A Phenolphthalein-Dummy Template Molecularly Imprinted Polymer for Highly Selective Extraction and Clean-Up of Bisphenol A in Complex Biological, Environmental and Food Samples
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemicals and Materials
2.2. Preparation of the PPMIP, BPAMIP, and Non-Imprinted Polymer (NIP)
2.3. Characterization of the PPMIP, BPAMIP, and NIP
2.4. Chromatographic Evaluation Experiments
2.5. Sorption Experiments
2.6. Analytical Procedures
2.6.1. Real Sample Preparation
2.6.2. SPE Procedure
2.6.3. HPLC Analyses
3. Results and Discussion
3.1. Characterization of the PPMIP, BPAMIP and NIP
3.2. Selectivity of the PPMIP and BPAMIP
3.3. Binding Properties of the PPMIP and NIP
3.4. Optimization of SPE Procedure
3.4.1. Selection of Sample Loading pH and Volume
3.4.2. Selection of Washing Solvent Volume
3.4.3. Selection of Elution Solvent Volume
3.5. Analysis of Spiked Biological, Environmental and Food Samples
4. Conclusions
Supplementary Materials
Author Contributions
Acknowledgments
Conflicts of Interest
References
- Hu, X.; Wu, X.; Yang, F.; Wang, Q.; He, C.; Liu, S. Novel surface dummy molecularly imprinted silica as sorbent for solid-phase extraction of bisphenol A from water samples. Talanta 2016, 148, 29–36. [Google Scholar] [CrossRef] [PubMed]
- Liao, C.; Liu, F.; Moon, H.B.; Yamashita, N.; Yun, S.; Kannan, K. Bisphenol analogues in sediments from industrialized areas in the United States, Japan, Korea: spatial and temporal distributions. Environ. Sci. Technol. 2012, 46, 11558–11565. [Google Scholar] [CrossRef] [PubMed]
- Liao, C.; Liu, F.; Kannan, K. Bisphenol S, a new bisphenol analogue, in paper products and currency bills and its association with bisphenol A residues. Environ. Sci. Technol. 2012, 46, 6515–6522. [Google Scholar] [CrossRef] [PubMed]
- Liao, C.; Kannan, K. Determination of free and conjugated of bisphenol A in human urine and serum by liquid chromatography-tandem mass spectrometry. Environ. Sci. Technol. 2012, 46, 5003–5009. [Google Scholar] [CrossRef] [PubMed]
- Chen, Y.; Fang, J.; Ren, L.; Fan, R.; Zhang, J.; Liu, G.; Zhou, L.; Chen, D.; Yu, Y.; Lu, S. Urinary bisphenol analogues and triclosan in children from south China and implications for human exposure. Environ. Pollut. 2018, 238, 299–305. [Google Scholar] [CrossRef] [PubMed]
- Yamazaki, E.; Yamashita, N.; Taniyasu, S.; Lam, J.; Lam, P.K.S.; Moon, H.B.; Jeong, Y.; Kannan, P.; Achyuthan, H.; Munuswamy, N. Bisphenol A and other bisphenol analogues including BPS and BPF in surface water samples from Japan, China, Korea and India. Ecotoxicol. Environ. Saf. 2015, 122, 565–572. [Google Scholar] [CrossRef] [PubMed]
- Wang, Q.; Zhu, L.; Chen, M.; Ma, X.; Wang, X.; Xia, J. Simultaneously determination of bisphenol A and its alternatives in sediment by ultrasound-assisted and solid phase extractions followed by derivatization using GC-MS. Chemosphere 2017, 169, 709–715. [Google Scholar] [CrossRef] [PubMed]
