Relative potency of PAHs and heterocycles as aryl hydrocarbon receptor agonists in fish

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. (C) 2004 Elsevier Ltd. All rights reserved.