Analytical challenges and recent advances in the determination of estrogens in water environments

Journal of Chromatographic Science

Volumn 47, Issue 2, 2009, Pages 127-139

  Briciu, Rodica Domnica ^a   Kot Wasik, Agata ^b   Namiesnik, Jacek ^b  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 60549111841     PISSN: 00219665     EISSN: None     Source Type: Journal    
DOI: 10.1093/chromsci/47.2.127     Document Type: Review

References (194)

1. http://en.wikipedia.org/wiki/Steroid-hormone.
2. E.C. Bonefeld-Jørgensen. The human health effect programme in Greenland, a review. Sci. Total Environ. 331: 215-31 (2004).
3. http://redpoll.pharmacy.ualberta.ca/drugbank.
4. L.S. Shore and M. Shemesh. Naturally produced steroid hormones and their release into the environment. Pure Appl. Chem. 75: 1859-71 (2003).
5. F. Ingerslev and B. Halling-Sørensen. Evaluation of analytical chemical methods for detection of estrogens in the environment. Danish Enviromental Protection Agency, Working Report 44:1-69 (2003).
6. A.C. Johnson, R.J. Williams, and P. Matthiessen. The potential steroid hormone contribution of farm animals to freshwaters, the United Kingdom as a case study. Sci. Total Environ. 362: 166-78 (2006).
7. E.P. Kolodziej and D.L. Sedlak. Rangeland grazing as a source of steroid hormones to surface waters. Environ. Sci. Technol. 41: 3514-20 (2007).
8. E.L. Bushee, D.R. Edwards, and P.A. Moore. Quality of runoff from plots treated with municipal sludge and horse bedding. Trans. ASAE 41: 1035-41 (1998).
9. B.K. Burnison, H. Hartmann, A. Lister, M.R. Servos, T. Ternes, and G. Van der Kraak. A toxicity identification evaluation approach to studying estrogenic substances in hog manure and agricultural runoff. Environ. Toxicol. Chem. 22: 2243-50 (2003).
10. M. Kuster, M.J. López de Alda, and D. Barcelo. Analysis and distribution of estrogens and progestogens in sewage sludge, soils and sediments. Trends Anal. Chem. 23: 790-98 (2004).
11. R.L. Gomes, E. Avcioglu, M.D. Scrimshaw, and J.N. Lester. Steroid estrogen determination in sediment and sewage sludge: a critique of sample preparation and chromatographic/mass spectrometry considerations, incorporating a case study in method development. Trends Anal. Chem. 23: 737-44 (2004).
12. C.R. Tyler, S. Jobling, and J.P. Sumpter. Endocrine disruption in wildlife: a criical review of the evidence. Crit. Rev. Toxicol. 28: 319-61 (1998).
13. J.G Vos, E. Dybing, H.A. Greim, O. Ladefoged, C. Lambre, J.V. Tarazona, I. Brandt, and A.D. Vethaak. Health effects of endocrine-disrupting chemicals on wildlife, with special reference to the European situation. Crit. Rev. Toxicol. 30: 71-133 (2000).
14. C.P. Yu, H. Roh, and K.-H. Chu. 17β-Estradiol-degrading bacteria isolated from activated sludge. Environ. Sci. Technol. 41:486-92 (2006).
15. S.J. Nivena, J. Snapeb, M. Hetheridgeb, M. Evansb, J. McEvoyc, and S.J. Rowlanda. Investigations of cholesterol transformation during sewage treatment: Relevance to estrogen formation pathways? Sci. Total Environ. 279: 75-86 (2001).
16. C.E. Purdom, P.A. Hardiman, V.J. Bye, N.C. Eno, C.R. Tyler, and J.P. Sumpter. Estrogenic effects of effluents from sewage treatment works. Chem. Ecol. 8: 275-86 (1994).
17. M. Auriol, Y. Filali-Meknassi, R.D. Tyagi, C.D. Adams, and R.Y. Surampalli. Endocrine disrupting compounds removal from wastewater, a new challenge. Proc. Biochem. 41: 525-39 (2006).
18. S. Hartmann, M. Lacorn, and H. Steinhart. Natural occurance of steroid hormonesin food. Food Chem. 6: 7-20 (1998).
19. K.G. Karthikeyan and M.T. Meyer. Occurrence of antibiotics in wastewater treatment facilities in Wisconsin, USA. Sci. Total Environ. 361: 196-207 (2006).
20. F. Sacher, F.T. Lange, H.-J. Brauch, and I. Blankenhorn. Pharmaceuticals in groundwaters. Analytical methods and results of a monitoring program in Baden-Wurttemberg, Germany. J Chromatogr. A 938:199-210 (2001).
21. Y. Lin, Y. Shi, M. Jiang, Y. Jin, Y. Peng, B. Lu, and K. Dai. Removal of phenolic estrogen pollutants from different sources of water using molecularly imprinted polymeric microspheres. Environ. Poll. 153:483-91 (2008).
22. G.-G. Ying, R.S. Kookana, and P. Dillon. Sorption and degradation of selected five endocrine disrupting chemicals in aquifer material. Water Res. 37: 3785-91 (2003).
23. M.J. Lopez de Alda, S. Diaz-Cruz, M. Petrovic, and D. Barcelo. Liquid chromatography-(tandem) mass spectrometry of selected emerging pollutants (steroid sex hormones, drugs and alkylphenolic surfactants) in the aquatic environment. J. Chromatogr. A 1000: 503-26 (2003).
24. R.L. Gomes, M.D. Scrimshaw, and J.N. Lester. Determination of endocrine disrupters in sewage treatment and receiving waters. Trends Anal. Chem. 22: 697-707 (2003).
25. S.D. Richardson. Water analysis: Emerging contaminants and current issues. Anal. Chem. 75: 2831-57 (2003).
26. S.D. Richardson and T.A. Ternes. Water analysis: Emerging contaminants and current issues. Anal. Chem. 77: 3807-38 (2005).
