Volume 12 Issue 5
Nov.  2022
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Qiqin Wang, Lingjue Sun, Huihui Wu, Ning Deng, Xianglong Zhao, Jingwei Zhou, Tingting Zhang, Hai Han, Zhengjin Jiang. Rapid fabrication of zwitterionic sulfobetaine vinylimidazole-based monoliths via photoinitiated copolymerization for hydrophilic interaction chromatography[J]. Journal of Pharmaceutical Analysis, 2022, 12(5): 783-790. doi: 10.1016/j.jpha.2022.05.008
Citation: Qiqin Wang, Lingjue Sun, Huihui Wu, Ning Deng, Xianglong Zhao, Jingwei Zhou, Tingting Zhang, Hai Han, Zhengjin Jiang. Rapid fabrication of zwitterionic sulfobetaine vinylimidazole-based monoliths via photoinitiated copolymerization for hydrophilic interaction chromatography[J]. Journal of Pharmaceutical Analysis, 2022, 12(5): 783-790. doi: 10.1016/j.jpha.2022.05.008

Rapid fabrication of zwitterionic sulfobetaine vinylimidazole-based monoliths via photoinitiated copolymerization for hydrophilic interaction chromatography

doi: 10.1016/j.jpha.2022.05.008
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This work was supported by the National Natural Science Foundation of China (Grant Nos.: 82173773 and 82073806), the Natural Science Foundation of Guangdong Province, China (Grant Nos.: 2020A1515010569 and 2021A0505030039), and Science and Technology Program of Guangzhou, China (Grant No.: 202102020729).

  • Received Date: Dec. 06, 2021
  • Accepted Date: May 22, 2022
  • Rev Recd Date: May 17, 2022
  • Publish Date: May 28, 2022
  • Zwitterionic sulfobetaine-based monolithic stationary phases have attracted increasing attention for their use in hydrophilic interaction chromatography. In this study, a novel hydrophilic polymeric monolith was fabricated through photo-initiated copolymerization of 3-(3-vinyl-1-imidazolio)-1-propanesulfonate (SBVI) with pentaerythritol triacrylate using methanol and tetrahydrofuran as the porogenic system. Notably, the duration for the preparation of this novel monolith was as little as 5 min, which was significantly shorter than that required for previously reported sulfobetaine-based monoliths prepared via conventional thermally initiated copolymerization. Moreover, these monoliths showed good morphology, permeability, porosity (62.4%), mechanical strength (over 15 MPa), column efficiency (51,230 plates/m), and reproducibility (relative standard deviations for all analytes were lower than 4.6%). Mechanistic studies indicated that strong hydrophilic and negative electrostatic interactions might be responsible for the retention of polar analytes on the zwitterionic SBVI-based monolith. In particular, the resulting monolith exhibited good anti-protein adhesion ability and low nonspecific protein adsorption. These excellent features seem to favor its application in bioanalysis. Therefore, the novel zwitterionic sulfobetaine-based monolith was successfully employed for the highly selective separation of small bioactive compounds and the efficient enrichment of N-glycopeptides from complex samples. In this study, we prepared a novel zwitterionic sulfobetaine-based monolith with good performance and developed a simpler and faster method for preparation of zwitterionic monoliths.
