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Solid-phase extraction combined with dispersive liquid-liquid microextraction and chiral liquid chromatography-tandem mass spectrometry for the simultaneous enantioselective determination of representative proton-pump inhibitors in water samples

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Abstract

This report describes, for the first time, the simultaneous enantioselective determination of proton-pump inhibitors (PPIs-omeprazole, lansoprazole, pantoprazole, and rabeprazole) in environmental water matrices based on solid-phase extraction combined with dispersive liquid-liquid microextraction (SPE-DLLME) and chiral liquid chromatography-tandem mass spectrometry. The optimized results of SPE-DLLME were obtained with PEP-2 column using methanol-acetonitrile (1/1, v/v) as elution solvent, dichloroethane, and acetonitrile as extractant and disperser solvent, respectively. The separation and determination were performed using reversed-phase chromatography on a cellulose chiral stationary phase, a Chiralpak IC (250 mm × 4.6 mm, 5 μm) column, under isocratic conditions at 0.6 mL min−1 flow rate. The analytes were detected in multiple reaction monitoring (MRM) mode by triple quadrupole mass spectrometry. Isotopically labeled internal standards were used to compensate matrix interferences. The method provided enrichment factors of around 500. Under optimal conditions, the mean recoveries for all eight enantiomers from the water samples were 89.3–107.3 % with 0.9–10.3 % intra-day RSD and 2.3–8.1 % inter-day RSD at 20 and 100 ng L−1 levels. Correlation coefficients (r 2) ≥ 0.999 were achieved for all enantiomers within the range of 2–500 μg L−1. The method detection and quantification limits were at very low levels, within the range of 0.67–2.29 ng L−1 and 2.54–8.68 ng L−1, respectively. This method was successfully applied to the determination of the concentrations and enantiomeric fractions of the targeted analytes in wastewater and river water, making it applicable to the assessment of the enantiomeric fate of PPIs in the environment.

Simultaneous enantioselective determination of representative proton-pump inhibitors in water samples

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References

  1. Pérez-Fernández V, Marchese S, Gentili A, García MÁ, Curini R, Caretti F, et al. Analysis of antithyroid drugs in surface water by using liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2014;1367:78–89.

    Article  Google Scholar 

  2. Gracia-Lor E, Sancho JV, Hernández F. Simultaneous determination of acidic, neutral and basic pharmaceuticals in urban wastewater by ultra high-pressure liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2010;1217:622–32.

    Article  CAS  Google Scholar 

  3. Celano R, Piccinelli AL, Campone L, Rastrelli L. Ultra-preconcentration and determination of selected pharmaceutical and personal care products in different water matrices by solid-phase extraction combined with dispersive liquid-liquid microextraction prior to ultra high pressure liquid chromatography tandem mass spectrometry analysis. J Chromatogr A. 2014;1355:26–35.

    Article  CAS  Google Scholar 

  4. Zhou JL, Maskaoui K, Lufadeju A. Optimization of antibiotic analysis in water by solid-phase extraction and high performance liquid chromatography-mass spectrometry/mass spectrometry. Anal Chim Acta. 2012;731:32–9.

    Article  CAS  Google Scholar 

  5. Varga R, Somogyvári I, Eke Z, Torkos K. Determination of antihypertensive and anti-ulcer agents from surface water with solid-phase extraction-liquid chromatography-electrospray ionization tandem mass spectrometry. Talanta. 2011;83:1447–54.

    Article  CAS  Google Scholar 

  6. Evans SE, Davies P, Lubben A, Kasprzyk-Hordern B. Determination of chiral pharmaceuticals and illicit drugs in wastewater and sludge using microwave assisted extraction, solid-phase extraction and chiral liquid chromatography coupled with tandem mass spectrometry. Anal Chim Acta. 2015;882:112–26.

    Article  CAS  Google Scholar 

  7. Kasprzyk-Hordern B, Kondakal VV, Baker DR. Enantiomeric analysis of drugs of abuse in wastewater by chiral liquid chromatography coupled with tandem mass spectrometry. J Chromatogr A. 2010;1217:4575–86.

    Article  CAS  Google Scholar 

  8. Ribeiro AR, Santos LH, Maia AS, Delerue-Matos C, Castro PM, Tiritan ME. Enantiomeric fraction evaluation of pharmaceuticals in environmental matrices by liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2014;1363:226–35.

    Article  CAS  Google Scholar 

  9. Caballo C, Sicilia MD, Rubio S. Enantioselective determination of representative profens in wastewater by a single-step sample treatment and chiral liquid chromatography-tandem mass spectrometry. Talanta. 2015;134:325–32.

