Table 1.
ER affinity and activity by individual PAH mixture parent, hydroxy, quinoid and ketone metabolite compounds
| ER | Parent compound | Hydroxy metabolite(s) | Quinoid metabolite(s) | Ketone metabolite(s) | ||||||
|---|---|---|---|---|---|---|---|---|---|---|
| PAH compound | Rings | Affinity | Activity | Affinity | Activity | Affinity | Activity | Affinity | Activity | References |
| Naphthalene | 2 | Weak inducer/ non-inducer | Inducer/ non-inducer | Binding | Non-inducer | (20,48,49,51,54) | ||||
| Phenanthrene | 3 | Non-binding | Non-inducer | Binding | Inducer | Binding | Non-inducer | (20,48–52) | ||
| Fluoranthene | 4 | Non-binding | Non-inducer | Binding | Inducer | (20,50,51) | ||||
| Acenaphthene | 3 | Non-binding/ weak binding | Non-inducer | Weak binding | Non-inducer | (20,48) | ||||
| Fluorene | 3 | Non-binding | Non-inducer | Weak binding | Inducer/weak inducer | Weak binding | Non-inducer | (20,48,50–52,54) | ||
| Pyrene | 4 | Non-binding | Weak inducer/ non-inducer | Weak binding | Inducer/ non-inducer | (20,49–51,54) | ||||
| Carbazole | 3 | Non-binding | Non-inducer | (52) | ||||||
| Dibenzofuran | 3 | Weak inducer | (54) | |||||||
| 1-Methylnaphthalene | 2 | Inducer/ non-inducer | (20,54) | |||||||
| Benz[a]anthracene | 4 | Non-binding | Weak inducer | Binding | Inducer | Weak binding | Non-inducer | Weak binding | Non-inducer | (20,47,48,50– 52,54) |
| Anthracene | 3 | Non-binding/ weak binding | Weak inducer/ non-inducer | Weak inducer | Binding/ weak binding | Weak inducer/ non-inducer | Weak binding | Non-inducer | (48,50,52,54) | |
| Benzo[b]fluoranthene | 5 | Non-binding | Weak inducer/ non-inducer | Weak binding | Inducer | Weak binding | Non-inducer | (20,48,50,51,54) | ||
| Dibenzothiophene | 3 | Weak inducer/ non-inducer | (52) | |||||||
| Chrysene | 4 | Non-binding | Weak inducer/ non-inducer | Binding | Inducer/ non-inducer | Binding | Inducer | (20,47,48,50–52) | ||
| 1,2-Benzofluorene/benzo(a) fluorene | 4 | Weak binding | Non-inducer | (48) | ||||||
| 2,6-Dimethylnaphthalene | 2 | Weak inducer | (54) | |||||||
| BaP | 5 | Non-binding | Weak inducer/ non-inducer | Binding | Inducer/ non-inducer | Binding | Inducer | Non-binding | Non-inducer | (20,48,50–52,54) |
| Retene | 3 | |||||||||
| 2-Methylphenanthrene | 3 | Non-inducer | (52) | |||||||
| Benzo[e]pyrene | 5 | Non-binding | Weak inducer/ non-inducer | Weak binding | Inducer | (50,51,54) | ||||
| Benzo[k]fluoranthene | 5 | Non-binding | Weak inducer/ non-inducer | Binding | Inducer | (20,50,51,54) | ||||
| 1-Methylphenanthrene | 3 | |||||||||
| Acenaphthylene | 3 | Non-inducer | (20) | |||||||
| Benzo[g,h,i]perylene | 6 | Weak binding | Weak inducer/ non-inducer | (20,50,54) | ||||||
| Picene | 5 | |||||||||
| 3,4-Benzofluorene/benzo(c) fluorene | 4 | |||||||||
| Perylene | 5 | |||||||||
| Benzo[a]fluoranthene | 5 | |||||||||
| Dibenz[a,l]pyrene | 6 | |||||||||
| Indeno[1,2,3-c,d]pyrene | 6 | Weak binding | Non-inducer | Non-inducer | (20,50,51) | |||||
| Benzo[b]chrysene | 5 | |||||||||
| Dibenz[a,j]anthracene | 5 | |||||||||
| Dibenz[a,h]anthracene | 5 | Weak binding | Weak inducer/ non-inducer | (20,50,54) | ||||||
| Benzo[c]phenanthrene | 4 | Non-binding | Non-inducer | Binding | Weak inducer/ non-inducer | Binding | (47,48,51) | |||
| 3-Methylcholanthrene | 5 | Weak binding | Weak inducer | (53,54) | ||||||
For all 36 compounds within our Superfund sediment-derived PAH mixture, in order of descending mixture concentration. Affinity is defined by binding or displacement assay, to either the alpha or beta subunit of ER. Activity is defined by one or more of multiple assays: B-galactosidase activity, MVLN estrogen-responsive luciferase assay, estrogen responsive element fold induction in MCF-7 or other cell lines, or Yeast 2 Hybrid Assay. For some compounds, literature finds conflicting binding affinity or activity, and some compounds may exhibit antiestrogenic properties (data not shown). MVLN = also known as “MCF-7 Vit Luc Neo”, a cell line based on MCF-7 that has been stably transfected so the luciferase gene is under the control of an estrogen-responsive element from the Xenopus vitellogenin A2 gene.