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  • B. Li, Z. Yuan, P. Jain, et al., De novo design of functional zwitterionic biomimetic material for immunomodulation, Sci. Adv. 6 (2020), eaba0754
    S. Jiang, Z. Cao, Ultralow-fouling, functionalizable, and hydrolyzable zwitterionic materials and their derivatives for biological applications, Adv. Mater. 22 (2010) 920-932
    F. Zaccarian, M.B. Baker, M.J. Webber, Biomedical uses of sulfobetaine-based zwitterionic materials, Org. Mater. 2 (2020) 342-357
    H.S. Sundaram, X. Han, A.K. Nowinski, et al., One-step dip coating of zwitterionic sulfobetaine polymers on hydrophobic and hydrophilic surfaces, ACS Appl. Mater. Interfaces 6 (2014) 6664-6671
    R.A. Sonnenberg, S. Naz, L. Cougnaud, et al., Comparison of underivatized silica and zwitterionic sulfobetaine hydrophilic interaction liquid chromatography stationary phases for global metabolomics of human plasma, J. Chromatogr. A 1608 (2019), 460419
    E. Wikberg, J.J. Verhage, C. Viklund, et al., Grafting of silica with sulfobetaine polymers via aqueous reversible addition fragmentation chain transfer polymerization and its use as a stationary phase in HILIC, J. Separ. Sci. 32 (2009) 2008-2016
    D. Yu, Z. Guo, A. Shen, et al., Synthesis and evaluation of sulfobetaine zwitterionic polymer bonded stationary phase, Talanta 161 (2016) 860-866
    X. Liu, Y. Jiang, F. Zhang, et al. Preparation and evaluation of a polymer-based sulfobetaine zwitterionic stationary phase, J. Chromatogr. A 1649 (2021), 462229
    L. Qiao, X. Shi, G. Xu, Recent advances in development and characterization of stationary phases for hydrophilic interaction chromatography, Trends Anal. Chem. 81 (2016) 23-33
    K. Broeckhoven, G. Desmet, Advances and innovations in liquid chromatography stationary phase supports, Anal. Chem. 93 (2021) 257-272
    Q. Wang, K. Peng, W. Chen, et al., Development of double chain phosphatidylcholine functionalized polymeric monoliths for immobilized artificial membrane chromatography, J. Chromatogr. A 1479 (2017) 97-106
    Q. Wang, Q. Zhang, H. Huang, et al., Fabrication and application of zwitterionic phosphorylcholine functionalized monoliths with different hydrophilic crosslinkers in hydrophilic interaction chromatography, Anal. Chim. Acta 1101 (2020) 222-229
    Z. Zajickova, L. Novakova, F. Svec, Monolithic poly(styrene-co-divinylbenzene) columns for supercritical fluid chromatography-mass spectrometry analysis of polypeptide, Anal. Chem. 92 (2020) 11525-11529
    F. Svec, Y. Lv, Advances and recent trends in the field of monolithic columns for chromatography, Anal. Chem. 87 (2015) 250-273
    Q. Wang, K. Peng, N. Gan, et al., Rapid fabrication of versatile zwitterionic super-hydrophilic polymers by sole-monomer system for biomolecules separation, Chem. Eng. J. 396 (2020), 125121
    L. Sun, D. Xu, Y. Shen, et al., Photo-assisted generation of versatile zwitterionic carboxybetaine-based hypercrosslinked polymers for separation science, Chem. Eng. J. 431 (2022), 133374
    Q. Wang, H. Wu, K. Peng, et al., Hydrophilic polymeric monoliths containing choline phosphate for separation science applications, Anal. Chim. Acta 999 (2018) 184-189
    J. Guo, Q. Wang, D. Xu, et al., Recent advances in preparation and applications of monolithic chiral stationary phases, Trends Anal. Chem. 123 (2020), 115774
    Z. Jiang, N.W. Smith, P.D. Ferguson, et al., Hydrophilic interaction chromatography using methacrylate-based monolithic capillary column for the separation of polar analytes, Anal. Chem. 79 (2007) 1243-1250
    H.C. Foo, J. Heaton, N.W. Smith, et al., Monolithic poly(SPE-co-BVPE) capillary columns as a novel hydrophilic interaction liquid chromatography stationary phase for the separation of polar analytes, Talanta 100 (2012) 344-348
    Y. Lv, Z. Lin, F. Svec, “Thiol-ene” click chemistry: a facile and versatile route for the functionalization of porous polymer monoliths, Analyst 137 (2012) 4114-4118
    X. Wang, X. Lin, Z. Xie, Preparation and evaluation of a sulfoalkylbetaine-based zwitterionic monolithic column for CEC of polar analytes, Electrophoresis 30 (2009) 2702-2710
    C. Viklund, A. Sjögren, K. Irgum, et al., Chromatographic interactions between proteins and sulfoalkylbetaine-based zwitterionic copolymers in fully aqueous low-salt buffers, Anal. Chem. 73 (2001) 444-452
    C. Viklund, K. Irgum, Synthesis of porous zwitterionic sulfobetaine monoliths and characterization of their interaction with proteins, Macromolecules 33 (2000) 2539-2544
