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A glassy carbon electrode modified with molecularly imprinted poly(aniline boronic acid) coated onto carbon nanotubes for potentiometric sensing of sialic acid

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Abstract

A potentiometric sensor for sialic acid (SA) was developed based on molecular imprinting technique. The sensor was fabricated by modifying carbon nanotubes (CNT) and an SA-imprinted poly(aniline boronic acid) (PABA) film on a glassy carbon electrode (GCE). The detection strategy capitalizes on the change of electrochemical potential resulting from boronic acid-SA interaction. The imprinted PABA combines the functions of SA-binding boronic acid groups and the imprinting effect, thus endowing it with both chemical and sterical recognition capability. The imprint factor (IF, compared to a non-molecularly imprinted polymer) is 1.74. The sensor can well differentiate SA from its analogs at physiological pH values and has a linear potentiometric response (R2 = 0.998) in 80 μM to 8.2 mM SA concentrations range with a detection limit of 60 μM (at S/N = 3). The sensor was applied to the determination of SA in serum samples and gave recoveries between 93% and 105%.

Schematic presentation of the fabrication of a sialic acid (SA) imprinted poly(aniline boronic acid) (PABA)/CNT modified electrode. The electrode can well differentiate SA from its analogs at physiological pH and determine SA in human serum samples with satisfactory recoveries of 93%–105%.

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References

  1. Mahajan VS, Pillai S (2016) Sialic acids and autoimmune disease. Immunol Rev 269:145–161

    Article  CAS  Google Scholar 

  2. Fukuda M (1996) Possible roles of tumor-associated carbohydrate antigens. Cancer Res 56:2237–2244

    CAS  PubMed  Google Scholar 

  3. Chari SN, Nath N (1984) Sialic acid content and sialidase activity of polymorphonuclear leucocytes in diabetes mellitus. Am J Med Sci 288:18–20

    Article  CAS  Google Scholar 

  4. Wang SS, Rymer DL, Good TA (2001) Reduction in cholesterol and sialic acid content protects cells from the toxiceffects of beta-amyloid peptides. J Biol Chem 276:42027–42034

    Article  CAS  Google Scholar 

  5. Sankoh S, Thammakhet C, Numnuam A, Limbut W, Kanatharana P, Thavarungkul P (2016) 4-mercaptophenyl- boronicacid functionalized gold nanoparticles for colorimetric sialic acid detection. Biosens Bioelectron 85:743–750

    Article  CAS  Google Scholar 

  6. Matsuno K, Suzuki S (2008) Simple fluorimetric method for quantification of sialic acids in glycoproteins. Anal Biochem 375:53–59

    Article  CAS  Google Scholar 

  7. Tebani A, Schlemmer D, Imbard A, Rigal O, Porquet D, Benoist JF (2011) Measurement of free and total sialic acid by isotopic dilution liquid chromatography tandem mass spectrometry method. J Chromatogr B Analyt Technol Biomed Life Sci 879:3694–3699

    Article  CAS  Google Scholar 

  8. Fatoni A, Numnuam A, Kanatharana P, Limbut W, Thavarungkul P (2014) A conductive porous structuredchitosan-grafted polyaniline cryogel for use as a sialic acid biosensor. Electrochim Acta 130:296–304

    Article  CAS  Google Scholar 

  9. James TD, Shinkai S (1996) Saccharide sensing with molecular receptors based on boronic acid. Angew Chem Int Ed 35:1910–1922

    Article  Google Scholar 

  10. Shoji E, Freund MS (2001) Potentiometric sensors based on the inductive effect on the pKa of poly(aniline): a nonenzymatic glucose sensor. J Am Chem Soc 123:3383–3384

    Article  CAS  Google Scholar 

  11. Shoji E, Freund MS (2002) Potentiometric saccharide detection based on the pK(a) changes of poly(aniline boronic acid). J Am Chem Soc 124:12486–12493

    Article  CAS  Google Scholar 

  12. Zhong X, Bai HJ, Xu JJ, Chen HY, Zhu YH (2010) A reusable interface constructed by 3-aminophenylboronic acid-functionalized multiwalled carbon nanotubes for cell capture, release, and cytosensing. Adv Funct Mater 20:992–999

    Article  CAS  Google Scholar 

  13. Matsumoto A, Sato N, Kataoka K, Miyahara Y (2009) Noninvasive sialic acid detection at cell membrane by using phenylboronic acid modified self-assembled monolayer gold electrode. J Am Chem Soc 131:12022–12023

    Article  CAS  Google Scholar 

  14. Qian DP, Han FF, Li WB, Bao N, Yu CM, Gu HY (2017) Sensitive determination of sialic acid expression on living cells by using an ITO electrode modified with graphene, gold nanoparticles and thionine for triple signal amplification. Microchim Acta 184:3841–3850

    Article  CAS  Google Scholar 

  15. Lorand JP, Edwards JO (1959) Polyol complexes and structure of the benzeneboronate ion. J Org Chem 24:769–774

    Article  CAS  Google Scholar 

  16. Deore B, Freund MS (2003) Saccharide imprinting of poly(aniline boronic acid) in the presence of fluoride. Analyst 128:803–806

    Article  CAS  Google Scholar 

  17. Otsuka H, Uchimura E, Koshino H, Okano T, Kataoka K (2003) Anomalous binding profile of phenylboronic acid with N-acetylneuraminic acid (Neu5Ac) in aqueous solution with varying pH. J Am Chem Soc 125:3493–3502