27. L.M. Hewitt and C.H. Marvin. Analytical methods in environmental effects- directed investigations of effluents. Mutation Res. 589: 208-32 (2005).
28. H.J. Stan and T. Heberer. Pharmaceuticals in the aquatic environment. Water Anal. M20-M23 (1997).
29. D. Bodzek, W. Bqkowski, T. Wielkoszynski, B. Janoszka, B. Jaremczuk, B. Tarnawski, R. Tarnawski, and K. Tyrpien. TLC and GC-MS determination of cholesterol in consumable fats. Acta Chrom. 8: 122-43 (1998).
30. M.S. Diaz-Cruz, M.J. Lopez de Alda, R. Lopez, and D. Barcelo. Determination of estrogens and progestogens by mass spectrometric techniques (GC/MS, LC/MS and LC/MS/MS). J. Mass Spectrom. 38: 917-23 (2003).
31. E.P. Kolodziej, T. Harter, and D.L. Sedlak, Dairy wastewater, aquaculture, and spawning fish as sources of steroid hormones in the aquatic environment. Environ. Sci. Technol. 38: 6377-84 (2004).
32. M. Farre, R. Brix, M. Kuster, F. Rubio, Y. Goda, M.J. López de Alda, and D. Barcelo. Evaluation of commercial immunoassays for the detection of estrogens in water by comparison with high-performance liquid chromatography tandem mass spectrometry HPLC-MS/MS (QqQ). Anal. Bioanal. Chem. 385: 1001-11 (2006).
33. C. Huang and D. L. Sedlak. Analysis of estrogenic hormones in municipal wastewater effluent and surface water using enzyme-linked immunosorbent assay and gas chromatography/tandem mass spectrometry. Environ. Toxicol. Chem. 20: 133-39 (2001).
34. J. Hu, H. Zhang, and H. Chang. Improved method for analyzing estrogens in water by liquid chromatography-electrospray mass spectrometry. J. Chromatogr. A 1070: 221-24 (2005).
35. D. Matejicek and V. Kuban. Enhancing sensitivity of liquid chromato- graphic/ion-trap tandem mass spectrometric determination of estrogens by on-line pre-column derivatization. J. Chromatogr. A 1192: 248-53 (2008).
36. D.A. Alvarez, J.D. Petty, J.N. Huckins, T.L. Jones-Lepp, D.T. Getting, and J.P. Goddard. Development of a passive, in situ, integrative sampler for hydrophilic organic contaminants in aquatic environments. Environ. Toxichol. Chem. 23: 1640-48 (2004).
37. T.L. Jones-Lepp, D.A. Alvarez, D.J. Petty, and J.N. Huckins. Polar organic chemical integrative sampling and liquid chromatography-electrospray/ ion-trap mass spectrometry for assessing selected prescription and illicit drugs in treated sewage effluents. Arch. Environ. Contam. Toxicol. 47: 427-39 (2004).
38. J.D. Petty, J.N. Huckins, D.A. Alvarez, W.G. Brumbaugh, W.L. Cranor, and R.W. Gale. A holistic passive integrative sampling approach for assessing the presence and potential impacts of waterborne environmental contaminants. Chemosphere 54: 695-705 (2004).
39. D.A. Alvarez, P.E. Stackelberg, J.D. Petty, J.N. Huckins, E.T. Furlong, and S.D. Zaugg. Comparison of a novel passive sampler to standard water-column sampling for organic contaminants associated with wastewater effluents entering a New Jersey stream. Chemosphere 61: 610-22 (2005).
40. P. Matthiessen, D. Arnold, A.C. Johnson, T.J. Pepper, T.G. Pottinger, and K.G.T. Pulman. Contamination of headwater streams in the United Kingdom by oestrogenic hormones from livestock farms. Sci. Total Environ. 367:616-30 (2006).
41. A. Arditsoglou and D. Voutsa. Passive sampling of selected endocrine disrupting compounds using polar organic chemical integrative samplers. Environ. Poll. in press.
42. Z. Zhang, A. Hibberd, and J.L. Zhou. Analysis of emerging contaminants in sewage effluent and river water: Comparison between spot and passive sampling. Anal. Chim. Acta 607: 37-44 (2008).
43. B. De. Steroidal compounds from in vitro regenerated shoots of Datura metel. Fitoterapia 74:14-17 (2003).
44. J.S. Ra, S.-Y. Oh, B.C. Lee, and S.D. Kim. The effect of suspended particles coated by humic acid on the toxicity of pharmaceuticals, estrogens, and phenolic compounds. Environ. Int. 34: 184-92 (2008).
45. S.X. Peng, T.M. Branch, and S.L. King. Fully automated 96-well liquid-liquid extraction for analysis of biological samples by liquid chromatography with tandem mass spectrometry. Anal. Chem. 73: 708-14 (2001).
46. S. Zorita, P. Hallgren, and L. Mathiasson. Steroid hormone determination in water using an environmentally friendly membrane based extraction technique. J. Chromatogr. A 1192: 1-8 (2008).
47. A. Laganá, A. Bacaloni, I. De Leva, A. Faberi, G. Fago, and A. Marino. Analytical methodologies for determining the occurrence of endocrine disrupting chemicals in sewage treatment plants and natural waters. Anal. Chim. Acta 501: 79-88 (2004).
48. A. Di Corcia, C. Crescenzi, R. Sampleri, and L. Scappaticcio. Trace analysis of sulfonylurea herbicides in water extraction and purification by a Carbograph 4 cartridge, followed by liquid chromatography with UV detection, and confirmatory analysis by an electrospray/mass detector. Anal. Chem. 69:2819-26 (1997).
49. R. Wissiak, M. Rosenberg, and M. Grasserbauer. Comparison of different sorbent materials for on-line solid-phase extraction with liquid chromatography- atmospheric pressure chemical ionization mass spectrometry of phenols. J. Chromatogr. A 896:159-70 (2000).
