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Analytical and Bioanalytical Chemistry

, Volume 411, Issue 5, pp 1075–1084 | Cite as

Entacapone detection by a GOQDs-molecularly imprinted silica fluorescent chemical nanosensor

  • Hamed Ahmadi
  • Farnoush FaridbodEmail author
  • Mina Mehrzad-Samarin
Research Paper

Abstract

A sensitive fluorescent chemical nanosensor for the detection of entacapone (EN) in pharmaceutical samples is introduced. EN is a nitrocatechol drug that functions as a selective and reversible inhibitor of catechol-O-methyl transferase and is widely prescribed in the treatment of Parkinson disease. Molecularly imprinting technology and graphene oxide quantum dots (GOQDs) were employed in designing the EN fluorescent nanosensor. GOQDs were embedded into an inorganic polymer while the imprinting process occurred. The synthesized GOQDs-embedded silica molecularly imprinting polymer (SMIP) showed strong fluorescent emission at 450 nm by exciting at 360 nm. The fluorescence intensity of GOQDs-embedded SMIP was quenched effectively by adsorption of EN as a template molecule. The quenching corresponded to EN concentration in a linear range of at least 0.40–6.00 μM with a limit of detection of 0.31 μM. The designed chemical nanosensor was successfully applied to the analysis of entacapone in some pharmaceutical tablets also containing carbidopa and levodopa (RSD 3.8%).

Keywords

Entacapone Nanosensor Fluorescence detection Graphene quantum dots Inorganic molecularly imprinted polymer 

Notes

Acknowledgements

The authors are grateful to the Research Council of University of Tehran for the financial support of this work.

Compliance with ethical standards

This research was performed in accordance with the Declaration of Helsinki and with approval of the ethics board of the University of Tehran. Human plasma sample used in this work was from a healthy volunteer with O-positive blood who signed an informed consent form in the Iranian Blood Transfusion Center. It was a fresh frozen plasma (Product Code: E070V00).

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

216_2018_1534_MOESM1_ESM.pdf (143 kb)
ESM 1 (PDF 142 kb)

