Effect-directed identification of naphthenic acids as important in vitro xeno-estrogens and anti-androgens in North Sea offshore produced water discharges

Environmental Science and Technology

Volumn 43, Issue 21, 2009, Pages 8066-8071

  Thomas, K V ^a   Langford, K ^a   Petersen, K ^a   Smith, A J ^b   Tollefsen, K E ^a  

^a NORWEGIAN INSTITUTE FOR WATER RESEARCH   (Norway)

^b CENTRE FOR ENVIRONMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AGONIST ACTIVITY; ALKYLPHENOLS; ANDROGEN RECEPTORS; COMPLEX MIXTURE; ESTROGEN RECEPTOR; IN-VITRO; LIGAND RECEPTORS; NAPHTHENIC ACID; NORTH SEA; OFFSHORE ENVIRONMENTS; OFFSHORE OIL PRODUCTION; PETROGENIC; PRODUCED WATER;

ARGON; AROMATIC HYDROCARBONS; CHROMATOGRAPHIC ANALYSIS; DRILLING PLATFORMS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH PRESSURE LIQUID CHROMATOGRAPHY; OFFSHORE OIL FIELDS; OFFSHORE OIL WELL PRODUCTION; ORGANIC ACIDS; POLYCYCLIC AROMATIC HYDROCARBONS; PRODUCTION PLATFORMS; WATER ANALYSIS;

EFFLUENTS;

ANDROGEN RECEPTOR; ANTIANDROGEN; ESTROGEN; ESTROGEN RECEPTOR; POLYCYCLIC AROMATIC HYDROCARBON;

ANDROGEN; DISCHARGE; EFFLUENT; ESTROGENIC COMPOUND; LIGAND; LIQUID CHROMATOGRAPHY; OIL PRODUCTION; ORGANIC ACID; PAH; SEAWATER; YEAST;

ARTICLE; ATLANTIC OCEAN; CHEMICAL STRUCTURE; CONTROLLED STUDY; EFFLUENT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; NONHUMAN; RECEPTOR BINDING; WATER POLLUTION;

ANDROGEN ANTAGONISTS; CARBOXYLIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIHYDROTESTOSTERONE; ESTROGENS; MASS SPECTROMETRY; NORTH SEA; RECEPTORS, ANDROGEN; RECEPTORS, ESTROGEN; SACCHAROMYCES CEREVISIAE; SEAWATER; TIME FACTORS; WATER POLLUTANTS, CHEMICAL;

ATLANTIC OCEAN; NORTH SEA;

EID: 70350767354     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es9014212     Document Type: Article

References (36)

