Analytical and Bioanalytical Chemistry. Electronic Supplementary Material
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1 Analytical and Bioanalytical Chemistry Electronic Supplementary Material Multi-residue enantiomeric analysis of human and veterinary pharmaceuticals and their metabolites in environmental samples by chiral liquid chromatography coupled with tandem mass spectrometry detection Dolores Camacho-Muñoz, Barbara Kasprzyk-Hordern 1
2 Table S1 Published enantioselective methods that employed AGP CSP and LC-MS/MS for the determination of cpacs in environmental matrices Compound Environmental matrix Sample treatment Analytical determination Method quantification limits Ibuprofen 1 Influent wastewater (1 ml) Effluent wastewater and river water (25 ml) SPE (Oasis HLB) LC-MS/MS (TQD) Chiral-AGP column (1 x 4 mm, 5 µm particle size) 1mM NH 4 OAc/ACN 98:2, v/v, (ph 7.);.2 ml/min 8-27 ng L -1 in wastewater 3-8 ng L -1 in river water Clotrimazole, econazole, miconazole, tebuconazole, propiconazole 2 Wastewater (1-2 ml) Sludge.1 g USE-SPE (Oasis HLB) UHPLC-MS/MS (TQD) Chiral-AGP column (1 x 4 mm, 5 µm particle size) 1mM NH 4 OAc/ACN 9:1, v/v, (ph 7.);.3 ml/min.3-1 ng L -1 in wastewater 3-29 ng g -1 in sewage sludge Ketoconazole 2 Deaminated metoprolol 3 Fluoxetine and norfluoxetine 4 Effluent wastewater (5 ml) Influent (2 ml) and effluent (5 ml) wastewater Chloramphenicol Soil (2 g) isomers 5 Plant samples (1 g) SPE (Oasis HLB) SPE (Evolute CX- 5 cartridges) Shaking- LLE Chiral-HSA column (1 x 2 mm, 5 µm particle size) LC-MS/MS (TQD) Chiral-AGP column (1 x 2 mm, 5 µm particle size) 1mM NH 4 OAc/MeOH 95:5: v/v, (ph 5.);.22 ml/min LC-MS/MS (TQD) Chiral-AGP column (1 x 2 mm, 5 µm particle size) 1mM NH 4 OAc/ACN 97:3, v/v, (ph 4.4);.22 ml/min LC-MS/MS (TQD) Chiral-AGP column (15 x 2 mm, 5 µm particle size) 1mM NH 4 OAc/ACN 98:2, v/v, (ph 4.);.4 ml/min 4.8 ng L -1 in effluent wastewater ng L -1 in influent wastewater.9-1. ng L -1 in effluent wastewater 2-5 ng g -1 TQD: Triple quadrupole detector; USE: Ultrasonic solvent extraction; LLE: liquid-liquid extraction; 1 Wang Z, Huang Q, Yu Y, Wang C, Ou W, Peng X (213) Environ Geochem Health 35:683 91; 2 Huang Q, Zhang K, Wang Z, Wang C, Peng X (212) Anal Bioanal Chem 43: ; 3 Barclay VKH, Tyrefors NL, Johansson IM, Pettersson CE (212) J Chromatogr A 1269:28 217; 4 Barclay VKH, Tyrefors NL, Johansson M, Pettersson CE (212) J Chromatogr A 1227: ; 5 Berendsen BJA, Zuidema T, de Jong J, Stolker LAM, Nielen MWF (211) Anal Chim Acta 7:
3 Table S2 Structures, molecular weighs, CAS numbers and physicochemical properties of the studied PACs Compound Structure CAS pk a Log K ow Solubility Uses (mg L -1 ) Anti-inflammatory drugs S-(+)-O-Desmethylnaproxen (M) C 13H 12O b 2.54 a 2296 a Metabolite 6α-Methylprednisolone C 22H 3O a 1.99 a 12 a Human/Veterinary Antibacterial drugs Amoxicillin C 16H 19N 3O 5S a.61 a 3433 a Human/Veterinary Ampicillin 3H2O C 16H 19N 3O 4S 3H 2O a 1.35 a 11 a Human/Veterinary 3
