9-Octadecynoic Acid: A Novel DNA Binding Agent

David E. Berry, James A. Chan, Laurie MacKenzie, Sidney M. Hecht

Research output: Contribution to journalArticlepeer-review

20 Scopus citations


A novel bioassay was developed to permit the identification of cytotoxic natural principles that bind to DNA. A hexane extract of Schoepfia californica cytotoxic to cultured KB cells displayed much less cytotoxic potential when the culture medium contained exogenously added calf thymus DNA. Fractionation of the extract afforded a purified principle shown to be 9-octadecynoic acid, an 18-carbon, unbranched acetylenic fatty acid. 9-Octadecynoic acid had an apparent DNA dissociation constant of 1.8 mM; it inhibited topoisomerase I mediated DNA filter binding but did not inhibit the DNA topoisomerase I mediated relaxation of a supercoiled plasmid DNA. The fatty acid was weakly inhibitory to DNA polymerase α. 9-Octadecynoic acid possesses none of the structural characteristics of known DNA binding molecules and may bind to DNA by some novel mechanism.

Original languageEnglish (US)
Pages (from-to)195-198
Number of pages4
JournalChemical Research in Toxicology
Issue number2
StatePublished - Mar 1 1991
Externally publishedYes

ASJC Scopus subject areas

  • Toxicology


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