Some heterocyclic aromatic compounds are Ah receptor agonists in the DR-CALUX assay and the EROD assay with RTL-W1 cells

Environmental Science and Pollution Research

Volumn 18, Issue 8, 2011, Pages 1297-1304

  Hinger, Gunnar ^e   Brinkmann, Markus ^a   Bluhm, Kerstin ^a   Sagner, Anne ^b   Takner, Helena ^c   Eisenträger, Adolf ^a,d   Braunbeck, Thomas ^e   Engwall, Magnus ^c   Tiehm, Andreas ^b   Hollert, Henner ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b Water Technology Center   (Germany)

^c ÖREBRO UNIVERSITY   (Sweden)

^d UMWELTBUNDESAMT   (Germany)

^e UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Ah receptor; DR CALUX; EROD; Heterocyclic aromatic compounds; NSO HET

Indexed keywords

AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450 1A1; HETEROCYCLIC COMPOUND; NITROGEN; OXYGEN; SULFUR;

AROMATIC HYDROCARBON; ATMOSPHERIC POLLUTION; BIOASSAY; CYTOLOGY; ENZYME ACTIVITY; MARINE POLLUTION; MOLECULAR ANALYSIS; NITROGEN; OXYGEN; PYRENE; SAMPLING; SOIL POLLUTION; SORPTION; SULFUR; VOLATILIZATION; WATER POLLUTION;

ANIMAL; ARTICLE; BIOASSAY; CELL LINE; CHEMISTRY; DRUG EFFECT; DRUG POTENTIATION; LIVER; MASS FRAGMENTOGRAPHY; METABOLISM; POLLUTANT; RAINBOW TROUT; RAT;

ANIMALS; BIOLOGICAL ASSAY; CELL LINE; CYTOCHROME P-450 CYP1A1; ENVIRONMENTAL POLLUTANTS; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HETEROCYCLIC COMPOUNDS; LIVER; NITROGEN; ONCORHYNCHUS MYKISS; OXYGEN; RATS; RECEPTORS, ARYL HYDROCARBON; SULFUR;

EID: 80051668115     PISSN: 09441344     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11356-011-0483-7     Document Type: Article

References (36)

