Analytical determination of oestrogenic endocrine disruptors: the method of choice for wastewater treatment plant effluents
Tereza Černá A B , Klára Michalíková A , Jaroslav Semerád A and Tomáš Cajthaml B CA Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, 14220 Prague 4, Czech Republic.
B Institute for Environmental Studies, Faculty of Science, Charles University, Benátská 2, 12801 Prague 2, Czech Republic.
C Corresponding author. Email: cajthaml@biomed.cas.cz
Environmental Chemistry 18(4) 143-155 https://doi.org/10.1071/EN21028
Submitted: 13 March 2021 Accepted: 9 June 2021 Published: 15 July 2021
Environmental context. Endocrine disrupting compounds (EDCs) are among the most recently targeted micropollutants detected in wastewater treatment plant (WWTP) effluents and in aquatic environments. There is a need for the development of robust analytical methods for most relevant estrogenic EDCs. This study provides optimisation of analytical techniques and addresses several relevant aspects that are often overlooked in the literature. The method was finally successfully employed for the analysis of WWTP effluents.
Abstract. Two analytical approaches – liquid chromatography–tandem mass spectrometry (LC-MS/MS) and gas chromatography–tandem mass spectrometry (GC-MS/MS) methods – were compared for the simultaneous determination of the 19 most important oestrogenic endocrine disrupting chemicals (EDCs), such as 17β-oestradiol, oestrone, 17α-ethinyloestradiol, bisphenol A and triclosan in wastewater treatment plant effluents. To lower the instrument limits of detection (ILODs), a derivatisation step preceded detection in both methods. The stability, sensitivity and ease of use of dansylation (Dns) for LC-MS/MS and trimethylsilylation (TMS) for GC-MS/MS derivatives were evaluated before method validation. TMS derivatisation products were highly unstable over time. Parameters such as susceptibility to matrix effects and the stability of monodansylated and didansylated derivatisation products of phytohormones are discussed. Lower ILODs of highly potent EDCs (0.11 ng mL−1 for 17β-oestradiol, 0.01 ng mL−1 for 17α-ethinyloestradiol and 0.22 ng mL−1 for oestrone) and stability of derivatisation products within 7 days were achieved using LC–MS/MS; therefore, further validation of this method at environmentally relevant concentrations was conducted. The method limits of detection (MLODs) met the requirements of the European Union defined in Directive 2008/105/ES for 17α-ethinyloestradiol (0.035 ng L−1) and 17β-oestradiol (0.4 ng L−1). Twenty samples of wastewater treatment plant effluent from the Czech Republic were screened using LC-MS/MS. Fifteen of the EDCs were detected in at least one sample. The most abundant EDCs were bisphenol A, with a concentration up to 1107 ng L−1, and triclosan, with a concentration up to 76 ng L−1. No seasonal trend between late spring and autumn samples was observed in the frequency or quantity of analytes.
Keywords: BSTFA, dansyl chloride, oestrogens, phytoestrogens, WWTP effluent, liquid chromatography, gas chromatography, mass spectrometry.
References
Adams NR (1998). Clover phyto-oestrogens in sheep in Western Australia. Pure and Applied Chemistry 70, 1855–1862.| Clover phyto-oestrogens in sheep in Western Australia.Crossref | GoogleScholarGoogle Scholar |
Anari MR, Bakhtiar R, Zhu B, Huskey S, Franklin RB, Evans DC (2002). Derivatization of ethinylestradiol with dansyl chloride to enhance electrospray ionization: Application in trace analysis of ethinylestradiol in rhesus monkey plasma. Analytical Chemistry 74, 4136–4144.
| Derivatization of ethinylestradiol with dansyl chloride to enhance electrospray ionization: Application in trace analysis of ethinylestradiol in rhesus monkey plasma.Crossref | GoogleScholarGoogle Scholar | 12199585PubMed |
Andaluri G, Suri RPS, Graham K (2017). Steroid hormones in environmental matrices: extraction method comparison. Environmental Monitoring and Assessment 189, 626
| Steroid hormones in environmental matrices: extraction method comparison.Crossref | GoogleScholarGoogle Scholar | 29124425PubMed |
Antignac JP, De Wasch K, Monteau F, De Brabander H, Andre F, Le Bizec B (2005). The ion suppression phenomenon in liquid chromatography–mass spectrometry and its consequences in the field of residue. Analytica Chimica Acta 529, 129–136.