50. S. Lacorte, M.-C. Perrot, D. Fraisse, and D. Barcelo. Determination of chlorobenzidines in industrial effluent by solid phase extraction and liquid chromatography with electrochemical and mass spectrometric detection. J. Chromatogr. A 833:181-94 (1999).
51. G. D'Ascengo, A. Di Corcia, A. Gentili, R. Manciny, R. Mastropasqua, M. Nazzari, and R. Samperi. Fate of natural estrogen conjugates in municipal sewage transport and treatment facilities. Sci. Total Environ. 302: 199-209 (2002).
52. P. Labadie and H. Budzinski. Development of an analytical procedure for determination of selected. Anal. Bioanal. Chem. 381: 1199-1205 (2005).
53. L.J. Meng and J. Sjöwall. Method for combined analysis of profiles of conjugated progesterone metabolites and bile acids in serum and urine of pregnant women. J. Chromatogr. B 688:11-26 (1997).
54. K. Majima, T. Fukui, J. Yuan, G. Wang, and K. Matsumoto. Quantitative measurement of 17β-estradiol and estriol in river water by time resolved fluoroimmunoassay. Anal. Sci. 18: 869-74 (2002).
55. A. Lagana, A. Bacaloni, G. Fago, and A. Marino. Trace analysis of estrogenic chemicals in sevage effluent using liquid chromatography combined with tandem mass spectrometry. Rapid Commun. Mass Spectrom. 14: 401-407 (2000).
56. O. Conroy, A. Eduardo-Sáez, D. Quanrud, W. Ela, and R.G. Arnold. Changes in estrogen/anti-estrogen activities inponded secondary effluent. Sci. Total Environ. 382: 311-23 (2007).
57. O. Conroy, D.M. Quanrud, W.P. Ela, D. Wicke, K.E. Lansey, and R.G. Arnold. Fate of wastewater effluent hER-Agonists and hER- Antagonists during soil aquifer treatment. Environ. Sci. Technol. 39: 2287-93 (2005).
58. R.D. Holbrook, N.G. Love, and J.T. Novak. Sorption of 17β-estradiol and 17α-ethinylestradiol by colloidal organic carbon derived from biological wastewater treatment systems. Environ Sci. Technol. 38: 3322-29 (2004).
59. M.J. Lopez de Alda and D. Barcelo. Use of solid-phase extraction in various of its modalities for sample preparation in the determination of estrogens and pro-gestogens in sediment and water. J. Chromatogr. A 938: 145-53 (2001).
60. Y. Filali-Meknassy, M. Auriol, C.D. Adams, and R.Y. Surampally. Quantification of the steroid sex hormones using solid phase extraction followed by liquid chromatography. Water Environ. Res. 79: 687-96 (2007).
61. M. Auriol, Y. Filali-Meknassi, C.D. Adams, R.D. Tyagi, T.-N. Noguerol, and B. Pina. Removal of estrogenic activity of natural and synthetic hormones from a municipal wastewater: Efficiency of horseradish peroxidase and laccase from Trametes versicolor. Chemosphere 70: 445-52 (2008).
62. S. Wang, W. Huang, G. Fang, J. He, and Y. Zhang. On-line coupling of solid- phase extraction to high-performance liquid chromatography for determination of estrogens in environment. Anal. Chim. Acta 606: 194-201 (2008).
63. M.J. López de Alda and D. Barcelo. Determination ofsteroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by liquid chromatography-diode array detection-mass spectrometry. J. Chromatogr. A 892: 391-406 (2000).
64. M. Seifert, G. Brenner-Weiß, S. Haindl, M. Nusser, U. Obst, and B. Hock. A new concept for the bioeffects-related analysis of xenoestrogens: Hyphenation of receptor assays with LC-MS. Fresenius' J. Anal. Chem. 363: 767-70 (1999).
65. A. Garcia-Prieto, L. Lunar, S. Rubio, and D. Perez-Bendito. Hemimicelle-based solid-phase extraction of estrogens from environmental water samples. Analyst 131: 107-14 (2006).
66. C. Kelly. Analysis of steroids in environmental water samples using solid-phase extraction and ion-trap gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry. J. Chromatogr. A 872: 309-14 (2000).
67. C.Y. Chen, T.Y. Wen, G.S. Wang, H.W. Cheng, Y.H. Lin, and G.W. Lien. Determining estrogenic steroids in Taipei waters and removal in drinking water treatment using high-flow solid-phase extraction and liquid chromatography/ tandem mass spectrometry. Sci. Total Environ. 378: 352-65 (2007).
68. K. Mitani, M. Fujioka, and H. Kataoka. Fully automated analysis of estrogens in environmental waters by in-tube solid-phase microextraction coupled with liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 1081: 218-24 (2005).
69. H. Kataoka, H.L. Lord, and J. Pawliszyn. Applications of solid-phase micro- extraction in food analysis. J. Chromatogr. A 880: 35-62 (2000).
70. H. Kataoka. Automated sample preparation using in-tube solid-phase micro-extraction and its application-a review. Anal. Bioanal. Chem. 373: 31-45 (2002).
71. H. Kataoka. New trends in sample preparation for clinical and pharmaceutical analysis. Trends Anal. Chem. 22: 232-44 (2003).
72. H. Kataoka. Recent advances in solid-phase microextraction and related techniques for pharmaceutical and biomedical analysis. Curr. Pharm. Anal. 1: 65-84 (2005).
73. H.L. Lord and J. Pawliszyn. Evolution of solid-phase microextraction technology. J. Chromatogr. A 885: 153-93 (2000).
74. H.L. Lord and J. Pawliszyn. Microextraction of drugs. J. Chromatogr. A 902: 17-63 (2000).
75. S. Rodriguez-Mozaz, M.J. Lopez de Alda, and D. Barceló. Advantages and limitations of on-line solid phase extraction coupled to liquid chromatography-mass spectrometry technologies versus biosensors for monitoring of emerging contaminants in water. J. Chromatogr. A 1152: 97-115 (2007).
