title: Relative potency of PAHs and heterocycles as aryl hydrocarbon receptor agonists in fish.
abstract: The relative potency of polycyclic aromatic compounds as aryl hydrocarbon receptor (AhR) agonists in fish was determined using data on CYP1A induction or AhR binding for 74 polycyclic aromatic hydrocarbons (PAHs) and heterocycles in teleost, avian, or mammalian systems from 18 published papers. Each PAH was assigned a fish potency factor relative to the potency of 2,3,7,8-tetrachlorodibenzo-p-dioxin as an AhR agonist. Two and three ring unsubstituted PAHs were generally inactive in fish, avian, and mammalian systems. Benzo[k]fluoranthene and indeno[1,2,3-cd]pyrene were consistently the most potent PAHs, with fish potency factors of 0.001-0.002. Common structural features associated with higher potency PAHs included 4-6 rings containing fluoranthene or phenanthrene structures with an exposed bay region. These results show that PAHs can have similar potency as many dioxin-like PCBs, and AhR mediated toxicity should be considered in assessing the risks of PAHs in fish.
authors.affiliation: P.E.A.K. Research, Longmont, Colorado, USA. barron.mace@epa.gov
authors.forename: Mace G
authors.initials: MG
authors.lastname: Barron
authors.forename: Ron
authors.initials: R
authors.lastname: Heintz
authors.forename: Stanley D
authors.initials: SD
authors.lastname: Rice
mesh_terms: D000818:Animals; D002460:Cell Line; D019363:Cytochrome P-450 CYP1A1 / Q000096:biosynthesis*; D004305:Dose-Response Relationship, Drug; D004790:Enzyme Induction / Q000187:drug effects; D005399:Fishes / Q000378:metabolism*; D006571:Heterocyclic Compounds / Q000378:metabolism / Q000633:toxicity*; D000072317:Polychlorinated Dibenzodioxins; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry / Q000378:metabolism / Q000633:toxicity*; D018336:Receptors, Aryl Hydrocarbon / Q000037:antagonists & inhibitors*
chemical_list: D006571:Heterocyclic Compounds; D000072317:Polychlorinated Dibenzodioxins; D011084:Polycyclic Aromatic Hydrocarbons; D018336:Receptors, Aryl Hydrocarbon; D019363:Cytochrome P-450 CYP1A1