| The ion suppression phenomenon in liquid chromatography–mass spectrometry and its consequences in the field of residue.Crossref | GoogleScholarGoogle Scholar |
Backe WJ (2015). An ultrasensitive (parts-per-quadrillion) and SPE-free method for the quantitative analysis of estrogens in surface water. Environmental Science & Technology 49, 14311–14318.
| An ultrasensitive (parts-per-quadrillion) and SPE-free method for the quantitative analysis of estrogens in surface water.Crossref | GoogleScholarGoogle Scholar |
Barreiros L, Queiroz JF, Magalhaes LM, Silva AMT, Segundo MA (2016). Analysis of 17-beta-estradiol and 17-alpha-ethinylestradiol in biological and environmental matrices – A review. Microchemical Journal 126, 243–262.
| Analysis of 17-beta-estradiol and 17-alpha-ethinylestradiol in biological and environmental matrices – A review.Crossref | GoogleScholarGoogle Scholar |
Bienvenu JF, Provencher G, Belanger P, Berube R, Dumas P, Gagne S, Gaudreau E, Fleury N (2017). Standardized procedure for the simultaneous determination of the matrix effect, recovery, process efficiency, and internal standard association. Analytical Chemistry 89, 7560–7568.
| Standardized procedure for the simultaneous determination of the matrix effect, recovery, process efficiency, and internal standard association.Crossref | GoogleScholarGoogle Scholar | 28682594PubMed |
Blair RM, Fang H, Branham WS, Hass BS, Dial SL, Moland CL, Tong WD, Shi LM, Perkins R, Sheehan DM (2000). The estrogen receptor relative binding affinities of 188 natural and xenochemicals: Structural diversity of ligands. Toxicological Sciences 54, 138–153.
| The estrogen receptor relative binding affinities of 188 natural and xenochemicals: Structural diversity of ligands.Crossref | GoogleScholarGoogle Scholar | 10746941PubMed |
Caballero-Casero N, Lunar L, Rubio S (2016). Analytical methods for the determination of mixtures of bisphenols and derivatives in human and environmental exposure sources and biological fluids. A review. Analytica Chimica Acta 908, 22–53.
| Analytical methods for the determination of mixtures of bisphenols and derivatives in human and environmental exposure sources and biological fluids. A review.Crossref | GoogleScholarGoogle Scholar | 26826686PubMed |
Cahill MG, Logrippo S, Dineen BA, James KJ, Caprioli G (2015). Development and validation of a high-resolution LTQ Orbitrap MS method for the quantification of isoflavones in wastewater effluent. Journal of Mass Spectrometry 50, 112–116.
| Development and validation of a high-resolution LTQ Orbitrap MS method for the quantification of isoflavones in wastewater effluent.Crossref | GoogleScholarGoogle Scholar | 25601682PubMed |
Celic M, Insa S, Skrbic B, Petrovic M (2017). Development of a sensitive and robust online dual column liquid chromatography–tandem mass spectrometry method for the analysis of natural and synthetic estrogens and their conjugates in river water and wastewater. Analytical and Bioanalytical Chemistry 409, 5427–5440.
| Development of a sensitive and robust online dual column liquid chromatography–tandem mass spectrometry method for the analysis of natural and synthetic estrogens and their conjugates in river water and wastewater.Crossref | GoogleScholarGoogle Scholar | 28573324PubMed |
Chimchirian RF, Suri RPS, Fu HX (2007). Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants. Water Environment Research 79, 969–974.
