Aryl Hydrocarbon Receptor-Mediated Effects of Chlorinated Polycyclic Aromatic Hydrocarbons

Abstract

Chlorinated polycyclic aromatic hydrocarbons (ClPAHs) with 3-5 rings are ubiquitous environmental contaminants. However, toxicities of ClPAHs remain unclear. In this study, aryl hydrocarbon receptor (AhR)-mediated activities of ClPAHs were investigated by using a yeast assay system. All environmentally relevant 18 ClPAHs showed the AhR activities in the test; the activities were elevated with the number of chlorine atoms on the lower molecular weight PAH ( approximately three-ring and fluoranthene derivatives) but not for higher molecular weight ClPAHs (>four-ring). The similar trends were also observed in certain ClPAHs-induced cytochrome P450 1A1 expression in MCF-7 cells. The structure-activity relationship between the AhR activity and the corresponding solvent accessible surface area of ClPAHs revealed a parabolic relationship, with approximately 350 A (2)/molecule as the optimal dimensions as the ligand for binding to AhR. These findings indicate that the spatial dimensions of ClPAHs apparently influence their ability to activate the AhR. Finally, we discussed the toxicity of exposure to ClPAHs based on the AhR activities, estimated that it would be approximately 30-50 times higher than that of dioxins.

Dechlorane Plus and decabromodiphenyl ether in atmospheric particles of northeast Asian cities

“…for mixtures of ClPAHs and PAHs in the air particulates have been calculated, using the same equation as in our previous report , using the PAHs and ClPAHs concentrations in PM sampling on 16 January 2015, and the degree of toxicity compared to BaP, as determined by Ohura et al (2007; for AhR-mediated activities of ClPAHs in a yeast assay. The calculated TEQs for Σ2ClPAH and Σ7PAH…”

“…The evidence suggests that the combustion of organic materials in combination with a chlorine source, or of organic materials containing chlorine, is a possible source of environmental ClPAH pollution. There are concerns that ClPAHs have adverse effects on humans, based on reports that some ClPAHs exhibited mutagenic potential in Salmonella Typhimurium strains TA98 and TA100 (Colmsjö et al, 1984;Bhatia et al, 1987), and showed stronger aryl hydrocarbon receptor (AhR)-mediated activities than those of the parent PAHs in yeast assays (Ohura et al, 2007). Due to the lack of authentic ClPAH analytical standards, their environmental chemistry has not yet been examined in detail.…”

“…However, the particle size distribution of atmospheric ClPAHs is still unknown. Moreover, there are concerns that ClPAHs can have an adverse effect on human health, based on reports that some ClPAHs exhibit a mutagenic potential in Salmonella Typhimurium strains TA98 and TA100 (Bhatia et al 1987, Colmsjö et al 1984, and show stronger aryl hydrocarbon receptor (AhR)-mediated activities than those of the parent PAHs in yeast assays (Ohura et al 2007). For this reason, atmospheric ClPAHs in fine particles that can easily reach the lung periphery are of particular concern, and thus we consider it important to determine the concentrations of ClPAHs with respect to particle size, and to evaluate the effects of ClPAHs in atmospheric PM on human health.…”

Water exposure assessment of aryl hydrocarbon receptor agonists in Three Gorges Reservoir, China using SPMD-based virtual organisms

“…In addition to the best-characterized high-affinity ligands abovementioned, there are numerous PAH-like chemicals (for example oxygenated, methylated PAHs or heterocyclic compounds), pesticide, fungicides and pharmaceutical compounds that are also relatively high-affinity AhR ligands (Denison and Nagy, 2003;Long et al, 2003;Ohura et al, 2007;Sergent et al, 2009;Wall et al, 2012). Our previous study indicated that there were relatively high concentrations of GJB BD1 BD2 WZ CS MP GJB BD1 WZ CS MP GJB BD1 BD2 WZ CS CQ MP GJB BD1 BD2 WZ CS CQ MP GJB BD1 BD2 FJ WZ CS CQ 2008_7d organochlorine pesticides (OCP) in TGR water (Wang et al, 2009(Wang et al, , 2013b.…”

Analysis of Halogenated Polycyclic Aromatic Hydrocarbons in the Air

“…It has been advanced the studies on not only environmental behaviors but also biological effects of ClPAHs. Indeed, the AhR-mediated activities of ClPAHs have been determined by using yeast and CULUX assay systems [13,14]. Although the activities were observed for all the 3-to 5-ring ClPAHs, which were at levels considerably lower (>80-times) than that of TCDD.…”