Skip to main content
Log in

A Zr(IV)-based porphyrinic metal-organic framework as a solid-phase sorbent for extraction of sulfonamides prior to their quantitation by LC-MS

  • Original Paper
  • Published:
Microchimica Acta Aims and scope Submit manuscript

Abstract

A porphyrinic metal–organic framework (PCN-224) was fabricated and used as an adsorbent for solid-phase extraction of ultratrace levels of polar sulfonamide antibiotics from food and drinking waters. The PCN-224 was characterized by scanning electron microscopy, Fourier transform infrared spectroscopy, and powder X-ray diffraction analyses. Parameters affecting the extraction efficiency were optimized. The sulfonamides were quantified by liquid chromatography-tandem mass spectrometry. Figures of merit include (a) low limits of detection (0.07–0.47 ng·L−1), (b) wide linear ranges (0.5–2000 ng·L−1), and (c) good repeatabilities (2.8%–6.7%) and reproducibilities (1.7%–5.1%). The method was successfully applied to the determination of sulfonamides in food and drinking water samples.

A Zr(IV)-based porphyrinic metal−organic framework (PCN-224) was synthesized from a Zr6 cluster and the H2TCPP ligand. It was used for solid-phase extraction of sulfonamides from food and drinking water samples coupled with liquid chromatography-tandem mass spectrometry (LC-MS/MS) for determination.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Chen ZH, Zhan CR, Guo P, Wang YX, Hu ZG (2007) Study on simultaneous determination of 13 sulfonamides residues in aquatic products by HPLC. J Food Sci 28:448–451

    CAS  Google Scholar 

  2. Ungemach F (2000) Figures on quantities of antibacterials used for different purposes in the EU countries and interpretation. Acta Vet Scand Suppl 93:89–97 discussion 97–98:111–117

    CAS  PubMed  Google Scholar 

  3. Kools SA, Moltmann JF, Knacker T (2008) Estimating the use of veterinary medicines in the European Union. Regul Toxicol Pharmacol 50(1):59–65

    Article  CAS  PubMed  Google Scholar 

  4. Zhou AX, Su XS, Gao S, Zhang YL, Lin XY, Zhang LY, An YL (2014) High performance liquid chromatography (HPLC) was used to determine four sulfonamide antibiotics in groundwater, soil and feces. Chin J Anal Chem 42:397–402

    CAS  Google Scholar 

  5. Li YW, Mo CH, Zhao N, Zhang RJ, Yi RH (2008) High performance liquid chromatography (HPLC) was used to determine the sulfonamide antibiotics in water and soil. Chin J Anal Chem 36:954–958

    Google Scholar 

  6. Lopes RP, Augusti DV, Souza LFD, Santos FA, Lima JA, Vargas EA, Augusti R (2011) Development and validation (according to the 2002/657/EC regulation) of a method to quantify sulfonamides in porcine liver by fast partition at very low temperature and LC-MS/MS. Anal Methods 3:606–613

    Article  CAS  Google Scholar 

  7. Lopes RP, Augusti DV, Oliveira AGM, Oliveira FAS, Vargas EA, Augusti R (2011) Development and validation of a methodology to qualitatively screening veterinary drugs in porcine muscle via an innovative extraction/clean-up procedure and LC-MS/MS analysis. Food Addit Contam A 28:1667–1676

    CAS  Google Scholar 

  8. Sun HW, Qi HJ, Li H (2013) Development of capillary electrophoretic method combined with accelerated solvent extraction for simultaneous determination of residual sulfonamides and their acetylated metabolites in aquatic products. Food Anal Methods 2013(6):1049–1055

    Article  Google Scholar 

  9. Zhang YP, Xu X, Qi X, Gao WQ, Sun S, Li XT, Jiang CF, Yu AM, Zhang HQ, Yu Y (2012) Determination of sulfonamides in livers using matrix solid-phase dispersion extraction high-performance liquid chromatography. J Sep Sci 35:45–52

    Article  CAS  PubMed  Google Scholar 

  10. Yu H, Mu H, Hu YM (2012) Determination of fluoroquinolones, sulfonamides, and tetracyclines multiresidues simultaneously in porcine tissue by MSPD and HPLC–DAD. J Pharm Anal 2:76–81