| Free synthetic and natural estrogen hormones in influent and effluent of three municipal wastewater treatment plants.Crossref | GoogleScholarGoogle Scholar | 17910365PubMed |
Desbrow C, Routledge EJ, Brighty GC, Sumpter JP, Waldock M (1998). Identification of estrogenic chemicals in STW effluent. 1. Chemical fractionation and in vitro biological screening. Environmental Science & Technology 32, 1549–1558.
| Identification of estrogenic chemicals in STW effluent. 1. Chemical fractionation and in vitro biological screening.Crossref | GoogleScholarGoogle Scholar |
Diaz-Cruz MS, De Alda MJL, Lopez R, Barcelo D (2003). Determination of estrogens and progestogens by mass spectrometric techniques (GC/MS, LC/MS and LC/MS/MS). Journal of Mass Spectrometry 38, 917–923.
| Determination of estrogens and progestogens by mass spectrometric techniques (GC/MS, LC/MS and LC/MS/MS).Crossref | GoogleScholarGoogle Scholar | 14505318PubMed |
Ding WH, Chiang CC (2003). Derivatization procedures for the detection of estrogenic chemicals by gas chromatography/mass spectrometry. Rapid Communications in Mass Spectrometry 17, 56–63.
| Derivatization procedures for the detection of estrogenic chemicals by gas chromatography/mass spectrometry.Crossref | GoogleScholarGoogle Scholar | 12478555PubMed |
European Chemicals Agency (ECHA) et al. (2018). Guidance for the identification of endocrine disruptors in the context of Regulations (EU) No 528/2012 and (EC) No 1107/2009. EFSA Journal 16, e05311
| Guidance for the identification of endocrine disruptors in the context of Regulations (EU) No 528/2012 and (EC) No 1107/2009.Crossref | GoogleScholarGoogle Scholar | 32625784PubMed |
Fairbairn DJ, Arnold WA, Barber BL, Kaufenberg EF, Koskinen WC, Novak PJ, Rice PJ, Swackhamer DL (2016). Contaminants of emerging concern: mass balance and comparison of wastewater effluent and upstream sources in a mixed-use watershed. Environmental Science & Technology 50, 36–45.
| Contaminants of emerging concern: mass balance and comparison of wastewater effluent and upstream sources in a mixed-use watershed.Crossref | GoogleScholarGoogle Scholar |
FDA (2018). ‘Bioanalytical Method Validation: Guidance for Industry.’ (US Department of Health and Human Services, Food and Drug Administration, Center for Drug Evaluation and Research and Center for Veterinary Medicine)
Frizzell C, Ndossi D, Verhaegen S, Dahl E, Eriksen G, Sorlie M, Ropstad E, Muller M, Elliott CT, Connolly L (2011). Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis. Toxicology Letters 206, 210–217.
| Endocrine disrupting effects of zearalenone, alpha- and beta-zearalenol at the level of nuclear receptor binding and steroidogenesis.Crossref | GoogleScholarGoogle Scholar | 21803136PubMed |
Glineur A, Nott K, Carbonnelle P, Ronkart S, Lognay G, Tyteca E (2018). Trace analysis of estrogenic compounds in surface and groundwater by ultra-high performance liquid chromatography–tandem mass spectrometry as pyridine-3-sulfonyl derivatives. Journal of Chromatography. A 1534, 43–54.
| Trace analysis of estrogenic compounds in surface and groundwater by ultra-high performance liquid chromatography–tandem mass spectrometry as pyridine-3-sulfonyl derivatives.Crossref | GoogleScholarGoogle Scholar | 29290395PubMed |
Golovko O, Sauer P, Fedorova G, Kroupova HK, Grabic R (2018). Determination of progestogens in surface and waste water using SPE extraction and LC-APCI/APPI-HRPS. The Science of the Total Environment 621, 1066–1073.
| Determination of progestogens in surface and waste water using SPE extraction and LC-APCI/APPI-HRPS.Crossref | GoogleScholarGoogle Scholar | 29102184PubMed |
Gorga M, Petrovic M, Barcelo D (2013). Multi-residue analytical method for the determination of endocrine disruptors and related compounds in river and waste water using dual column liquid chromatography switching system coupled to mass spectrometry. Journal of Chromatography. A 1295, 57–66.