76. J. Bones, K. Thomas, P.N. Nesterenko, and B. Paull. On-line preconcentration of pharmaceutical residues from large volume water samples using shortreversed- phase monolithic cartridges coupled to LC-UV-ESI-MS. Talanta 70: 1117-28 (2006).
77. K.-S. Boos and C.-H. Grimm. High-performance liquid chromatography integrated solid-phase extraction in bioanalysis using restricted access precolumn packings. Trends Anal. Chem. 18:175-80 (1999).
78. H. Sabik, R. Jeannot, and B. Rondeau. Multiresidue methods using solid-phase extraction techniques for monitoring priority pesticides, including triazines and degradation products, in ground and surface waters. J. Chromatogr. A 885: 217-36 (2000).
79. M. Ibänez, J. Sancho, W. Pozo, W. Niessen, and F. Hernández. Use of quadrupole time-of-flight mass spectrometry in the elucidation of unknown compounds present in environmental water. Rapid Commun. Mass Spectrom. 19: 169-78 (2005).
80. M. Gilar, E.S.P. Bouvier, and B.J. Compton. Advances in sample preparation in electromigration chromatographic and mass spectrometric separation methods. J. Chromatogr. A 909: 111-35 (2001).
81. S. Rodriguez-Mozaz, M.J. López de Alda, and D. Barcelo. Picogram per liter level determination of estrogens in natural waters and waterworks by a fully automated on-line solid-phase extraction-liquid chromatography- electrospray tandem mass spectrometry method. Anal. Chem. 76: 6998-7006 (2004).
82. L. Brossa, R.M. Marce, F. Borrull, and E. Pocurull. Occurrence of twenty-six endocrine-disrupting compounds in environmental water samples from Catalonia, Spain. Environ. Toxicol. Chem. 24: 261-67 (2005).
83. K. Zhang and Y. Zuo. Pitfalls and solution for simultaneous determination of estrone and 17α-ethinylestradiol by gas chromatography-mass spectrometry after derivatization with N,O-bis(trimethylsilyl) trifluoroacetamide. Anal. Chim. Acta 554: 190-196 (2005).
84. E.P. Kolodziej, J.L. Gray, and D.L. Sedlak. Quantification of steroid hormones with pheromonal properties in municipal wastewater effluent. Environ. Toxicol. Chem. 22: 2622-29 (2003).
85. T. Heberer, K. Schmidt-Baumler, and H.J. Stan. Occurrence and distribution of organic contaminants in the aquatic system in Berlin. Part I: Drug residues and other polar contaminants in Berlin surface and groundwater. Acta Hydrochim. Hydrobiol. 26: 272-79 (1998).
86. M. Del Olmo, A. González-Casado, N.A. Navas, and J.L. Vilchez. Determination of bisphenol A (BPA) in water by gas chromatography-mass spectrometry. Anal. Chim. Acta 346: 87-92 (1997).
87. Y. Hadef, J. Kaloustian, H. Portugal, and A. Nicolay. Multivariate optimization of a derivatisation procedure for the simultaneous determination of nine anabolic steroids by gas chromatography coupled with mass spectrometry. J. Chromatogr. A 1190: 278-85 (2008).
88. H.H. Zhang and J. Henion. Quantitative and qualitative determination of estrogen sulfates in human urine by liquid chromatography/tandem mass spectrometry using 96-well technology. Anal. Chem. 71: 3955-64 (1999).
89. X.-Y. Xiao, D.V. McCalley, and J. McEvoy. Analysis of estrogens in river water and effluents using solid-phase extraction and gas chromatography-negative chemical ionisation mass spectrometry of the pentafluorobenzoyl derivatives. J. Chromatogr. A 923: 195-204 (2001).
90. F. Courant, J.-P. Antignac, D. Maume, F. Monteau, A.-M. Andersson, N. Skakkebaek, F. Andre, and B. Le Bizec. Exposure assessmentofprepubertal children to steroid endocrine disrupters 1. Analytical strategy for estrogens measurement in plasma at ultra-trace level. Anal. Chim. Acta 586:105-14 (2007).
91. D.D. Fine, G.P. Breidenbach, T.L. Price, and S.R. Hutchins. Quantitation of estrogens in ground water and swine lagoon samples using solid-phase extraction, pentafluorobenzyl/trimethylsilyl derivatizations and gas chromatography-negative ion chemical ionization tandem mass spectrometry. J. Chromatogr. A 1017:167-85 (2003).
92. L. Mao, C. Sun, H. Zhang, Y. Li, and D. Wu. Determination of environmental estrogens in human urine by high performance liquid chromatography after fluorescent derivatizationwith p-nitrobenzoyl chloride. Anal. Chim. Acta 522: 241-46 (2004).
93. S. Weigel, R. Kallenborg, and H. Huhnerfuss. Simultaneous solid-phase extraction of acidic, neutral and basic pharmaceuticals from aqueous samples at ambient (neutral) pH and their determination by gas chromatography-mass spectrometry. J. Chromatogr. A 1023:183-95 (2004).
94. W.Z. Shou, X. Jiang, and W. Naidong. Development and validation of a high-sensitivity liquid chromatography/tandem mass spectrometry (LC/MS/MS) method with chemical derivatization for thedetermination ofethinyl estradiol in human plasma. Biomed. Chromatogr. 18: 414-21 (2004).
95. F. Zhang, M.J. Bartels, J.C. Brodeur, E.L. McClymont, and K.B. Woodburn. Quantitation of 17α-ethinylestradiol in aquatic samples using liquid-liquid phase extraction, dansyl derivatization, and liquid chromatography/positive electrospray tandem mass spectrometry. Rapid Commun. Mass Spectrom. 18: 2739-2742 (2004).
96. M.R. Anari, R. Bakhtiar, B. Zhu, S. Huskey, R.B. Franklin, and D.C. Evans. Derivatization of ethinylestradiol with dansyl chloride to enhance electrospray ionization: application in trace analysis of ethinylestradiol in Rhesus Monkey plasma. Anal. Chem. 74: 4136-44 (2002).