1. Alinsafi A, Md M, Bonte SL, Pons MN, Benhammou A (2006) Effect of variability on the treatment of textile dyeing wastewater by activated sludge. Dyes Pigm 69: 31-39.
2. Andersson E, Rotander A, Engwall M, von Kronhelm T, Berggren A, Ivarsson P, Hollert H (2009) AhR agonist and genotoxicant bioavailability in a PAH-contaminated soil undergoing biological treatment. Environ Sci Pollut Res 16: 521-530.
3. Barron MG, Heintz R, Rice SD (2004) Relative potency of PAHs and heterocycles as aryl hydrocarbon receptor agonists in fish. Mar Environ Res 58: 95-100.
4. Behrens A, Schirmer K, Bols NC, Segner H (1998) Microassay for rapid measurement of 7-ethoxyresorufin-o-deethylase activity in intact fish hepatocytes. Mar Environ Res 46: 369-373.
5. Blotevogel J, Reineke AK, Hollender J, Held T (2008) Identifikation NSO-heterocyclischer Prioritärsubstanzen zur Erkundung und Überwachung Teeröl-kontaminierter Standorte. Grundwasser-Zeitschrift der Fachsektion Hydrogeologie 13: 147-157.
6. Brack W, Schirmer K (2003) Effect-directed identification of oxygen and sulfur heterocycles as major polycyclic aromatic cytochrome P4501A-inducers in a contaminated sediment. Environ Sci Technol 37: 3062-3070.
7. Brack W, Segner H, Möder M, Schüürmann G (2000) Fixed-effect-level toxicity equivalents-a suitable parameter for assessing ethoxyresorufin-O-deethylase induction potency in complex environmental samples. Environ Toxicol Chem 19: 2493-2501.
8. Broughton HB, Watson IA (2004) Selection of heterocycles for drug design. J Mol Graph Model 23: 51-58.
9. Brunström B, Halldin K (1998) EROD induction by environmental contaminants in avian embryo livers. Comp Biochem Physiol C 121: 213-219.
10. Clemons JH, Dixon DG, Bols NC (1997) Derivation of 2, 3, 7, 8-TCDD toxic equivalent factors (TEFs) for selected dioxins, furans and PCBs with rainbow trout and rat liver cell lines and the influence of exposure time, 15th International Symposium on Chlorinated Dioxins, PCB and Related Compounds, Edmonton, Canada, pp. 1105-1119.
11. Cripps C, Bumpus JA, Aust SD (1990) Biodegradation of azo and heterocyclic dyes by Phanerochaete chrysosporium. Appl Environ Microbiol 56: 1114-1118.
12. Dyreborg S, Arvin E, Broholm K (1997) Biodegradation of NSO-compounds under different redox-conditions. J Contam Hydrol 25: 177-197.
13. Eisentraeger A, Brinkmann C, Hollert H, Sagner A, Tiehm A, Neuwoehner J (2008) Heterocyclic compounds: toxic effects using algae, daphnids, and the Salmonella/microsome test taking methodical quantitative aspects into account. Environ Toxicol Chem 27: 1590-1596.
14. Fernández-Alba AR, Guil MDH, López GD, Chisti Y (2002) Comparative evaluation of the effects of pesticides in acute toxicity luminescence bioassays. Anal Chim Acta 451: 195-202.
15. Garrison PM, Tullis K, Aarts JMMJG, Brouwer A, Giesy JP, Denison MS (1996) Species-specific recombinant cell lines as bioassay systems for the detection of 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin-like chemicals. Fundam Appl Toxicol 30: 194-203.
16. Gustavsson L, Klee N, Olsmann H, Hollert H, Engwall M (2004) Fate of Ah receptor agonists during biological treatment of an industrial sludge containing explosives and pharmaceutical residues. Environ Sci Pollut Res 11: 379-387.
17. Hollert H, Dürr M, Olsman H, Halldin K, van Bavel B, Brack W, Tysklind M, Engwall M, Braunbeck T (2002) Biological and chemical determination of dioxin-like compounds in sediments by means of a sediment triad approach in the catchment area of the Neckar River. Ecotoxicology 11: 323-336.
18. Jacob J, Karcher W, Wagstaffe PJ (1984) Polycyclic aromatic compounds of environmental and occupational importance-their occurrence, toxicity and the development of high purity certified reference materials. Part I. Fresenius J Anal Chem 317: 101-114.
19. Keiter S, Grund S, van Bavel B, Hagberg J, Engwall M, Kammann U, Klempt M, Manz W, Olsman H, Braunbeck T, Hollert H (2008) Activities and identification of aryl hydrocarbon receptor agonists in sediments from the Danube river. Anal Bioanal Chem 390: 2009-2019.
