Determination of Estrogenic Endocrine Disruptors in Environmental Samples—A Review of Chromatographic Methods

REFERENCES

• Soto , A. M. , Calabro , J. M. , Prechtl , N. , Yau , A. , Orlando , E. , Daxenberger , A. , Kolok , A. L. , Guillette , J. , Bizec , B. L. , Lange , I. and Sonnenschein , C. 2004 . Androgenic and estrogenic activity in water bodies receiving cattle feedlot effluent in Eastern Nebraska . Environ. Health Perspec , 112 : 346 – 352 .
   PubMed Web of Science ®Google Scholar
• Brian , J. , Harris , C. , Scholze , M. , Backhaus , T. , Booy , P. , Lamoree , M. , Pojana , G. , Jonkers , N. , Runnalls , T. , Bonfa , A. , Marcomini , A. and Sumpter , J. 2005 . Accurate prediction of the response of freshwater fish to a mixture of estrogenic chemicals . Environ. Health Perspec. , 113 : 721 – 728 .
   PubMed Web of Science ®Google Scholar
• Fernandez , M. P. , Ikonomou , M. G. and Buchanan , I. 2007 . An assessment of estrogenic organic contaminants in Canadian wastewaters . Sci. Total Environ. , 373 : 250 – 269 .
   PubMed Web of Science ®Google Scholar
• Vulliet , E. , Baugros , J. B. , Flament-Waton , M. M. and Grenier-Loustalot , M. F. 2007 . Analytical methods for the determination of selected steroid sex hormones and corticosteriods in wastewater . Anal. Bioanal. Chem , 387 : 2143 – 2149 .
   PubMed Web of Science ®Google Scholar
• Korner , W. , Speengler , P. , Bolz , U. , Schuller , W. , Hanf , V. and Metzger , J. 2001 . Substances with estrogenic activity in effluents of sewage treatment plants in southwestern Germany. 2. Biological analysis . Environ. Toxicol. Chem , 20 : 2142 – 2152 .
   PubMed Web of Science ®Google Scholar
• Gutendorf , B. and Wastendorf , J. 2001 . 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 – 87 .
   PubMed Web of Science ®Google Scholar
• Sumpter , J. P. and Jobling , S. 1995 . Vitellogenesis as a biomarker for estrogenic contamination of the aquatic environment . Environ. Health Perspect. , 103 : 173 – 180 .
   PubMed Web of Science ®Google Scholar
• Larsson , D. G. J. , Adolfsson-Erici , M. , Parkkonen , J. , Patterson , M. , Berg , A. H. , Olsson , P. E. and Förlin , L. 1999 . Ethinyloestradiol—An undesired fish contraceptive? . Aquat. Toxicol. , 45 : 91 – 97 .
   Web of Science ®Google Scholar
• Koodziej , E. P. , Harter , T. and Sedlak , D. L. 2004 . Dairy wastewater, aquaculture, and spawning fish as sources of steroid hormones in the aquatic environment . Environ. Sci. Technol. , 38 : 6377 – 6383 .
   PubMed Web of Science ®Google Scholar
• Fry , D. M. and Toone , C. K. 1981 . DDT–induced feminization of gull embryos . Science , 213 : 922 – 924 .
   PubMed Web of Science ®Google Scholar
• Fertuck , K. C. , Kumar , S. , Sikka , H. C. , Matthews , J. B. and Zacharewski , T. R. 2001 . Interaction of PAH-related compounds with the α and β isoforms of the estrogen receptor . Toxicol. Let. , 121 : 167 – 177 .
   PubMed Web of Science ®Google Scholar
• Harris , C. A. , Henttu , P. , Parker , M. G. and Sumpter , J. P. 1997 . The estrogenic activity of phthalate esters in vitro . Environ. Health. Perspect. , 105 : 802 – 809 .
   PubMed Web of Science ®Google Scholar
• Kim , H. S. , KIM , T. S. , Shin , J. H. , Moon , H. J. , Kang , I. H. , Kim , I. Y. , Oh , J. Y. and Han , S. Y. 2004 . Neonatal exposure to di(n-butyl) phthalate (dbp) alters male reproductive-tract development . J. Toxicol. Environ. Health Part B , 67 : 2045 – 2060 .