    Z.J. Jiang, N.W. Smith, P.D. Ferguson, et al., Novel highly hydrophilic zwitterionic monolithic column for hydrophilic interaction chromatography, J. Separ. Sci. 32 (2009) 2544-2555
    G. Yuan, Y. Peng, Z. Liu, et al., A facile and efficient strategy to enhance hydrophilicity of zwitterionic sulfoalkylbetaine type monoliths, J. Chromatogr. A 1301 (2013) 88-97
    H. Wu, H. Jin, G. Yuan, et al., Simultaneous quantification of urea and allantoin in cosmetic products by nano-HPLC using a highly hydrophilic monolith, J. Liq. Chromatogr. Relat. Technol. 41 (2018) 780-785
    Z.H. Liu, Y.B. Peng, T.T. Wang, et al., Preparation and application of novel zwitterionic monolithic column for hydrophilic interaction chromatography, J. Separ. Sci. 36 (2013) 262-269
    C. Liu, W. Chen, G. Yuan, et al., Influence of the crosslinker type on the chromatographic properties of hydrophilic sulfoalkylbetaine-type monolithic columns, J. Chromatogr. A 1373 (2014) 73-80
    H. Li, C. Liu, Q. Wang, et al., The effect of charged groups on hydrophilic monolithic stationary phases on their chromatographic properties, J. Chromatogr. A 1469 (2016) 77-87
    H. Li, C. Liu, L. Zhao, et al., A systematic investigation of the effect of sample solvent on peak shape in nano- and microflow hydrophilic interaction liquid chromatography columns, J. Chromatogr. A 1655 (2021), 462498
    C. Liu, H. Li, Q. Wang, et al., Preparation and evaluation of 400 μm I.D. polymer-based hydrophilic interaction chromatography monolithic columns with high column efficiency, J. Chromatogr. A 1509 (2017) 83-90
    Y. Huang, Z.J. Jiang, Supercritical fluid chromatography using methacrylate-based monolithic column for the separation of polar analytes, J. Separ. Sci. 44 (2021) 3324-3332
    L. Carr, G. Cheng, H. Xue, et al., Engineering the polymer backbone to strengthen nonfouling sulfobetaine hydrogels, Langmuir 26 (2010) 14793-14798
    R. Quintana, D. Jańczewski, V.A. Vasantha, et al., Sulfobetaine-based polymer brushes in marine environment: is there an effect of the polymerizable group on the antifouling performance? Colloids Surf. B Biointerfaces 120 (2014) 118-124
    W. Zhao, Q. Ye, H. Hu, et al., Grafting zwitterionic polymer brushes via electrochemical surface-initiated atomic-transfer radical polymerization for anti-fouling applications, J. Mater. Chem. B 2 (2014), 5352
    M. Ezzat, C.J. Huang, Zwitterionic polymer brush coatings with excellent anti-fog and anti-frost properties, RSC Adv. 6 (2016) 61695-61702
    M. Catalá-Icardo, S. Torres-Cartas, E.F. Simó-Alfonso, et al., Influence of photo-initiators in the preparation of methacrylate monoliths into poly(ethylene-co-tetrafluoroethylene) tubing for microbore HPLC, Anal. Chim. Acta 1093 (2020) 160-167
    P. Zhu, W. Chen, Q. Wang, et al., Phosphatidylethanolamine functionalized biomimetic monolith for immobilized artificial membrane chromatography, J. Pharm. Anal. 12 (2022) 332-338
    Z. Jiang, J. Reilly, B. Everatt, et al., Novel zwitterionic polyphosphorylcholine monolithic column for hydrophilic interaction chromatography, J. Chromatogr. A 1216 (2009) 2439-2448
    P.A. Bristow, J.H. Knox, Standardization of test conditions for high performance liquid chromatography columns, Chromatographia 10 (1977) 279-289
    J.B. Schlenoff, Zwitteration: coating surfaces with zwitterionic functionality to reduce nonspecific adsorption, Langmuir 30 (2014) 9625-9636
    J. Nilsson, U. Rüetschi, A. Halim, et al., Enrichment of glycopeptides for glycan structure and attachment site identification, Nat. Methods 6 (2009) 809-811
    G. Qing, J. Yan, X. He, et al., Recent advances in hydrophilic interaction liquid interaction chromatography materials for glycopeptide enrichment and glycan separation, Trends Anal. Chem. 124 (2020), 115570
    Y. Wu, N. Sun, C. Deng, Construction of magnetic covalent organic frameworks with inherent hydrophilicity for efficiently enriching endogenous glycopeptides in human saliva, ACS Appl. Mater. Interfaces 12 (2020) 9814-9823
    Y.Y. Zhou, X. Sheng, J. Garemark, et al., Enrichment of glycopeptides using environmentally friendly wood materials, Green Chem. 22 (2020) 5666-5676
    Q.Q. Zhang, Y.Y. Huang, B.Y. Jiang, et al., In situ synthesis of magnetic mesoporous phenolic resin for the selective enrichment of glycopeptides, Anal. Chem. 90 (2018) 7357-7363
    C. Xia, F. Jiao, F. Gao, et al., Two-dimensional MoS2-based zwitterionic hydrophilic interaction liquid chromatography material for the specific enrichment of glycopeptides, Anal. Chem. 90 (2018) 6651-6659
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