Abstract
A pair of permanently positively charged stable isotope labeling (SIL) agents, 2-(4-(((2,5-dioxopyrrolidin-1-yl)oxy)carbonyl)phenyl)-1,3-dimethyl-benzimidazolium iodides (d0-DPDBM) and its deuterated counterpart d6-DPDBM, were designed and synthesized for the analysis of bisphenols with the aid of ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC–MS/MS). The UHPLC–MS/MS sensitivity of bisphenols was enhanced due to the introduction of positively charged DPDBM moiety into the molecules. Bisphenols were purified by a simple n-hexane extraction and subsequent alkaline back-extraction method, which could remove both hydrophilic and hydrophobic matrices. Matrix effect was effectively minimized by this strategy and the SIL strategy during which samples and standards experienced identical ionization process. The developed method was applied to the simultaneous determination of bisphenols in food and food contact materials with limits of detection (LODs) of 1.5–6.5 ng·L−1, and the limits of quantitation (LOQs) of 4.9 − 21.5 ng·L−1. Correlation coefficients for all analytes were higher than 0.9964. The intra-day precision for all analytes was in the range of 2.7–4.1%, whereas the inter-day precision was in the range of 4.6–6.3%. The recoveries were in the range of 90.2 − 96.4%, and the matrix effects for all analytes ranged from –5.6 to 4.5%.
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All data generated or analyzed during this study are included in this published article (and its supplementary information files).
References
Alshana U, Ertas N, Goger NG (2015) Determination of parabens in human milk and other food samples by capillary electrophoresis after dispersive liquid-liquid microextraction with back-extraction. Food Chem 181:1–8. https://doi.org/10.1016/j.foodchem.2015.02.074
Ao J, Zhang Q, Tang W, Yuan T, Zhang J (2021) A simple, rapid and sensitive method for the simultaneous determination of eighteen environmental phenols in human urine. Chemosphere 278:130494. https://doi.org/10.1016/j.chemosphere.2021.130494
Bjornsdotter MK, de Boer J, Ballesteros-Gomez A (2017) Bisphenol A and replacements in thermal paper: a review. Chemosphere 182:691–706. https://doi.org/10.1016/j.chemosphere.2017.05.070
Caban M, Stepnowski P (2020) The application of isotopically labeled analogues for the determination of small organic compounds by GC/MS with selected ion monitoring. Anal Methods 12:3854–3864. https://doi.org/10.1039/d0ay00723d
Chen S, Kong H, Lu X, Li Y, Yin P, Zeng Z, Xu G (2013) Pseudotargeted metabolomics method and its application in serum biomarker discovery for hepatocellular carcinoma based on ultra high-performance liquid chromatography/triple quadrupole mass spectrometry. Anal Chem 85:8326–8333. https://doi.org/10.1021/ac4016787
Chen X, Chen W, Lu S, Tang Z, Zhu Z, Zhong W, Kang L, Liao S (2019) Development and validation of HPLC–MS/MS method for the simultaneous determination of 8-hydroxy-2′-deoxyguanosine and twelve cosmetic phenols in human urine. Chromatographia 82:1415–1421. https://doi.org/10.1007/s10337-019-03757-2
den Braver-Sewradj SP, van Spronsen R, Hessel EVS (2020) Substitution of bisphenol A: a review of the carcinogenicity, reproductive toxicity, and endocrine disruption potential of alternative substances. Crit Rev Toxicol 50:128–147. https://doi.org/10.1080/10408444.2019.1701986
Donato FF, Martins ML, Munaretto JS, Prestes OD, Adaime MB, Zanella R (2015) Development of a multiresidue method for pesticide analysis in drinking water by solid phase extraction and determination by gas and liquid chromatography with triple quadrupole tandem mass spectrometry. Journal of the Brazilian Chemical Society. https://doi.org/10.5935/0103-5053.20150192
El-Maghrabey MH, Kishikawa N, Kuroda N (2020) Current trends in isotope-coded derivatization liquid chromatographic-mass spectrometric analyses with special emphasis on their biomedical application. Biomed Chromatogr 34:e4756. https://doi.org/10.1002/bmc.4756
