Research into pharmaceutical compounds as present in the watercycle
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1 Research into pharmaceutical compounds as present in the watercycle Merijn Schriks, Ton van Leerdam KWR, (Nieuwegein, NL)
2 Presentation outline Introduction Stress hormones in wastewater: in vitro bioassay results in relation to analytical chemistry Discussion and conclusions Questions 2
3 Watercycle 3
4 Micropollutants in the watercycle chemicals registered in EINECS inventory (Schwartzenbach et al., 2006); in daily use (Schwartzenbach et al., 2006) 4
5 Application of in vitro bioassays for waterquality assessment Mixture interactions - Analytical chemistry Specificity (targets) +++ Sensitivity (LOD/LOQ) +++ Regulatory acceptance +++ Biological relevance +/- In vitro bioassay +/ /
6 CALUX bioassays biological measurement of hormone activity Compound x Compound y Compound z Integrated biological response, relative to a reference compound 6
7 ER-CALUX in surface water Rhine-Lobith ng E2 EQ/L Spring Summer Fall Winter Spring Summer Lekkanaal-Nieuwegein Puijker, Estrogenic activity in Dutch surface waters. RIWA report. ISBN
8 van der Linden et al. study (2008) Multiple types of hormone activity (CALUX bioassays)? Van der Linden et al., ES&T 2008??? Legend: B/blanc, D/drinking Watercycle water, Research I/industrial Institute wastewater, H/hospital wastewater, PM/paper mill 8 treated wastewater, STP/sewage treatment plant, W/surface water
9 Aim of the present research Attempt to identify/quantify responsible active glucocorticoids by means of LC-MS/MS and link the results to bioassay response 9
10 Glucocorticoids (stress hormones) cortisol Glucocorticoids Released under stress-conditions Many effects on metabolism Gluconeogenesis; Inhibition of glucose utilization; Promotion of lipolysis; Major medical application (suppression of immuno/allergic reactions). Examples: dexamethasone, prednisone 10
11 Pharmaceuticals and glucocorticoids Drug (US RX-list top 200 rating, 2009) Nasonex (29) Nasacort AQ (86) Rhinocort Aqua (111) Pulmicort Respules (122) Tobradex (131) Ciprodex Otic (145) Compound Mometasone furoate Triamcinolone acetonide Budesonide Budesonide Dexamethasone Dexamethasone Human disease Hay fever (adults, children > 2 yrs) Hay fever (adults, children > 2 yrs) Hay fever (adults, children > 6 yrs) Asthma Infection of the eyes Infection of the ears Prescribed compounds in the NL (Source RIVM, 2009) Cortisol Prednisolone Prednisone Triamcinolone acetonide Cortisone Dexamethasone Amount (kg/yr) 11
12 Methodology CALUX Orbitrap LC-MS/MS KWR: BDS: sample collection-preparation-extraction-lc-ms/ms; CALUX bioassays (endpoints PR, GR, AR, ER). 12
13 Methodology chemical analysis Carried out with LC high resolution Orbitrap MS Confimation criteria: 1. Retention time; 2. Accurate mass; 3. Product ion masses. 13
14 Results chemical analysis NL: 9.05E8 TIC MS pos Relative abundance Relative abundance Prednisolone m/z cortisol m/z cortisone m/z prednisone m/z Time (min) triamcinolone acetonide m/z N L : E 6 m /z= F : F TM S + p E S I F ull m s [ ] M S p o s N L : E 6 m /z= F : F TM S + p E S I F ull m s [ ] M S p o s N L : E 6 m /z= F : F TM S + p E S I F ull m s [ ] M S p o s N L : E 4 m /z= F : F TM S + p E S I F ull m s [ ] M S p o s Full scan LC-Orbitrap MS chromatogram Extracted-ion chromatograms (pos ion mode) 14 Schriks et al., ES&T 2010
15 Results chemical analysis High res full scan MS spectrum of Cortisol incl. low-res product ion spectrum 15 Schriks et al., ES&T 2010
16 Results: CALUX results and chemical results on ref standards No Compound CALUX EC50 REP (nm) 1 Aldosterone ± Amicinonide 0.49 ± 0.04 Betamethasone 1.02 ± 0.05 Cortisone >1000 Desoximethasone 0.66 ± 1.3 Dexamethasone 0.84 ± 1 Flunisolide 0.49 ± 1.7 Fluorometholone 0.59 ± 1.4 Cortisol 11.4 ± 0.07 Methylprednisolone 2.25 ± 0.4 Paramethasone 1.14 ± 0.7 Prednicarbate 4.75 ± 0.2 Prednisolone 3.68 ± 0.2 Prednisone >500 Remexolone 0.83 ± 1 Triamcinolone 5.67 ± 0.2 Triamcinoloneacetonide 0.37 ± Triamcinolonehexaacetonide 3.40 ± < < Retention time (min.) m/z [M+H] % recovery 43 ± 5 44 ± 3 94 ± 5 77 ± 4 77 ± 7 90 ± 6 90 ± 6 89 ± 4 91 ± ± 6 84 ± 7 46 ± 1 73 ± 3 77 ± 6 67 ± 5 61 ± 5 74 ± ± 7
17 Results Chemical analysis High recovery (LC-MS/MS) of 18 glucocorticoid standards (~80% in wastewater); LOD (LC-MS/MS) ~ 10 ng/l; CALUX bioassay Most potent standard is triamcinolone acetonide (REP = 2.3) Least potent standard is cortisone (REP < ) Reference standard is dexamethasone (REP = 1) 17
18 Thank you for your attention! Ton van Leerdam, Annemarie van Wezel, Pim de Voogt Sander van der Linden, Bart van der Burg Dennis van der Vught, Rene van Doorn, Pascal Kooij, Hans van Beveren This research was funded by the Joint Research Programme of the Dutch Water Utilities (BTO) and the EU TECHNEAU project 18
19 Results Analysis in wastewater effluents (van der Linden et al., 2008) Water sample GR-CALUX (ng dex EQs/L) (vd Linden et al., 2008) Detected glucocorticoids (LC-MS/MS) Conc. LC-MS/MS [ng/l] REP x conc (ng dex EQs/L) Industry wastewater 243 Prednisolone Dexamethasone Cortisone Cortisol Fluocortin/fluprednidene Hydrocortisone aceponate Not confirmed Not confirmed Max Hospital wastewater 96 Cortisone Prednisolone Cortisol Prednisone Triamcinolone acetonide Fluocortin/fluprednidene Hydrocortisone aceponate Not confirmed Not confirmed Max Paper mill treated wastewater 11 No compounds detected STP effluent 38 Triamcinolone acetonide Hydrocortisone aceponate Not confirmed
20 CALUX response versus chemical concentrations Measured GR CALUX bioassay response Predicted GR CALUX bioassay response Unexplained result 20 Schriks et al., ES&T 2010
21 Discussion / conclusions 1) Various glucocorticoids present in wastewaters (low ug/l range). Good recoveries in wastewater; 2) Bioassay results can be explained to a fairly large extent by chemical analysis; 3) Gaps between bioassay results and chemical analysis can be explained by: 1) Unknown agonists in the sample extracts; 2) Unknown compounds that modulate glucocorticoid action in the CALUX bioassay; 3) Interexperimental variation in the REP; 4) Surface water concentrations most probably in the low ng/l range (Chang et al., 2008; Tölgyesi et al., 2010). KWR results: max. 2.7 ng dex EQs/L (remains to be published). 5) The significance for human and/or ecosystem health is poorly understood at present Watercycle and deserves Research Institute more research attention. 21
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