Skip to main content
SpringerLink
Log in

A molecularly imprinted polymer based on MOF and deep eutectic solvent for selective recognition and adsorption of bovine hemoglobin

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

In this study, a novel kind of imprinted polymers based on metal–organic frameworks (MOF@DES-MIPs) was prepared, using bovine hemoglobin (BHb) as template molecules and deep eutectic solvents (DES) as functional monomers for selective recognition and adsorption of BHb. MOF were used as the substrates to improve the accessibility of imprinted sites and DES as the functional monomers to produce different forces for BHb to help the formation of imprinted sites. Imprinted polymer films were taken to provide analyte selectivity. The MOF@DES-MIPs prepared were characterized and evaluated by scanning electron microscope, X-ray diffraction, and Fourier transform infrared spectrometer. We also investigated the influences of BHb concentration and adsorption time on the performance of MOF@DES-MIPs. The maximal adsorption capacity of MOF@DES-MIPs to BHb reached 151.28 mg g−1, and the MOF@DES-MIPs showed good selectivity and fast adsorption equilibrium, which might offer a novel method for the preparation and research of molecularly imprinted polymers of biomacromolecules. In addition, MOF@DES-MIPs were successfully applied in the selective recognition of BHb from a real bovine blood sample.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Shi W, Zhang S, Li K, Jia W, Han D. Integration of mixed-mode chromatography and molecular imprinting technology for double recognition and selective separation of proteins. Sep Purif Technol. 2018;202:165–73.

    Article  CAS  Google Scholar 

  2. Xie X, Hu Q, Ke R, Zhen X, Bu Y, Wang S. Facile preparation of photonic and magnetic dual responsive protein imprinted nanomaterial for specific recognition of bovine hemoglobin. Chem Eng J. 2019;371:130–7.

    Article  CAS  Google Scholar 

  3. Zhang J, Wang Y, Lu X. Molecular imprinting technology for sensing foodborne pathogenic bacteria. Anal Bioanal Chem. 2021;413:1–18.

    Article  Google Scholar 

  4. Han S, Yao A, Wang Y. An ionic liquid-molecularly imprinted composite based on graphene oxide for the specific recognition and extraction of cancer antigen 153. RSC Adv. 2021;11(22):13085–90.

    Article  CAS  Google Scholar 

  5. Pichon V, Delaunay N, Combes A. Sample preparation using molecularly imprinted polymers. Anal Chem. 2020;92:16–33.

    Article  CAS  Google Scholar 

  6. Dinc M, Esen C, Mizaikoff B. Recent advances on core-shell magnetic molecularly imprinted polymers for biomacromolecules. Trends Anal Chem. 2019;114:202–17.

    Article  CAS  Google Scholar 

  7. Xu W, Wang Y, Wei X, Chen J, Xu P, Ni R, et al. Fabrication of magnetic polymers based on deep eutectic solvent for separation of bovine hemoglobin via molecular imprinting technology. Anal Chim Acta. 2019;1048:1–11.

    Article  CAS  Google Scholar 

  8. Gao R, Mu X, Hao Y, Zhang L, Zhang J, Tang Y. Combination of surface imprinting and immobilized template techniques for preparation of core-shell molecularly imprinted polymers based on directly amino-modified Fe3O4 nanoparticles for specific recognition of bovine hemoglobin. J Mater Chem B. 2014;2:1733–41.

    Article  CAS  Google Scholar 

  9. Zhang Q, Karine D, Royer S, Francois J. Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev. 2012;41(21):7108–46.

    Article  CAS  Google Scholar 

  10. Lyu H, Hu K, Chu Q, Su Z, Xie Z. Preparation of ionic liquid mediated molecularly imprinted polymer and specific recognition for bisphenol A from aqueous solution. Microchem J. 2020;158:105293–9.