97. A. Salvador, C. Moretton, A. Piram, and R.A. Faure. On-line solid-phase extraction with on-support derivatization for high-sensitivity liquid chromatography tandem mass spectrometry of estrogens in influent/effluent of wastewater treatment plants. J. Chromatogr. A 1145: 102-109 (2007).
98. P.D. Okeyo and N.H. Snow. Analysis of estrogens and anabolic steroids by SPME with on-fiber derivatization and GC/MS. J. Microcol. Sep. 10: 551-556 (1998).
99. S. Nakamura, M. Takino, and S. Daishima. Determination of chlorophenols, bisphenol A and 17β-estradiol by gas chromatography/negative-ion chemicalionization mass spectrometry. Bunseki Kagaku 49: 181-87 (2000).
100. G. Singh, A. Gutierrez, K. Xu, and I.A. Blair. Liquid chromatography/electron capture atmospheric pressure chemical ionization/mass spectrometry: Analysis of pentafluorobenzyl derivatives of biomolecules and drugs in the Attomole Range. Anal. Chem. 72: 3007-3013 (2000).
101. K. Shimada, K. Mitamura, and T. Higashi. Gaschromatographyand high-performance liquid chromatography of natural steroids. J. Chromatogr. A 935:141-72 (2001).
102. Y.-H. Lin, C.-Y. Chen, and G.-S. Wang. Analysis of steroid estrogens in water using liquid chromatography/tandem mass spectrometry with chemical derivatizations. Rapid Commun. Mass Spectrom. 21: 1973-83 (2007).
103. Z. Li, S. Wang, N.A. Lee, R.D. Allan, and I.R. Kennedy. Development of a solid- phase extraction-enzyme-linked immunosorbent assay method for the determination of estrone in water. Anal. Chim. Acta 503: 171-77 (2004).
104. B.G. Wolthers and G.B.P. Kraan. Clinical applications of gas chromatography and gas chromatography-mass spectrometry of steroids. J. Chromatogr. A 843: 247-74 (1999).
105. O.J. Pozo, J.V. Sancho, M. Ibanez, F. Hernández, and W.M.A. Niessen. Confirmation of organicmicropollutants detected in environmental samples by liquid chromatography tandem mass spectrometry: Achievements and pitfalls. Trends Anal. Chem. 25: 1030-42 (2006).
106. F. Hernandez, J.V. Sancho, M. Ibanez, and C. Guerrero. Antibiotic residuedetermination in environmental waters by LC-MS. Trends Anal. Chem. 26: 466-85 (2007).
107. V. Gabet, C. Miege, P. Bados, and M. Coquery. Analysis of estrogensin environmental matrices. Trends Anal. Chem. 26:1113-31 (2007).
108. C. Baronti, R. Curini, G. D'Ascenzo, A. Di Corcia, A. Gentili, and R. Samperi. Monitoringnatural and synthetic estrogens atactivated sludgesewagetreatment plants and in a receiving river water. Environ. Sci. Technol. 34: 5059-66 (2000).
109. M. Avery. Quantitative characterization of differential ion suppression on liquid chromatography/atmospheric pressure ionization mass spectrometric bioanalytical methods. Rapid Commun. Mass Spectrom. 17: 197-201 (2003).
110. M. van Hout, H. Niederlander, R. de Zeeuw, and G. de Jong. Ion suppression in the determination of clenbuterol in urine by solid-phase extraction atmospheric pressure chemical ionisation ion-trap mass spectrometry. Rapid Commun. Mass Spectrom. 17: 245-50 (2003).
111. L. Sojo, G. Lum, and P. Chee. Internal standard signal suppression by co-eluting analyte in isotope dilution LC-ESI-MS. Analyst 128: 51-54 (2003).
112. K.H. DeSilva, F.B. Vest, and H.T. Karnes. Pyrene sulphonyl chloride as a reagent for quantitation of oestrogens in human serum using HPLC with conventional and laser-induced fluorescence detection. Biomed. Chromatogr. 10: 318-24 (1996).
113. H. Yamada, Y. Kuwahara, Y. Takamatsu, and T. Hayase. A new sensitive determination method of estradiol in plasma using peroxyoxalate ester chemiluminescence combined with an HPLC system. Biomed. Chromatogr. 14:333-37 (2000).
114. K. Takanashi, T. Honma, T. Kashiwagi, H. Honjo, and I. Yoshizawa. Detection and measurement of urinary 2-hydroxyestradiol 17-sulfate, a potential placental antioxidant during pregnancy. Clin. Chem. 46: 373-78 (2000).
115. A. Chandrasekaran, M. Osman, S.J. Adelman, J. Warsheski, J. Scatina, and S.F. Sisenwine. Determination of 17cr-dihydroequilenin in rat, rabbit and monkey plasma by high-performance liquid chromatography with fluorimetric detection. J. Chromatogr. B 676: 69-75 (1996).
116. R. Gatti, M. Franchina, M.G. Gioia, and V. Cavrini. HPLC-fluorescence determination of equilin and equilenin in postmenopausal women's urine. Biomed. Chromatogr. 14: 82-88 (2000).
117. S. Ikegawa, M. Itoh, N. Murao, H. Kijima, M. Suzuki, T. Fujiyma, J. Goto, and M. Tohma. Immunoaffinity extraction for liquid chromatographic determination of equilin and its metabolites in plasma. Biomed. Chomatogr. 10: 73-77 (1996).
118. C. van Aerden, L. Debrauwer, J.C. Tabet, and A. Paris. Analysis of nucleoside-estrogen adducts by LC-ESI-MS-MS. Analyst 123: 2677-80 (1998).
119. P. Volin. Analysis of steroidal lipids by gas and liquid chromatography. J. Chromatogr. A 935:125-40 (2001).
120. C. Li, X.Z. Li, N. Graham, and N.Y. Gao. The aqueous degradation of bisphenol A and steroid estrogens by ferrate. Water Res. 42: 109-20 (2008).
