Toxic and Genotoxic Effects of Azaarenes: Isomers and Metabolites

Carbamazepine, an anti-epileptic pharmaceutical agent commonly found in wastewater, is highly recalcitrant to standard wastewater treatment practices. This study investigated the mixture toxicity of carbamazepine transformation products formed during UV photolysis using three standard ecotoxicity assays (representing bacteria, algae and crustaceans). UV-treatment of 6 mg L -1 carbamazepine solution was carried out over a 120 min period and samples were removed periodically over the course of the experiment. Quantification results confirmed the degradation of carbamazepine throughout the treatment period, together with concurrent increases in acridine and acridone concentrations. Ecotoxicity was shown to increase in parallel with carbamazepine degradation indicating that the mixture of degradation products formed was more toxic than the parent compound. In fact, ecotoxicity was still greater than 60 % for all three endpoints even when the carbamazepine concentration had decreased to < 1 % of the starting concentration, and acridine and acridone had decreased to < 10 % of their maximum measured concentrations. Single compound toxicity testing also confirmed the higher toxicity of measured degradation products relative to the parent compound. These results show that transformation products considerably more toxic than carbamazepine itself are likely to be produced during UV treatment of wastewater effluents and/or photo-induced degradation of carbamazepine in natural waters. This study highlights the need to consider mixture toxicity and the formation and persistence of toxicologically relevant transformation products when assessing the environmental risks posed by pharmaceutical compounds.

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“…Benthic invertebrate, midge (Chironomus riparius); 96h; survival (first instar larvae Bleeker et al (1999). Table S2.…”

Section: Supplementary Materialsmentioning

confidence: 99%

Ecotoxicity of carbamazepine and its UV photolysis transformation products

Donner

Kosjek

Qualmann

et al. 2013

Science of The Total Environment

167

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“…Azaarenes and their transformation products, more polar than their homocyclic analogues, can interact specifically with cell membranes and DNA, and this interaction may influence their toxicity (De Voogt et al, 1999). Since isomer specific toxicity of PACs has been established in several studies (Kraak et al, 1997;Bleeker et al, 1999a;De Voogt et al, 1999;Wiegman et al, 2001;Droge et al, 2006), three isomer pairs were selected: two three-ringed homocyclic compounds, two three-ringed azaarenes and the two main transformation products of the two azaarenes. The aim of this study was to determine if the closely related homo-and heterocyclic compounds affected emergence of the midge Chironomus riparius during chronic exposure to PAC spiked sediments.…”

Section: Introductionmentioning

confidence: 99%

Life cycle responses of the midge Chironomus riparius to polycyclic aromatic compound exposure

Paumen

Borgman

Kraak

et al. 2008

Environmental Pollution

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General rightsIt is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), other than for strictly personal, individual use, unless the work is under an open content license (like Creative Commons). Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. Emergence of Chironomus riparius is a sensitive endpoint to detect life cycle effects of PACs. AbstractDuring acute exposure, polycyclic aromatic compounds (PACs) act mainly by narcosis, but during chronic exposure the same compounds may exert sublethal life cycle effects. The aim of this study was therefore to evaluate the chronic effects of sediment spiked PACs on the emergence of the midge Chironomus riparius. Three isomer pairs were selected, and 28-day LC 50 values and 50% emergence times (EMt 50 ) were determined. Concentrationeresponse relationships were observed for phenanthrene, acridine, phenanthridine and acridone. Anthracene and phenanthridone had no effect on total emergence, but did cause a delay in emergence. Calculated porewater LC 50 values correlated well with logK ow values, suggesting narcosis as mode of action. In contrast, effect concentrations for delay in emergence (EMt 50 ) deviated from narcosis, suggesting a specific mode of action during chronic exposure. It is concluded that emergence is a powerful endpoint to detect life cycle effects of PACs on a key sediment inhabiting invertebrate. Ó 2007 Elsevier Ltd. All rights reserved.Keywords: Chironomus riparius; Polycyclic aromatic compounds; Emergence IntroductionPolycyclic aromatic compounds (PACs) are ubiquitous contaminants, present in the environment mainly as a result of anthropogenic activities (industry, oil drilling and vehicle emissions). Smaller amounts of PACs are generated in natural processes, like volcanism and forest fires (Neilson, 1998). Because of their hydrophobicity, PACs tend to accumulate in sediments and soils, which act not only as a sink, but also as a source of PACs for benthic organisms (Wilcke, 2000;Van Metre and Mahler, 2005). In sediment cores from 38 urban and reference lakes across the United States, total sediment SPAH concentrations (SPAH ¼ sum of 13 homocyclic PACs used for the consensus-based sediment quality guidelines in the USA) ranged from 0.5 to 10 mg/kg (Van Metre and Mahler, 2005).Populations of benthic invertebrates are exposed to a variety of PACs in the sediment, but little is known about their chronic effects, since research has mainly focused on acute exposure (Bleeker et al., 1998; Neilson, 199...