   Web of Science ®Google Scholar
• McKinney , J. D. and Waller , C. L. 1998 . Molecular determinants of hormone mimicry: Halogenated aromatic hydrocarbon environmental agents . J. Toxicol. Environ. Heath Part B. Crit Rev. , 1 : 27 – 58 .
   PubMed Web of Science ®Google Scholar
• Yadetie , F. and Male , F. 2002 . Effects of 4-nonylphenol on gene expression of pituitary hormones in juvenile Atlantic salmon (Salmo salar) . Aquat. Toxicol. , 58 : 113 – 129 .
   PubMed Web of Science ®Google Scholar
• EPA , U. S. 2006 . Special report on environmental endocrine disruption: an effect assessment and analysis, Office of Research and Development EPA/630/R–96/012
   Google Scholar
• Environmental Agency . 1998 . “Endocrine—disrupting substances in environment; what should be done?” Environmental Issue series, Consultative Report
   Google Scholar
• European Commission . 1996 . “European workshop on the impact of endocrine disrupters on human health and wildlife.” Report of the Proceeding, 2–4 December 1996, Weybridge, UK, Report EUR 17549
   Google Scholar
• Waste Water Cluster . 1999 . “ European Commission-DG XII-DI ” . In Water Technologies WWC Newsletter No. 2
   Google Scholar
• 1996 . The Identification and Assessment of Estrogenic Substances in Sewage Treatment Effluents , Bristol : The Environment Agency . R&D Publication, Nov. 1996
   Google Scholar
• Campbell , C. G. , Borglin , S. E. , Green , F. B. , Grayson , A. , Wozei , E. and Stringfellow , W. 2006 . Biologically directed environmental monitoring, fate, and transport of estrogenic endocrine disrupting compounds in water: A review . Chemosphere , 65 : 1265 – 1280 .
   PubMed Web of Science ®Google Scholar
• Fan , Y. , Zhang , M. , Da , S.-L. and Feng , Y.-Q. 2005 . Determination of endocrine disruptors in environmental waters using poly(acrylamide-vinylpyridine) monolithic capillary for in-tube solid-phase microextraction coupled to high-performance liquid chromatography with fluorescence detection . Analyst , 130 : 1065 – 1069 .
   PubMed Web of Science ®Google Scholar
• Huang , C. H. and Sedlak , D. L. 2001 . 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 – 139 .
   PubMed Web of Science ®Google Scholar
• Histerkamp , I. , Ganrass , J. and Ruck , W. 2004 . Bioassay-directed chemical analysis utilizing LC–MS: A tool for identifying estrogenic compounds in water samples? . Anal. Bioanal. Chem. , 378 : 709 – 715 .
   PubMed Web of Science ®Google Scholar
• Zhang , F. , Bartels , M. J. , Kookana , R. , Brodeur , J. C. , McClymont , E. L. and Woodburn , K. B. 2004 . Quantitation of 17-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 .
   PubMed Web of Science ®Google Scholar
• López de Alda , M. J. , Díaz-Cruz , S. , Petrowic , M. and Barceló , D. 2003 . 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 – 526 .
   PubMed Web of Science ®Google Scholar
• Gadzaa-Kopciuch , R. , Ričanyová , J. and Buszewski , B. 2009 . Isolation and detection of steroids from human urine by molecularly imprinted solid–phase extraction and liquid chromatography . J. Chromatogr. B , 877 : 1177 – 1184 .
   PubMed Web of Science ®Google Scholar
• Voulvoulis , N. 2003 . “ Methods for the determination of endocrine disrupters ” . In Endocrine Disrupters in Wastewater and Sludge Treatment Processes , 59 – 101 . New York : CRC Press LLC . Ch. 3
   Google Scholar
• Desbrow , C. , Routledge , E. J. , Brighty , G. C. , Sumpter , J. P. and Waldock , M. 1998 . Identification of estrogenic chemicals in STW effluent. 1. chemical fractionation and in vitro biological screening . Environ. Sci. Tech. , 32 : 1549 – 1558 .