121. M.H. Choi, K.R. Kim, and B.C. Chung. Determination of estrone and 17β-estradiol in human hair by gas chromatography-mass spectrometry. Analyst 125: 711-14 (2000).
122. G. Beaumier-Gallon, J. Lanfranchi, M.-F. Vergnes, D. Lairon, J. Pastor, A.M. Pauli, and H. Portugal. Method for simultaneous measurements of traces of heptadeuterated cholesterol and cholesterol by gas chromatography-mass spectrometry: application in humans. J. Chromatogr. B 718: 23-32 (1998).
123. F. Tilton, W.H. Benson, and D. Schlenk. Evaluation of estrogenic activity from a municipal wastewater treatment plant with predominantly domestic input. Aqua. Toxicol. 61: 211-24 (2002).
124. M. Ma, K. Rao, and Z. Wang. Occurrence of estrogenic effects in sewage and industrial wastewaters in Beijing, China. Environ. Pollut. 147: 331-36 (2007).
125. O.L. Curieux-Belfond, B. Fievet, G.E. Séralini, and M. Mathieu. Short-term bioaccumulation, circulation and metabolism ofestradiol-17β in the oyster Crassostrea gigas. J. Exp. Mar. Biol. Ecol. 325: 125-33 (2005).
126. L.J. Fono, L.P. Kolodziej, and L.P. Sedlak. Attenuation of wastewater-derived contaminants in an effluent-dominated river. Environ. Sci. Technol. 40: 7257-62 (2006).
127. M.N. Andrew, R.H. Dunstan, W.A. O'Connor, L. Van Zwieten, B. Nixon, and G.R. MacFarlane. Effects of 4-nonylphenol and 17β-ethynylestradiol exposure in the Sydney rockoyster, Saccostrea glomerata: Vitellogenin induction and gonadal development. Aqua. Toxicol., in press.
128. P. Labadieand H. Budzinski. Determination of steroidal hormone profiles along the Jalle d'Eysines River (near Bordeaux, France). Environ. Sci. Technol. 39: 5113-20 (2005).
129. R. Jeannot, H. Sabik, E. Sauvard, T. Dagnak, and K. Dohrendorf. Determination of endocrine-disrupting compounds in environmental samples using gas and liquid chromatography with mass spectrometry. J. Chromatogr. A 974: 143-59 (2002).
130. T.A. Hanselman, D.A. Graetz, A.C. Wilkie, N.J. Szabo, and C.S. Diaz. Determination of steroidal estrogens in flushed dairy manure wastewater by gas chromatography-mass spectrometry. J. Environ. Qual. 35: 695-700 (2006).
131. B.D. Stanford and H.S. Weinberg. Isotope dilution for quantitation of steroid estrogens and nonylphenols by gas chromatography with tandem mass spectrometry in septic, soil, and groundwater matrices. J. Chromatogr. A 1176:26-36 (2007).
132. X. Penga, Y. Yua, C. Tanga, J. Tan, Q. Huanga, and Z. Wang. Occurrence of steroid estrogens, endocrine-disrupting phenols and acid pharmaceutical residues in urban riverine water of the Pearl River Delta, South China. Sci. Total Environ. 397: 158-166 (2008).
133. C. Kelly. Analysis of steroids in environmental water samples using solid- phase extraction and ion-trap gas chromatography-mass spectrometry and gas chromatography-tandem mass spectrometry. J. Chromatogr. A 872: 309-14 (2000).
134. S. Nakamura, T.H. Sian, and S.J. Daishima. Determination of estrogens in river water by gas chromatography-negative-ion chemical-ionization mass spectrometry. J. Chromatogr. A 919: 275-82 (2001).
135. H.M. Kuch and K. Ballschmiter. Determination of endocrine-disrupting phenolic compounds and estrogens in surface and drinking water by HRGC-(NCI)-MS in the picogram per liter range. Environ. Sci. Technol. 35: 3201-3206 (2001).
136. H.M. Kuch and K. Ballschmiter. Determination of endogenous and exogenous estrogens in effluents from sewage treatment plants at the ng/L-level. Fresenius' J. Anal. Chem. 366: 392-395 (2001).
137. A.C. Belfroid, A. Van der Horst, A.D. Vethaak, A.J. Schäfer, G.B.J. Rijs, J. Wegener, and W.P. Cofino. Analysis and occurrence of estrogenic hormones and their glucuronides in surface water and waste water in The Netherlands. Sci. Total Environ. 225: 101-108 (1999).
138. M.A. Soliman, J.A. Pedersen, and I.H. Suffet. Rapid gas chromatography-mass spectrometry screening method for human pharmaceuticals, hormones anti- oxidants and plasticizers in water. J. Chromatogr. A 1029: 223-37 (2004).
139. J. Hu, S. Cheng, T. Aizawa, Y. Terao, and S. Kunikane. Products of aqueous chlorination of 17β-estradiol and their estrogenic activities. Environ. Sci. Technol. 37: 5665-70 (2003).
140. K. Moriyama, H. Matsufuji, M. Chino, and M. Takeda. Identification and behavior of reaction products formed by chlorination of ethynylestradiol. Chemosphere 55: 839-47 (2004).
141. H. Nakamura, R. Kuruto-Niwa, M. Uchida, and Y. Terao. Formation of chlorinated estrones via hypochlorous disinfection of wastewater effluent containing estrone. Chemosphere 66: 1441-48 (2007).
142. A.K. Sarmah, G.L. Northcott, F.D.L. Leusch, and L.A. Tremblay. A survey of endocrine disrupting chemicals (EDCs) in municipal sewage and animal waste effluents in the Waikato region of New Zealand. Sci. Total Environ. 355: 135-44 (2006).
143. M.R. Servos, D.T. Bennie, B.K. Burnison, A. Jurkovik, R. McInnis, T. Neheli, A. Schnell, P. Seto, S.A. Smyth, and T.A. Ternes. Distribution of estrogens, 17β-estradiol and estrone, in Canadian municipal wastewater treatment plants. Sci. Total Environ. 336: 155-70 (2005).