Gallo P, Di Marco PI, Esposito F, Fasano E, Scognamiglio G, Mita GD, Cirillo T (2017) 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 220:406–412. https://doi.org/10.1016/j.foodchem.2016.10.005
Gao S, Zhang ZP, Karnes HT (2005) Sensitivity enhancement in liquid chromatography/atmospheric pressure ionization mass spectrometry using derivatization and mobile phase additives. J Chromatogr B 825:98–110. https://doi.org/10.1016/j.jchromb.2005.04.021
Gonzalez O, van Vliet M, Damen CW, van der Kloet FM, Vreeken RJ, Hankemeier T (2015) Matrix effect compensation in small-molecule profiling for an LC-TOF platform using multicomponent postcolumn infusion. Anal Chem 87:5921–5929. https://doi.org/10.1021/ac504268y
Hao Z, Xiao Y, Jiang L, Bai W, Huang W, Yuan L (2017) Simultaneous determination of bisphenol A, bisphenol F, 4-nonylphenol, 4-n-nonylphenol, and octylphenol in grease-rich food by Carb/PSA solid-phase extraction combined with high-performance liquid chromatography tandem mass spectrometry. Food Anal Methods 11:589–597. https://doi.org/10.1007/s12161-017-1029-5
Ji Z, Cheng J, Song C, Hu N, Zhou W, Suo Y, Sun Z, You J (2019) A highly sensitive and selective method for determination of phenoxy carboxylic acids from environmental water samples by dispersive solid-phase extraction coupled with ultra high performance liquid chromatography-tandem mass spectrometry. Talanta 191:313–323. https://doi.org/10.1016/j.talanta.2018.08.055
Li Q, Liu J, Zhang L, Shi Y, Li G (2022) Click isotope mass probe for highly selective determination of trace steroid hormones in food samples. J. Agric. Food Chem. https://doi.org/10.1021/acs.jafc.1c07323
Li Y, Ruan Q, Li Y, Ye G, Lu X, Lin X, Xu G (2012a) A novel approach to transforming a non-targeted metabolic profiling method to a pseudo-targeted method using the retention time locking gas chromatography/mass spectrometry-selected ions monitoring. J. Chromatogr. A 1255:228-236. https://doi.org/10.1016/j.chroma.2012a.01.076
Li Y, Zhang S, Song C, You J (2012b) Determination of bisphenol A and alkylphenols in soft drinks by high-performance liquid chromatography with fluorescence detection. Food Anal Methods 6:1284–1290. https://doi.org/10.1007/s12161-012-9541-0
Ma C, Zhang S, Wu X, You J (2020) Permanently positively charged stable isotope labeling agents and its application in the accurate quantitation of alkylphenols migrated from plastics to edible oils. J Agric Food Chem 68:9024–9031. https://doi.org/10.1021/acs.jafc.0c03413
Munaretto JS, Ferronato G, Ribeiro LC, Martins ML, Adaime MB, Zanella R (2013) Development of a multiresidue method for the determination of endocrine disrupters in fish fillet using gas chromatography-triple quadrupole tandem mass spectrometry. Talanta 116:827–834. https://doi.org/10.1016/j.talanta.2013.07.047
Niu Y, Wang B, Zhao Y, Zhang J, Shao B (2017) Highly sensitive and high-throughput method for the analysis of bisphenol analogues and their halogenated derivatives in breast milk. J Agric Food Chem 65:10452–10463. https://doi.org/10.1021/acs.jafc.7b04394
Regueiro J, Wenzl T (2015) Determination of bisphenols in beverages by mixed-mode solid-phase extraction and liquid chromatography coupled to tandem mass spectrometry. J Chromatogr A 1422:230–238. https://doi.org/10.1016/j.chroma.2015.10.046
Russo G, Barbato F, Grumetto L (2016) Development and validation of a LC-FD method for the simultaneous determination of eight bisphenols in soft drinks. Food Anal Methods 9:2732–2740. https://doi.org/10.1007/s12161-016-0458-x
Sadeghi M, Nematifar Z, Fattahi N, Pirsaheb M, Shamsipur M (2015) Determination of bisphenol A in food and environmental samples using combined solid-phase extraction–dispersive liquid–liquid microextraction with solidification of floating organic drop followed by HPLC. Food Anal Methods 9:1814–1824. https://doi.org/10.1007/s12161-015-0357-6
Sang S, Yang CS (2008) Structural identification of novel glucoside and glucuronide metabolites of (-)-epigallocatechin-3-gallate in mouse urine using liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 22:3693–3699. https://doi.org/10.1002/rcm.3786