References

  1. 1.
    Almeida SAC, Silva MJB, da Luz FAC, Silva DP, de Deus SLV, Oliveira Dantas N. Controlling the cytotoxicity of CdSe magic-sized quantum dots as a function of surface defect density. Nano Lett. 2014;14:5452–7.CrossRefGoogle Scholar
  2. 2.
    Kairdolf BA, Smith AM, Stokes TH, Wang MD, Young AN, Nie S. Semiconductor quantum dots for bioimaging and biodiagnostic applications. Annu Rev Anal Chem. 2013;6:143–62.CrossRefGoogle Scholar
  3. 3.
    Liu S, Zhang X, Yu Y, Zou G. A Monochromatic electrochemiluminescence sensing strategy for dopamine with dual-stabilizers-capped CdSe quantum dots as emitters. Anal Chem. 2014;86:2784–8.CrossRefGoogle Scholar
  4. 4.
    Liu Y, Wu P. Graphene quantum dot hybrids as efficient metal-free electrocatalyst for the oxygen reduction reaction. ACS Appl Mater Interf. 2013;5:3362–9.CrossRefGoogle Scholar
  5. 5.
    Duran G, Contento MA, Rios A. Sensoring strategies using quantum dots: a critical view. Current Org Chem. 2015;19:1134–49.CrossRefGoogle Scholar
  6. 6.
    Zhu S, Song Y, Zhao X. The photoluminescence mechanism in carbon dots (graphene quantum dots, carbon nanodots, and polymer dots): current state and future perspective. Nano Res. 2015;8:355–81.CrossRefGoogle Scholar
  7. 7.
    Bao L, Zhang ZL, Tian ZQ, Zhang L, Liu C, Lin Y, et al. Electrochemical tuning of luminescent carbon nanodots: from preparation to luminescence mechanism. Adv Mater. 2011;23:5801–6.CrossRefGoogle Scholar
  8. 8.
    Zheng H, Wang Q, Long Y, Zhang H, Huang X, Zhu R. Enhancing the luminescence of carbon dots with a reduction pathway. Chem Commun. 2011;47:10650–2.CrossRefGoogle Scholar
  9. 9.
    Jin SH, Kim DH, Jun GH, Hong SH, Jeon S. Tuning the photoluminescence of graphene quantum dots through the charge transfer effect of functional groups. ACS Nano. 2013;7:1239–45.CrossRefGoogle Scholar
  10. 10.
    Yan X, Li B, Li LS. Colloidal graphene quantum dots with well-defined structures. Acc Chem Res. 2013;46:2254–62.CrossRefGoogle Scholar
  11. 11.
    Al-Ogaidi I, Gou H, Aguilar ZP, Guo S, Melconian AK, Al-kazaz AKA, et al. Detection of the ovarian cancer biomarker CA-125 using chemiluminescence resonance energy transfer to graphene quantum dots. Chem Commun. 2014;50:1344–6.CrossRefGoogle Scholar
  12. 12.
    Russo P, Hu A, Compagnini G, Duley WW, Zhou NY. Femtosecond laser ablation of highly oriented pyrolytic graphite: a green route for large-scale production of porous graphene and graphene quantum dots. Nanoscale. 2014;6:2381–9.CrossRefGoogle Scholar
  13. 13.
    Dong Y, Shao J, Chen C, Li H, Wang R, Chi Y, et al. Blue luminescent graphene quantum dots and graphene oxide prepared by tuning the carbonization degree of citric acid. Carbon. 2012;50:4738–43.CrossRefGoogle Scholar
  14. 14.
    Zhou X, Wang A, Yu C, Wu S, Shen J. Facile synthesis of molecularly imprinted graphene quantum dots for the determination of dopamine with affinity-adjustable. ACS Appl Mater Interf. 2015;7:11741–7.CrossRefGoogle Scholar
  15. 15.
    Ganjali MR, Faridbod F, Norouzi P. Biomimetic molecularly imprinted polymers as smart materials and future perspective in health care. Adv Health Mater 2014;465-492.Google Scholar
  16. 16.
    Lofgreen JE, Ozin GA. Controlling morphology and porosity to improve performance of molecularly imprinted sol-gel silica. Chem Soc Rev. 2014;43:911–33.CrossRefGoogle Scholar
  17. 17.
    Liu J, Chen H, Lin Z, Lin JM. Preparation of surface imprinting polymer capped Mn-doped ZnS quantum dots and their application for chemiluminescence detection of 4-nitrophenol in tap water. Anal Chem. 2010;82:7380–6.CrossRefGoogle Scholar
  18. 18.
    Hou J, Li H, Wang L, Zhang P, Zhou T, Ding H, et al. Rapid microwave-assisted synthesis of molecularly imprinted polymers on carbon quantum dots for fluorescent sensing of tetracycline in milk. Talanta. 2016;146:34–40.CrossRefGoogle Scholar
  19. 19.
    Liu G, Chen Z, Jiang X, Feng DQ, Zhao J, Fan D, et al. In-situ hydrothermal synthesis of molecularly imprinted polymers coated carbon dots for fluorescent detection of bisphenol A. Sens Actuators B. 2016;228:302–7.CrossRefGoogle Scholar
  20. 20.
    Chantada-Vázquez MP, Sánchez-González J, Peña-Vázquez E, Tabernero MJ, Bermejo AM, Bermejo-Barrera P, et al. Synthesis and characterization of novel molecularly imprinted polymer – coated Mn-doped ZnS quantum dots for specific fluorescent recognition of cocaine. Biosens. 2016;75:213–21.CrossRefGoogle Scholar
  21. 21.
