Octadecynoic acid: a novel DNA binding agent.

D E Berry1, J A Chan, L MacKenzie

  • 1Department of Biomolecular Discovery, Smith Kline Beecham Pharmaceuticals, King of Prussia, Pennsylvania 19406-0939.

Chemical Research in Toxicology
|March 1, 1991
PubMed
Summary

Researchers identified 9-octadecynoic acid, a novel fatty acid from Schoepfia californica, that binds to DNA. This cytotoxic compound may interact with DNA via a new mechanism, distinct from known DNA-binding molecules.

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Area of Science:

  • Natural Product Chemistry
  • Molecular Biology
  • Biochemistry

Background:

  • Cytotoxic natural products are crucial for drug discovery.
  • Identifying compounds that interact with DNA is a key area of research.
  • Schoepfia californica is a plant source with potential bioactive compounds.

Purpose of the Study:

  • To develop a bioassay for identifying DNA-binding cytotoxic natural products.
  • To isolate and characterize the DNA-binding cytotoxic principle from Schoepfia californica.
  • To investigate the mechanism of DNA interaction for the isolated compound.

Main Methods:

  • Development of a novel bioassay using cultured KB cells and calf thymus DNA.
  • Hexane extraction and fractionation of Schoepfia californica.

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  • Characterization of the purified compound using biochemical assays, including DNA binding and enzyme inhibition studies.

    • Main Results:

    • A hexane extract of Schoepfia californica showed reduced cytotoxicity in the presence of DNA.
    • 9-Octadecynoic acid, an acetylenic fatty acid, was isolated as the active principle.
    • 9-Octadecynoic acid exhibited DNA binding (Kd = 1.8 mM), inhibited topoisomerase I DNA binding, but not DNA relaxation, and weakly inhibited DNA polymerase alpha.

    Conclusions:

    • 9-Octadecynoic acid is a novel cytotoxic natural product that binds to DNA.
    • The mechanism of DNA binding for 9-octadecynoic acid appears novel, as it lacks structural similarities to known DNA-binding agents.
    • This study highlights the potential of Schoepfia californica as a source of unique bioactive compounds.