1. Roe Utvik, T. I. Chemical characterization of produced water from four offshore oil production platforms in the North Sea. Chemosphere 1999, 39, 2593-2606.
2. Thomas, K. V.; Balaam, J. B.; Hurst, M. R.; Thain, J. E. Bio-analytical and chemical characterization of offshore produced water effluents for estrogen receptor (ER) agonists. J. Environ. Monit. 2004, 6, 593-598. (Pubitemid 38998226)
3. Thomas, K. V.; Balaam, J.; Hurst, M. R.; Thain, J. E. Identification of in vitro estrogen and androgen receptor agonists in North Sea offshore produced water discharges. Environ. Toxicol. Chem./SETAC 2004, 23, 1156-1163.
4. Boitsov, S.; Mjos, S. A.; Meier, S. Identification of estrogen-like alkylphenols in produced water from offshore oil installations. Mar. Environ. Res. 2007, 64, 651-665. (Pubitemid 47539582)
5. Hurst, M. R.; Chan-Man, Y. L.; Balaam, J.; Thain, J. E.; Thomas, K. V. The stable aryl hydrocarbon receptor agonist potency of United Kingdom Continental Shelf (UKCS) offshore produced water effluents. Mar. Pollut. Bull. 2005, 50, 1694-1698.
6. Tollefsen, K. E.; Harman, C.; Smith, A.; Thomas, K. V. Estrogen receptor (ER) agonists and androgen receptor (AR) antagonists in effluents from Norwegian North Sea oil production platforms. Mar. Pollut. Bull. 2007, 54, 277-283.
7. Myhre, L. P., Bausant, T., Sundt, R., Sanni, S., Vabø, R., Skjoldal, H. R., Klungsøyr, J. Risk Assessment of Reproductive Effects of Alkyl Phenols in Produced Water on Fish Stocks in the North Sea; Norwegian Institute of Marine Research, 2004.
8. Balaam, J. L.; Chan-Man, Y.; Roberts, P. H.; Thomas, K. V. Identification of non-regulated pollutants in North Sea produced water discharges. Environ. Toxicol. Chem./SETAC 2009, 28, 1159-1167.
9. Kelce, W. R.; Gray, L. E.; Wilson, E. M. Antiandrogens as environmental endocrine disruptors. Reprod. Fertil. Dev. 1998, 10, 105-112.
10. Sohoni, P.; Sumpter, J. P. Several environmental oestrogens are also anti-androgens. J. Endocrinol. 1998, 158, 327-329.
11. Guillette, L. J.; Crain, D. A.; Rooney, A. A.; Pickford, D. B. Organization versus activation: the role of endocrine-disrupting contaminants (EDCs) during embryonic development in wildlife. Environ. Health Perspect. 1995, 103, 157-164.
12. Scott, A. P.; Katsiadaki, I.; Kirby, M. F.; Thain, J. E. Relationship between Sex Steroid and Vitellogenin Concentrations in Flounder (Platichthys flesus) Sampled from an Estuary Contaminated with Estrogenic Endocrine-Disrupting Compounds. Environ. Health Perspect. 2006, 114, 27-31.
13. Scott, A. P.; Katsiadaki, I.; Witthames, P. R.; Hylland, K.; Davies, I. M.; McIntosh, A. D.; Thain, J. Vitellogenin in the blood plasma of male cod (Gadus morhua): A sign of oestrogenic endocrine disruption in the open sea. Mar. Environ. Res. 2006, 61, 149-170. (Pubitemid 43199621)
14. Scott, A. P.; Sanders, M.; Stentiford, G. D.; Reese, R. A.; Katsiadaki, I. Evidence for estrogenic endocrine disruption in an offshore flatfish, the dab (Limanda limanda L.). Mar. Environ. Res. 2007, 64, 128-148. (Pubitemid 46990517)
15. Fossi, C. M.; Casini, S.; Marsili, L.; Ancora, S.; Mori, G.; Neri, G.; Romeo, T.; Ausili, A. Evaluation of ecotoxicological effects of endocrine disrupters during a four-year survey of the Mediterranean population of swordfish (Xiphias gladius). Mar. Environ. Res. 2004, 58, 425-429. (Pubitemid 38738910)
16. Fossi, M. C.; Casini, S.; Marsili, L. Potential toxicological hazard due to endocrine-disrupting chemicals on Mediterranean top predators: State of art, gender differences and methodological tools. Environ. Res. 2007, 104, 174-182. (Pubitemid 46560489)
17. Fossi, M. C.; Casini, S.; Marsili, L.; Neri, G.; Mori, G.; Ancora, S.; Moscatelli, A.; Ausili, A.; Notarbartolo-di-Sciara, G. Biomarkers for endocrine disruptors in three species of Mediterranean large pelagic fish. Mar. Environ. Res. 2002, 54, 667-671.
18. Thomas, K. V.; Hurst, M. R.; Matthiessen, P.; McHugh, M.; Smith, A.; Waldock, M. J. An assessment of in vitro androgenic activity and the identification of environmental androgens in United Kingdom estuaries. Environ. Toxicol. Chem./SETAC 2002, 21, 1456-1461.
