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Solid-Phase Extraction and Simultaneous Fluorescence Detection of Cis-Diol-Containing Biomolecules Based on a Novel Boronate Affinity Material

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Abstract

Boronate affinity materials have been widely studied in separation science, chemical sensing, drug delivery and nanomedicine due to their unique recognition mechanism towards cis-diol-containing biomolecules (cis-diols). In this paper, a new phenylboronic acid (PBA)-functionalized silica particle was prepared by one-pot synthetic strategy based on a PBA-coupled silane reagent, which was synthesized using 1,3,5-benzenetricarboxaldehyde as a spacer arm to covalently link 3-aminophenylboronic acid and 3-aminopropyltriethoxysiliane. Such PBA-functionalized silica particles displayed wrinkle shape with large surface area of 192 m2 g−1, resulting in its high binding capacities of 480 µmol g−1 for catechol and 63 µmol g−1 for adenosine. Moreover, the PBA-functionalized silica particles could rapidly extract the cis-diols in 10 min with a high binding recovery of 83–92%, much higher than its control polymers (1 ~ 47%). In addition to the good extraction performances, the PBA-functionalized silica particles also exhibited fluorescence responses to the cis-diols using two different excitation lights at 300 nm and 470 nm, giving emission lights at 379 nm and 631 nm, respectively, whose fluorescence-responsive mechanism was preliminarily studied. In summary, the developed boronate affinity silica particles can be used not only for the solid-phase extraction of cis-diols, but also to report the recognition events through the fluorescence signals, providing an idea to develop multi-functional boronate affinity materials for simultaneous enrichment and detection of cis-diols in biological samples.

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Data availability

The data that support the findings of this study are available from the corresponding authors upon reasonable request.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (21705073) and the Starting Research Fund of Nanjing Normal University (164320H133-12).

Funding

National Natural Science Foundation of China, 21705073, Starting Research Fund of Nanjing Normal University, 164320H133-12.

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Authors and Affiliations

  1. School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing, 210023, Jiangsu, China

    Qianjin Li, Tingting Wang, Yadan Hou & Shuqing Xiong

  2. College of Chemistry, Nanchang University, Nanchang, 330031, Jiangxi, China

    Dan Wang, Qianyong Cao & Fenying Wang

  3. Anhui Costar Biochemical Co. LTD, Dangtu, 243100, Anhui, China

    Chenhong Wei

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  1. Qianjin Li
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Contributions

QL, Conceptualization, Methodology, Supervision, Writing- Reviewing and Editing; TW, Investigation, Validation, Data curation; YH, Investigation, Validation, Data curation; DW, Investigation, Validation; SX, Investigation; CW, Investigation; QC, Manuscript revision, Funding acquisition; FW, Manuscript revision, Funding acquisition.

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Correspondence to Qianjin Li, Qianyong Cao or Fenying Wang.

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Li, Q., Wang, T., Hou, Y. et al. Solid-Phase Extraction and Simultaneous Fluorescence Detection of Cis-Diol-Containing Biomolecules Based on a Novel Boronate Affinity Material. Chromatographia 86, 387–399 (2023). https://doi.org/10.1007/s10337-023-04252-5

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