    Article  CAS  Google Scholar 

  10. Petrie B, Barden R, Kasprzyk-Hordern B. A review on emerging contaminants in wastewaters and the environment: current knowledge, understudied areas and recommendations for future monitoring. Water Res. 2014;72:3–27.

    Article  Google Scholar 

  11. Kasprzyk-Hordern B. Pharmacologically active compounds in the environment and their chirality. Chem Soc Rev. 2010;39:4466–503.

    Article  CAS  Google Scholar 

  12. Huang Q, Wang Z, Wang C, Peng X. Chiral profiling of azole antifungals in municipal wastewater and recipient rivers of the Pearl River Delta. China Environ Sci Pollut Res Int. 2013;20:8890–9.

    Article  CAS  Google Scholar 

  13. Borgå K, Bidleman TF. Enantiomer fractions of organic chlorinated pesticides in arctic marine ice fauna, zooplankton, and benthos. Environ Sci Technol. 2005;39:3464–73.

    Article  Google Scholar 

  14. Liu T, Wang P, Lu Y, Zhou G, Diao J, Zhou Z. Enantioselective bioaccumulation of soil-associated fipronil enantiomers in Tubifex tubifex. J Hazard Mater. 2012;219-220:50-6.

  15. Hashim NH, Shafie S, Khan SJ. Enantiomeric fraction as an indicator of pharmaceutical biotransformation during wastewater treatment and in the environment--a review. Environ Technol. 2010;31:1349–70.

    Article  CAS  Google Scholar 

  16. Sachs G, Shin JM, Besancon M, Prinz C. The continuing development of gastric acid pump inhibitors. Aliment Pharmacol Ther. 1993;7:29–31.

    Google Scholar 

  17. Agranat II, Caner H. Intellectual property and chirality of drugs. Drug Discov Today. 1999;4:313–21.

    Article  CAS  Google Scholar 

  18. Andersson T, Weidolf L. Stereoselective disposition of proton pump inhibitors. Clin Drug Investig. 2008;28:263–79.

    Article  CAS  Google Scholar 

  19. Nödler K, Licha T, Bester K, Sauter M. Development of a multi-residue analytical method, based on liquid chromatography-tandem mass spectrometry, for the simultaneous determination of 46 micro-contaminants in aqueous samples. J Chromatogr A. 2010;1217:6511–21.

    Article  Google Scholar 

  20. Gros M, Petrović M, Barceló D. Development of a multi-residue analytical methodology based on liquid chromatography-tandem mass spectrometry (LC-MS/MS) for screening and trace level determination of pharmaceuticals in surface and wastewaters. Talanta. 2006;70:678–90.

    Article  CAS  Google Scholar 

  21. Barreiro JC, Vanzolini KL, Madureira TV, Tiritan ME, Cass QB. A column-switching method for quantification of the enantiomers of omeprazole in native matrices of waste and estuarine water samples. Talanta. 2010;82:384–91.

    Article  CAS  Google Scholar 

  22. Barreiro JC, Vanzolini KL, Cass QB. Direct injection of native aqueous matrices by achiral-chiral chromatography ion trap mass spectrometry for simultaneous quantification of pantoprazole and lansoprazole enantiomers fractions. J Chromatogr A. 2011;1218:2865–70.

    Article  CAS  Google Scholar 

  23. Fattahi N, Samadi S, Assadi Y, Hosseini MR. Solid-phase extraction combined with dispersive liquid-liquid microextraction-ultra preconcentration of chlorophenols in aqueous samples. J Chromatogr A. 2007;1169:63–9.

    Article  CAS  Google Scholar 

  24. Latrous EI, Atrache L, Ben Sghaier R, Bejaoui Kefi B, Haldys V, Dachraoui M, et al. Factorial design optimization of experimental variables in preconcentration of carbamates pesticides in water samples using solid phase extraction and liquid chromatography-electrospray-mass spectrometry determination. Talanta. 2013;117:392–8.

    Article  Google Scholar 

  25. Li Y, Dong F, Liu X, Xu J, Li J, Kong Z, et al. Simultaneous enantioselective determination of triazole fungicides in soil and water by chiral liquid chromatography/tandem mass spectrometry. J Chromatogr A. 2012;1224:51–60.

    Article  CAS  Google Scholar 

  26. Berijani S, Assadi Y, Anbia M, Milani Hosseini MR, Aghaee E. Dispersive liquid-liquid microextraction combined with gas chromatography-flame photometric detection. Very simple, rapid and sensitive method for the determination of organophosphorus pesticides in water. J Chromatogr A. 2006;1123:1–9.