    Article  CAS  PubMed  Google Scholar 

  11. Aguileraluiz MM, Martínez VJL, Romerogonzález R, Garrido Frenich A (2012) Multiclass method for fast determination of veterinary drug residues in baby food by ultra-high-performance liquid chromatography–tandem mass spectrometry. Food Chem 132:2171–2180

    Article  CAS  Google Scholar 

  12. Lopes RP, Reyes RC, Romero-González R, Frenich AG, Vidal JLM (2012) Development and validation of a multiclass method for the determination of veterinary drug residues in chicken by ultra high performance liquid chromatography–tandem mass spectrometry. Talanta 89:201–208

    Article  CAS  PubMed  Google Scholar 

  13. Han J, Wang Y, Liu Y, Li YF, Lu Y, Yan YS, Ni L (2013) Ionic liquid-salt aqueous two-phase extraction based on salting-out coupled with high-performance liquid chromatography for the determination of sulfonamides in water and food. Anal Bioanal Chem 405:1245–1255

    Article  CAS  PubMed  Google Scholar 

  14. Arroyo-Manzanares N, Gámiz-Gracia L, García-Campaña AM (2014) Alternative sample treatments for the determination of sulfonamides in milk by HPLC with fluorescence detection. Food Chem 143:459–564

    Article  CAS  PubMed  Google Scholar 

  15. Xie W, Han C, Hou JB, Wang F, Qian Y, Xi JY (2012) Simultaneous determination of multiveterinary drug residues in pork meat by liquid chromatography-tandem mass spectrometry combined with solid phase extraction. J Sep Sci 35:3447–3454

    Article  CAS  PubMed  Google Scholar 

  16. D'Orazio G, Rocchi S, Fanali S (2012) Nano-liquid chromatography coupled with mass spectrometry: separation of sulfonamides employing non-porous core-shell particles. J Chromatogr A 1255:277–285

    Article  CAS  PubMed  Google Scholar 

  17. Frenich AG, Aguilera-Luiz MDM, Vidal JLM, Romero-González R (2010) Comparison of several extraction techniques for multiclass analysis of veterinary drugs in eggs using ultra-high pressure liquid chromatography–tandem mass spectrometry. Anal Chim Acta 661:150–160

    Article  CAS  Google Scholar 

  18. Hou J, Yan J, Zhang FS, Zhao Q, Chen HY, Zhang YQ, Li GJ, Li Y, Ding L (2014) Evaluation of intercalated α-zirconium phosphate as sorbent in separation and detection of sulfonamides in honey. Food Chem 150:58–64

    Article  CAS  PubMed  Google Scholar 

  19. Chen LG, Zhang XP, Sun L, Xu Y, Zeng QL, Wang H, Xu HY, Yu AM, Zhang HQ, Ding L (2009) Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer. J Agric Food Chem 57:10073–10080

    Article  CAS  PubMed  Google Scholar 

  20. Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM (2013) The chemistry and applications of metal-organic frameworks. Science 341:1230444

    Article  CAS  Google Scholar 

  21. Allendorf MD, Bauer CA, Bhaktaa RK, Houk RJT (2009) Luminescent metal–organic frameworks. Chem Soc Rev 38:1330–1352

    Article  CAS  PubMed  Google Scholar 

  22. Aziz-Zanjani MO, Mehdinia A (2014) A review on procedures for the preparation of coatings for solid phase microextraction. Microchim Acta 181:1169–1190

    Article  CAS  Google Scholar 

  23. Chen JJ, Wang LJ, Xu GJ, Wang X, Zhao RS (2018) Highly stable Zr(IV)-based porphyrinic metal organic frameworks as an adsorbent for the effective removal of gatifloxacin from aqueous solution. Molecules 23(937):1–11

    Google Scholar 

  24. Park J, Jiang Q, Feng DW, Mao LJ, Zhou HC (2016) Size-controlled synthesis of Porphyrinic metal−organic framework and functionalization for targeted photodynamic therapy. J Am Chem Soc 138:3518–3525