- Schecter, A.; Malik, N.; Haffner, D.; Smith, S.; Harris, T.R.; Paepke, O.; Birnbaum, L. Bisphenol a (BPA) in U.S. food. Environ. Sci. Technol. 2010, 44, 9425–9430. [Google Scholar] [CrossRef] [PubMed]
- Zimmers, S.M.; Browne, E.P.; O’Keefe, P.W.; Anderton, D.L.; Kramer, L.; Reckhow, D.A.; Arcaro, K.F. Determination of free bisphenol A (BPA) concentrations in breast milk of U. S. women using a sensitive LC/MS/MS method. Chemosphere 2014, 104, 237–243. [Google Scholar] [CrossRef] [PubMed]
- Yang, Y.; Guan, J.; Yin, J.; Shao, B.; Li, H. Urinary levels of bisphenol analogues in residents living near a manufacturing plant in south China. Chemosphere 2014, 112, 481–486. [Google Scholar] [CrossRef] [PubMed]
- Wu, Y.T.; Zhang, Y.H.; Zhang, M.; Liu, F.; Wan, Y.C.; Huang, Z.; Ye, L.; Zhou, Q.; Shi, Y.; Lu, B. Selective and simultaneous determination of trace bisphenol A and tebuconazole in vegetable and juice samples by membrane-based molecularly imprinted solid-phase extraction and HPLC. Food Chem. 2014, 164, 527–535. [Google Scholar] [CrossRef] [PubMed]
- Lorber, M.; Schecter, A.; Paepke, O.; Shropshire, W.; Christensen, K.; Birnbaum, L. Exposure assessment of adult intake of bisphenol A (BPA) with emphasis on canned food dietary exposures. Environ. Int. 2015, 77, 55–62. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Tamayo, F.G.; Turiel, E.; Martín-Esteban, A. Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: recent developments and future trends. J. Chromatogr. A 2007, 1152, 32–40. [Google Scholar] [CrossRef] [PubMed]
- Gallo, P.; Pisciottano, I.D.M.; Esposito, F.; Fasano, E.; Scognamiglio, G.; Mita, G.D.; Cirillo, T. Determination of BPA, BPB, BPF, BADGE and BFDGE in canned energy drinks by molecularly imprinted polymer cleaning up and UPLC with fluorescence detection. Food Chem. 2017, 220, 406–412. [Google Scholar] [CrossRef] [PubMed]
- Zhou, H.; Xu, Y.P.; Tong, H.W.; Liu, Y.X.; Han, F.; Yan, X.Y.; Liu, S.M. Direct synthesis of surface molecularly imprinted polymers based on vinyl-SiO2 nanospheres for recognition of bisphenol A. J. Appl. Polym. Sci. 2013, 128, 3846–3852. [Google Scholar] [CrossRef]
- Bi, X.; Liu, Z. Facile preparation of glycoprotein-imprinted 96-well microplates for enzyme-linked immunosorbent assay by boronate affinity-based oriented surface imprinting. Anal. Chem. 2014, 86, 959–966. [Google Scholar] [CrossRef] [PubMed]
- Yang, J.; Li, Y.; Wang, J.; Sun, X.; Cao, R.; Sun, H.; Huang, C.; Chen, J. Molecularly imprinted polymer microspheres prepared by Pickering emulsion polymerization for selective solid-phase extraction of eight bisphenols from human urine samples. Anal. Chim. Acta 2015, 872, 35–45. [Google Scholar] [CrossRef] [PubMed]
- Sun, H.; Li, Y.; Yang, J.; Sun, X.; Huang, C.; Zhang, X.; Chen, J. Preparation of dummy imprinted polymers by Pickering emulsion polymerization for the selective determination of seven bisphenols from sediment samples. J. Sep. Sci. 2016, 39, 2188–2195. [Google Scholar] [CrossRef] [PubMed]
- Yang, Y.; Yu, J.; Yin, J.; Shao, B.; Zhang, J. Molecularly imprinted solid-phase extraction for selective extraction of bisphenol analogues in beverages and canned food. J. Agric. Food Chem. 2014, 62, 11130–11137. [Google Scholar] [CrossRef] [PubMed]