| Multi-residue analytical method for the determination of endocrine disruptors and related compounds in river and waste water using dual column liquid chromatography switching system coupled to mass spectrometry.Crossref | GoogleScholarGoogle Scholar | 23683400PubMed |
Gross-Sorokin MY, Roast SD, Brighty GC (2006). Assessment of feminization of male fish in English rivers by the environment agency of England and Wales. Environmental Health Perspectives 114, 147–151.
| Assessment of feminization of male fish in English rivers by the environment agency of England and Wales.Crossref | GoogleScholarGoogle Scholar | 16818261PubMed |
Grover DP, Zhang ZL, Readman JW, Zhou JL (2009). A comparison of three analytical techniques for the measurement of steroidal estrogens in environmental water samples. Talanta 78, 1204–1210.
| A comparison of three analytical techniques for the measurement of steroidal estrogens in environmental water samples.Crossref | GoogleScholarGoogle Scholar | 19269495PubMed |
Ieda T, Horii Y, Petrick G, Yamashita N, Ochiai N, Kannan K (2005). Analysis of nonylphenol isomers in a technical mixture and in water by comprehensive two-dimensional gas chromatography-mass spectrometry. Environmental Science & Technology 39, 7202–7207.
| Analysis of nonylphenol isomers in a technical mixture and in water by comprehensive two-dimensional gas chromatography-mass spectrometry.Crossref | GoogleScholarGoogle Scholar |
Jarosova B, Ersekova A, Hilscherova K, Loos R, Gawlik BM, Giesy JP, Blaha L (2014). Europe-wide survey of estrogenicity in wastewater treatment plant effluents: the need for the effect-based monitoring. Environmental Science and Pollution Research International 21, 10970–10982.
| Europe-wide survey of estrogenicity in wastewater treatment plant effluents: the need for the effect-based monitoring.Crossref | GoogleScholarGoogle Scholar | 24870285PubMed |
Jaukovic ZD, Grujic SD, Bujagic IVM, Lausevic MD (2017). Determination of sterols and steroid hormones in surface water and wastewater using liquid chromatography–atmospheric pressure chemical ionization mass spectrometry. Microchemical Journal 135, 39–47.
| Determination of sterols and steroid hormones in surface water and wastewater using liquid chromatography–atmospheric pressure chemical ionization mass spectrometry.Crossref | GoogleScholarGoogle Scholar |
Kidd KA, Blanchfield PJ, Mills KH, Palace VP, Evans RE, Lazorchak JM, Flick RW (2007). Collapse of a fish population after exposure to a synthetic estrogen. Proceedings of the National Academy of Sciences of the United States of America 104, 8897–8901.
| Collapse of a fish population after exposure to a synthetic estrogen.Crossref | GoogleScholarGoogle Scholar | 17517636PubMed |
Kolpin DW, Schenzel J, Meyer MT, Phillips PJ, Hubbard LE, Scott TM, Bucheli TD (2014). Mycotoxins: Diffuse and point source contributions of natural contaminants of emerging concern to streams. The Science of the Total Environment 470–471, 669–676.
| Mycotoxins: Diffuse and point source contributions of natural contaminants of emerging concern to streams.Crossref | GoogleScholarGoogle Scholar | 24184544PubMed |
Konemann S, Kase R, Simon E, Swart K, Buchinger S, Schlusener M, Hollert H, Escher BI, Werner I, Ait-Aissa S, Vermeirssen E, Dulio V, Valsecchi S, Polesello S, Behnisch P, Javurkova B, Perceval O, Di Paolo C, Olbrich D, Sychrova E, Schlichting R, Leborgne L, Clara M, Scheffknecht C, Marneffe Y, Chalon C, Tusil P, Soldan P, Von Danwitz B, Schwaiger J, Becares MIS, Bersani F, Hilscherova K, Reifferscheid G, Ternes T, Carere M (2018). Effect-based and chemical analytical methods to monitor estrogens under the European Water Framework Directive. Trends in Analytical Chemistry 102, 225–235.
