Citation: Qian-Chun Zhang, Ying-Yi Cheng, Gong-Ke Li, Xiao-Hua Xiao. Porous boronate affinity monolith for on-line extraction coupled to high-performance liquid chromatography for sensitive analysis of heterocyclic aromatic amines in food samples[J]. Chinese Chemical Letters, ;2015, 26(12): 1470-1477. doi: 10.1016/j.cclet.2015.10.023 shu

Porous boronate affinity monolith for on-line extraction coupled to high-performance liquid chromatography for sensitive analysis of heterocyclic aromatic amines in food samples

  • Corresponding author: Gong-Ke Li,  Xiao-Hua Xiao, 
  • Received Date: 25 August 2015
    Available Online: 27 October 2015

  • A novel on-line solid-phase microextraction-high-performance liquid chromatography (SPME-HPLC) system was developed for the determination of heterocyclic aromatic amines (HAAs) in food samples. A poly(vinylphenylboronic acid-co-ethylene glycol dimethacrylate) polymer monolith was prepared for on-line efficient extraction and large-volume injection was used to increase the sensitivity of detection. The polymermonolith, based on a ternary porogen, was prepared by in situ polymerization of vinylphenylboronic acid (VPBA) and ethylene glycol dimethacrylate (EGDMA) in a fused-silica capillary column. It showed good permeability, high extraction capacity, and high selectivity. The column-tocolumn reproducibility was satisfactory, and the enrichment factors for HAAs were 3746-7414. Conditions influencing the on-line extraction efficiency, including pH of sample solutions, flow rate of extraction and desorption, and desorption volume, were investigated. The proposed method had low limit of detection (0.10-0.15 ng/L) and good linearity. Trace HAAs in roast beef and lamb samples were determined, and the amounts of 2-amino-3-methylimidazo[4,5-f]quinoline, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline, 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline, 2-amino-3,4,8-trimethylimidazo[ 4,5-f]quinoxaline, and 2-amino-3,4,7,8-tetramethyl-3H-imidazo[4,5-f]quinoxaline in these samples were 0.235-2.08 ng/g. The recoveries for the five HAAs ranged from74.3% to 119%, and the relative standard deviation (RSDs) were less than 8.2%. The results showed that the proposed on-line method was highly sensitive for monitoring HAAs in different food samples.
  • 加载中
    1. [1]

      [1] T. Sugimura, Nutrition and dietary carcinogens, Carcinogenesis 21 (2000) 387- 395.

    2. [2]

      [2] L.R. Ferguson, M. Philpott, N. Karunasinghe, Dietary cancer and prevention using antimutagens, Toxicology 198 (2004) 147-159.

    3. [3]

      [3] K. Puangsombat, P. Gadgil, J. Scott Smith, et al., Occurrence of heterocyclic amines in cooked meat products, Meat Sci. 90 (2012) 739-746.

    4. [4]

      [4] A. Shin, M.J. Shrubsole, R.M. Ness, et al., Meat and meat-mutagen intake, doneness preference and the risk of colorectal polyps: the tennessee colorectal polyp study, Int. J. Cancer 121 (2007) 136-142.

    5. [5]

      [5] F. OZ, M. Kaya, Heterocyclic aromatic amines in meat, J. Food Process. Preserv. 35 (2011) 739-753.

    6. [6]

      [6] H. Kataoka, T. Inoue, N. Ikekita, K. Saito, Development of exposure assessment method based on the analysis of urinary heterocyclic amines as biomarkers by online in-tube solid-phase microextraction coupled with liquid chromatography- tandem mass spectrometry, Anal. Bioanal. Chem. 406 (2014) 2171-2178.

    7. [7]

      [7] Y.F. Fu, G. Zhao, S. Wang, et al., Simultaneous determination of fifteen heterocyclic aromatic amines in the urine of smokers and nonsmokers using ultra-high performance liquid chromatography-tandem mass spectrometry, J. Chromatogr., A 1333 (2014) 45-53.

    8. [8]

      [8] H. Kataoka, T. Inoue, K. Saito, et al., Analysis of heterocyclic amines in hair by online in-tube solid-phase microextraction coupled with liquid chromatography tandem mass spectrometry, Anal. Chim. Acta 786 (2013) 54-60.

