Polychlorinated naphthalenes (PCNs) are ubiquitous
environmental pollutants that are structurally similar to
other polychlorinated diaromatic hydrocarbons (PCDHs),
such as polychlorinated dibenzo-p-dioxins (PCDDs),
dibenzofurans (PCDFs), and biphenyls (PCBs). Despite
being ubiquitous, much less is known about the fate, transport,
and biological effects of individual PCN congeners than
other PCDHs. The purpose of the current study was to utilize
an in vitro assay (H4IIE-luc) to determine potencies
relative to 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) for
20 individual PCNs (from 75 possible congeners) and 6 Halowax
mixtures. H4IIE rat hepatoma cells (H4IIE-Luc), which
are stably transfected with an Ah receptor (AhR)-controlled
luciferase reporter gene construct, respond specifically
to AhR agonists and are thus a reasonable measure of AhR-mediated, or dioxin-like, activity. The most potent
congeners were 1,2,3,4,6,7-hexa-CN (PCN 66), 1,2,3,5,6,7-hexa-CN (PCN 67), and 1,2,3,4,5,6,7-hepta-CN (PCN 73), with
relative potencies as compared to TCDD of 0.004, 0.001,
and 0.001, respectively. Significant structure−activity
relationships were observed. For example, lateral substitution
is an important determinant of AhR-mediated activity,
but not sufficient, as illustrated by the inactivity of 2,3,6,7-tetra-CN to elicit AhR-mediated activity. Relative potencies
of the Halowax mixtures with AhR-mediated activity were
0.0089, 0.000038, and 0.0000018 for 1051, 1014, and 1013,
respectively. The relative potencies derived from this study
were applied to literature-derived data on concentrations
of PCN congeners in environmental mixtures to assess
the potential contribution of PCNs to total TCDD equivalents
(TEQs) in environmentally weathered complex mixtures.