    Article  CAS  Google Scholar 

  11. Fu N, Li L, Liu K, Kim C, Li J, Zhu T. A choline chloride-acrylic acid deep eutectic solvent polymer based on Fe3O4 particles and MoS2 sheets (poly(ChCl-AA DES)@Fe3O4@MoS2) with specific recognition and good antibacterial properties for β-lactoglobulin in milk. Talanta. 2019;197:567–77.

    Article  CAS  Google Scholar 

  12. Zhang Y, Cao H, Huang Q, Liu X, Zhang H. Isolation of transferrin by imprinted nanoparticles with magnetic deep eutectic solvents as monomer. Anal Bioanal Chem. 2018;410:6237–45.

    Article  CAS  Google Scholar 

  13. Liu Y, Wang Y, Dai Q, Zhou Y. Magnetic deep eutectic solvents molecularly imprinted polymers for the selective recognition and separation of protein. Anal Chim Acta. 2016;936:168–78.

    Article  CAS  Google Scholar 

  14. Nadim AH, El-Aal M, Al-Ghobashy MA, El-Saharty YS. Facile imprinted polymer for label-free highly selective potentiometric sensing of proteins: case of recombinant human erythropoietin. Anal Bioanal Chem. 2021;413:3611–23.

    Article  CAS  Google Scholar 

  15. Li L, Chen Y, Yang L, Wang Z, Liu H. Recent advances in applications of metal-organic frameworks for sample preparation in pharmaceutical analysis. Coordin Chem Rev. 2020;411:213235.

    Article  CAS  Google Scholar 

  16. Li Z, Xi Y, Zhao A, Jiang J, Li B, Yang X. Cobalt-imidazole metal-organic framework loaded with luminol for paper-based chemiluminescence detection of catechol with use of a smartphone. Anal Bioanal Chem. 2021;413:3541–50.

    Article  CAS  Google Scholar 

  17. Mirzajani R, Kardani F, Ramezani Z. Fabrication of UMCM-1 based monolithic and hollow fiber-metal-organic framework deep eutectic solvents/molecularly imprinted polymers and their use in solid phase microextraction of phthalate esters in yogurt, water and edible oil by GC-FID-ScienceDi. Food Chem. 2020;314:126179–89.

    Article  CAS  Google Scholar 

  18. Kang Y, Zhang L, Lai Q, Lin C, Wu K, Dang L, et al. Molecularly imprinted polymer based on metal-organic frameworks: synthesis and application on determination of dibutyl phthalate. Polym-Plast Tech Mat. 2020;2:1–10.

    Google Scholar 

  19. Li J, Ma M, Zhang C, Lu R, Zhang L, Zhang W. Synthesis of a molecularly imprinted polymer using MOF-74(Ni) as matrix for selective recognition of lysozyme. Anal Bioanal Chem. 2020;412(24):7227–36.

    Article  CAS  Google Scholar 

  20. Wu X, Chen X, Zhong G, Chen C, Cai C. A novel Wulff-type boronate acid-functionalized magnetic metal, organic framework imprinted polymer for specific recognition of glycoproteins under physiological pH. J Sep Sci. 2020;43(19):3715–824.

    Article  Google Scholar 

  21. Han S, Ding Y, Teng F, Yao A, Leng Q. Determination of chloropropanol with an imprinted electrochemical sensor based on multi-walled carbon nanotubes/metal-organic framework composites. RSC Adv. 2021;11:18468–75.

    Article  CAS  Google Scholar 

  22. Zhang H, Yang C, Geng Q, Fan H, Wang B, Wu M, et al. Adsorption of hydrogen sulfide by amine-functionalized metal organic framework (MOF-199): an experimental and simulation study. Appl Surf Sci. 2019;497:143815–43.

    Article  CAS  Google Scholar 

  23. Shadpour M, Maryam M. The effect of the coupling agents KH550 and KH570 on the nanostructure and interfacial interaction of zinc oxide/chiral poly(amide-imide) nanocomposites containing l-leucine amino acid moieties. J Mater Sci. 2014;49(14):5112–8.

