A Fast and Effective Approach for Running EPA Method 539: Determination of Hormones in Drinking Water using SPE and LC/MS/MS

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1 A Fast and Effective Approach for Running EPA Method 539: Determination of Hormones in Drinking Water using SPE and LC/MS/MS Xianrong (Jenny) Wei 1, Matthew Trass 1, Ali Haghani 2, Andy Eaton 2 1 Phenomenex, Inc., 411 Madrid Ave., Torrance, CA USA 2 Eurofins, 750 Royal Oaks Drive, Monrovia, CA USA PO _W_1 PO _W_2

2 Introduction Hormones have been found in a wide range of water supplies throughout the world. Compounds such as ethinylestradiol, the active ingredient in a commonly prescribed birth-control medication, can cause detrimental affects to both aquatic life and humans 1. Because of this public risk, there is a rapidly growing interest in monitoring these compounds, and EPA method 539 was specifically developed to monitor this growing problem. EPA method 539 is a challenging analysis because it not only requires very low detection limits (0.1 part per trillion for some compounds), it also requires mass-spectrometer analysis in both positive and negative ion mode. Despite these challenges, more than 1,000 water utilities are running EPA 539 in the United States alone. Therefore, it is extremely important to have a fast, accurate and reproducible analytical testing method. This work follows the EPA method extraction protocol, but we offer an optimized LC/MS/MS method that utilizes a high ph mobile phase in order to maximize the LC/MS/MS response. Because conventional silica-based HPLC media is not stable under alkaline conditions, an organosilica hybrid column (Gemini 3 µm NX-C18; Phenomenex, Inc.) was used to perform these analyses.

3 Structure 17- -Ethinyl Estradiol ( da) 17- -Estradiol ( da) Estriol ( da) Testosterone ( da) Equilin ( da) Estrone ( da) 4-Androstene-3,17-dione ( da)

4 Material and Methods Sample Preparation Pre-treatment: Per the EPA method protocol, 1 L water samples are dechlorinated, preserved, collected and stored. Surrogate standards are then added prior to solid phase extraction. SPE disk: 47 mm Octadecyl sorbent (Fisher CAT: ). Disk cleaning: Rinse disk with 10 ml of methanol followed by 5 ml of methanol. Conditioning: Condition with 10 ml of methanol followed by 10 ml of water. Load: Load entire (1 L) sample under vacuum. Without letting the disk go dry, wash with 10 ml of 15 % methanol. Dry: Dry the disk under full vacuum for min. Elution: Elute with 3 x 5 ml of methanol (allow time for the disk to soak for 1 min during first elution step). Evaporation: Dry samples under Nitrogen gas at 45 ºC. Reconstitute: Add 500 µl of 50 % methanol and transfer to a 1 ml volumetric flask. Add internal standard and adjust to 1 ml volume with 50 % methanol. Filtration (optional): Not necessary for drinking water sample LC/MS/MS Parameters: APP ID: Column: Gemini 3 μm NX-C18 Dimensions: 100 x 2.0 mm Part No.: 00D-4453-B0 Mobile Phase: A: 0.2 % NH 4 OH in Water B: 0.2 % NH 4 OH in Methanol Gradient: Time (min) B (%) Flow Rate: 0.2 ml/min Inj. Volume: 10 µl Temperature: Ambient Detection: API 4000 (AB SCIEX) Backpressure: 1700 psi Sample: 1 ml of drinking water extract Negative Mode Q1 Q2 RT (min) Polarity Estriol / ESI- Estriol-D2 (I.S.) ESI- Bisphenol A-D16 (SURR) / ESI- Equilin / ESI- Estrone / ESI- 17-β-Estradiol / ESI- 13 C 6 -Estradiol (I.S.) ESI- 17-α-Ethinyl Estradiol / ESI- Ethinyl Estradiol-D4 (SURR) / ESI- 13 C 2 -Ethinyl Estradiol (I.S.) ESI- 4-Androstene-3,17-dione / ESI+ Testosterone / ESI+ Testosterone-D3 (I.S.) / ESI+

