Polar Forms of Benzo[<i>a</i>]pyrene May Be Ubiquitous in the Environment

Ismail, Yasser; Lafleur, and Arthur L.; Giese, Roger W.

doi:10.1021/es9710722

Cited by 6 publications

(1 citation statement)

References 31 publications

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“…A number of them are mutagenic, have the capacity to form DNA and protein adducts and to activate aryl hydrocarbon receptor (AhR)–mediated activity, and may interfere with estrogen receptor (ER)–mediated signaling [3–7]. Although oxidized and nitrated PAH derivatives and azaarenes are also significant environmental contaminants [8–11], their toxicity mechanisms are understood less than those of the parent PAHs. Oxygenated (oxy)‐PAHs contain one or more keto‐ groups, whereas azaarenes are polycyclic aromatic heterocycles in which nitrogen replaces a carbon in one of the rings (Fig.…”

Section: Introductionmentioning

confidence: 99%

Aryl hydrocarbon receptor‐mediated and estrogenic activities of oxygenated polycyclic aromatic hydrocarbons and azaarenes originally identified in extracts of river sediments

Machala

Cigánek

Bláha

et al. 2001

Enviro Toxic and Chemistry

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Reproductive dysfunction in wildlife populations can be a result of environmental contaminants binding to aryl hydrocarbon receptor (AhR) or estrogenic receptors. Signaling by both types of receptors can be affected by polycyclic aromatic hydrocarbons (PAHs), which are potential endocrine disruptors. However, our knowledge regarding the effects of oxygenated (oxy)-PAHs and azaarenes on AhR-mediated and estrogenic activities is incomplete. In the present study, we have identified 9-fluorenone, anthrone, anthraquinone, benzanthrone, benz[a]anthracene-7,12-dione, benz[c]acridine, and dibenz[a,h]acridine as prevalent oxy-PAHs and azaarenes found in river sediments. Their concentrations in sediment samples ranged from 2.1 to 165.2 ng g(-1) for oxy-PAHs and up to 27.3 ng g(-1) for azaarenes. Their relative AhR-inducing and estrogenic potencies were quantified in vitro using two cell lines that were stably transfected with a luciferase reporter gene system and expressed as induction equivalency factors (IEFs). The only oxy-PAHs with detectable levels of in vitro AhR-mediated activity were benzanthrone and benz[a]anthracene-7,12-dione. However, their IEFs were approximately three to four orders of magnitude lower than those of benzo[a]pyrene. On the other hand, azaarenes showed a strong AhR-mediated activity, with dibenzo[a,h]acridine being a far more potent inducer of activity than benzo[a]pyrene. Benzanthrone, benz[a]anthracene-7,12-dione, anthraquinone, and benz[a]acridine were weak inducers of in vitro estrogenic activity, with IEFs similar to that of benzo[a]pyrene. Based on concentrations and relative potencies, our results suggest that dibenzo[a,h]acridine can significantly contribute to the overall AhR-mediated activity in river sediments, whereas the remaining compounds do not. No studied compound was found to contribute significantly to estrogen receptor-mediated activity in vitro.

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Section: Introductionmentioning

confidence: 99%