    Liu H, Zhou K, Wu D, Wang J, Sun B. A novel quantum dots-labeled on the surface of molecularly imprinted polymer for turn-off optosensing of dicyandiamide in dairy products. Biosens Bioelectron. 2016;77:512–7.CrossRefGoogle Scholar
  22. 22.
    Mehrzad-Samarin M, Faridbod F, Dezfuli AS, Ganjali MR. A novel metronidazole fluorescent nanosensor based on graphene quantum dots embedded silica molecularly imprinted polymer. Biosens Bioelectron. 2017;92:618–23.CrossRefGoogle Scholar
  23. 23.
    Holm KJ, Spencer CM. Entacapone. Drugs. 1999;58:159–77.CrossRefGoogle Scholar
  24. 24.
    Brooks DJ, Agid Y, Eggert K, Widner H, Østergaard K, Holopainen A. Treatment of end-of-dose wearing-off in Parkinson’s disease: Stalevo® (levodopa/carbidopa/entacapone) and levodopa/DDCI given in combination with Comtess®/Comtan® (entacapone) provide equivalent improvements in symptom control superior to that of traditional levodopa/DDCI treatment. Europ Neurolog. 2005;53:197–202.CrossRefGoogle Scholar
  25. 25.
    Rizk M, Attia AK, Elshahed MS, Farag AS. Validated voltammetric method for the determination of antiparkinsonism drug entacapone in bulk, pharmaceutical formulation and human plasma. J Electroanal Chem. 2015;743:112–9.CrossRefGoogle Scholar
  26. 26.
    Dong Y, Wang R, Li H, Shao J, Chi Y, Lin X, et al. Polyamine-functionalized carbon quantum dots for chemical sensing. Carbon. 2012;50:2810–5.CrossRefGoogle Scholar
  27. 27.
    Mao Y, Bao Y, Han D, Li F, Niu L. Efficient one-pot synthesis of molecularly imprinted silica nanospheres embedded carbon dots for fluorescent dopamine optosensing. Biosens Bioelectron. 2012;38:55–60.CrossRefGoogle Scholar
  28. 28.
    Lin Y, Jin J, Song M. Preparation and characterisation of covalent polymer functionalized graphene oxide. J Mater Chem. 2011;21:3455–61.CrossRefGoogle Scholar
  29. 29.
    Zhou Y, Qu ZB, Zeng Y, Zhou T, Shi G. A novel composite of graphene quantum dots and molecularly imprinted polymer for fluorescent detection of paranitrophenol. Biosens Bioelectron. 2014;52:317–23.CrossRefGoogle Scholar
  30. 30.
    Howarter JA, Youngblood JP. Surface modification of polymers with 3-aminopropyltriethoxysilane as a general pretreatment for controlled wettability. Macromolecules. 2007;40:1128–32.CrossRefGoogle Scholar
  31. 31.
    Sun J, Zhuang JQ, Guan SW, Yang WS. Synthesis of robust water-soluble ZnS:Mn/SiO2 core/shell nanoparticles. J Nanopart Res. 2008;10:653–8.CrossRefGoogle Scholar
  32. 32.
    Koradia SK, Jivani NP, Malaviya SV, Chauhan SP, Vaghani SS. Development and validation of spectrophotometric method for the estimation of entacapone in pharmaceutical formulations. Int J Chem Sci. 2009;7:349–52.Google Scholar
  33. 33.
    Ramaiyan S, Anubala S, Nagaiah K. Analytical methods for determination of entacapone in pharmaceuticals and urine. Eurasian J Anal Chem. 2015;10:150–62.Google Scholar
  34. 34.
    Abdel-Ghany MF, Hussein LA, Ayad MF, Youssef MM. Investigation of different spectrophotometric and chemometric methods for determination of entacapone, levodopa and carbidopa in ternary mixture. Spectrochim Acta A Mol Biomol Spectrosc. 2017;171:236–45.CrossRefGoogle Scholar
  35. 35.
    Shoghi-Kalkhoran M, Faridbod F, Norouzi P, Ganjali MR. Praseodymium molybdate nanoplates/reduced graphene oxide nanocomposite based electrode for simultaneous electrochemical determination of entacapone, levodopa and carbidopa. J Mater Sci Mater Electron. 2018;29:20–31.CrossRefGoogle Scholar
  36. 36.
    Bugamelli F, Marcheselli C, Barba E, Raggi MA. Determination of l-dopa, carbidopa, 3-O-methyldopa and entacapone in human plasma by HPLC–ED. J Pharm Biomed Anal. 2011;54:562–7.CrossRefGoogle Scholar
  37. 37.
    Gumustas M, Uslu B, Ozkan SA, Aboul-Enein HY. Validated stability-indicating HPLC and UPLC assay methods for the determination of entacapone in pharmaceutical dosage forms. Chromatographia. 2014;77:1721–6.CrossRefGoogle Scholar
  38. 38.
    Belal F, Ibrahim F, Sheribah ZA, Alaa H. Micellar HPLC-UV method for the simultaneous determination of levodopa, carbidopa and entacapone in pharmaceuticals and human plasma. J Chromatogr B. 2018;1091:36–45.CrossRefGoogle Scholar
  39. 39.
    Belal F, Ibrahim F, Sheribah ZA, Alaa H. Micelle-enhanced spectrofluorimetric method for quantification of entacapone in tablets and human plasma. Luminescence. 2017;32:713–22.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Analytical Chemistry Department, School of Chemistry, College of ScienceUniversity of TehranTehranIran

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