Determination of macrolide antibiotics, their intermediates and transformation products in solid environmental matrices
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1 Determination of macrolide antibiotics, their intermediates and transformation products in solid environmental matrices Ivan Senta, I. Krizman, M. Ahel, N. Udiković-Kolić, S. Terzic Rudjer Boskovic Institute, Zagreb, Croatia ICCE, slo, 21 June 217 Page 1
2 Introduction Antibiotic residues in the environment possible contribution to selection and spread of antibiotic resistance Numerous analytical methods for determination of antibiotics in environmental samples Focus on parent compounds The contribution of transformation products (TPs), synthesis intermediates and byproducts to the total mass loads mostly unknown Page 2
3 Macrolide antibiotics Among the top 3 mostly consumed classes of antibiotics Incomplete removal during wastewater treatment and relatively high sorption affinity occurrence in sludge and sediments Erythromycin (ERY) Azithromycin (AZI) Clarithromycin (CLA) Roxithromycin (RX) Page 3
4 Metabolites and TPs N -desmethyl AZI (N -DMA) Anhydro ERY (ERY-H 2 ) N-desmethyl CLA (DMC) Descladinosyl AZI (DCA) ERY enol ether (EEE) Descladinosyl CLA (DCC) C H 3 H 3 C CH 3 H 3 C H N H H 3 C CH 3 CH H H 3 3 C H P H CH 3 H H N CH 3 CH 3 CH 3 CH 3 H CH 3 Phosphorylated AZI (AZI-P4) N-demethyl ERY (DME) ERY oxime (EX) Page 4
5 Intermediates in AZI synthesis Erythromycin (ERY) Azithromycin (AZI) Erythromycin oxime (EX) Erythromycin imino ether (EIE) N-desmethyl azithromycin (N-DMA) Page 5
6 Analytical procedure Sample (sediment, sludge) Addition of surrogate standards (AZI-d 3 and CLA-d 3 ) Pressurized liquid extraction (PLE) 1 % NH 3 in MeH 8 C, 15 psi Static time: 1 min 2 cycles Evaporation (N 2 ) and reconstitution LC-MS/MS analysis (ESI+, MRM) Page 6
7 MS/MS parameters (MRM) CMPUND ABBREVIATIN PRECURSR IN (m/z) PRDUCT IN 1 (m/z) CE 1 / V PRDUCT IN 2 (m/z) DESCLADINSYL AZITHRMYCIN DCA PHSPHRYLATED AZITHRMYCIN AZI-P N- DESMETHYL AZITHRMYCIN N-DMA N'- DESMETHYL AZITHRMYCIN N'-DMA AZITHRMYCIN AZI DESCLADINSYL CLARITHRMYCIN DCC ERYTHRMYCIN IMIN ETHER EIE N-DEMETHYL ERYTHRMYCIN DME ERYTHRMYCIN ERY ERYTHRMYCIN XIME EX ANHYDRERYTHRMYCIN ERY-H N'-DEMETHYL CLARITHRMYCIN DMC CLARITHRMYCIN CLA RXITHRMYCIN RX ERYTHRMYCIN ENL ETHER ERY-EE AZITHRMYCIN -d 3 AZI-d CLARITHRMYCIN -d 3 CLA-d CE 2 / V I. Senta, I.Krizman-Matasić, S. Terzic, M. Ahel, J Chromatogr A (in press, DI: 1.116/j.chroma ) Page 7