    Article  CAS  Google Scholar 

  27. Rezaee M, Yamini Y, Faraji M. Evolution of dispersive liquid-liquid microextraction method. J Chromatogr A. 2010;1217:2342–57.

    Article  CAS  Google Scholar 

  28. Peng G, He Q, Al-Hamadani SM, Zhou G, Liu M, Zhu H, et al. Dispersive liquid-liquid microextraction method based on solidification of floating organic droplet for the determination of thiamphenicol and florfenicol in environmental water samples. Ecotoxicol Environ Saf. 2015;115:229–33.

    Article  CAS  Google Scholar 

  29. Zgoła-Grześkowiak A. Application of DLLME to isolation and concentration of non-steroidal anti-inflammatory drugs in environmental water samples. Chromatographia. 2010;72:671–8.

    Article  Google Scholar 

  30. Luo M, Liu D, Zhou Z, Wang P. A new chiral residue analysis method for triazole fungicides in water using dispersive liquid-liquid microextraction (DLLME). Chirality. 2013;25:567–74.

    Article  CAS  Google Scholar 

  31. Huang P, Zhao P, Dai X, Hou X, Zhao L, Liang N. Trace determination of antibacterial pharmaceuticals in fishes by microwave-assisted extraction and solid-phase purification combined with dispersive liquid-liquid microextraction followed by ultra-high performance liquid chromatography-tandem mass spectrometry. J Chromatogr B. 2016;1011:136–44.

    Article  CAS  Google Scholar 

  32. Liang N, Huang P, Hou X, Li Z, Tao L, Zhao L. Solid-phase extraction in combination with dispersive liquid-liquid microextraction and ultra-high performance liquid chromatography-tandem mass spectrometry analysis: the ultra-trace determination of 10 antibiotics in water samples. Anal Bioanal Chem. 2016;408:1701–13.

    Article  CAS  Google Scholar 

  33. Alves AC, Gonçalves MM, Bernardo MM, Mendes BS. Determination of organophosphorous pesticides in the ppq range using a simple solid-phase extraction method combined with dispersive liquid-liquid microextraction. J Sep Sci. 2011;34:2475–81.

    Article  CAS  Google Scholar 

  34. Carpinteiro I, Abuín B, Rodríguez I, Ramil M, Cela R. Mixed-mode solid-phase extraction followed by dispersive liquid-liquid microextraction for the sensitive determination of ethylphenols in red wines. J Chromatogr A. 2012;1229:79–85.

    Article  CAS  Google Scholar 

  35. Zhao RS, Diao CP, Chen QF, Wang X. Sensitive determination of amide herbicides in environmental water samples by a combination of solid-phase extraction and dispersive liquid-liquid microextraction prior to GC-MS. J Sep Sci. 2009;32:1069–74.

    Article  CAS  Google Scholar 

  36. Dixit S, Dubey R, Bhushan R. Normal and polar-organic-phase high-performance liquid chromatographic enantioresolution of omeprazole, rabeprazole, lansoprazole and pantoprazole using monochloro-methylated cellulose-based chiral stationary phase and determination of dexrabeprazole. Biomed Chromatogr. 2014;28:112–9.

    Article  CAS  Google Scholar 

  37. Balamurugan P, Basha KA, Jayachandran J, Gangrade M, Parthiban P. Simultaneous chemo/enantioseparation and assay of R-(+)-rabeprazole and related impurities in pharmaceutical formulations. Chromatographia. 2015;78:1–9.

    Article  Google Scholar 

  38. Sun L, Cao Y, Jiao H, Fang Y, Yang Z, Bian M, et al. Enantioselective determination of (R)- and (S)-lansoprazole in human plasma by chiral liquid chromatography with mass spectrometry and its application to a stereoselective pharmacokinetic study. J Sep Sci. 2015;38:3696–703.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the Large Instrument Sharing Service Construction Special of Shenyang Science and Technology Innovation Fund (No. F14-195-4-00) and the National Natural Science Foundation of China (No. 81503029).

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Authors and Affiliations

  1. School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, 110016, China

    Pengfei Zhao, Miaoduo Deng, Jia Yu, Xingjie Guo & Longshan Zhao

  2. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, Liaoning Province, 110016, China

    Peiting Huang

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Zhao, P., Deng, M., Huang, P. et al. Solid-phase extraction combined with dispersive liquid-liquid microextraction and chiral liquid chromatography-tandem mass spectrometry for the simultaneous enantioselective determination of representative proton-pump inhibitors in water samples. Anal Bioanal Chem 408, 6381–6392 (2016). https://doi.org/10.1007/s00216-016-9753-z

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