Renzo BAGNATI Mario Negri Institute of Pharmacological Research- IRCCS Milano - Italy
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1 STEROIDS IN WASTE WATERS AS MARKERS OF ABUSE Renzo BAGNATI Mario Negri Institute of Pharmacological Research- IRCCS Milano - Italy
2 A first attempttoapplythe sewage epidemiologyapproachin doping Compare urban waste water samples with samples taken in sites during sport events. Major methodological problems: very small populations (hundreds ), only spot sampling available, presence of mixed population. This study tried to obtain a first results about the presence of significative chemicals in waste waters from amateur sport sites.
3 Sampling site 1 Sampling well of sewage waters in the University Sport Center (CUS) - Università della Calabria - Arcavacata di Rende (Cs) South of Italy. Practised sports: basket, volley, football, rugby, martial arts etc. People: about 150 athletes/day; age: 18-25, mostly registered to the University, with some external addition. 2 samplings: june and october 2011
4 Sampling site 2 Sampling well of sewage waters, School Camp (FIDAL), Via degli Stadi, Cosenza - Italy. Samplings: a) Regional Athletics Masters (june 2011); about 200 participants, age b) Italian Athletics Masters (october 2011); about 2500 participants, age Praticed sports: shot put, discus, javelin, hammer throw, high and long jump, all running specialities (short and long distances).
5 Compounds analyzed Doping substances: anabolic steroids, aromatase inhibitors Pharmaceuticals: anti-acids, antibiotics, anti-convulsive, analgesics, anti-hyperlipidemics, β-blockers, diuretics Illicit drugs: amphetamines, cocaine, morphine, codeine, cannabinoids
6 Doping substances Anabolic steroids α- and β-testosterone androstenedione α- and β-boldenone α- and β-19-nortestosterone β-trenbolone 17-α-methyltestosterone 4-chloro-1,2-dehydromethyltestosterone mesterolone methandrostenolone oxymetolone Aromatase inhibitors anastrozole exemestane letrozole
7 Some steroids and aromatase inhibitors structures
8 Sample preparation 1. Double filtration (1.2 e 0.45 μm) 2. Internal standars spiking 3. Acidification (HCl 37%), purification and pre-concentration with SPE (Oasis)
9 Instrumental analysis HPLC-MS Quantitative analysis Triple quadrupole API-5500 Qualitative analysis High resolution LTQ-Orbitrap XL
10 Quantitation by MRM using a triple quadrupole
11 Isotopic dilution Addition of known amounts of isotope labelled substances
12 MS/MS instrumental conditions Substance declustering potential (DP) (V) Precursor ion (m/z) Product ion I (m/z) and collision energy (ev) Product ion II (m/z) and collision energy (ev) β-trenbolone (34) (44) α-19-nortestosterone β-19-nortestosterone α-boldenone β-boldenone α-testosterone β-testosterone β-testosterone-d3 (IS) (32) (32) (32) (32) 97.0 (28) 97.0 (28) 97.0 (28) 79.0 (62) 79.0 (62) (20) (20) (32) (32) (32) Methandrostenolone (40) (22) 17α-methyltestosterone 17α-methylestosterone-d3 (IS) (32) 97.0 (32) (34) (34) Mesterolone (66) (30) Oxymetolone (40) 43.0 (120) 4-chloro-1-dehydro-17αmethyltestosterone (44) (44) Anastrozole (32) (76) Exemestane (26) (22) Letrozole (20) (44)
13 HPLC conditions for quantitative analysis Column: Xterra MS C18, 100x1 mm, 3.5 μm Eluent A: acetic acid (0.1%) in water Eluent B: acetonitrile Agilent API 5500 ESI source triple quadrupole
14 Substance Retention time (min.) Method characteristics LOQ in samples (ng/l) Relative Standard Deviation % "intraday" Relative Standard Deviation % "interday" Recovery tests from water samples Reccovery % SD % 17-α-methyltestosterone chloro-1,2-dehydrometiltestosterone α-19-nortestosterone α-boldenone α-testosterone anastrozolo androstenedione β-19-nortestosterone β-boldenone β-testosterone exemestane letrozole mesterolone methandrostenolone trenbolone oxymetolone
15 HPLC-MRM chromatograms of a standard mix of steroids [API 5500 positive ions] XIC of +MRM (38 pairs): / Da ID: Androstenedione 1 from Sample 1 (06 St_ pg) of 06 St_ pg.wiff (... Max. 1.9e5 cps. Intensity, cps e5 1.5e5 1.0e5 androstenedione 5.0e Time, min XIC of +MRM (38 pairs): / Da ID: Boldenone 1 from Sample 1 (06 St_ pg) of 06 St_ pg.wiff (Turb... Max. 2.4e5 cps. Intensity, cps Intensity, cps Intensity, cps 2.0e5 1.0e5 β - boldenone α - boldenone Time, min XIC of +MRM (38 pairs): / Da ID: Testosterone 1 from Sample 1 (06 St_ pg) of 06 St_ pg.wiff (Tur... Max. 2.9e5 cps. 2.9e5 2.0e5 1.0e Time, min XIC of +MRM (38 pairs): / Da ID: Testosterone-D3 1 from Sample 1 (06 St_ pg) of 06 St_ pg.wiff (... Max. 2.2e5 cps. 2.0e5 1.0e5 β - testosterone Time, min α - testosterone testosterone D3