- Li, J.; Zhang, X.B.; Liu, Y.X.; Tong, H.W.; Xu, Y.P.; Liu, S.M. Preparation of a hollow porous molecularly imprinted polymer using tetrabromobisphenol A as a dummy template and its application as SPE sorbent for determination of bisphenol A in tap water. Talanta 2013, 117, 281–287. [Google Scholar] [CrossRef] [PubMed]
- Sun, H.; Li, Y.; Huang, C.; Peng, J.; Yang, J.; Sun, X.; Zang, S.; Chen, J.; Zhang, X. Solid-phase extraction based on a molecularly imprinted polymer for the selective determination of four benzophenones in tap and river water. J. Sep. Sci. 2015, 38, 3412–3420. [Google Scholar] [CrossRef] [PubMed]
- Pichon, V. Selective sample treatment using molecularly imprinted polymers. J. Chromatogr. A 2007, 1152, 41–53. [Google Scholar] [CrossRef] [PubMed]
- Sun, X.; Wang, J.; Li, Y.; Yang, J.; Jin, J.; Shah, S.M.; Chen, J. Novel dummy molecularly imprinted polymers for matrix solid-phase dispersion extraction of eight fluoroquinolones from fish samples. J. Chromatogr. A 2014, 1359, 1–7. [Google Scholar] [CrossRef] [PubMed]
- Chen, L.; Xu, S.; Li, J. Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem. Soc. Rev. 2011, 40, 2922–2942. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Sambe, H.; Hoshina, K.; Hosoya, K.; Haginaka, J. Direct injection analysis of bisphenol A in serum by combination of isotope imprinting with liquid chromatography-mass spectrometry. Analyst 2005, 130, 38–40. [Google Scholar] [CrossRef] [PubMed]
- Sambe, H.; Hoshina, K.; Hosoya, K.; Haginaka, J. Simultaneous determination of bisphenol A and its halogenated derivatives in river water by combination of isotope imprinting and liquid chromatography-mass spectrometry. J. Chromatogr. A 2006, 1134, 16–23. [Google Scholar] [CrossRef] [PubMed]
- Yin, J.F.; Meng, Z.H.; Zhu, Y.S.; Song, M.Y.; Wang, H.L. Dummy molecularly imprinted polymer for selective screening of trace bisphenols in river water. Anal. Methods 2011, 3, 173–180. [Google Scholar] [CrossRef]
- Sun, X.; Wang, J.; Li, Y.; Jin, J.; Zhang, B.; Shah, S.M.; Wang, X.; Chen, J. Highly selective dummy molecularly imprinted polymers as a solid-phase extraction sorbent for five bisphenols in tap and river water. J. Chromatogr. A 2014, 1343, 33–41. [Google Scholar] [CrossRef] [PubMed]
- Hiratsuka, Y.; Funaya, N.; Matsunaga, H.; Haginaka, J. Preparation of magnetic molecularly imprinted polymers for bisphenol A and its analogues and their application to the assay of bisphenol A in river water. J. Pharm. Biomed. Anal. 2013, 75, 180–185. [Google Scholar] [CrossRef] [PubMed]
- Yu, D.; Hu, X.; Wei, S.; Wang, Q.; He, C.; Liu, S. Dummy molecularly imprinted mesoporous silica prepared by hybrid imprinting method for solid-phase extraction of bisphenol A. J. Chromatogr. A 2015, 1396, 17–24. [Google Scholar] [CrossRef] [PubMed]