20. Keiter S, Braunbeck T, Heise S, Pudenz S, Manz W, Hollert H (2009) A fuzzy logic-classification of sediments based on data from in vitro biotests. J Soils Sediments 9: 168-179.
21. Lee LE, Clemons JH, Bechtel DG, Caldwell SJ, Han KB, Pasitschniak-Arts M, Mosser D, Bols NC (1993) Development and characterization of a rainbow trout liver cell line expressing cytochrome P450-dependent monooxygenase activity. Cell Biol Toxicol 9: 279-294.
22. Licht D, Ahring BK, Arvin E (1996) Effects of electron acceptors, reducing agents, and toxic metabolites on anaerobic degradation of heterocyclic compounds. Biodegradation 7: 83-90.
23. Long M, Laier P, Vinggaard AM, Andersen HR, Lynggaard J, Bonefeld-Jorgensen EC (2003) Effects of currently used pesticides in the AhR-CALUX assay: comparison between the human TV101L and the rat H4IIE cell line. Toxicology 194: 77-93.
24. Louiz I, Kinani S, Gouze ME, Ben-Attia M, Menif D, Bouchonnet S, Porcher JM, Ben-Hassine OK, Ait-Aissa S (2008) Monitoring of dioxin-like, estrogenic and anti-androgenic activities in sediments of the Bizerta lagoon (Tunisia) by means of in vitro cell-based bioassays: contribution of low concentrations of polynuclear aromatic hydrocarbons (PAHs). Sci Total Environ 402: 318-329.
25. Meyer S (1999) Mikrobieller Abbau typischer Teeröl-PAK und Hetero-PAK (N, S, O) in einem Modellbodenhorizont. PhD thesis, Hamburg University, Hamburg, Germany, 148 pp.
26. Murk AJ, Legler J, Denison MS, Giesy JP, van de Guchte C, Brouwer A (1996) Chemical-activated luciferase gene expression (CALUX): a novel in vitro bioassay for Ah receptor active compounds in sediments and pore water. Fundam Appl Toxicol 33: 149-160.
27. Neal JJ, Wu D (1994) Inhibition of insect cytochromes P450 by furanocoumarins. Pestic Biochem Physiol 50: 43-50.
28. Nielsen T, Siigur K, Helweg C, Jørgensen O, Hansen PE, Kirso U (1997) Sorption of polycyclic aromatic compounds to humic acid as studied by high-performance liquid chromtography. Environ Sci Technol 31: 1102-1108.
29. Olsman H, Engwall M, Kammann U, Klempt M, Otte J, van Bavel B, Hollert H (2007) Relative differences in aryl hydrocarbon receptor-mediated response for 18 polybrominated and mixed halogenated dibenzo-p-dioxins and -furans in cell lines from four different species. Environ Toxicol Chem 26: 2448-2454.
30. Rasmussen G, Olsena RA (2004) Sorption and biological removal of creosote-contaminants from groundwater in soily sand vegetated with orchard grass (Dactylis glomerata). Adv Environ Res 8: 313-327.
31. Robbiano L, Baroni D, Carrozzino R, Mereto E, Brambilla G (2004) DNA damage and micronuclei induced in rat and human kidney cells by six chemicals carcinogenic to the rat kidney. Toxicology 204: 187-195.
32. Sovadinová I, Bláha L, Janosek J, Hilscherová K, Giesy JP, Jones PD, Holoubek I (2006) Cytotoxicity and aryl hydrocarbon receptor-mediated activity of N-heterocyclic polycyclic aromatic hydrocarbons: structure-activity relationships. Environ Toxicol Chem 25: 1291-1297.
33. Tiehm A, Müller A, Alt S, Jacob H, Schad H, Weingran C (2008) Development of a groundwater biobarrier for the removal of PAH, BTEX, and heterocyclic hydrocarbons. Water Sci Technol 58: 1349-1355.
34. Vondrácek J, Chramstová K, Plíšková M, Bláha L, Brack W, Kozubík A, Machala M (2004) Induction of aryl hydrocarbon receptor-mediated and estrogen receptor-mediated activities, and modulation of cell proliferation by dinaphthofurans. Environ Toxicol Chem 23: 2214-2220.
35. Wölz J, Engwall M, Maletz S, Takner HO, van Bavel B, Kammann U, Klempt M, Weber R, Braunbeck T, Hollert H (2008) Changes in toxicity and Ah receptor agonist activity of suspended particulate matter during flood events at the rivers Neckar and Rhine-a mass balance approach using in vitro methods and chemical analysis. Environ Sci Pollut Res 15: 536-553.
36. Zedeck MS (1980) Polycyclic aromatic hydrocarbons-a review. J Environ Pathol Toxicol 3: 537-567.