16 HPLC-MRM chromatograms of a waste water sample [API 5500 positive ions] I n t e n s i t y, I n c t p e s n s i t y, I c n p t e s n s i t y, c p s XIC of +MRM (38 pairs): / Da ID: Boldenone 1 from Sample 1 (18 Mi_Nosedo_10) of 18 Mi_Nosedo_10.wiff (Turbo S e6 1.0e6 5.0e5 β - boldenone α - boldenone Max. 1.4e6 cps Time, min XIC of +MRM (38 pairs): / Da ID: Androstenedione 1 from Sample 1 (18 Mi_Nosedo_10) of 18 Mi_Nosedo_10.wiff (Tur... Max. 8.4e5 cps. 8.0e5 6.0e5 4.0e5 2.0e Time, min XIC of +MRM (38 pairs): / Da ID: Testosterone 1 from Sample 1 (18 Mi_Nosedo_10) of 18 Mi_Nosedo_10.wiff (Turbo... Max. 2.5e5 cps. 2.5e5 2.0e5 1.5e5 β - testosterone 1.0e e Time, min androstenedione α - testosterone
17 Resultsforthe analysisofdoping substances α- and β-testosterone, androstenedione and α- and β-boldenone were found in similar concentrations in all samples coming from sport sampling sites. α-testosterone and androstenedione are metabolic products of β-testosterone α- and β-boldenone are not normally present in natural conditions. None of the other artificial anabolic steroids and aromatase inhibitors were found.
18 Result comparisons boldenone and testosterone Urban and sport sites waste waters (ng/l) β-boldenone α-boldenone β-testosterone α-testosterone CUS event Calabria (Site 1) Master events Calabria (Site 2) Milano waste Bologna waste Cagliari waste water plant (mean) water plant (mean) water plant (mean)
19 Boldenone and testosterone concentrations in urine and waste waters Human urine (non diluted (ng/ml) Human urine (non diluted) incubated with β-glucoronidase /arylsulfatase(ng/ml) Human urine diluted 5 timeswithwaste water and incubated (ng/ml) Wastewater used for dilution (ng/ml) β-boldenone < α-boldenone < β-testosterone α-testosterone < 0.4
20 Finalconsiderationsabout anaboliccompoundsin wastewaters The only anabolic compounds identified in waste waters are β-testosterone and some of its metabolic and/or bacterial products (α-testosterone, α- boldenone and β-boldenone). A comparison with data from urban waste waters and a sample of normal clean urine showed that boldenone is most probably derived from testosterone excretion of normal individuals and subsequent bacterial transformation in waste waters, not from its use as anabolic agent.
21 Pharmaceuticals in urban and sport sites waste waters (ng/l) CUS event Calabria (Site 1) Master events Calabria (Site 2) Milano waste water plant
22 Considerationsaboutpharmaceuticals in wastewatersduringsport events Most of the pharmaceuticals found in waste waters of general population are also present in samples from sport dedicated areas There is a trend toward (to be confirmed) of a higher levels of consumption of analgesic/anti-inflammatory drugs, despite a prevalence of a young healthy population in one of the sampling sites Also the presence of high concentrations of β-blockers and diuretics should be confirmed Anti hyperlipidemics are less used among sport practising people.
23 Results - Illicit drugs in waste waters (ng/l) CUS event Calabria (Site 1) Master events Calabria (Site 2) Milano waste water plant 100 0
24 Considerationsaboutillicitdrugsin wastewatersduringsport events Measurable levels of illicit drugs residues were found in this study (cocaine, morphine, cannabis) In contrast with levels found in large urban settings (Milano) cannabis use looks higher than cocaine Illicit drug consumption is higher in younger amateur athletes.
25 Qualitative analysis with LTQ Orbitrap XL - nano-esi source Column: Zorbax SB C18, 50x0.5 mm, 5 μm Eluente A: formic acid (0.05%) in water Eluente B: acetonitrile
26 LTQ- Orbitrap scheme
27 Quadrupoleand Orbitrapresolutions Quadrupole Orbitrap
28 LTQ-Orbitrap analysis TIC - FTMS TIC MS2 β-boldenone α-boldenone cocaina
29 Boldenone confirmation by high resolution HPLC-MS β-boldenone FT-MS MS2 spectrum
30 LTQ ORBITRAP XL Mario Negri
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