8 Relative Abundance Chromatographic separation D:\Data\...\16517_makrolidi_RW_SE\Std_7 17-May-16 21:43:29 1 pg/ul + I.S. 1 pg/ul RT: RT: 4.5 DCA RT: 9.9 RT: 1.8 RT: 1.8 RT: 11. AZI-P4 RT: 12.8 N-DMA N -DMA AZI RT: 13.8 RT: 14.5 AX DCC CLA-H RT: Time (min) D:\Data\...\16517_makrolidi_RW_SE\Std_7 17-May-16 21:43:29 1 pg/ul + I.S. 1 pg/ul NL: 5.17E5 RT: TIC F: + c ESI sid=14. 1 SRM ms @cid15. [ ] 5 NL: 2.18E5 TIC F: + c ESI sid=1. 1 SRM ms @cid35. [ ] 5 NL: 5.95E5 TIC F: + c ESI sid=14. 1 SRM ms @cid19. [ ] 5 NL: 1.2E6 TIC F: + c ESI sid=14. 1 SRM ms @cid16. [ ] 5 NL: 7.15E5 TIC F: + c ESI sid=8. 1 SRM ms @cid16. [ ] 5 NL: 4.E6 TIC F: + c ESI sid=14. 1 SRM ms @cid11. [ ] 5 NL: 4.66E6 TIC F: + c ESI sid=14. 1 SRM ms2 59.4@cid18. [ ] 5 NL: 2.51E5 TIC F: + p ESI sid=14. 1 SRM ms @cid33. [ ] 5 RT: 1.2 RT: 11.1 RT: 1.1 RT: 11. RT: 14.6 RT: 15.5 RT: 16.2 ERY-H2 RT: 16.8 EIE DME ERY EX RT: 19.6 RT: 21.8 RT: 23.6 RT: 22.9 RT: 23.1 DMC ERY-EE CLA RX Time (min) NL: 1.75E5 TIC F: + c ESI sid=14. SRM ms @cid8. [ ] NL: 1.18E6 TIC F: + c ESI sid=14. SRM ms2 72.5@cid24. [ ] NL: 2.31E4 TIC F: + c ESI sid=12. SRM ms @cid25. [ ] NL: 9.68E5 TIC F: + c ESI sid=14. SRM ms @cid16. [ ] NL: 1.72E6 TIC F: + c ESI sid=8. SRM ms @cid19. [ ] NL: 1.4E6 TIC F: + c ESI sid=14. SRM ms @cid23. [ ] NL: 2.6E6 TIC F: + c ESI sid=1. SRM ms @cid34. [ ] NL: 1.1E6 TIC F: + c ESI sid=8. SRM ms @cid42. [ ] Column: ACE C18 PFP (15 x 3 mm; 3 μm) Eleunt A:.1 % HCH in water Eluent B: ACN I. Senta, I.Krizman-Matasić, S. Terzic, M. Ahel, J Chromatogr A (in press, DI: 1.116/j.chroma ) Page 8
9 Recovery (%) Extraction recovery (preliminary experiments) 12 MeH ACN MeH + 1 % NH3 ACN + 1 % NH3 MeH/acetone 8/ Page 9
10 Method validation river sediment Compound Recovery (%) Matrix effect (%) Accuracy (%) MDL (μg/kg) MQL (μg/kg) DCA AZI-P N-DMA N'-DMA AZI DCC EIE EX ERY-H ERY-EE DMC CLA RX DME Spiking level: 2 ng/g, n=4 MDL = method detection limit; MQL = method quantification limit Page 1
11 c (μg/kg) Application to real samples suspended solids (WWTP of the city of Zagreb) Raw wastewater 1 Raw wastewater 2 Aeration tank 1 5 Page 11
12 c (μg/kg) Application to real samples sediments (Sava river) 1 9 Upstream Discharge Krapina confluence Zagreb Page 12
13 Conclusions The developed method allows quantitative determination of an extended range of macrolide compounds in solid environmental samples Several synthesis intermediates and TPs were determined for the first time Some of them significantly contributes to the overall mass balance of macrolides Pharmaceutical industry facilities can be important source of sediment pollution with antibiotics and related compounds Page 13
14 Acknowledgements Croatian Science Foundation: Project CMPASS (grant number IP ) Project WINAR (grant number UIP ) The staff of the wastewater treatment plant of the city of Zagreb Thank you for your attention! Page 14
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