    9. [9]

      [9] R. Gonzalo-Lumbreras, N. Rosales-Conrado, M.E. Leó n-Gonzá lez, et al., Capillary liquid chromatography with diode array and mass spectrometry detection for heterocyclic aromatic amine determination in ready-to-eat food treated with electron-beam irradiation, J. Chromatogr., A 1217 (2010) 6778-6784.

    10. [10]

      [10] A. Martín-Calero, P. Veró nica, A.M. Afonso, et al., Ionic liquids as mobile phase additives in high-performance liquid chromatography with electrochemical detection: application to the determination of heterocyclic aromatic amines in meat-based infant foods, Talanta 79 (2009) 590-597.

    11. [11]

      [11] A. Martín-Calero, J.H. Ayala, A.M. Afonso, et al., Determination of less polar heterocyclic amines in meat extracts: fast sample preparation method using solid-phase microextraction prior to high-performance liquid chromatography fluorescence quantification, Anal. Chim. Acta 582 (2007) 259-266.

    12. [12]

      [12] B. Janoszka, U. Blaszczyk, L. Warzecha, et al., Clean-up procedures for the analysis of heterocyclic aromatic amines (aminoazaarenes) from heat-treated meat samples, J. Chromatogr., A 938 (2001) 155-165.

    13. [13]

      [13] S. Casal, E. Mendes, J.O. Fernandes, et al., Analysis of heterocyclic aromatic amines in foods by gas chromatography-mass spectrometry as their tert-butyldimethylsilyl derivatives, J. Chromatogr., A 1040 (2004) 105-114.

    14. [14]

      [14] S. Hegstad, R. Reistad, J. Alexander, et al., Eumelanin is a major determinant for 2- amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) incorporation into hair of mice, Pharmacol. Toxicol. 90 (2002) 333-337.

    15. [15]

      [15] M. Kobayashi, T. Hanaoka, H. Hashimoto, S. Tsugane, 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) level in human hair as biomarkers for dietary grilled/stir-fried meat and fish intake, Mutat. Res. 588 (2005) 136-142.

    16. [16]

      [16] M. Kobayashi, T. Hanaoka, S. Tsugane, Validity of a self-administered food frequency questionnaire in the assessment of heterocyclic amine intake using 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) levels in hair, Mutat. Res. 630 (2007) 14-19.

    17. [17]

      [17] E.E. Bessette, I. Yasa, R.J. Turesky, et al., Biomonitoring of carcinogenic heterocyclic aromatic amines in hair: a validation study, Chem. Res. Toxicol. 22 (2009) 1454-1463.

    18. [18]

      [18] D. Gu, Z.L. Neuman, R.J. Turesky, et al., Biomonitoring the cooked meat carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in canine fur, J. Agric. Food Chem. 60 (2012) 9371-9375.

    19. [19]

      [19] L.B. Agudelo Mesa, J.M. Padró, M. Reta, Analysis of non-polar heterocyclic aromatic amines in beefburguers by using microwave-assisted extraction and dispersive liquid-ionic liquid microextraction, Food Chem. 141 (2013) 1694-1701.

    20. [20]

      [20] F. Oz, Quantitation of heterocyclic aromatic amines in ready to eat meatballs by ultra fast liquid chromatography, Food Chem. 126 (2011) 2010-2016.

    21. [21]

      [21] Q.C. Zhang, G.K. Li, X.H. Xiao, Acrylamide-modified graphene for online microsolid- phase extraction coupled to high-performance liquid chromatography for sensitive analysis of heterocyclic amines in food samples, Talanta 131 (2015) 127-135.

    22. [22]

      [22] A. Martín-Calero, J.H. Ayala, A.M. Afonso, et al., Ionic liquids as desorption solvents and memory effect suppressors in heterocyclic aromatic amines determination by SPME-HPLC fluorescence, Ana. Bioanal. Chem. 394 (2009) 937-946.

    23. [23]

      [23] Y.Y. Zhong, W.F. Zhou, Y. Zhu, et al., Trace analysis of anions in organic matrices by ion chromatography coupled with a novel reversed-phase column for on-line sample pretreatment, Chin. Chem. Lett. 22 (2011) 461-464.

