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A poly(5-indolylboronic acid) based molecular imprint doped with carbon dots for fluorometric determination of glucose

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Abstract

A hybrid nanomaterial was synthesized that consists of poly(5-indolylboronic acid) acting as a molecular imprint (MIP), and of fluorescent carbon dots (CDs). The combination of CDs and MIP endowed the hybrid with stable fluorescence and template selectivity. The addition of glucose causes aggregation and quenching of fluorescence. Aggregation is due to the formation of covalent bonds between the cis-diols of glucose molecules and boronic acid side groups. The fluorometric signal, obtained at excitation/emission wavelengths of 350/450 nm, varies in the 5 to 750 μM glucose concentration range, with a 0.5 μM detection limit. The assay is not interfered by various biomolecules including fructose and was successful applied to the determination of glucose in (spiked) serum. In our perception, the results make this glucose assay an attractive new tool for clinical applications.

Schematic presentation of a hybrid nanomaterial that consists of poly(5-indolylboronic acid) acting as a molecular imprint, and of carbon dots. The addition of glucose causes fluorescence quenching in the range of 5–750 μM with a 0.5 μM detection limit.

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References

  1. Zhang ZY, Chen ZP, Cheng FB, Zhang YW, Chen LX (2017) Highly sensitive on-site detection of glucose in human urine with naked eye based on enzymatic-like reaction mediated etching of gold nanorods. Biosens Bioelectron 89:932–936

    Article  CAS  Google Scholar 

  2. Steiner MS, Duerkop A, Wolfbeis OS (2011) Optical methods for sensing glucose. Chem Soc Rev 40:4805–4839

    Article  CAS  Google Scholar 

  3. Arakawa T, Kuroki Y, Nitta H, Chouhan P, Toma K, Sawada S, Takeuchi S, Sekita T, Akiyoshi K, Minakuchi S, Mitsubayashi K (2015) Mouthguard biosensor with telemetry system for monitoring of saliva glucose: a novel cavitas sensor. Biosens Bioelectron 84:106–111

    Article  Google Scholar 

  4. Hoa LT, Chung JS, Hur SH (2016) A highly sensitive enzyme-free glucose sensor based on Co3O4 nanoflowers and 3D graphene oxide hydrogel fabricated via hydrothermal synthesis. Sens Actuators B Chem 223:76–82

    Article  CAS  Google Scholar 

  5. Lin LP, Song XH, Chen YY, Rong MC, Zhao TT, Wang YR, Jiang YQ, Chen X (2015) Intrinsic peroxidase-like catalytic activity of nitrogen-doped graphene quantum dots and their application in the colorimetric detection of H2O2 and glucose. Anal Chim Acta 869:89–95

    Article  CAS  Google Scholar 

  6. Chen S, Hai X, Chen XW, Wang JH (2014) In situ growth of silver nanoparticles on graphene quantum dots for ultrasensitive colorimetric detection of H2O2 and glucose. Anal Chem 86:6689–6694

    Article  CAS  Google Scholar 

  7. Hao TF, Wei X, Nie YJ, Xu YQ, Lu K, Yan YS, Zhou ZP (2016) Surface modification and ratiometric fluorescence dual function enhancement for visual and fluorescent detection of glucose based on dual-emission quantum dots hybrid. Sens Actuators B Chem 230:70–76

    Article  CAS  Google Scholar 

  8. Liu XJ, Yang WX, Chen LL, Jia JB (2016) Synthesis of copper nanorods for non-enzymatic amperometric sensing of glucose. Microchim Acta 183:2369–2375

    Article  CAS  Google Scholar 

  9. Yuan J, Cen Y, Kong XJ, Wu S, Liu CLW, Yu RQ, Chu X (2015) MnO2-nanosheet-modified upconversion nanosystem for sensitive turn-on fluorescence detection of H2O2 and glucose in blood. ACS Appl Mater Interfaces 7:10548–10555

