Boronate affinity-based surface molecularly imprinted polymers using glucose as fragment template for excellent recognition of glucosides

Journal of Chromatography A

Volumn 1474, Issue , 2016, Pages 8-13

  Peng, Mijun ^a,b   Xiang, Haiyan ^c   Hu, Xin ^b   Shi, Shuyun ^b   Chen, Xiaoqing ^b  

^a JISHOU UNIVERSITY   (China)

^b CENTRAL SOUTH UNIVERSITY   (China)

^c SOUTHERN MEDICAL UNIVERSITY   (China)

Author keywords

Boronic acid; Glucoside; Segment template; Selective extraction; Surface molecularly imprinted polymers

Indexed keywords

ADSORPTION; CARBOHYDRATES; EXTRACTION; GLUCOSE; MASS TRANSFER; POLYMERS; SUGARS;

BORONIC ACID; GLUCOSIDE; SEGMENT TEMPLATE; SELECTIVE EXTRACTION; SURFACE MOLECULARLY IMPRINTED POLYMERS;

GLYCOSIDES;

BORONIC ACID DERIVATIVE; DAIDZEIN; GENISTEIN; GLUCOSE; GLUCOSIDE; GLYCITEIN; IRON OXIDE; MOLECULARLY IMPRINTED POLYMER; MONOMER; TETRAETHOXYSILANE; AFFINITY LABELING; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FERRIC ION; FERRIC OXIDE; POLYMER; SILANE DERIVATIVE;

ADSORPTION; AQUEOUS SOLUTION; ARTICLE; COVALENT BOND; CROSS LINKING; EXTRACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHILICITY; MAGNET; MOLECULAR RECOGNITION; PH; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SOYBEAN; AFFINITY LABELING; ALGORITHM; CHEMISTRY; MOLECULAR IMPRINTING; SOLID PHASE EXTRACTION; SURFACE PROPERTY; THERMODYNAMICS;

AFFINITY LABELS; ALGORITHMS; BORONIC ACIDS; FERRIC COMPOUNDS; GLUCOSE; GLUCOSIDES; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; MOLECULAR IMPRINTING; POLYMERS; SILANES; SOLID PHASE EXTRACTION; SOYBEANS; SURFACE PROPERTIES; THERMODYNAMICS;

EID: 84995679687     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2016.10.059     Document Type: Article

References (30)

