title: 1H NMR studies on mutagenic nitrofluoranthenes and exposure risk assessment.
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.
authors: Department of Chemistry, Louisiana State University, Baton Rouge 70803.
authors: G L
authors: GL
authors: Squadrito
authors: B S
authors: BS
authors: Shane
authors: F R
authors: FR
authors: Fronczek
authors: D F
authors: DF
authors: Church
authors: W A
authors: WA
authors: Pryor
mesh_terms: D002273:Carcinogens / Q000633:toxicity; D005449:Fluorenes / Q000737:chemistry / Q000633:toxicity*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D015394:Molecular Structure; D009152:Mutagenicity Tests; D012307:Risk Factors; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D002273:Carcinogens; D005449:Fluorenes; C033643:3-nitrofluoranthene; C049030:2-nitrofluoranthene