LC-MS and GC-MS Approaches for the Analysis of Emerging Contaminants in Water Samples
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1 LC-MS and GC-MS Approaches for the Analysis of Emerging Contaminants in Water Samples Imma Ferrer and Mike Thurman () JerryA. Zweigenbaum, MelissaChurleyandPhilStremple(2) () Center for Environmental Mass Spectrometry, University of Colorado, Boulder, CO, USA (2) Agilent Technologies, Inc.
2 Outline. LC-TOF-MS Approach for Analysis of EPA 694 Pharmaceuticals in Water Samples. 2. LC-QqQ-MS Approach using Jet Stream as a highly sensitive methodology for the identification of Pharmaceuticals in the Environment. 3. Rapid Resolution chromatography: examples using UHPLC (290 Infinity). 4. GC-MS-MS for the analysis of Phytoestrogens.
3 Instrumentation LC-TOF-MS Agilent Model 6220 Specifications: 4 GHz detector rate 0,000 resolving power < 2 ppm accuracy LC-QqQ-MS Agilent Model UHPLC Infinity (Also Model 6460 with Jet Stream) GC-MS-MS (QqQ) Agilent Model 7000
4 Analytical Conditions Extraction procedure (Water Samples): Gilson GX-27 ASPEC automated SPE system. Solid-phase extraction with Oasis HLB cartridges. L sample to ml extract or 00 ml sample to 500 µl extract. LC Conditions: Columns: Zorbax Eclipse Plus and SB: C 8, 2. x 00 mm, 3.5 µm particles C 8, 2. x 50 mm,.8 µm particles C 8 2. x 00 mm,.8 µm particles Mobile phase Acetonitrile and water with 0. % formic acid. Gradient: 0 % ACN to 00 % in, 0 or 20 min. Flow = 0.6 ml/min and.2 ml/min.
5 . LC-TOF-MS for the Analysis of Pharmaceuticals Target Analytes EPA Method 694 Group Group 3 Acetaminophen,7-dimethylxanthine Roxithromycin Gemfibrozil Ampicillin Diphenhydramine Sarafloxacin Ibuprofen Azithromycin Caffeine Carbadox Carbamazepine Cefotaxime Ciprofloxacin Clarithromycin Cloxacillin Codeine Enrofloxacin Erythromycin Erythromycin Anhydrate Flumequine Fluoxetine Lincomycin Lomefloxacin Miconazole Norfloxacin Sulfachloropyridazine Sulfadiazine Sulfadimethoxine Sulfamerazine Sulfamethazine Sulfamethizole Sulfamethoxazole Sulfanilamide Sulfathiazole Naproxen Triclocarban Warfarin Group 4 Albuterol Cimetidine Metformin Ranitidine Macrolides Benzomidazoles Penicillines Quinolones Sulfonamides Pyrimidines NSAIDs Cotinine Ofloxacin Thiabendazole Dehydronifedipine Oxacillin Trimethoprim Digoxigenin Oxolinic Acid Tylosin Digoxin Penicillin G Virginiamycin Diltiazem Penicillin V
6 . LC-TOF-MS for the Analysis of Pharmaceuticals x0 x Drinking Water Sample, spiked at 0 ug/l + TIC Scan Mix_60_Oasis_Hot water_final volume ml_5ul.d Cpd :+ ECC Scan Mix_60_Oasis_Hot water_final volume ml_5ul.d Counts vs. Acquisition Time (min) Sulfanilamide Acetaminophen Caffeine Ampicillin Cotinine,7-dimethylxanthine Lincomycin + Sulfadiazine Thiabendazole Sulfamerazine Sulfamethazine Cefotaxime Sulfamethizole Norfloxacin + Ofloxacin Ciprofloxacin Lomefloxacin Enrofloxacin Sulfachloropyridazine Sarafloxacin Digoxigenin Sulfamethoxazole + Azithromycin Oxolinic Acid Sulfadimethoxine Erythromycin Diphenhydramine Penicillin G Tylosin Carbamazepine Flumequine Fluoxetine Oxacillin Virginiamycin Cloxacillin Dehydronifedipine Miconazole Trimethoprim Diltiazem + Digoxin Clarithromycin Roxithromycin + Penicillin V Counts vs. Acquisition Time (min)
7 Screening and Use of Databases Cotinine Wastewater Sample Caffeine Carbamazepine Diphenhydramine Sulfamethoxazole DEET Thiabendazole Trimethoprim
8 Non-target Analysis Carbamazepine x0 5 + EIC( ) Scan Boulder WWO_9June08.d N Extracted Chromatogram m/z = 94 N H 2 C 4 H 2 N + Exact Mass: O NH 2 C 5 H 3 N 2 O + Exact Mass: Counts vs. Acquisition Time (min) x HO C 5 H 5 N 2 O ppm N O NH Counts vs. Mass-to-Charge (m/z) C 5 H 5 N 2 O 2 + Exact Mass:
9 2. LC-QqQ-MS for the Analysis of Pharmaceuticals Jetstream Technology Agilent Jet Stream gradient focusing technology delivers many more ions to the mass spectrometer while reducing the number of neutral solvent clusters. The result is stronger signals with lower RSD s at the limit of detection.
