9-Octadecynoic acid

A novel DNA binding agent

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

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

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
Volume4
Issue number2
StatePublished - 1991
Externally publishedYes

Fingerprint

Type I DNA Topoisomerase
DNA
Olacaceae
Fatty Acids
Superhelical DNA
KB Cells
Hexanes
DNA-Directed DNA Polymerase
Biological Assay
Culture Media
Cultured Cells
Plasmids
Carbon
Bioassay
Fractionation
9-stearolic acid
Molecules
calf thymus DNA
2-hexadecynoic acid

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Toxicology
  • Health, Toxicology and Mutagenesis

Cite this

Berry, D. E., Chan, J. A., MacKenzie, L., & Hecht, S. (1991). 9-Octadecynoic acid: A novel DNA binding agent. Chemical Research in Toxicology, 4(2), 195-198.

9-Octadecynoic acid : A novel DNA binding agent. / Berry, David E.; Chan, James A.; MacKenzie, Laurie; Hecht, Sidney.

In: Chemical Research in Toxicology, Vol. 4, No. 2, 1991, p. 195-198.

Research output: Contribution to journalArticle

Berry, DE, Chan, JA, MacKenzie, L & Hecht, S 1991, '9-Octadecynoic acid: A novel DNA binding agent', Chemical Research in Toxicology, vol. 4, no. 2, pp. 195-198.
Berry, David E. ; Chan, James A. ; MacKenzie, Laurie ; Hecht, Sidney. / 9-Octadecynoic acid : A novel DNA binding agent. In: Chemical Research in Toxicology. 1991 ; Vol. 4, No. 2. pp. 195-198.
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