| Effect-based and chemical analytical methods to monitor estrogens under the European Water Framework Directive.Crossref | GoogleScholarGoogle Scholar |
Kramer RD, Filippe TC, Prado MR, De Azevedo JCR (2018). The influence of solid–liquid coefficient in the fate of pharmaceuticals and personal care products in aerobic wastewater treatment. Environmental Science and Pollution Research International 25, 25515–25525.
| The influence of solid–liquid coefficient in the fate of pharmaceuticals and personal care products in aerobic wastewater treatment.Crossref | GoogleScholarGoogle Scholar | 29956261PubMed |
Kresinova Z, Linhartova L, Filipova A, Ezechias M, Masin P, Cajthaml T (2018). Biodegradation of endocrine disruptors in urban wastewater using Pleurotus ostreatus bioreactor. New Biotechnology 43, 53–61.
| Biodegradation of endocrine disruptors in urban wastewater using Pleurotus ostreatus bioreactor.Crossref | GoogleScholarGoogle Scholar | 28502780PubMed |
Kuster M, Azevedo DA, De Alda MJL, Neto FRA, Barcelo D (2009). Analysis of phytoestrogens, progestogens and estrogens in environmental waters from Rio de Janeiro (Brazil). Environment International 35, 997–1003.
| Analysis of phytoestrogens, progestogens and estrogens in environmental waters from Rio de Janeiro (Brazil).Crossref | GoogleScholarGoogle Scholar | 19467706PubMed |
Laborie S, Moreau-Guigon E, Alliot F, Desportes A, Oziol L, Chevreuil M (2016). A new analytical protocol for the determination of 62 endocrine-disrupting compounds in indoor air. Talanta 147, 132–141.
| A new analytical protocol for the determination of 62 endocrine-disrupting compounds in indoor air.Crossref | GoogleScholarGoogle Scholar | 26592587PubMed |
Lindholm-Lehto PC, Ahkola HSJ, Knuutinen JS, Herve SH (2016). Widespread occurrence and seasonal variation of pharmaceuticals in surface waters and municipal wastewater treatment plants in central Finland. Environmental Science and Pollution Research International 23, 7985–7997.
| Widespread occurrence and seasonal variation of pharmaceuticals in surface waters and municipal wastewater treatment plants in central Finland.Crossref | GoogleScholarGoogle Scholar | 26769590PubMed |
Locatelli M, Sciascia F, Cifelli R, Malatesta L, Bruni P, Croce F (2016). Analytical methods for the endocrine disruptor compounds determination in environmental water samples. Journal of Chromatography A 1434, 1–18.
| Analytical methods for the endocrine disruptor compounds determination in environmental water samples.Crossref | GoogleScholarGoogle Scholar | 26805600PubMed |
Loos R, Carvalho R, Comero S, António DC, Ghiani M, Lettieri T, Locoro G, Paracchini B, Tavazzi S, Gawlik BM, Blaha L, Jarosova B, Voorspoels S, Schwesig D, Haglund P, Fick J, Gans O (2012). EU Wide Monitoring Survey on Waste Water Treatment Plant Effluents. JRC76400, EUR 25563 EN. JRC scientific and policy reports. (Publications Office of the European Union: Luxembourg)
Matejicek D, Vlcek J, Buresova A, Pelcova P (2013). Online molecularly imprinted solid-phase extraction coupled to liquid chromatography–tandem mass spectrometry for the determination of hormones in water and sediment samples. Journal of Separation Science 36, 1509–1515.
| Online molecularly imprinted solid-phase extraction coupled to liquid chromatography–tandem mass spectrometry for the determination of hormones in water and sediment samples.Crossref | GoogleScholarGoogle Scholar | 23441059PubMed |
Matuszewski BK, Constanzer ML, Chavez-Eng CM (2003). Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Analytical Chemistry 75, 3019–3030.
| Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS.Crossref | GoogleScholarGoogle Scholar | 12964746PubMed |
Miege C, Bados P, Brosse C, Coquery M (2009). Method validation for the analysis of estrogens (including conjugated compounds) in aqueous matrices. Trends in Analytical Chemistry 28, 237–244.