- Sun, X.; Wang, J.; Li, Y.; Jin, J.; Yang, J.; Li, F.; Shah, S.M.; Chen, J. Highly class-selective solid-phase extraction of bisphenols in milk, sediment and human urine samples using well-designed dummy molecularly imprinted polymers. J. Chromatogr. A 2014, 1360, 9–16. [Google Scholar] [CrossRef] [PubMed]
- Rezaee, M.; Yamini, Y.; Shariati, S.; Esrafili, A.; Shamsipur, M. Dispersive liquid-liquid microextraction combined with high-performance liquid chromatography-UV detection as a very simple, rapid and sensitive method for the determination of bisphenol A in water samples. J. Chromatogr. A 2009, 1216, 1511–1514. [Google Scholar] [CrossRef] [PubMed]
- Reyes-Gallardo, E.M.; Lucena, R.; Cárdenas, S.; Valcárcel, M. Dispersive micro-solid phase extraction of bisphenol A from milk using magnetic nylon 6 composite and its final determination by HPLC-UV. Microchem. J. 2016, 124, 751–756. [Google Scholar] [CrossRef]
Template Molecule | IF Value for BPA | Sample Type | Reference |
---|---|---|---|
BPA | 6.4 | Human urine | [17] |
BPAP | About 4.0 | River sediment | [18] |
BPS | 8.7 | Tap and river water | [28] |
BPB | About 5.0 | River water | [29] |
BPAF | Not shown | Environmental water | [30] |
PP | 9.0 | Human urine, bovine serum, sediment, milk, edible oil and soybean sauce | This work |
Sample Type | LOD (ng·mL−1) | Spiked Level a (ng) | Sample 1 | Sample 2 | Sample 3 | |||
---|---|---|---|---|---|---|---|---|
Recovery (%) | RSD (%, n = 3) | Recovery (%) | RSD (%, n = 3) | Recovery (%) | RSD (%, n = 3) | |||
Human urine | 2.6 | 100 | 97.3 | 6.2 | 90.5 | 1.2 | 91.4 | 3.2 |
500 | 94.7 | 3.7 | 103.8 | 2.6 | 98.2 | 4.4 | ||
Bovine serum | 1.3 | 100 | 95.1 | 5.8 | 99.1 | 2.9 | 97.3 | 1.6 |
500 | 93.3 | 1.2 | 97.5 | 5.8 | 99.2 | 3.1 | ||
Sediment | 1.3 b | 100 | 103.4 | 2.2 | 104.7 | 4.3 | 97.9 | 1.3 |
500 | 91.2 | 3.5 | 95.7 | 1.6 | 98.1 | 5.7 | ||
Milk | 1.3 | 100 | 98.8 | 1.5 | 96.4 | 6.3 | 98.1 | 3.3 |
500 | 100.6 | 4.1 | 102.8 | 5.0 | 99.0 | 2.7 | ||
Edible oil | 2.6 | 100 | 96.1 | 2.9 | 94.6 | 4.8 | 97.2 | 6.0 |
500 | 103.2 | 7.7 | 106.9 | 6.4 | 100.4 | 5.2 | ||
Soybean sauce | 5.2 | 100 | 83.6 | 2.1 | 82.1 | 1.8 | 87.2 | 3.6 |
500 | 87.9 | 1.7 | 90.2 | 1.6 | 89.0 | 2.9 |
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Yang, J.; Li, Y.; Huang, C.; Jiao, Y.; Chen, J. A Phenolphthalein-Dummy Template Molecularly Imprinted Polymer for Highly Selective Extraction and Clean-Up of Bisphenol A in Complex Biological, Environmental and Food Samples. Polymers 2018, 10, 1150. https://doi.org/10.3390/polym10101150
Yang J, Li Y, Huang C, Jiao Y, Chen J. A Phenolphthalein-Dummy Template Molecularly Imprinted Polymer for Highly Selective Extraction and Clean-Up of Bisphenol A in Complex Biological, Environmental and Food Samples. Polymers. 2018; 10(10):1150. https://doi.org/10.3390/polym10101150
Chicago/Turabian StyleYang, Jiajia, Yun Li, Chaonan Huang, Yanna Jiao, and Jiping Chen. 2018. "A Phenolphthalein-Dummy Template Molecularly Imprinted Polymer for Highly Selective Extraction and Clean-Up of Bisphenol A in Complex Biological, Environmental and Food Samples" Polymers 10, no. 10: 1150. https://doi.org/10.3390/polym10101150