19. Thomas, K. V.; Hurst, M. R.; Matthiessen, P.; Waldock, M. J. Characterization of estrogenic compounds in water samples collected from United Kingdom estuaries. Environ. Toxicol. Chem./SETAC 2001, 20, 2165-2170.
20. Routledge, E. J.; Sumpter, J. P. Estrogenic activity of surfactants and some of their degradation products assessed using a recombinant yeast screen. Environ. Toxicol. Chem. 1996, 15, 241-248.
21. Clemente, J. S.; Fedorak, P. M. Evaluation of the analyses of tert-butyldimethylsilyl derivatives of naphthenic acids by gas chromatography-electron impact mass spectrometry. J. Chromatogr. A 2004, 1047, 117-128.
22. Grung, M.; Lichtenthaler, R.; Ahel, M.; Tollefsen, K.-E.; Langford, K.; Thomas, K. V. Effects-directed analysis of organic toxicants in wastewater effluent from Zagreb, Croatia. Chemosphere 2007, 67, 108-120.
23. Christiaens, V.; Berckmans, P.; Haelens, A.; Witters, H.; Claessens, F. Comparison of different androgen bioassays in the screening for environmental (anti-)androgenic activity. Environ. Toxicol Chem./SETAC 2005, 24, 2646-2656. (Pubitemid 41445202)
24. Jobling, S.; Burn, R. W.; Thorpe, K.; Williams, R.; Tyler, C. Statistical Modeling Suggests that Antiandrogens in Effluents from Wastewater Treatment Works Contribute to Widespread Sexual Disruption in Fish Living in English Rivers. Environ. Health Perspect. 2009, 117, 797-802.
25. Portolés, T.; Francisco, J.; López Juan, V.; Sancho, F. H. Methodical approach for the use of GC-TOF MS for screening and confirmation of organic pollutants in environmental water. J. Mass Spectrom. 2007, 42, 1175-1185. (Pubitemid 47401841)
26. Tollefsen, K.-E.; Julie Nilsen, A. Binding of alkylphenols and alkylated non-phenolics to rainbow trout (Oncorhynchus mykiss) hepatic estrogen receptors. Ecotoxicol. Environ. Saf.2008, 69, 163-172. (Pubitemid 350181079)
27. Clemente, J. S.; Fedorak, P. M. A review of the occurrence, analyses, toxicity, and biodegradation of naphthenic acids. Chemosphere 2005, 60, 585-600. (Pubitemid 40814384)
28. Brient, J. A.; Wessner, P. J.; Doly, M. N. Naphthenic acids. In Encyclopedia of Hemical Technology, 4th ed.; Kroschwitz, J. I, Ed.; Wiley: New York, 1995; Vol.16, pp 1017-1029.
29. Smith, B. E.; Lewis, C. A.; Belt, S. T.; Whitby, C.; Rowland, S. J. Effects of alkyl chain branching on the biotransformation of naphthenic acids. Environ. Sci. Technol. 2008, 42, 9323-9328.
30. Smith, B. E.; Rowland, S. J. A derivatisation and liquid chromatography/ electrospray ionisation multistage mass spectrometry method for the characterization of naphthenic acids. Rapid Commun. Mass Spectrom. 2008, 22, 3909-3927.
31. Singh, S. M.; Gauthier, S.; Labrie, F. Androgen Receptor Antagonists (Antiandrogens): Structure activity relationships. Curr. Med. Chem. 2000, 7, 211-247. (Pubitemid 30396447)
32. Tamura, H.; Ishimoto, Y.; Fujikawa, T.; Aoyama, H.; Yoshikawa, H.; Akamatsu, M. Structural basis for androgen receptor agonists and antagonists: Interaction of SPEED 98-listed chemicals and related compounds with the androgen receptor based on an in vitro reporter gene assay and 3D-QSAR. Bioorg. Med. Chem. 2006, 14, 7160-7174. (Pubitemid 44404243)
33. Bataineh, M.; Scott, A. C.; Fedorak, P. M.; Martin, J. W. Capillary HPLC/QTOF-MS for Characterizing Complex Naphthenic Acid Mixtures and Their Microbial Transformation. Anal. Chem. 2006, 78, 8354-8361.
34. Martin, J. W.; Xiumei, H.; Peru, K. M.; Headley, J. V. Comparison of high- and low-resolution electrospray ionization mass spectrometry for the analysis of naphthenic acid mixtures in oil sands process water. Rapid Commun. Mass Spectrom. 2008, 22, 1919-1924.
35. Lister, A.; Nero, V.; Farwell, A.; Dixon, D. G.; Van Der Kraak, G. Reproductive and stress hormone levels in goldfish (Carassius auratus) exposed to oil sands process-affected water. Aquat. Toxicol. 2008, 87, 170-177.
36. Paris, F.; Balaguer, P.; Terouanne, B.; Servant, N.; Lacoste, C.; Cravedi, J.-P.; Nicolas, J.-C.; Sultan, C. Phenylphenols, biphenols, bisphenol-A and 4-tert-octylphenol exhibit α and β estrogen activities and antiandrogen activity in reporter cell lines. Mol. Cell. Endocrinol. 2002, 193, 43-49.