    Article  CAS  Google Scholar 

  10. Wang H, Yi JH, Velado D, Yu YY, Zhou SQ (2015) Immobilization of carbon dots in molecularly imprinted microgels for optical sensing of glucose at physiological pH. ACS Appl Mater Interfaces 7:15735–15745

    Article  CAS  Google Scholar 

  11. Bradley SJ, Kroon K, Laufersky G, Röding M, Goreham RV, Gschneidtner T, Schroeder K, Moth-Poulsen K, Andersson M, Nann T (2017) Heterogeneity in the fluorescence of graphene and graphene oxide quantum dots. Microchim Acta 184:871–878

    Article  CAS  Google Scholar 

  12. Zhang FW, Wen QJ, Hong MZ, Zhuang ZY, Yu Y (2017) Efficient and sustainable metal-free GR/C3N4/CDots ternary heterostructrues for versatile visible-light-driven photoredox applications: towards synergistic interaction of carbon materials. Chem Eng J 307:593–603

    Article  CAS  Google Scholar 

  13. Arcudi F, Dordevic L, Prato M (2016) Synthesis, separation, and characterization of small and highly fluorescent nitrogen-doped carbon nanodots. Angew Chem Int Ed 55:2107–2112

    Article  CAS  Google Scholar 

  14. Li Y, Zhao Y, Cheng HH, Hu Y, Shi GQ, Dai LM, Qu LT (2011) Nitrogen-doped graphene quantum dots with oxygen-rich functional groups. J Am Chem Soc 134:15–18

    Article  Google Scholar 

  15. Niu MC, Pham-Huy C, He H (2016) Core-shell nanoparticles coated with molecularly imprinted polymers: a review. Microchim Acta 183:2677–2695

    Article  CAS  Google Scholar 

  16. Dai H, Xiao DL, He H, Li H, Yuan DH, Zhang C (2015) Synthesis and analytical applications of molecularly imprinted polymers on the surface of carbon nanotubes: a review. Microchim Acta 182:893–908

    Article  CAS  Google Scholar 

  17. Zhou X, Wang AQ, Yu CF, Wu SS, Shen J (2015) Facile synthesis of molecularly imprinted graphene quantum dots for the determination of dopamine with affinity-adjustable. ACS Appl Mater Interfaces 7:11741–11747

    Article  CAS  Google Scholar 

  18. Wu WT, Shen J, Li YX, Zhu HB, Banerjee P, Zhou SQ (2012) Specific glucose-to-SPR signal transduction at physiological pH by molecularly imprinted responsive hybrid microgels. Biomaterials 33:7115–7125

    Article  CAS  Google Scholar 

  19. Zhou X, Ma PP, Wang AQ, Yu CF, Qian T, Wu SS, Shen J (2015) Dopamine fluorescent sensors based on polypyrrole/graphene quantum dots core/shell hybrids. Biosens Bioelectron 64:404–410

    Article  CAS  Google Scholar 

  20. Pringsheim BE, Terpetschnig E, Piletsky SA, Wolfbeis OS (1999) A polyaniline with near-infrared optical response to saccharides. Adv Mater 10:865–868

    Article  Google Scholar 

  21. Shen PF, Xia YS (2014) Synthesis-modification integration: one-step fabrication of boronic acid functionalized carbon dots for fluorescent blood sugar sensing. Anal Chem 86:5323–5329

    Article  CAS  Google Scholar 

  22. Na WD, Liu H, Wang MY, Su XG (2017) A boronic acid based glucose assay based on the suppression of the inner filter effect of gold nanoparticles on the orange fluorescence of graphene oxide quantum dots. Microchim Acta 184:1463–1470

    Article  CAS  Google Scholar 

  23. Mader HS, Wolfbeis OS (2008) Boronic acid based probes for microdetermination of saccharides and glycosylated biomolecules. Microchim Acta 162:1–34

    Article  CAS  Google Scholar 

  24. Pan D, Zhang J, Li Z, Wu M (2010) Hydrothermal route for cutting graphene sheets into blue-luminescent graphene quantum dots. Adv Mater 22:734–738