   Web of Science ®Google Scholar
• Barber , L. B. , Brown , G. K. and Zaugg , S. D. 2000 . Potential endocrine disrupting organic chemicals in treated municipal wastewater and river water . ACS Symposium Series, Analysis of Environmental Endocrine Disruptors , 747 : 97 – 123 .
   Google Scholar
• Kuch , H. M. and Ballschmiter , K. 2000 . Determination of endogenous and exogenous estrogens in effluents from sewage treatment plants at ng/l-level . J. Anal. Chem. , 366 : 392 – 395 .
   Web of Science ®Google Scholar
• Rogers-Gray , T. P. , Jobling , S. , Morris , S. , Kelly , C. , Kirby , S. , Janbakhsh , A. , Harries , J. E. , Waldock , M. J. , Stumper , J. P. and Tyler , C. R. 2000 . Long-term temporal changes in the estrogenic composition of treated sewage effluent and its biological effects on fish . Environ. Sci. Technol. , 34 : 1521 – 1528 .
   Web of Science ®Google Scholar
• Siegener , R. and Chen , R. F. 2000 . Detection of pharmaceuticals entering Boston Harbor . Anal. Environ. Endoc. Disrupt ACS Symp. Ser. , 747 : 125 – 132 .
   Google Scholar
• Möder , M. , Braun , P. , Lange , F. , Schrader , S. and Lorenz , W. 2007 . Determination of endocrine disrupting compounds and acidic drugs in water by coupling of derivatization, gas chromatography and negative-chemical ionization mass spectrometry . Clean. , 35 : 444 – 451 .
   Google Scholar
• Belfroid , A. C. , Van der Horst , A. , Vethaak , A. D. , Schäfer , A. J. , Rijs , G. B. J. , Wegener , J. and Cofino , W. P. 1999 . Analysis and occurrence of estrogenic hormones and their glucuronides in surface water and waste water in The Netherlands . Sci. Tot. Environ. , 225 : 101 – 108 .
   PubMed Web of Science ®Google Scholar
• Ternes , T. A. , Stumpf , M. , Mueller , J. , Haberer , K. , Wilken , D. and Servos , M. 1999 . Behavior and occurrence of estrogens in municipal sewage treatment plants—I. Investigations in Germany, Canada and Brazil . Sci. Total Environ. , 225 : 81 – 88 .
   PubMed Web of Science ®Google Scholar
• Johnson , A. C. , Belfroid , A. and Di Corcia , A. 2000 . Estimating steroid oestrogen inputs into activated sludge treatment works and observations on their removal from the effluent . Sci. Total Environ. , 256 : 163 – 171 .
   PubMed Web of Science ®Google Scholar
• Kelly , C. 2000 . 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 – 314 .
   PubMed Web of Science ®Google Scholar
• Quintana , J. B. , Carpinterio , J. , Rodríguez , I. , Lorenzo , R. A. , Carro , A. M. and Cela , R. 2004 . Determination of natural and synthetic estrogens in water by gas chromatography with mass spectrometric detection . J. Chromatogr. A , 1024 : 177 – 185 .
   PubMed Web of Science ®Google Scholar
• López de Alda , M. J. and Barceló , D. 2001 . Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction–liquid chromatography–diode array detection . J. Chromatogr. A , 911 : 203 – 210 .
   PubMed Web of Science ®Google Scholar
• Almeida , C. and Nogueira , J. M. F. 2006 . Determination of steroid sex hormones in water and urine matrices by stir bar sorptive extraction and liquid chromatography with diode array detection . Pharm. Biomed. Analysis , 41 : 303 – 311 .
   Web of Science ®Google Scholar
• López de Alda , M. J. and Barceló , D. 2000 . Determination of steroid 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 .
   PubMed Web of Science ®Google Scholar
• López de Alda , M. J. and Barceló , D. 2001 . Review of analytical methods for the determination of estrogens and progestogens in waste waters . Fresenius J. Anal. Chem. , 371 : 437 – 447 .
   PubMedGoogle Scholar
• Rodriguez-Mozaz , S. , López de Alda , M. J. M. J. and Barceló , D. 2004 . Monitoring of estrogens, pesticides and bisphenol A in natural waters and drinking water treatment plants by solid–phase extraction–liquid chromatography–mass spectrometry . J. Chromatogr. A , 1045 : 85 – 92 .