4 Table S2(Continued) Compound Structure CAS pk a Log K ow Solubility Uses (mg L -1 ) Danofloxacin C 19H 2FN 3O , 9.43 d.39 d 65.6 d Veterinary Penicillin G sodium salt C 16H 17N 2NaO 4S a 1.67 a 21 a Human/Veterinary Penicillin V potassium salt C 16H 17N 2O 5SK a 1.88 a 65 a Human/Veterinary Ceftiofur C 19H 17N 5O 7S a 2.5 a 4 e Veterinary 4
5 Table S2(Continued) Compound Structure CAS pk a Log K ow Solubility Uses (mg L -1 ) Doxycycline hyclate C 23H 29ClN 2O , 7.7, 9.5 f -3.4 b 63 b Human/Veterinary Erythromycin C 37H 67NO a 3.6 a 1437 a Human/Veterinary Minocycline HCl C 23H 28ClN 3O b.5 g g Human Oxytetracycline HCl C 22H 25ClN 2O a -.9 a 313 a Human/Veterinary 5
6 Table S2(Continued) Compound Structure CAS pk a Log K ow Solubility Uses (mg L -1 ) Tetracycline HCl C 22H 25ClN 2O a -1.3 a a Human/Veterinary 1R,2R-(-)-Chloramphenicol base C 9H 12N 2O n.a a 26 a Metabolite 1R,2S-(-)-Florfenicol C 12H 14Cl 2FNO 4S a -.12 a 132 h Veterinary Antifungal drug (+)-Griseofulvin C 17H 17ClO >9 i 2.18 i 8.64 i Veterinary 6
7 Table S3 Optimized MRM conditions for the analysis of the target analytes by LC-MS/MS Compound CV/CE MRM 1 (quantification) CV/CE MRM 2 (confirmation) Mode Amoxicillin 28/ > / > ESI + Ampicillin 44/1 35.3> / > 16.5 ESI + Ceftiofur 5/2 524.> /5 524.> 125. ESI + 1R,2R-(-)-Chloramphenicol base 3/ > / > 132. ESI + Danofloxacin 65/ > / > ESI + S-(+)-O-Desmethylnaproxen 2/1 215.> 17.5 ESI - Doxycycline hyclate 4/ > / >154. ESI + Erythromycin 12/ > / > ESI + 1R,2S-(-)-Florfenicol 25/ > / > 185. ESI + (+)-Griseofulvin 45/ > / > 165. ESI + 6α-Methylprednisolone 48/ > /2 375.> 357. ESI + Minocycline 44/ > ESI + Oxytetracycline 4/ > / > 21.4 ESI + Penicillin G 48/ > / > 176. ESI + Penicillin V 54/ > / > 16.1 ESI + Tetracycline 32/ > / > 427. ESI + Table S4 Linearity and range, enantiomeric fraction, instrumental and method detection and quantification limits Compound Linearity range (µg L -1 ) R 2 IDL S/N (µg L -1 ) IQL S/N (µg L -1 ) Surface water (n=3) MDL calc (ng L -1 ) MQL calc (ng L -1 ) Effluent wastewater (n=3) MDL calc (ng L -1 ) MQL calc (ng L -1 ) Amoxicillin a Ampicillin a Ceftiofur a R,2R-(-)-Chloramphenicol base b S-(+)-O-Desmethylnaproxen c R,2S-(-)-Florfenicol c Griseofulvin d α-Methylprednisolone d Penicillin G a Penicillin V a IS used: a Ketoprofen-d3, b Ifosfamide-d4, c Naproxen-d3, d Tetramisole-d5, : Enantiomeric fraction (x: mean, σ: standard deviation; Absolute shown in brackets); IDL S/N: Instrumental detection limit based on signal to noise approach; IQL S/N: Instrumental quantification limit based on signal to noise approach; MDL calc: Method detection limit; MQL calc: Method quantification limit 7
