Methylated polycyclic aromatic hydrocarbons and/or their metabolites are important contributors to the overall estrogenic activity of polycyclic aromatic hydrocarbon–contaminated soils

Lam, Monika M.; Engwall, Magnus; Denison, Michael S.; Larsson, Maria

doi:10.1002/etc.3958

Cited by 27 publications

(16 citation statements)

References 45 publications

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“…However, the dimethylation of dibenzothiophene increased the potency of the parent compound. The derivatives of acridine, 9‐methylacridine and 9‐(10H)acridone, tested in the present study failed to induce AhR‐mediated response in the H4IIE‐ luc assay, which is consistent with results of a previous study, in which those compounds failed to induce ethoxyresorufin‐ O ‐deethylase activity in breast cancer cells (Lam et al ). However, the small concentrations tested in the present study might be a reason why those compounds were not able to activate the AhR.…”

Section: Discussionsupporting

confidence: 92%

Methylated PACs are more potent than their parent compounds: A study of aryl hydrocarbon receptor–mediated activity, degradability, and mixture interactions in the H4IIE‐luc assay

Lam

Bülow

Engwall

et al. 2018

Enviro Toxic and Chemistry

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Twenty-six polycyclic aromatic compounds (PACs; including native polycyclic aromatic hydrocarbons [PAHs], hydroxylated PAHs, alkylated and oxygenated PAHs, and [alkylated] heterocyclic compounds) were investigated for their aryl hydrocarbon receptor (AhR)-mediated potencies in the H4IIE-luc bioassay. Potential degradabilities of PACs were investigated by use of various durations of exposure (24, 48, or 72 h), and various mixtures of PACs including PAHs, alkylated and oxygenated PAHs, and heterocyclic compounds were tested for their joint AhR-mediated potency. Additive behaviors of PACs in mixtures were studied by comparing observed mixture potencies with mixture potencies predicted by use of the concentration addition model. Methylated derivatives were more potent than their parent compounds in the H4IIE-luc assay. A time-dependent decrease in relative potency was observed for all AhR-active compounds, which may be indicative of in vitro biotransformation. Monomethylated compounds seemed to be more rapidly transformed than analogous unsubstituted compounds. In addition, the results showed that the predictive power of the concentration addition model increased with the number of compounds, suggesting additivity in multicomponent mixtures. Due to the greater potency of methylated derivatives and their ubiquitous occurrence, there is a need for further research on the toxicity and mixture behavior of these environmentally and toxicologically relevant compounds. Environ Toxicol Chem 2018;37:1409-1419. © 2018 SETAC.

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Section: Discussionsupporting

confidence: 92%

Methylated PACs are more potent than their parent compounds: A study of aryl hydrocarbon receptor–mediated activity, degradability, and mixture interactions in the H4IIE‐luc assay

Lam

Bülow

Engwall

et al. 2018

Enviro Toxic and Chemistry

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“…Supplementary data to this article can be found online at: Flupentixol 2709-56-0 27 37 78 114 < 30 51 91 197 Fluphenazine 5002-47-1 268 114 66 133 < 60 82 334 165 Propiconazole 1.9×10 -5 EC50 2,8, h PCB 7.0×10 -3 EC20 3,13, t Estrone 1.1×10 -1 ECIR1.5 3,10, a TDCPP w 0.33 IC20 3,12, r Pyrene 4.1×10 -6 EC25 1,5, b,c PCB 138 5.3×10 -3 EC20 3,13, s Formononetin 2.3×10 -4 EC50 3,11, m Verapamil hydrochloride 0.27 IC20 3,12, r Terbuthylazine 1.3×10 -5 EC50 2,8, h PCB 153 6.0×10 -3 EC20 3,13, s Genistein 2.0×10 -4 EC10 3,10, a PCB 180 6.0×10 -3 EC20 3,13, s Naringenin 2.2×10 -5 EC50 3,11, m Propiconazole 5.4×10 -3 EC10 3,13, a Terbuthylazine 1.6×10 -7 EC10 3,10, a Terbuthylazine 4.1×10 -3 EC10 3,13, s Triphenyl phosphate 1.4×10 -6 EC10 3,10, a Triphenyl phosphate 1.7×10 -2 EC10 3,13, a 1 rat-based cell line 5 H4EII-luc 9 Hepa1c1c7 13 HG5LN-hPXR a (Neale et al, 2017) e (current study) i (Kinani et al, 2010) m (Procházková et al, 2017) q (Lam et al, 2017) u (Escher et al, 2013) 2 mouse-based cell line 6 H4G1.1c2 10 MELN 14 AREc32 b (Larsson et al, 2012) f (Denison et al, 1998) j (Pillon et al, 2005) n r (US EPA ToxCast) v 3 human-based cell line 7 H4L1.1c4 11 HeLa9903 15 p53RE-bla c g (Takeuchi et al, 2008) k (Creusot et al, 2013) o s (Creusot et al, 2010) w Tris(1,3-Dichloro-2propyl)phosphate 4 DR-CALUX 8 Hepa1.12cR 12 MDA-kb2 d (Behnisch et al, 2003) h (Ghisari et al, 2015) l (Leusch et al, 2010) p (Ceger et al, 2015) t (Creusot, 2011) x Tris(2-butoxyethyl) phosphate…”