    Article  Google Scholar 

  24. Liu Z, Wang Y, Xu F, Wei X, Chen J, Li H, et al. A new magnetic molecularly imprinted polymer based on deep eutectic solvents as functional monomer and cross-linker for specific recognition of bovine hemoglobin. Anal Chim Acta. 2020;1129:1129–92.

    Article  Google Scholar 

  25. Guan X, Li Q, Maimaiti T, Lan S, Ouyang P, Ouyang B, et al. Toxicity and photosynthetic inhibition of metal-organic framework MOF-199 to pea seedlings. J Hazard Mater. 2020;409:124521–52.

    Article  Google Scholar 

  26. Chen F, Xie X, Shi Y. Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine. J Chromatogr A. 2013;1300(14):112–8.

    Article  CAS  Google Scholar 

  27. Gao R, Hao Y, Zhang L, Cui X, Liu D, Zhang M, et al. A facile method for protein imprinting on directly carboxyl-functionalized magnetic nanoparticles using non-covalent template immobilization strategy. Chem Eng J. 2016;284:139–48.

    Article  CAS  Google Scholar 

  28. Zhang M, Wang Y, Jia X, He M, Xu M, Yang S, et al. The preparation of magnetic molecularly imprinted nanoparticles for the recognition of bovine hemoglobin. Talanta. 2014;120(4):376–85.

    Article  CAS  Google Scholar 

  29. Sun Y, Zhong S. Nanoscale trifunctional bovine hemoglobin for fabricating molecularly imprinted polydopamine via Pickering emulsions-hydrogels polymerization. Colloid Surface B. 2017;159:131–8.

    Article  CAS  Google Scholar 

  30. Wang P, Tang X, Hu L, Yin Y, Chen S, Xu J, et al. Preparation of bovine hemoglobin surface molecularly imprinted cotton for selective protein recognition-ScienceDirect. Process Biochem. 2020;88:31–7.

    Article  CAS  Google Scholar 

  31. Zhao Y, Chen Y, Fang M, Tian Y, Bai G, Zhuo K. Silanized carbon dot-based thermo-sensitive molecularly imprinted fluorescent sensor for bovine hemoglobin detection. Anal Bioanal Chem. 2020;412(23):5811–7.

    Article  CAS  Google Scholar 

  32. Li D, He X, Chen Y, Li W, Zhang Y. Novel hybrid structure silica/CdTe/molecularly imprinted polymer: synthesis, specific recognition, and quantitative fluorescence detection of bovine hemoglobin. ACS Appl Mater Inter. 2013;5(23):12609–16.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was funded by Heilongjiang Province Science Foundation for Youths (No. QC2018073), the Fundamental Research Funds in Heilongjiang Provincial Universities (No. 135409210), and Social Development Public Relations Project of Qiqihar Science and Technology Bureau (No. SFZD-2019151).

Author information

Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Qiqihar University, Qiqihar, 161006, China

    Shuang Han, Aixin Yao, Yuxin Ding, Qiuxue Leng & Fu Teng

  2. Heilongjiang Provincial Key Laboratory of Catalytic Synthesis for Fine Chemicals, Qiqihar University, Qiqihar, 161006, China

    Shuang Han

Authors
  1. Shuang Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Aixin Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yuxin Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Qiuxue Leng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fu Teng
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shuang Han.

Ethics declarations

Competing interests

The authors declare no competing interests.

Additional information

Publisher’s note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Han, S., Yao, A., Ding, Y. et al. A molecularly imprinted polymer based on MOF and deep eutectic solvent for selective recognition and adsorption of bovine hemoglobin. Anal Bioanal Chem 413, 5409–5417 (2021). https://doi.org/10.1007/s00216-021-03520-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-021-03520-3

Keywords

Search

Navigation