1H NMR studies on mutagenic nitrofluoranthenes and exposure risk assessment

Chem Res Toxicol. 1990 May-Jun;3(3):231-5. doi: 10.1021/tx00015a007.

Abstract

The 1H NMR spectra of the nitrofluoranthene isomers are presented to allow gas chromatographic analysis of environmental samples suspected of containing nitrofluoranthenes. The mutagenic isomers 1-, 2-, 3-, 7-, and 8-nitrofluoranthene and 1,2- and 1,3-dinitrofluoranthene and a nonmutagenic analogue, 1-phenyl-4-nitronaphthalene, have been studied by using nuclear Overhauser effects and 2D shift-correlated 1H NMR spectroscopy. The X-ray crystal structure of 1-phenyl-4-nitronaphthalene is also reported. Reduction potentials and coplanarity of the nitro group have been used to correlate the mutagenicity of nitrated polycyclic aromatic hydrocarbons (nitro-PAH) measured by the Ames assay, but our data suggest that these parameters are not sufficient for the prediction of mutagenic potency in the nitrofluoranthene series.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carcinogens / toxicity
  • Fluorenes / chemistry
  • Fluorenes / toxicity*
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Structure
  • Mutagenicity Tests
  • Risk Factors
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Carcinogens
  • Fluorenes
  • 3-nitrofluoranthene
  • 2-nitrofluoranthene