Section: Appendix a Supplementary Datamentioning

confidence: 87%

Effect-based monitoring of the Danube River using mobile passive sampling

Novák

Vrana

Rusina

et al. 2018

Science of The Total Environment

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Many aquatic pollutants can be present at low concentrations, but their mixtures can still affect health or behavior of exposed organisms. In this study, toxicological and chemical analyses were combined for spatial contamination profiling using an innovative passive sampling approach. A novel Dynamic Passive Sampler (DPS) was employed as a mobile sampler from a ship cruising along 2130km of the Danube river during the Joint Danube Survey 3 (JDS3). The sampling was performed in eight subsequent river stretches with two types of complementary passive samplers: silicone rubber sheets (SR) used for non-polar chemicals and SDB-RPS Empore™ disks (ED) for more hydrophilic compounds. Besides extensive chemical analyses, the bioactivity of samples was characterized by a battery of reporter gene bioassays. Cross-calibration of the employed passive samplers enabled robust estimation of water concentrations applicable for compounds with a wide range of physicochemical properties. DPS was suitable for sampling of water contaminants even at pgL levels, with 209 of 267 analyzed compounds detected in the samples. Biological effects were detected in both ED and SR extracts across all river stretches by bioassays focused on xenobiotic metabolism mediated by the aryl hydrocarbon and pregnane X receptors, endocrine disruptive potential mediated by estrogen and androgen receptors and the oxidative stress response. The bioassay responses expressed as bioanalytical equivalent concentrations (BEQ) were comparable with data obtained from large volume active sampling. The extracts of the ED samplers were more biologically active than extracts of SR samplers. Except of estrogenicity, where the analyzed chemicals explained on average 62% of the effects in ED samples, the detected chemicals explained <8% of BEQ values. The study shows the utility of the combination of the innovative passive sampling approach with effect-based tools for efficient and fast monitoring even in water bodies with relatively low levels of contamination.

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“…Soil has received far less attention with bioanalytical tools (Xiao et al, 2006). The few studies available focus on soils in connection with the application of sewage sludge to agricultural soils (Liu et al, 2014) or soil of e-waste recycling sites (Shen et al, 2008) or other contaminated areas (Sidlova et al, 2009;Lam et al, 2018).…”

Section: Soilmentioning

confidence: 99%

Bioanalytical Tools in Water Quality Assessment

Neale¹,

Leusch²,

Escher³

2021

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The first edition of Bioanalytical Tools in Water Quality Assessment was released in 2012. The field has exploded since and the second edition updates and reviews the application of bioanalytical tools for water quality assessment including surveillance monitoring. The book focuses on applications to water quality assessment ranging from wastewater to drinking water, including recycled water, as well as treatment processes and advanced water treatment. Emerging applications for other environmental matrices are also included. Bioanalytical Tools in Water Quality Assessment, Second Edition, not only demonstrates applications but also fills in the background knowledge in toxicology/ecotoxicology needed to appreciate these applications. Each chapter summarises fundamental material in a targeted way so that information can be applied to better understand the use of bioanalytical tools in water quality assessment. The book can be used by lecturers teaching academic and professional courses and also by risk assessors, regulators, experts, consultants, researchers and managers working in the water sector. It can also be a reference manual for environmental engineers, analytical chemists and toxicologists. ISBN: 9781789061970 (Paperback) ISBN: 9781789061987 (eBook)

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Methylated polycyclic aromatic hydrocarbons and/or their metabolites are important contributors to the overall estrogenic activity of polycyclic aromatic hydrocarbon–contaminated soils

Cited by 27 publications

References 45 publications

Methylated PACs are more potent than their parent compounds: A study of aryl hydrocarbon receptor–mediated activity, degradability, and mixture interactions in the H4IIE‐luc assay

Methylated PACs are more potent than their parent compounds: A study of aryl hydrocarbon receptor–mediated activity, degradability, and mixture interactions in the H4IIE‐luc assay

Effect-based monitoring of the Danube River using mobile passive sampling

Bioanalytical Tools in Water Quality Assessment

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