| Method validation for the analysis of estrogens (including conjugated compounds) in aqueous matrices.Crossref | GoogleScholarGoogle Scholar |
Nash JP, Kime DE, Van Der Ven LTM, Wester PW, Brion F, Maack G, Stahlschmidt-Allner P, Tyler CR (2004). Long-term exposure to environmental concentrations of the pharmaceutical ethynylestradiol causes reproductive failure in fish. Environmental Health Perspectives 112, 1725–1733.
| Long-term exposure to environmental concentrations of the pharmaceutical ethynylestradiol causes reproductive failure in fish.Crossref | GoogleScholarGoogle Scholar | 15579420PubMed |
Nie YF, Qiang ZM, Zhang HQ, Ben WW (2012). Fate and seasonal variation of endocrine-disrupting chemicals in a sewage treatment plant with A/A/O process. Separation and Purification Technology 84, 9–15.
| Fate and seasonal variation of endocrine-disrupting chemicals in a sewage treatment plant with A/A/O process.Crossref | GoogleScholarGoogle Scholar |
Preindl K, Braun D, Aichinger G, Sieri S, Fang ML, Marko D, Warth B (2019). A generic liquid chromatography–tandem mass spectrometry exposome method for the determination of xenoestrogens in biological matrices. Analytical Chemistry 91, 11334–11342.
| A generic liquid chromatography–tandem mass spectrometry exposome method for the determination of xenoestrogens in biological matrices.Crossref | GoogleScholarGoogle Scholar | 31398002PubMed |
Rodil R, Quintana JB, Concha-Grana E, Lopez-Mahia P, Muniategui-Lorenzo S, Prada-Rodriguez D (2012). Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain). Chemosphere 86, 1040–1049.
| Emerging pollutants in sewage, surface and drinking water in Galicia (NW Spain).Crossref | GoogleScholarGoogle Scholar | 22189380PubMed |
Rodriguez-Mozaz S, De Alda MJL, Barcelo D (2004). 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. Analytical Chemistry 76, 6998–7006.
| 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.Crossref | GoogleScholarGoogle Scholar | 15571352PubMed |
Ronderos-Lara JG, Saldarriaga-Norena H, Murillo-Tovar MA, Vergara-Sanchez J (2018). Optimization and application of a GC-MS method for the determination of endocrine disruptor compounds in natural water. Separations 5, 33
| Optimization and application of a GC-MS method for the determination of endocrine disruptor compounds in natural water.Crossref | GoogleScholarGoogle Scholar |
Routledge EJ, Sheahan D, Desbrow C, Brighty GC, Waldock M, Sumpter JP (1998). Identification of estrogenic chemicals in STW effluent. 2. In vivo responses in trout and roach. Environmental Science & Technology 32, 1559–1565.
| Identification of estrogenic chemicals in STW effluent. 2. In vivo responses in trout and roach.Crossref | GoogleScholarGoogle Scholar |
Salste L, Leskinen P, Virta M, Kronberg L (2007). Determination of estrogens and estrogenic activity in wastewater effluent by chemical analysis and the bioluminescent yeast assay. The Science of the Total Environment 378, 343–351.
| Determination of estrogens and estrogenic activity in wastewater effluent by chemical analysis and the bioluminescent yeast assay.Crossref | GoogleScholarGoogle Scholar | 17428521PubMed |
Samaras V, Thomaidis N, Stasinakis A, Lekkas T (2011). An analytical method for the simultaneous trace determination of acidic pharmaceuticals and phenolic endocrine disrupting chemicals in wastewater and sewage sludge by gas chromatography–mass spectrometry. Analytical and Bioanalytical Chemistry 399, 2549–2561.