   PubMed Web of Science ®Google Scholar
• Laganá , A. , Bacaloni , A. , Fago , G. and Marino , A. 2000 . Trace analysis of estrogenic chemicals in sewage effluent using liquid chromatography combined with tandem mass spectrometry . Rapid Commun. Mass Spectrom. , 14 : 401 – 407 .
   PubMed Web of Science ®Google Scholar
• Baronti , C. , Curini , R. , D'Ascenzo , G. , Di Corcia , A. , Centili , A. and Samperi , R. 2000 . Monitoring natural and synthetic estrogens at activated sludge sewage treatment plants and in a receiving river water . Environ. Sci. Technol. , 34 : 5059 – 5066 .
   Web of Science ®Google Scholar
• Ingrand , V. , Herry , G. , Beausse , J. and de Roubin , M-R. 2003 . Analysis of steroid hormones in effluents of wastewater treatment plants by liquid chromatoraphy–tandem mass spectrometry . J. Chromatogr. A , 1020 : 99 – 104 .
   PubMed Web of Science ®Google Scholar
• Cen , C.-Y. , Wen , T.-Y. , Wang , G.-S. , Cheng , H.-W. , Lin , Y.-H. and Lin , G.-W. 2007 . 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 – 359 .
   PubMed Web of Science ®Google Scholar
• Lin , Y.-H. , Chen , C.-Y. and Wand , G.-S. 2007 . Analysis of steroid estrogens in water using liquid chromatography/tandem mass spectrometry with chemical derivatizations . Rapid Commun. Mass Spectrom. , 21 : 1973 – 1983 .
   PubMed Web of Science ®Google Scholar
• Snyder , S. A. , Keith , T. L. , Verbrugge , D. A. , Synder , E. M. , Gross , T. S. , Kannan , K. and Giesy , J. P. 1999 . Analytical methods for detection of selected estrogenic compounds in aqueous mixtures . Environ. Sci. Technol , 33 : 2814 – 2820 .
   Web of Science ®Google Scholar
• Tabak , H. H. , Bloomhuff , R. N. and Bunch , R. L. 1981 . Steroid hormones as water pollutants. II. Studies on the persistence and stability of natural urinary and synthetic ovulation-inhibiting hormones in untreated and treated wastewaters . Dev. Ind. Microbiol. , 22 : 497 – 519 .
   Google Scholar
• Xiao , X. Y. , McCalley , D. V. and McEvoy , J. 2001 . 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 .
   PubMed Web of Science ®Google Scholar
• Courant , F. , Antignac , J.-P. , Maume , D. , Monteau , F. , Andersson , A.-M. , Skakkebaek , N. , Andre , F. and Le Bizec , B. 2007 . Exposure assessment of prepubertal children to steroid endocrine disrupters: 1. Analytical strategy for estrogens measurement in plasma at ultra-trace level . Anal. Chim. Acta , 586 : 105 – 114 .
   PubMed Web of Science ®Google Scholar
• Fine , D. D. , Breidenbach , G. P. , Price , T. L. and Hutchins , S. R. 2003 . 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 – 185 .
   PubMed Web of Science ®Google Scholar
• Shou , W. Z. , Jiang , X. Y. and Weng , N. D. 2004 . Development and validation of a high-sensitivity liquid chromatography/tandem mass spectrometry (LC/MS/MS) method with chemical derivatization for the determination of ethinyl estradiol in human plasma . Biomed. Chromatogr. , 18 : 414 – 421 .
   PubMed Web of Science ®Google Scholar
• Zhang , F. , Bartels , M. J. , Brodeur , J. C. , McClymont , E. L. and Woodburn , K. B. 2004 . Quantitation of 17a-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 .
   PubMed Web of Science ®Google Scholar
• Anari , M. R. , Burton , R. W. , Gopaul , S. and Abbott , F. S. 2000 . Metabolic profiling of valproic acid by cDNA-expressed human cytochrome P450 enzymes using negative–ion chemical ionization gas chromatography–mass spectrometry . J. Chromatogr. B , 742 : 217 – 227 .
   PubMed Web of Science ®Google Scholar