    24. [24]

      [24] Ö . Ö zdestan, E. Kaçar, H. Keş kekoğlu, et al., Development of a new extraction method for heterocyclic aromatic amines determination in cooked meatballs, Food Anal. Method 7 (2014) 116-126.

    25. [25]

      [25] Q.B. Zhang, N. Tang, J.W.C. Brock, et al., Enrichment and analysis of nonenzymatically glycated peptides: boronate affinity chromatography coupled with electron-transfer dissociation mass spectrometry, J. Proteome Res. 6 (2007) 2323-2330.

    26. [26]

      [26] R. Tuytten, F. Lemiere, W. Van Dongen, et al., Development of an on-Line SPE-LC- ESI-MS method for urinary nucleosides: hyphenation of aprotic boronic acid chromatography with hydrophilic interaction LC-ESI-MS, Anal. Chem. 80 (2008) 1263-1271.

    27. [27]

      [27] O.G. Potter, M.C. Breadmore, E.F. Hilder, Boronate functionalised polymer monoliths for microscale affinity chromatography, Analyst 131 (2006) 1094-1096.

    28. [28]

      [28] X.T. Yang, Y.F. Hu, G.K. Li, Online micro-solid-phase extraction based on boronate affinity monolithic column coupled with high-performance liquid chromatography for the determination of monoamine neurotransmitters in human urine, J. Chromatogr., A 1342 (2014) 37-43.

    29. [29]

      [29] Z.A. Lin, H. Huang, G.N. Chen, et al., Preparation of phenylboronic acid-silica hybrid monolithic column with one-pot approach for capillary liquid chromatography of biomolecules, J. Chromatogr., A 1271 (2013) 115-123.

    30. [30]

      [30] L.B. Ren, Y.C. Liu, Z. Liu, et al., Synthesis of hydrophilic boronate affinity monolithic capillary for specific capture of glycoproteins by capillary liquid chromatography, J. Chromatogr., A 1216 (2009) 8421-8425.

    31. [31]

      [31] L.B. Ren, Z. Liu, Y.C. Liu, P. Dou, H.Y. Chen, Ring-opening polymerization with synergistic co-monomers: access to a boronate-functionalized polymeric monolith for the specific capture of cis-diol-containing biomolecules under neutral conditions, Angew. Chem. Int. Ed. 121 (2009) 6832-6835.

    32. [32]

      [32] Q.C. Zhang, X.H. Xiao, G.K. Li, Porous molecularly imprinted monolithic capillary column for on-line extraction coupled to high-performance liquid chromatography for trace analysis of antimicrobials in food samples, Talanta 123 (2014) 63-70.

    33. [33]

      [33] Y.L. Hu, Y.F. Fan, G.K. Li, Preparation and evaluation of a porous monolithic capillary column for microextraction of estrogens from urine and milk samples online coupled to high-performance liquid chromatography, J. Chromatogr., A 1228 (2012) 205-212.

    34. [34]

      [34] C. Cakal, J.P. Ferrance, P. Caglar, et al., Microchip extraction of catecholamines using a boronic acid functional affinity monolith, Anal. Chim. Acta 690 (2011) 94-100.

    35. [35]

      [35] Z.A. Lin, J.L. Pang, Y. Lin, et al., Preparation and evaluation of a phenylboronate affinity monolith for selective capture of glycoproteins by capillary liquid chromatography, Analyst 136 (2011) 3281-3288.

    36. [36]

      [36] Y.C. Liu, L.B. Ren, Z. Liu, A unique boronic acid functionalized monolithic capillary for specific capture, separation and immobilization of cis-diol biomolecules,, Chem Commun. 47 (2011) 5067-5069.

    37. [37]

      [37] H.Y. Li, Z. Liu, Recent advances in monolithic column-based boronate-affinity chromatography, TrAC. Trends Anal. Chem. 37 (2012) 148-161.

  • 加载中
    1. [1]

      Jiajia LvJie GaoHongyu LiZeli YuanNan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940

Metrics
  • PDF Downloads(0)
  • Abstract views(630)
  • HTML views(26)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return