Aryl hydrocarbon receptor ligand activity of polycyclic aromatic ketones and polycyclic aromatic quinones

Abstract

Polycyclic aromatic ketones (PAKs) and polycyclic aromatic quinones (PAQs) are oxygenated polycyclic aromatic hydrocarbons (PAHs), and reports about the aryl hydrocarbon receptor (AhR) ligand activities of these compounds are few. In this study, activation of AhR by 41 polycyclic aromatic compounds (PACs), focusing especially on PAKs and PAQs, was determined by measuring beta-galactosidase activity from a reporter plasmid in yeast engineered to express human AhR and the AhR nuclear translocator proteins and by measuring luciferase activity from mouse hepatoma (H1L1) cells (chemical-activated luciferase expression [CALUX] assay). The PACs used in these experiments included 11 PAKs, seven PAQs, and 21 PAHs. In this study, the PAKs 11H-benzo[a]fluoren-11-one (B[a]FO), 11H-benzo[b]fluoren-11-one (B[b]FO) and 7H-benzo[c]fluoren-7-one and the PAQs 5,12-naphthacenequinone, 1,4-chrysenequinone, and 7,12-benz[a]anthracenequinone showed high AhR activities in H1L1 cells, although these values were not as high as that for benzo[a]pyrene (B[a]P). These PAKs and PAQs showed significantly stronger activities in yeast cells relative to B[a]P. It was predicted that PAKs such as B[a]FO and B[b]FO occupied 0.06% to 1.3% of the total induction equivalents, and each contribution matched the contribution of PAHs such as B[a]P, chrysene, and benz[a]anthracene in gasoline exhaust particulates and airborne particulates using data of CALUX assay.