    Article  CAS  PubMed  Google Scholar 

  25. Zhao RS, Wang X, Yuan JP (2010) Highly sensitive determination of tetrabromobisphenol A and bisphenol A in environmental water samples by solid-phase extraction and liquid chromatography-tandem mass spectrometry. J Sep Sci 33:1652–1657

    Article  CAS  PubMed  Google Scholar 

  26. Sheridan R, Policastro B, Thomas S, Rice D (2008) Analysis and occurrence of 14 sulfonamide antibacterials and chloramphenicol in honey by solid-phase extraction followed by LC/MS/MS analysis. J Agric Food Chem 56:3509–3516

    Article  CAS  PubMed  Google Scholar 

  27. Turnipseed SB, Storey JM, Clark SB, Miller KE (2011) Analysis of veterinary drugs and metabolites in milk using quadrupole time-of-flight liquid chromatography-mass spectrometry. J Agric Food Chem 59:7569–7581

    Article  CAS  PubMed  Google Scholar 

  28. Zhao RS, Wang X, Wang X, Lin JM, Yuan JP, Chen LZ (2008) Using bamboo charcoal as solid-phase extraction adsorbent for the ultratrace-level determination of perfluorooctanoic acid in water samples by high-performance liquid chromatography–mass spectrometry. Anal Bioanal Chem 390:1671–1676

    Article  CAS  PubMed  Google Scholar 

  29. Xue Q, Qi YJ, Liu F (2015) Ultra-high performance liquid chromatography-electrospray tandem mass spectrometry for the analysis of antibiotic residues in environmental waters. Environ Sci Pollut Res 22:16857–16867

    Article  CAS  Google Scholar 

  30. García-Galána MJ, Díaz-Cruza MS, Barceló D (2010) Determination of 19 sulfonamides in environmental water samples by automated on-line solid-phase extraction-liquid chromatography–tandem mass spectrometry (SPE-LC–MS/MS). Talanta 81:355–366

    Article  CAS  Google Scholar 

  31. Hu SP, Zhao M, Xi YY, Mao QQ, Zhou XD, Chen DW, Yan PC (2017) Nontargeted screening and determination of sulfonamides: a dispersive micro solid-phase extraction approach to the analysis of milk and honey samples using liquid chromatography−high resolution mass spectrometry. J Agric Food Chem 65:1984–1991

    Article  CAS  PubMed  Google Scholar 

  32. He J, Tang H, You L, Zhan H, Zhu J, Lu K (2013) Fragment-imprinted microspheres for the extraction of sulfonamides. Microchim Acta 180(9–10):903–910

    Article  CAS  Google Scholar 

  33. Ling X, Zhang W, Chen Z (2016) Electrochemically modified carbon fiber bundles as selective sorbent for online solid-phase microextraction of sulfonamides. Microchim Acta 183(2):813–820

    Article  CAS  Google Scholar 

  34. Zhang CL, Wang Y (2008) Study on correlation between 1-octanol and water partition coefficient and molecular valance connectivity index for sulfonamides. Comput Appl Chem 25(11):1465–1468

    CAS  Google Scholar 

  35. Li YQ, Si HZ, Xiao YL, Liu CH, Xia CC, Li K, Qi YX (2009) Quantitative structure activity relationship models based on heuristic method and gene expression programming for the prediction of the pKa values of sulfa drugs. Acta Pharm Sin 44(5):486–490

    Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21777089 and 21477068), the Natural Science Foundation of Shandong Province (ZR2018MB040), the Key Research and Development Program of Shandong Province (2017GSF17107 and 2018GSF117036), and Shandong Province Taishan Scholar Program (ts201712063).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ru-Song Zhao.

Ethics declarations

The author(s) declare that they have no competing interests.

Electronic supplementary material

ESM 1

(DOC 28640 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Deng, ZH., Xu, GJ., Wang, XL. et al. A Zr(IV)-based porphyrinic metal-organic framework as a solid-phase sorbent for extraction of sulfonamides prior to their quantitation by LC-MS. Microchim Acta 185, 450 (2018). https://doi.org/10.1007/s00604-018-2985-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s00604-018-2985-1

Keywords

Navigation