Tan D, Jin J, Wang L, He X, Guo C, Dhanjai LuX, Chen J (2018) Quantification of bisphenol A and its selected analogs in serum using pre-column derivatization with high-performance liquid chromatography and tandem mass spectrometry. J Sep Sci 42:991–998. https://doi.org/10.1002/jssc.201800847
Taylor PJ (2005) Matrix effects: the Achilles heel of quantitative high-performance liquid chromatography-electrospray-tandem mass spectrometry. Clin Biochem 38:328–334. https://doi.org/10.1016/j.clinbiochem.2004.11.007
Wang H, Li X, Shao M, Lin L, Mu T, Liu Y (2021) Simultaneous determination of 9 environmental pollutants including bisphenol A in vegetable oil by solid phase extraction-liquid chromatography-tandem mass spectrometry. Anal Methods 13:3527–3534. https://doi.org/10.1039/d1ay00801c
Wang Z, Cui M, Ma B, Yang L, Yu Y, Cui H, Jin D, Shang H, Li D (2022) Rapid and one-step screening of taxane compounds by a two-dimensional carbon microfiber fractionation system combined with tandem mass spectrometry. J Agric Food Chem 70:4774–4782. https://doi.org/10.1021/acs.jafc.2c00573
Xu J, Li J, Zhang R, He J, Chen Y, Bi N, Song Y, Wang L, Zhan Q, Abliz Z (2019) Development of a metabolic pathway-based pseudo-targeted metabolomics method using liquid chromatography coupled with mass spectrometry. Talanta 192:160–168. https://doi.org/10.1016/j.talanta.2018.09.021
Xuan Q, Hu C, Yu D, Wang L, Zhou Y, Zhao X, Li Q, Hou X, Xu G (2018) Development of a high coverage pseudotargeted lipidomics method based on ultra-high performance liquid chromatography-mass spectrometry. Anal Chem 90:7608–7616. https://doi.org/10.1021/acs.analchem.8b01331
Yang J, Jin W, Liu D, Zhong Q, Zhou T (2020) Enhanced pseudotargeted analysis using a segment data dependent acquisition strategy by liquid chromatography-tandem mass spectrometry for a metabolomics study of liquiritin in the treatment of depression. J Sep Sci 43:2088–2096. https://doi.org/10.1002/jssc.202000107
Zhang S, Li Y, You J, Wang H, Zheng Y, Suo Y (2012) Improved method for the extraction and determination of bromophenols in seafoods by high-performance liquid chromatography with fluorescence detection. J Agric Food Chem 60:10985–10990. https://doi.org/10.1021/jf302882f
Zhang J, Zhao C, Zeng Z, Luo P, Zhao Y, Zhao J, Li L, Lu X, Xu G (2016) Sample-directed pseudotargeted method for the metabolic profiling analysis of rice seeds based on liquid chromatography with mass spectrometry. J Sep Sci 39:247–255. https://doi.org/10.1002/jssc.201500858
Zhou W, Yang S, Wang P G (2017) Matrix effects and application of matrix effect factor. Bioanalysis 9: 1839-1844. https://doi.org/10.4155/bio-2017-0214
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The work was supported by National Natural Science Foundation of China (No. 31801624).
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Xueting Wang: methodology, data curation, formal analysis. Rui Chang: data curation, formal analysis, investigation, methodology. Zhongyin Ji: HPLC–MS/MS analysis. Jinying Song: synthesis. Fei Yuan: purification. Shijuan Zhang: conceptualization, supervision, writing–review and editing.
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Xueting Wang declares that she has no conflict of interest. Rui Chang declares that she has no conflict of interest. Zhongyin Ji declares that she has no conflict of interest. Jinying Song declares that she has no conflict of interest. Fei Yuan declares that she has no conflict of interest. Shijuan Zhang declares that she has no conflict of interest.
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Wang, X., Chang, R., Ji, Z. et al. Improved Extraction and Detection Method for Bisphenols Using Stable Isotope Labeling Technique. Food Anal. Methods 16, 281–292 (2023). https://doi.org/10.1007/s12161-022-02413-0
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DOI: https://doi.org/10.1007/s12161-022-02413-0