| An analytical method for the simultaneous trace determination of acidic pharmaceuticals and phenolic endocrine disrupting chemicals in wastewater and sewage sludge by gas chromatography–mass spectrometry.Crossref | GoogleScholarGoogle Scholar | 21197532PubMed |
Shareef A, Angove MJ, Wells JD (2006). Optimization of silylation using N-methyl-N-(trimethylsilyl)-trifluoroacetamide, N,O-bis-(trimethyl.silyl)-trifluoroacetamide and N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide for the determination of the estrogens estrone and 17 alpha-ethinylestradiol by gas chromatography-mass spectrometry. Journal of Chromatography A 1108, 121–128.
| Optimization of silylation using N-methyl-N-(trimethylsilyl)-trifluoroacetamide, N,O-bis-(trimethyl.silyl)-trifluoroacetamide and N-(tert-butyldimethylsilyl)-N-methyltrifluoroacetamide for the determination of the estrogens estrone and 17 alpha-ethinylestradiol by gas chromatography-mass spectrometry.Crossref | GoogleScholarGoogle Scholar | 16445920PubMed |
Shelver WL, Kamp LM, Church JL, Rubio FM (2007). Measurement of triclosan in water using a magnetic particle enzyme immunoassay. Journal of Agricultural and Food Chemistry 55, 3758–3763.
| Measurement of triclosan in water using a magnetic particle enzyme immunoassay.Crossref | GoogleScholarGoogle Scholar | 17455947PubMed |
Shrivastava A, Gupta V (2011). Methods for the determination of limit of detection and limit of quantitation of the analytical methods. Chronicles of Young Scientists 2, 21–25.
| Methods for the determination of limit of detection and limit of quantitation of the analytical methods.Crossref | GoogleScholarGoogle Scholar |
Sosvorova LK, Chlupacova T, Vitku J, Vlk M, Heracek J, Starka L, Saman D, Simkova M, Hampl R (2017). Determination of selected bisphenols, parabens and estrogens in human plasma using LC-MS/MS. Talanta 174, 21–28.
| Determination of selected bisphenols, parabens and estrogens in human plasma using LC-MS/MS.Crossref | GoogleScholarGoogle Scholar |
Szarka S, Nguyen V, Prokai L, Prokai-Tatrai K (2013). Separation of dansylated 17 beta-estradiol, 17 alpha-estradiol, and estrone on a single HPLC column for simultaneous quantitation by LC-MS/MS. Analytical and Bioanalytical Chemistry 405, 3399–3406.
| Separation of dansylated 17 beta-estradiol, 17 alpha-estradiol, and estrone on a single HPLC column for simultaneous quantitation by LC-MS/MS.Crossref | GoogleScholarGoogle Scholar | 23371528PubMed |
Ting YF, Praveena SM, Aris AZ, Ismail SNS, Rasdi I (2017). Mathematical modeling for estrogenic activity prediction of 17 beta-estradiol and 17 alpha-ethynylestradiol mixtures in wastewater treatment plants effluent. Ecotoxicology 26, 1327–1335.
| Mathematical modeling for estrogenic activity prediction of 17 beta-estradiol and 17 alpha-ethynylestradiol mixtures in wastewater treatment plants effluent.Crossref | GoogleScholarGoogle Scholar | 28975452PubMed |
Tomsikova H, Aufartova J, Solich P, Sosa-Ferrera Z, Santana-Rodriguez JJ, Novakova L (2012). High-sensitivity analysis of female-steroid hormones in environmental samples. Trends in Analytical Chemistry 34, 35–58.
| High-sensitivity analysis of female-steroid hormones in environmental samples.Crossref | GoogleScholarGoogle Scholar |
Tousova Z, Oswald P, Slobodnik J, Blaha L, Muz M, Hu M, Brack W, Krauss M, Di Paolo C, Tarcai Z, Seiler TB, Hollert H, Koprivica S, Ahel M, Schollee JE, Hollender J, Suter MJF, Hidasi AO, Schirmer K, Sonavane M, Ait-Aissa S, Creusot N, Brion F, Froment J, Almeida AC, Thomas K, Tollefsen KE, Tufi S, Ouyang XY, Leonards P, Lamoree M, Torrens VO, Kolkman A, Schriks M, Spirhanzlova P, Tindall A, Schulze T (2017). European demonstration program on the effect-based and chemical identification and monitoring of organic pollutants in European surface waters. The Science of the Total Environment 601–602, 1849–1868.