5 FIGURE 1. Gemini NX-C18 high ph-stable particle Ethane cross-linking stabilizes the silica particle providing resistance to high ph attack, while maintaining high efficiency and mechanical strength. O O O O O O O Si Si O Si S Si O Si O Si Si O O O O O O O O C Si O Si Si O Si Si O Si Si O Si C O O O O O O O O C O Si Si O Si Si O Si Si O Si Si O O O O O O Conventional silica-based particles are not stable under alkaline conditions, but the presence of the ethane linkages in the Gemini NX-C18 particle allows it to be run under high ph conditions without significant degradation. Figure 2. Representative chromatogram of a standard injection, TIC. Conditions as above Intensity, cps 4.0e5 3.8e5 3.6e5 3.4e5 3.2e5 3.0e5 2.8e5 2.6e5 2.4e5 2.2e5 2.0e5 1.8e5 1.6e5 1.4e5 1.2e5 1.0e5 8.0e4 6.0e4 4.0e4 2.0e Estriol 2. Estriol-d2 (IS) 3. Bisphenol A-d16 4. Equilin 5. Estrone 6. Beta-estradiol 7. 13C6-estradiol (IS) 1, , 13 App ID min 8. Ethinyl Estradiol-d a-Ethinyl Estradiol C2-Ethinyl Estradiol (IS) 11. Androstenedione 12. Testosterone-d3 13. Testosterone

6 Figure 3. Mid-level extracted drinking water sample (spiked with analytes and I.S.) APP ID: Column: Gemini 3 µm NX-C18 Dimensions: 100 x 2.0 mm Part No.: 00D-4453-B0 Mobile Phase: A: 0.2 % NH 4 OH in Water B: 0.2 % NH 4 OH in Methanol Gradient: Time (min) B (%) Flow Rate: 0.2 ml/min Inj. Volume: 10 µl Temperature: Ambient Detection: API 4000 (AB SCIEX) Backpressure: 1700 psi Sample: 1 ml of drinking water extract

7 table 1. Method reporting limit and linearity for each analyte Compound MRL (ng/l) Linearity (R²) Estriol Equilin Estrone β-estradiol α-Ethinyl Estradiol Androstene-3,17-dione Testosterone

8 Results and Discussion Following extraction, EPA 539 requires LC/MS/MS analysis using high ph mobile phase. The high ph mobile phase is required to impart a charge on certain analytes for mass spectrometric analysis. Specifically, the compounds containing phenol functionality are deprotonated at high ph, allowing them to be analyzed in the negative mode. However, running high ph mobile phase severely limits the choice of HPLC columns that can be used (typical HPLC media is unstable above neutral ph). Therefore, we used Gemini NX-C18, an organo-silica-hybrid particle (figure 1) that is specially designed for high ph analysis. The optimized chromatographic method results in a fast analysis time, with all analytes eluting in less than 10 minutes. The total run time including equilibration is only 15 minutes (figure 2). In comparison, the EPA 539 method specifies a total run time of 50 minutes. The fast analysis time on Gemini NX-C18 is very beneficial since laboratories are required to acquire a multitude of check standards aside from actual drinking water samples. These check standards include: calibration data, MRL standards and QC samples. Over time, an optimized analysis time allows a laboratory to be significantly more productive. Aside from a fast analysis time, an effective analytical method also needs to be accurate with low limits of detection. Table 1 lists the method reporting limits and linearity values for each compound. The MRLs range from 0.1 ng/l for testosterone to 4.0 ng/l for equilin. Excellent linearity values were achieved with all compounds exceeding R 2 values of 0.99.

9 Conclusion EPA Method 539 was developed in response to widespread reports of hormones being present in water supplies. The health risk associated with these compounds is significant. Accordingly, more than 1,000 utilities in the US are testing water samples for hormones using EPA Method 539. The presented method follows the EPA method extraction protocol but utilizes an optimized chromatographic method. The optimized method significantly reduces analysis time (35 minutes per sample) while maintaining excellent linearity (0.99 R 2 value or greater for each compound) and low MRLs. Because EPA 539 is such an important and widely used assay, the presented method is of great assistance to laboratories desiring improved efficiency and productivity.

10 References 1. Benotti, M. J., Trenholm, R. A., Vanderford, B. J., Holady, J. C., Stanford, B. Snyder, S. A. (2009). Pharmaceuticals and endocrine disrupting compounds in U.S. drinking water. Environ, Sci, Technol., 43, p Trademarks Gemini is a registered trademark of Phenomenex, Inc. API 4000 is a trademark of AB SCIEX. Gemini is patented by Phenomenex. U.S. Patent No. 7,563, Phenomenex, Inc. All rights reserved.

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