1. [1] Hofer, B., Recent developments in the enzymatic O-glycosylation of flavonoids. Appl. Microbiol. Biotechnol. 100 (2016), 4269–4281.
2. [2] Li, H.M., Lee, J.K., Nie, L.J., Huo, Q., Ma, T., Sohng, J.K., Hong, Y.S., Wu, C.Z., Enzymatic synthesis of novel isobavachalcone glucosides via a UDP-glycosyltransferase. Arch. Pharm. Res. 38 (2015), 2208–2215.
3. [3] de Souza, L.M., Dartora, N., Scoparo, C.T., Gorin, P.A.J., Iacomini, M., Sassaki, G.L., Differentiation of flavonol glucoside and galactoside isomers combining chemical isopropylidenation with liquid chromatography–mass spectrometry analysis. J. Chromatogr. A 1447 (2016), 64–71.
4. [4] Zhao, H.D., Hu, X., Chen, X.Q., Shi, S.Y., Jiang, X.Y., Liang, X.J., Chen, W., Zhang, S.H., Analysis and improved characterization of minor antioxidants from leaves of Malus doumeri using a combination of major constituents’ knockout with high-performance liquid chromatography-diode array detector-quadrupole time-of-flight tandem mass spectrometry. J. Chromatogr. A 1398 (2015), 57–65.
5. [5] Barahona, F., Díaz-Álvarez, M., Turiel, E., Martín-Esteban, A., Molecularly imprinted polymer-coated hollow fiber membrane for the microextraction of triazines directly from environmental waters. J. Chromatogr. A 1442 (2016), 12–18.
6. [6] Contin, M., Bonelli, P., Lucangioli, S., Cukierman, A., Tripodi, V., Synthesis and characterization of molecularly imprinted polymer nanoparticles for coenzyme Q10 dispersive micro solid phase extraction. J. Chromatogr. A 1456 (2016), 1–9.
7. [7] Li, H., Hu, X., Zhang, Y.P., Shi, S.Y., Jiang, X.Y., Chen, X.Q., High-capacity magnetic hollow porous molecularly imprinted polymers for specific extraction of protocatechuic acid. J. Chromatogr. A 1404 (2015), 21–27.
8. [8] Safdarian, M., Ramezani, Z., Ghadiri, A.A., Facile synthesis of magnetic molecularly imprinted polymer: perphenazine template and its application in urine and plasma analysis. J. Chromatogr. A 1455 (2016), 28–36.
9. [9] Hu, X., Xie, L.W., Guo, J.F., Li, H., Jiang, X.Y., Zhang, Y.P., Shi, S.Y., Hydrophilic gallic acid-imprinted polymers over magnetic mesoporous silica microspheres with excellent molecular recognition ability in acqueous fruit juices. Food Chem. 179 (2015), 206–212.
10. [10] Xie, L.W., Guo, J.F., Zhang, Y.P., Hu, Y.C., You, Q.P., Shi, S.Y., Novel molecular imprinted polymers over magnetic mesoporous silica microspheres for selective and efficient determination of protocatechuic acid in Syzygium aromaticum. Food Chem. 178 (2015), 18–25.
11. [11] Bie, Z., Chen, Y., Ye, J., Wang, S., Liu, Z., Boronate-affinity glycan-oriented surface imprinting: a new strategy to mimic lectins for the recognition of an intact glycoprotein and its characteristic fragments. Angew. Chim. Int. Ed. 54 (2015), 10211–10215.
12. [12] Ji, W., Zhang, M., Liu, W., Wang, X., Duan, W., Xie, H., Wang, X., Development of hydrophilic magnetic molecularly imprinted polymers by directly coating onto Fe3O4 with a water-miscible functional monomer and application in a solid-phase extraction procedure for iridoid glycosides. RSC Adv. 6 (2016), 50487–50496.
13. [13] Ji, W., Zhang, M., Gao, Q., Cui, L., Chen, L., Wang, X., Preparation of hydrophilic molecularly imprinted polymers via bulk polymerization combined with hydrolysis of ester groups for selective recognition of iridoid glycosides. Anal. Bioanal. Chem. 408 (2016), 5319–5328.
14. [14] Ji, W., Ma, X., Zhang, J., Xie, H., Liu, F., Wang, X., Preparation of the high purity gingerols from ginger by dummymolecularly imprinted polymers. J. Chromatogr. A 1387 (2015), 24–31.
15. [15] You, Q.P., Peng, M.J., Zhang, Y.P., Guo, J.F., Shi, S.Y., Preparation of magnetic dummy molecularly imprinted polymers for selective extraction and analysis of salicyclic acid in Actinidia chinensis. Anal. Bioanal. Chem. 406 (2014), 831–839.
16. [16] Chen, L., Wang, X., Lu, W., Wu, X., Li, J., Molecular imprinting: perspectives and applications. Chem. Soc. Rev. 45 (2016), 2137–2211.
17. [17] Minami, K., Ihara, M., Kuroda, S., Tsuzuki, H., Ueda, H., Open-sandwich molecular imprinting: making a recognition matrix with antigen-imprinted antibody fragments. Bioconjugate Chem. 23 (2012), 1463–1469.
18. [18] Li, D.J., Chen, Y., Liu, Z., Boronate affinity materials for separation and molecular recognition: structure, properties and applications. Chem. Soc. Rev. 44 (2015), 8097–8123.
19. [19] Li, H.Y., Liu, Z., Recent advances in monolithic column-based boronate-affinity chromatography. Trend. Anal. Chem. 37 (2012), 148–161.
20. [20] Sun, X., Zhai, W., Fossey, J.S., James, T.D., Boronic acids for fluorescence imaging of carbohydrates. Chem. Commun. 52 (2016), 3456–3469.
21. [21] Li, L., Lu, Y., Bie, Z., Chen, H.Y., Liu, Z., Photolithographic boronate affinity molecular imprinting: a general and facile approach for glycoprotein imprinting. Angew. Chim. Int. Ed. 52 (2013), 7451–7454.
22. [22] Lin, Z.A., Wang, J., Tan, X.Q., Sun, L.X., Yu, R.F., Yang, H.H., Chen, G.N., Preparation of boronate-functionalized molecularly imprinted monolithic column with polydopamine coating for glycoprotein recognition and enrichment. J. Chromatogr. A 1319 (2013), 141–147.
23. [23] Wang, S.S., Ye, J., Bie, Z.J., Liu, Z., Affinity-tunable specific recognition of glycoproteins via boronate affinity-based controllable oriented surface imprinting. Chem. Sci. 5 (2014), 1135–1140.
24. [24] Bi, X.D., Liu, Z., Enzyme activity assay of glycoprotein enzymes based on a boronate affinity molecularly imprinted 96-well microplate. Anal. Chem. 86 (2014), 12382–12389.
25. [25] Kunath, S., Panagiotopoulou, M., Maximilien, J., Marchyk, N., Sänger, J., Haupt, K., Cell and tissue imaging with molecularly imprinted polymers as plastic antibody mimics. Adv. Healthc. Mater. 4 (2015), 1322–1326.
26. [26] Shinde, S., El-Schich, Z., Malakpour, A., Wan, W., Dizeyi, N., Mohammadi, R., Rurack, K., Wingren, A.G., Sellergren, B., Sialic acid-imprinted fluorescent core-shell particles for selective labeling of cell surface glycans. J. Am. Chem. Soc. 137 (2015), 13908–13912.
27. [27] Yin, D.Y., Wang, S.S., He, Y.J., Liu, J., Zhou, M., Ouyang, J., Liu, B.R., Chen, H.Y., Liu, Z., Surface-enhanced Raman scattering imaging of cancer cells and tissues via sialic acid-imprinted nanotags. Chem. Commun. 51 (2015), 17696–17699.
28. [28] Wang, S.S., Yin, D.Y., Wang, W.J., Shen, X.J., Zhu, J.J., Chen, H.Y., Liu, Z., Targeting and imaging of cancer cells via monosaccharide-imprinted fluorescent nanoparticles. Sci. Rep., 6, 2016, 22757.
29. [29] Liu, L.L., Shi, S.Y., Chen, X.Q., Peng, M.J., Analysis of tyrosinase binders from Glycyrrhiza uralensis root: evaluation and comparison of tyrosinase immobilized magneticfishing-HPLC and reverse ultrafiltration-HPLC. J. Chromatogr. B 932 (2013), 19–25.
30. [30] Ma, J., Wang, C., Wei, Y., Polyethyleneimine-facilitated high-capacity boronate affinity membrane and its application for the adsorption and enrichment of cis-diol-containing molecules. RSC Adv. 6 (2016), 43648–43655.