8 Table S5 Inter- and intra-day precision (RSD ), retention time and resolution of the studied PACs Intra-day RSD (n=3) 1 (μg L -1 ) 5 (μg L -1 ) 1 (μg L -1 ) 3 (μg L -1 ) 1 T (μg L -1 R (min) R S D1 D2 D3 D1 D2 D3 D1 D2 D3 D1 D2 D3 ) Inter-day RSD (n=9) Amoxicillin Ampicillin Ceftiofur R,2R-(-)-Chloramphenicol base S-(+)-O-Desmethylnaproxen R,2S-(-)-Florfenicol Griseofulvin α-Methylprednisolone Penicillin G Penicillin V T R: Retention time; R S: Resolution 5 (μg L -1 ) 1 (μg L -1 ) 3 (μg L -1 ) 8
9 Table S6 Recovery (), intra-day precision (RSD ), enantiomeric fraction and matrix effect () in surface water and effluent wastewater Surface water (n=3) Effluent wastewater (n=3) Recovery Recovery ME Recovery Recovery ME Compound () a () b () () c () d () Amoxicillin 35.8 ± ± Ampicillin 62.1 ± ± Ceftiofur 1.7 ± R,2R-(-)-Chloramphenicol base 26.5 ± ± ± ± S-(+)-O-Desmethylnaproxen 14.8 ± ± R,2S-(-)-Florfenicol Griseofulvin 98.1 ± ± α-Methylprednisolone ± ± Penicillin G ± n.a Penicillin V 38. ± n.a ME: Matrix effect; a Concentration level:.6 µg L -1 ; b Concentration level:.1 µg L -1 ; c Concentration level: 1.2 µg L -1 ; d Concentration level:.2 µg L -1 9
10 Conditioning and equilibration 4 ml methanol + 2 ml deionized water (ph 7.5) Sample load 5 ml filtered river water 25 ml filtered effluent wastewater 2 ml deionized water Wash 2 ml deionized water (5 NH 4 OH) Elution 1 4 x 1 ml methanol Elution 2 2 x 1 ml methanol (2 CH 2 O 2 ) HLB HLB HLB MAX HLB MAX Evaporation, reconstitution and injection on HPLC-MS/MS MAX MAX MAX Combine eluates Fig. S1 Flow chart Amoxicillin Ampicillin S-(+)-O-Desmethyl naproxen Penicillin G Ceftiofur Penicillin V Florfenicol Chloramphenicol base α-Methylprednisolone (+)-Griseofulvin Praziquantel-d11 E1 E2 E1 E2 E1 E Praziquantel E1 E2 E1 E2 E1 E (min) (min) (min) Fig. S2 Chromatogram of PACs sold as enantiomerically pure (except praziquantel) in standard solution (left) and surface water (center) and effluent wastewater (right) spiked at 3 μg L -1 of each enantiomer 1
11 12 1 Recovery () Pharmacologically active compound HLB (ph 7.5) HLB (ph 2.) MAX (ph 7.5) HLB-MAX (ph 7.5) MCX (ph 2.) Fig. S3 Optimization of SPE conditions 1. Enantiomeric fraction Pharmaceutically active compound HLB (ph 7.5) HLB (ph 2.) MAX (ph 7.5) HLB-MAX (ph 7.5) MCX (ph 2.) Fig. S4 Enantiomeric fraction of cpacs in different SPE conditions 11
12 1..8 Aminorex 1..8 Naproxen Tetramisole 1. Ketoprofen N-Dechloroethylifosfamide 1. Praziquantel Ifosfamide 1. Ibuprofen ,11-Dihydro-1-hydroxy carbamazepine Dihydroketoprofen E1+E2 E3 E Fexofenadine 1..8 Chloramphenicol Concentration (µg L -1 ) Concentration (µg L -1 ) Fig. S5 Enantiomeric fraction of cpacs in standard solutions prepared at different concentrations 12
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