| European demonstration program on the effect-based and chemical identification and monitoring of organic pollutants in European surface waters.Crossref | GoogleScholarGoogle Scholar | 28629112PubMed |
Tyler CR, Filby AL, Bickley LK, Cumming RI, Gibson R, Labadie P, Katsu Y, Liney KE, Shears JA, Silva-Castro V, Urushitani H, Lange A, Winter MJ, Iguchi T, Hill EM (2009). Environmental health impacts of equine estrogens derived from hormone replacement therapy. Environmental Science & Technology 43, 3897–3904.
| Environmental health impacts of equine estrogens derived from hormone replacement therapy.Crossref | GoogleScholarGoogle Scholar |
Valitalo P, Perkola N, Seiler TB, Sillanpaa M, Kuckelkorn J, Mikola A, Hollert H, Schultz E (2016). Estrogenic activity in Finnish municipal wastewater effluents. Water Research 88, 740–749.
| Estrogenic activity in Finnish municipal wastewater effluents.Crossref | GoogleScholarGoogle Scholar | 26584345PubMed |
Vanderford BJ, Pearson RA, Rexing DJ, Snyder SA (2003). Analysis of endocrine disruptors, pharmaceuticals, and personal care products in water using liquid chromatography/tandem mass spectrometry. Analytical Chemistry 75, 6265–6274.
| Analysis of endocrine disruptors, pharmaceuticals, and personal care products in water using liquid chromatography/tandem mass spectrometry.Crossref | GoogleScholarGoogle Scholar | 14616010PubMed |
Vargas-Berrones K, De Leon-Martinez LD, Bernal-Jacome L, Rodriguez-Aguilar M, Avila-Galarza A, Flores-Ramirez R (2020). Rapid analysis of 4-nonylphenol by solid-phase microextraction in water samples. Talanta 209, 120546
| Rapid analysis of 4-nonylphenol by solid-phase microextraction in water samples.Crossref | GoogleScholarGoogle Scholar | 31891999PubMed |
Vidova V, Spacil Z (2017). A review on mass spectrometry-based quantitative proteomics: Targeted and data independent acquisition. Analytica Chimica Acta 964, 7–23.
| A review on mass spectrometry-based quantitative proteomics: Targeted and data independent acquisition.Crossref | GoogleScholarGoogle Scholar | 28351641PubMed |
Vystavna Y, Frkova Z, Celle-Jeanton H, Diadin D, Huneaud F, Steinmann M, Crini N, Loup C (2018). Priority substances and emerging pollutants in urban rivers in Ukraine: Occurrence, fluxes and loading to transboundary European Union watersheds. The Science of the Total Environment 637–638, 1358–1362.
| Priority substances and emerging pollutants in urban rivers in Ukraine: Occurrence, fluxes and loading to transboundary European Union watersheds.Crossref | GoogleScholarGoogle Scholar | 29801228PubMed |
Wang S, Cyronak M, Yang E (2007). Does a stable isotopically labeled internal standard always correct analyte response? A matrix effect study on a LC/MS/MS method for the determination of carvedilol enantiomers in human plasma. Journal of Pharmaceutical and Biomedical Analysis 43, 701–707.
| Does a stable isotopically labeled internal standard always correct analyte response? A matrix effect study on a LC/MS/MS method for the determination of carvedilol enantiomers in human plasma.Crossref | GoogleScholarGoogle Scholar | 16959461PubMed |
Zhang ZL, Hibberd A, Zhou JL (2006). Optimisation of derivatisation for the analysis of estrogenic compounds in water by solid-phase extraction gas chromatography–mass spectrometry. Analytica Chimica Acta 577, 52–61.
| Optimisation of derivatisation for the analysis of estrogenic compounds in water by solid-phase extraction gas chromatography–mass spectrometry.Crossref | GoogleScholarGoogle Scholar | 17723653PubMed |