    Article  Google Scholar 

  25. Qu ZB, Zhou XG, Gu L, Lan RM, Sun DD, Yu DJ, Shi GY (2013) Boronic acid functionalized graphene quantum dots as a fluorescent probe for selective and sensitive glucose determination in microdialysate. Chem Commun 49:9830–9832

    Article  CAS  Google Scholar 

  26. Zhang L, Zhang ZY, Liang RP, Li YH, Qiu JD (2014) Boron-doped graphene quantum dots for selective glucose sensing based on the “abnormal” aggregation-induced photoluminescence enhancement. Anal Chem 86:4423–4430

    Article  CAS  Google Scholar 

  27. Fuyuno N, Kozawa D, Miyauchi Y, Mouri S, Kitaura R, Shinohara H, Yasuda T, Komatsu N, Matsuda K (2014) Drastic change in photoluminescence properties of graphene quantum dots by chromatographic separation. Adv Opt Mater 2:983–989

    Article  CAS  Google Scholar 

  28. Wu WT, Zhou T, Berliner A, Banerjee P, Zhou SQ (2010) Glucose-mediated assembly of phenylboronic acid modified CdTe/ZnTe/ZnS quantum dots for intracellular glucose probing. Angew Chem Int Ed 49:6554–6558

    Article  CAS  Google Scholar 

  29. Freeman R, Bahshi L, Finder T, Gill R, Willner I (2009) Competitive analysis of saccharides or dopamine by boronic acid-functionalized CdSe–ZnS quantum dots. Chem Commun 7:764–766

    Article  Google Scholar 

  30. Valipour M, Banihabib ME, Behbahani SMR (2013) Comparison of the ARMA, ARIMA, and the autoregressive artificial neural network models in forecasting the monthly inflow of Dez dam reservoir. J Hydrol 476:433–441

    Article  Google Scholar 

  31. Viero DP, Valipour M (2017) Modeling anisotropy in free-surface overland and shallow inundation flows. Adv Water Resour 104:1–14

    Article  Google Scholar 

  32. Valipour M (2017) Global experience on irrigation management under different scenarios. J Water Land Dev 32:95–102

    Article  Google Scholar 

  33. Valipour M (2016) Variations of land use and irrigation for next decades under different scenarios. Braz J Irrig Drain 88:262–288

    Google Scholar 

  34. Valipour M (2016) How much meteorological information is necessary to achieve reliable accuracy for rainfall estimations? Agriculture 6:53

    Article  Google Scholar 

  35. Valipour M, Peng D, Sefidkouhi MAG, Raeini−Sarjaz M (2017) Selecting the best model to estimate potential evapotranspiration with respect to climate change and magnitudes of extreme events. Agric Water Manag 180:50–60

    Article  Google Scholar 

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Acknowledgments

This work was supported by the Fundamental Research Funds for the Central Non-profit Research Institution of CAF (CAFYBB2017ZX003), the Fundamental Research Funds of Research Institute of Forest New Technology (CAFYBB2017SY033).

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Authors and Affiliations

  1. Institute of Chemical Industry of Forestry Products, Chinese Academy of Forestry; National Engineering Laboratory on Biomass Chemical Utilization; Key Laboratory of Biomass Energy and Material of Jiangsu province, Nanjing, 210042, China

    Xi Zhou, Xuexia Gao, Meihong Liu, Chunpeng Wang & Fuxiang Chu

  2. Institute of Forest New Technology, Chinese Academy of Forestry, Beijing, 100091, China

    Xi Zhou, Chunpeng Wang & Fuxiang Chu

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  1. Xi Zhou
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  2. Xuexia Gao
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  3. Meihong Liu
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  4. Chunpeng Wang
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  5. Fuxiang Chu
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Correspondence to Fuxiang Chu.

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Zhou, X., Gao, X., Liu, M. et al. A poly(5-indolylboronic acid) based molecular imprint doped with carbon dots for fluorometric determination of glucose. Microchim Acta 184, 4175–4181 (2017). https://doi.org/10.1007/s00604-017-2448-0

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