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“…Many of these compounds have carcinogenic and/or mutagenic properties. Increasingly, their presence in the ecosystem has been the cause of much concern and used as markers of human activity (Halsall et al, 1994;Bleeker et al, 1999;Jeanneau et al, 2006). PACs are a complex class of condensed multinumbered benzenoid ring compounds.…”

Section: Introductionmentioning

confidence: 99%

“…The parent homocyclic species, which contain only carbon and hydrogen, are the familiar polycyclic aromatic hydrocarbons (PAHs). However, the relatively low numbers of studies on heterocyclic substances in which two-thirds of the 4 million known organic compounds have been recognized as heterocyclic are in contrast with the number of PAHs (Adrian and Suflita, 1994;Bleeker et al, 1999). Consequently, their availability to organisms was higher than that of their homocyclic analogues, because their higher water solubility can imply higher water concentrations (Bleeker et al, 2002).…”

Section: Introductionmentioning

confidence: 99%

Occurrence of azaarenes in sediments of the Danshuei River, Taiwan—The use of azaarenes as indicator of anthropogenic source to the estuarine system

Chen

Hung

et al. 2008

Environmental Toxicology

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Azaarenes belong to the newly identified classes of anthropogenic pollutants. To our knowledge, this study presents the first result of pollution history of azaarenes and their controlling factors in estuary. To understand the transport mechanisms, surface sediment samples were collected from 18 sites of the Danshuei River during the summer and the winter of 2005. The highest concentrations of azaarene, 21.9 ng g 21 for 2-ring, 9.89 ng g 21 for 3-ring, and 9.17 ng g 21 for 4-ring, were observed in midstream surface sediments near the Shi-Zi-Tou waste water pumping station. Therefore, this waste water pumping station not only provides a good sediment accumulation environment but also discharges small particle size sediments, which contain mass amounts of azaarenes into the Danshuei River. This research also finds highly significant covariations among 3-ring and 4-ring azaarenes, which suggests similar source strengths and transport mechanisms for these compounds. Additionally, core samples were collected from two sites of the Danshuei River and analyzed to determine the pollution history. Values found in the core sediments correspond to pollution events in recent history. Contaminant inputs via in situ burning of dumping field and wastewater discharge for the periods of 1975-1985 and 2004-2005

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Toxic and Genotoxic Effects of Azaarenes: Isomers and Metabolites

Cited by 58 publications

References 25 publications

Ecotoxicity of carbamazepine and its UV photolysis transformation products

Ecotoxicity of carbamazepine and its UV photolysis transformation products

Life cycle responses of the midge Chironomus riparius to polycyclic aromatic compound exposure

Occurrence of azaarenes in sediments of the Danshuei River, Taiwan—The use of azaarenes as indicator of anthropogenic source to the estuarine system

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