144. S.A. Snyder, D.L. Villeneuve, E.M. Synder, and J.P. Giesy. Identification and quantification of estrogen receptor agonists in wastewater effluents. Environ. Sci. Technol. 35: 3620-25 (2001).
145. H.R. Andersen, M. Hansen, J. Kjølholt, F. Stuer-Lauriden, T. Ternes, and B. Halling-Sørensen. Assessment of the importance of sorption for steroid estrogens removal during activated sludge treatment. Chemosphere 61: 139-146 (2005).
146. M. Beck and M. Radke. Determination of sterols, estrogens and inorganic ions in waste water and size-segregated aerosol particles emitted from waste water treatment. Chemosphere 64: 1134-40 (2006).
147. O. Braga, G.A. Smythe, A.I. Schäfer, and A.J. Feitz. Fate of steroid estrogens in Australian inland and coastal wastewater treatment plants. Environ. Sci. Technol. 39: 3351-58 (2005).
148. Y. Zuo, K. Zhang, and Y. Deng. Occurrence and photochemical degradation of 17α-ethinylestradiol in Acushnet River Estuary. Chemosphere 63: 1583-90 (2006).
149. www.arcem.at
150. P. Hohenblum, O. Gans, W. Moche, S. Scharf, and G. Lorbeer. Monitoring of selected estrogenic hormones and industrial chemicals in groundwaters and surface waters in Austria. Sci. Total Environ. 333: 185-93 (2004).
151. A. Belfroid, M. van Velzen, B. van der Horst, and D. Vethaak. Occurrence of bisphenol A in surface water and uptakein fish: Evaluation of field measurements. Chemosphere 49: 97-103 (2002).
152. O.P. Heemken, H. Reincke, B. Stackel, and N. Theobald. The occurrence of xenoestrogens in the Elbe River and the North Sea. Chemosphere 45: 245-259 (2001).
153. A. Latorre, S. Lacorte, and D. Barceló. Presence of nonylphenol, octyphenol and bisphenol a in two aquifers close to agricultural, industrial and urban areas. Chromatographia 57: 111-16 (2003).
154. T. Reemtsma. The use of liquid chromatography-atmospheric pressure ionization-mass spectrometry in water analysis Part II: Obstacles. Trends Anal. Chem. 20: 533-42 (2001).
155. P.L. Skipper. Precision and sensitivity of aminobiphenyl hemoglobin adduct assays in a long-term population study. J. Chromatogr. B 778: 375-81 (2002).
156. M. Petrovic, E. Eljarrat, M.J. Lopez de Alda, and D. Barcelo. Recent advances in the mass spectrometric analysis related to endocrine disrupting compounds in aquatic environmental samples. J. Chromatogr. A 974: 23-51 (2002).
157. M.D. Jürgens, K.I.E. Holthaus, A.C. Johnson, J.L. Smith, M. Heteridge, and R.J. Williams. The potential for estradiol and ethinylestradiol degradation in English rivers. Environ. Toxicol. Chem. 21: 480-88 (2002).
158. L.D. Bowers. Analytical advances in detection of performance enhancing compounds. Clin. Chem. 43:1299-1304 (1997).
159. V. Ferchaud, P. Courcoux, B. Le Bizec, F. Monteau, and F. André. Enzymatic hydrolysis of conjugated steroid metabolites: search for optimum conditions using response surface methodology. Analyst 25: 2255-59 (2000).
160. C. Ayotte, D. Goudreault, and A. Charlebois. Testing for natural and synthetic anabolic agents in human urine. J. Chromatogr. B 687: 3-25 (1996).
161. A. Jacobsen, A. Lorenzen, R. Chapman, and E. Topp. Persistence of testosterone and 17β-estradiol in soils receiving swine manure or municipal biosolids. J. Environ. Qual. 34: 861-71 (2005).
162. Z. Fan, F.X.M. Casey, H. Hakk, and G.L. Larsen. Persistence and fate of 17β-estradiol and testosterone in agricultural soils. Chemosphere 67: 886-95 (2007).
163. F.X.M. Casey, G.L. Larsen, H. Hakk, and J. Sim nek. Fate and transport of 17β-estradiol in soil-water systems. Environ. Sci. Technol. 37: 2400-2409 (2003).
164. H.R. Anderson, M. Hansen, J. Kjølholt, F. Stuer-Lauridsen, T. Ternes, and B. Halling-Sørensen. Assessment of the importance of sorption for steroid estrogens removal during activated sludge treatment. Chemosphere 61: 139-46 (2005).
165. M.S. Colucci, H. Bork, and E. Topp. Persistence of estrogenic hormones in agricultural soils: II. 17α-ethynylestradiol. J. Environ. Qual. 30: 2070-80 (2001).
166. L.S. Shore, Y. Kapulnik, M. Gurevich, S. Wininger, H. Badamy, and M. Shemesh. Introduction of phytoestrogen production in Medicago Sativa leaves by irrigation with sewage water. Environ. Exp. Bot. 35: 363-69 (1995).
167. K.M. Lai, K.L. Johnson, M.D. Scrimshaw, and J.N. Lester. Binding of waterborne steroid estrogens to solid phases in river and estuarine systems. Environ. Sci. Technol. 34: 3890-94 (2000).
168. R.W. Giese. Measurement of endogenous estrogens: analytical challenges and recent advances. J. Chromatogr. A 1000: 401-12 (2003).
169. H. Mei, Y. Hsieh, C. Nardo, X. Xu, S. Wang, K. Ng, and W.A. Korfmacher. Investigation of matrix effects in bioanalytical high-performance liquid chromatography/tandem mass spectrometric assays: Application to drug discovery. Rapid Commun. Mass Spectrom. 17: 97-103 (2003).
170. I.C. Beck, R. Bruhn, and J. Gandrass. Analysis of estrogenic activity in coastal surface waters of the Baltic Sea using the yeast estrogen screen. Chemosphere 63: 1870-78 (2006).