10 High sensitivity achieved with Jet Stream Technology Drinking water, spiked at ppb concentration x ESI MRM Frag=75.0V CID@5.0 ( > 6.0) ppb_all Groups+Extras.d C 8 Eclipse Plus 2. x 00mm (3.5 μm) column Counts vs. Acquisition Time (min) Comparison 640 and 6460 with Jetstream QqQ 640 QqQ 6460 Jet Stream Comparison Acetaminophen 2 ppb 0.06 ppb 30 times Caffeine 0 ppb 0.5 ppb 20 times Carbamazepine 3 ppb 0.06 ppb 50 times Sulfadimethoxine 3 ppb 0.05 ppb 60 times
11 Instrumental LOD s for Pharmaceuticals Compound LOD Jetstream 6460 (µg/l),7-dimethylxanthine 0.6 Acetaminophen 0.06 Albuterol 0.02 Ampicillin 0.6 Azithromycin 6.0 Caffeine 0.5 Carbadox 0.3 Carbamazepine 0.06 Cefotaxime 2 Cimetidine 0.0 Ciprofloxacin 0.5 Clarithromycin 0. Cloxacillin 3.0 Codeine 0.3 Cotinine 0.05 Dehydronifedipine 0.03 Digoxigenin 0.4 Diltiazem 0. Diphenhydramine 0.05 Enrofloxacin 0.3 Erythromycin 0.3 Erythromycin 0.3 Anhydrate Flumequine 0.05 Fluoxetine 0.4 Gemfibrozil 0. Ibuprofen 7.0 Compound LOD Jetstream 6460 (µg/l) Lomefloxacin 0.4 Metformin 0.05 Miconazole 0.5 Naproxen.0 Norfloxacin.0 Ofloxacin 0.4 Oxolinic Acid 0.03 Penicillin G.0 Penicillin V.0 Ranitidine 0.05 Roxithromycin 0.5 Sarafloxacin 0.5 Sulfachloropyridazine 0.2 Sulfadiazine 0.5 Sulfadimethoxine 0.05 Sulfamerazine 0. Sulfamethazine 0.3 Sulfamethizole 0.3 Sulfamethoxazole 0.2 Sulfanilamide 4.0 Sulfathiazole 0.4 Thiabendazole 0.05 Triclocarban 0. Triclosan.0 Trimethoprim 0.5 Tylosin 6.0 Virginiamycin 0.4 Warfarin 0. After SPE concentration, more than 90% compounds are detectable at < ng/l in water
12 Analysis of Wastewater Sample Analysis of a Boulder Wastewater Outfall for EPA 694 x0 7 + TIC Scan Boulder WWO_9June08.d Carbamazepine Counts vs. Acquisition Time (min) Diphenhydramine CH 3 N m/z=79 O NH2 m/z=94 O m/z=52 N CH 3 m/z= > 94.0, > 79.0 x0 5 Ratio=2.5 Counts MRM ( min, 55 scans) ( > **) Boulder Counts x > 67.0, > 52.0 x0 4 Ratio=30.0 Counts MRM ( min, 46 scans) ( > **) Boulder Counts x
13 3. Rapid Resolution Chromatography: UHPLC EPA Method 694 Group Analytes (46 pharmaceuticals) separation on the 290 Infinity in half the time. C 8 Eclipse Plus 2. x 00mm (.8 μm) column Gradient: t 0 =0% ACN t 3.4 =0% ACN t 20 = 00% ACN t 20.3 =00% ACN Flow-rate: 0.6 ml/min Pressure: 750 Bar C 8 Eclipse Plus 2. x 50mm (.8 μm) column Gradient: t 0 =0% ACN t.7 =0% ACN t 0 = 00% ACN t 0.3 =00% ACN Flow-rate: 0.6 ml/min Pressure: 375 Bar
14 Faster and faster: Gone in 60 seconds to.5 second peak widths for pharmaceuticals using LC-MS MS-MS with a 5-ms dwell time and 20 points across the peak. C 8 Eclipse Plus 2. x 50mm (.8 μm) column Gradient: t 0 =0% ACN t.5 =00% ACN Flow-rate:.2 ml/min Pressure: 750 Bar x ESI MRM Frag=90.0V CID@35.0 ( > ) Boulder effluent_c8_speed grad_5comp.d Cotinine Thiabendazole 0.9 sec Trimethoprim Sulfamethoxazole Diphenhydramine Roxyithromycin TIC in Black Diltiazem Counts vs. Acquisition Time (min)
15 Fast analysis of pharmaceuticals in water following EPA Method 694: Applications of UHPLC-MS/MS Michael Thurman WOG pm 3:30 pm MS and Emerging Environmental Contaminants
16 Silk Heart Health 4. Analysis of Phytoestrogens by GC-MS-MS Beneficial effects of flavonoids (water-soluble plant pigments derived from the 2-phenyl-,4-benzopyrone structure) on humans have been reported. Phytoestrogens are a group of nonsteroidal polyphenolic compounds that occur naturally in plants (soy, alfalfa, clover ). They are used widely in several foods and beverages as food suplements. Because of their structural similarity with estradiol (7-β-estradiol), have the ability to cause estrogenic or/and antiestrogenic effects.