    Article  CAS  Google Scholar 

  18. Matsumoto A, Cabral H, Sato N, Kataoka K, Miyahara Y (2010) Assessment of tumor metastasis by the direct determination of cell-membrane sialic acid expression. Angew Chem Int Ed 49:5494–5497

    Article  CAS  Google Scholar 

  19. Yin DY, Wang SS, He YJ, Liu J, Zhou M, Ouyang J, Liu BR, Chen HY, Liu Z (2015) Surface-enhanced Raman scattering imaging of cancer cells and tissues via sialic acid-imprinted nanotags. Chem Commun 51:17696–17699

    Article  CAS  Google Scholar 

  20. Liu RH, Cui QL, Wang C, Wang XY, Yang Y, Li LD (2017) Preparation of sialic acid-imprinted fluorescent conjugated nanoparticles and their application for targeted cancer cell imaging. ACS Appl Mater Interfaces 9:3006–3015

    Article  CAS  Google Scholar 

  21. Lv CC, Li HY, Wang HY, Liu Z (2013) Probing the interactions between boronic acids and cis-diol-containingbiomolecules by affinity capillary electrophoresis. Anal Chem 85:2361–2369

    Article  Google Scholar 

  22. Sellergren B, Lepistoe M, Mosbach K (1988) Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition. J Am Chem Soc 110:5853–5860

    Article  CAS  Google Scholar 

  23. Macdiarmid AG, Epstein AJ (1989) The polyanilines: a novel class of conducting polymers. Faraday Discuss Chem Soc 88:317–332

    Article  CAS  Google Scholar 

  24. Rick J, Chou TC (2006) Amperometric protein sensor-fabricated as a polypyrrole, poly-aminophenylboronic acid bilayer. Biosens Bioelectron 22:329–335

    Article  CAS  Google Scholar 

  25. Baughman RH, Zakhidov AA, Heer WA (2002) Carbon nanotubes-the route toward applications. Science 297:787–792

    Article  CAS  Google Scholar 

  26. Shieh YT, Tsai YC, Twu YK (2013) Electrocatalytic behavior and H2O2 detection of carbon nanotube/chitosan nanocomposites prepared via different acidic aqueous solutions. Int J Electrochem Sci 8:831–845

    CAS  Google Scholar 

  27. Sainz R, Benito AM, Martínez MT, Galindo JF, Sotres J, Baró AM, Corraze B, Chauvet O, Maser WK (2010) Soluble self-aligned carbon nanotube/polyaniline composites. Adv Mater 17:278–281

    Article  Google Scholar 

  28. Takahashi S, Anzai J (2005) Phenylboronic acid monolayer-modified electrodes sensitive to sugars. Langmuir 21:5102–5107

    Article  CAS  Google Scholar 

  29. Djanashvili K, Frullano L, Peters JA (2005) Molecular recognition of sialic acid end groups by phenylboronates. Chemistry 11:4010–4018

    Article  CAS  Google Scholar 

  30. Yan J, Springsteen G, Deeter S, Wang B (2004) The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols: it is not as simple as it appears. Tetrahedron 60:11205–11209

    Article  CAS  Google Scholar 

  31. Springsteen G, Wang B (2001) Alizarin red S. As a general optical reporter for studying the binding of boronic acids with carbohydrates. Chem Commun 7:1608–1609

    Article  Google Scholar 

  32. Liu TL, Fu B, Chen JC, Yan ZH, Li K (2018) A non-enzymatic electrochemical sensor for detection of sialic acid based on a porphine/graphene oxide modified electrode via indicator displacement assay. Electrochim Acta 269:136–143

    Article  CAS  Google Scholar 

  33. Guo X, Liu J, Liu FY, She F, Zheng Q, Tang H, Ma M, Yao SZ (2017) Label-free and sensitive sialic acid biosensor based on organic electrochemical transistors. Sens Actuators B Chem 240:1075–1082

    Article  CAS  Google Scholar 

  34. Jayeoye TJ, Cheewasedtham W, Putson C, Rujiralai T (2018) Colorimetric determination of sialic acid based on boronic acid-mediated aggregation of gold nanoparticles. Microchim Acta 185:409–416

    Article  Google Scholar 

  35. Zhou YL, Dong H, Liu LT, Liu J, Xu MT (2014) A novel potentiometric sensor based on a poly(anilineboronic acid)/graphene modified electrode for probing sialic acid through boronic acid-diol recognition. Biosens Bioelectron 60:231–236

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to the financial support by the National Natural Science Foundation of China (51503126 and 21534008) and the kind help of Ms. Fan Yang from Guanghan Chenglin Hospital.

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Authors and Affiliations

  1. College of Polymer Science and Engineering, Sichuan University, Chengdu, 610065, China

    Fuhui Huang, Bengao Zhu, Haochen Zhang, Yue Gao, Chunmei Ding, Hong Tan & Jianshu Li

  2. State Key Laboratory of Polymer Materials Engineering, Sichuan University, Chengdu, 610065, China

    Jianshu Li

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  1. Fuhui Huang
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  2. Bengao Zhu
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  3. Haochen Zhang
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  4. Yue Gao
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  5. Chunmei Ding
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  7. Jianshu Li
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Correspondence to Chunmei Ding or Jianshu Li.

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Huang, F., Zhu, B., Zhang, H. et al. A glassy carbon electrode modified with molecularly imprinted poly(aniline boronic acid) coated onto carbon nanotubes for potentiometric sensing of sialic acid. Microchim Acta 186, 270 (2019). https://doi.org/10.1007/s00604-019-3387-8

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  • DOI: https://doi.org/10.1007/s00604-019-3387-8

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