171. P.P. Ferguson, C.R. Iden, A.E. McElroy, and B.J. Brownawell. Determination of steroid estrogens in wastewater by immunoaffinity extraction coupled with HPLC-electrospray-MS. Anal. Chem. 73: 3890-95 (2001).
172. T. Isobe, H. Shiraishi, M. Yasuda, A. Shinoda, H. Suzuki, and M. Morita. Determination of estrogens and their conjugates in water using solid-phase extraction followed by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 984: 195-202 (2003).
173. A. Gentili, D. Perret, S. Marchese, R. Mastropasqua, R. Curini, and A. Di Corcia. Analysis of free estrogens and their conjugates in sewage and river waters by solid-phase extraction then liquid chromatography electrospray-tandem mass spectrometry. Chromatographia 26: 25-32 (2002).
174. S. Reddy, C.R. Iden, and J.B. Brownawell. Analysis of steroid conjugates in sewage influent and effluent by liquid chromatography-tandem mass spectrometry. Anal. Chem. 77: 7032-38 (2005).
175. A. Yamamoto, N. Kakutani, K. Yamamoto, and H. Myiakoda. Steroid hormone profiles of urban and tidal rivers using LC/MS/MS equipped with electrospray ionization and atmospheric pressure photoionization sources. Environ. Sci. Technol. 40: 4132-37 (2006).
176. T. Benijts, R. Dams, W. Gunther, W. Lamnert, and A. De Leenheer. Analysis of estrogenic contaminants in river water using liquid chromatography coupled to ion trap based mass spectrometry. Rapid Commun. Mass Spectrom. 16: 1358-64 (2002).
177. T.R. Croley, R.J. Hughes, B.G. Koening, C.D. Metcalfe, and R.E. March. Mass spectrometry applied to the analysis of estrogens in the environment. Rapid Commun. Mass Spectrom. 14: 1087-93 (2000).
178. Y.K.K. Koh, T.Y. Chiu, A. Boobis, E. Cartmell, J.N. Lester, and M.D. Scrimshawc. Determination of steroid estrogens in wastewater by high performance liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 1173: 81-87 (2007).
179. P.M. Palmer, L.R. Wilson, P. O'Keefe, R. Sheridan, T. King, and C.-Y. Chen. Sources of pharmaceutical pollution inthe New York City Watershed. Sci. Total Environ. 394: 90-102 (2008).
180. Y. Watabe, T. Kondo, T. Nishikawa, T. Fujita, K. Kaya, and K. Hosoya. Fully automated liquid chromatography-mass spectrometry determination of 17β- estradiol in river water. J. Chromatogr. A1120: 252-59 (2006).
181. B.J. Vanderford and S.A. Snyder. Analysis of pharmaceuticals in water by isotope dilution liquid chromatography/tandem mass spectrometry. Environ. Sci. Technol. 40: 7312-20 (2006).
182. T. Reemtsma. Liquid chromatography-mass spectrometry and strategies for trace-level analysis of polar organic pollutants. J. Chromatogr. A 1000: 477-501 (2003).
183. T. Delatour. Performance of quantitative analyses by liquid chromatography-electrospray ionisation tandem mass spectrometry: From external calibration to isotopomer-based exact matching. Anal. Bioanal. Chem. 380: 515-23 (2004).
184. A. Kloepfer, J. B. Quintana, and T. Reemtsma. Operational options to reduce matrix effects in liquid chromatography-electrospray ionization-mass spectrometry analysis of aqueous environmental samples. J. Chromatogr. A 1067: 153-60 (2005).
185. P. Labadie and E.M. Hill. Analysis of estrogens in river sediments by liquid chromatography-electrospray ionisation mass spectrometry. Comparison of tandem mass spectrometry and time-of-flight mass spectrometry. J. Chromatogr. A 1141: 174-81 (2007).
186. Z.Yang. Analysis of nitrofurans metabolites by positive ion electrospray LC/MS/MS. Varian. LC/MC Application Note 2: 1-2 (2003).
187. B. Gutendorf and J. Westendorf. Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology 166: 79-89 (2001).
188. W.N. Sawaya, K.P. Lone, A. Husain, B. Dashti, and S. Al-Zenki. Screening for estrogenic steroids in sheep and chicken by the application of enzyme-linked immunosorbent assay and a comparison with analysis by gas chromatography-mass spectrometry. FoodChem. 63: 563-69 (1998).
189. J.E. Drewes, J. Hemming, S.J. Ladenburger, J. Schauer, and W. Sonzogn. An assessment of endocrine disrupting activity changes during wastewater treatment through the use of bioassays and chemical measurements. Water Environ. Res. 77: 12-23 (2005).
190. R.D. Holbrook, J.T. Novak, T.J. Grizzard, and N.G. Love. Estrogen receptor agonist fate during wastewater and biosolids treatment processes: A mass balance analysis. Environ. Sci. Technol. 36: 4533-39 (2002).
191. L. Salste, P. Laskinen, M. Virta, and L. Kronberg. Determination of estrogens and estrogenic activity in wastewater effluent by chemical analysis and the bioluminescent yeast assay. Sci. Total Environ. 378: 343-51 (2007).
192. C.J. Houtman, P. Booij, E. Jover, D.P. del Rio, K. Swart, M. van Velzen, R. Vreuls, J. Legler, A. Brouwer, and M.H. Lamoree. Estrogenic and dioxin-like compounds in sediment from Zierikzee Harbour identified with CALUX assay-directed fractionation combined with one and two dimensional gas chromatography analyses. Chemosphere 65: 2244-52 (2006).
193. W. Brack. Effect-directed analysis: A promising tool for the identification of organic toxicants in complex mixtures? Anal. Bioanal. Chem. 377: 397-407 (2003).
194. M. Petrovic, S. Tavazzi, and D. Barcelo. Column-switching system with restricted access pre-column packing for an integrated sample cleanup and liquid chromatographic-mass spectrometric analysis of alkylphenolic compounds and steroid sex hormones in sediment. J. Chromatogr. A 971: 37-45 (2002).