17 Analysis of Phytoestrogens in Soy Milk and Water Analytes studied: Biochanin A Coumestrol Daidzein Equol Formononetin Genistein Glycitein Prunetin Derivatization of Phytoestrogens (USGS Method ) Extraction of Soy Milk (ml) and Water Samples (00mL) With Ethyl Acetate (0mL) Evaporation of EtAc to dryness Derivatization with 200uL of 0% TMCS/BSTFA ( hour at 60C) Si(CH 3 ) 3 HO Biochanin A O Evaporation to dryness Addition of 200uL of BSTFA/Pyridine (5:) OH O OCH 3 Injection of ul into GC-MS-MS
18 GC-MS-MS Parameters Rate (ºC/min) Value (ºC/min) Hold Time (min) Run Time (min) Column: HP5 30m x 250 μm x 0.25 μm Initial Ramp Ramp x EI MRM CID@** ( > ) Mix_Phytos_50ppb_MRM_gain30.D MRM chromatogram of the Phyto Mix Equol Formononetin Biochanin A Prunetin Genistein Daidzein Coumestrol Glycitein Counts vs. Acquisition Time (min)
19 GC-MS-MS Fragmentation of Phytoestrogens Fragmentation pathway for Daidzein x EI Product Ion: ( min, 4 scans) CID@30.0 (398. -> **) Daidzein_PI_ Counts vs. Mass-to-Charge (m/z) (H 3 C) 3 SiO O + C 2 H 26 O 4 Si 2 m/z 398 (H 3 C) 3 SiO O OH O -CH 3 -C=O OSi OSi(CH 3 ) 3 C 20 H 23 O 4 Si 2 + m/z 383 (H 3 C) 3 SiO H O + C 9 H 23 O 3 Si 2 m/z 355 OSi
20 Analysis of Soy Milk Standard Soy Milk Extract Daidzein I.S. Genistein Glycitein (H 3 C) 3 SiO Genistein O 47-> >327 OSi(CH 3 ) 3 O m/z = 486 OSi(CH 3 ) 3
21 Backflush experiments Without Backflush With Backflush
22 Conclusions LC-TOF-MS useful for screening and non-target identification (e.g. degradation products). LC-QqQ-MS offers high sensitivity for analysis of target pharmaceuticals (low ng/l detections). Use of UHPLC to reduce total analysis time and enhances peak capacity on.8 μm columns. GC-MS-MS is a robust and highly selective instrument for analysis of emerging contaminants in environmental samples.
23 Acknowledgments Agilent Technologies for instrument support and providing standards. Special Thanks to personnel in Little Falls (Wilmington, DE) and Santa Clara (CA) Agilent sites: Melissa Churley, Chin-Kai Meng, Harry Prest, Phil Stremple, Phil Wylie and Jerry Zweigenbaum. Gilson Inc. for SPE support. Larry Barber (from USGS) for sample collection in Boulder, CO. University of Colorado for Lab space and support.
24 MRM transitions for Pharmaceuticals I. Ferrer, E.M. Thurman and J.A. Zweigenbaum, App Note EN, 2008
25 Analysis of Phytoestrogens LOD s range from ppb to 0 ppb R 2 > 0.999
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