Abstract
A sensitive molecular imprinted (MIP) electrochemical sensor for the rapid detection of coumarin was successfully constructed by modifying gold nanoparticles (AuNPs) improved reduced graphene oxide (rGO) on glassy carbon electrode (GCE). The modification of AuNPs/rGO was achieved by introducing/eluting coumarin template molecules. Imprinting parameters (template molecule to functional monomer ratio, pH value of electro-polymerization solution, polymerization cycles and types of eluent) of the sensor were experimentally optimized. The prepared nano-materials were characterized by scanning electron microscope (SEM), energy dispersion spectrum (EDS) and transmission electron microscope (TEM). The optimized imprinted electrochemical sensor was characterized by (cyclic voltammetry) CV (electrochemical impedance spectroscopy) and EIS and validated by standard linearity of current–concentration relation. The linear range and the detection of limit (LOD) of the molecular imprinted AuNPs/rGO/GCE sensor for coumarin detection were obtained from 1.0 × 10–7 to 1.8 × 10–5 M and 1.15 × 10–8 M (S/N = 3), respectively. The developed sensor is expected to be widely used in real sample detection due to the desirable features of high sensitivity and stability, and rapid response.
Graphical Abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bahadır EB, Sezgintürk MK (2016) Applications of graphene in electrochemical sensing and biosensing. TrAC-Trend Anal Chem 76:1–14. https://doi.org/10.1016/j.trac.2015.07.008
Blanco-López M, Lobo-Castanon M, Miranda-Ordieres A, Tunon-Blanco P (2004) Electrochemical sensors based on molecularly imprinted polymers. TrAC-Trend Anal Chem 23:36–48. https://doi.org/10.1016/S0165-9936(04)00102-5
Breslin CB, Branagan D, Garry LM (2019) Electrochemical detection of Cr(VI) with carbon nanotubes decorated with gold nanoparticles. J Appl Electrochem 49:195–205. https://doi.org/10.1007/s10800-018-1259-2
Cinti S, Arduini F (2017) Graphene-based screen-printed electrochemical (bio) sensors and their applications: Efforts and criticisms. Biosens Bioelectron 89:107–122. https://doi.org/10.1016/j.bios.2016.07.005
Emami S, Dadashpour S (2015) Current developments of coumarin-based anti-cancer agents in medicinal chemistry. Eur J Med Chem 102:611–630. https://doi.org/10.1016/j.ejmech.2015.08.033
Fajardo A, Tapia D, Pizarro J, Segura R, Jara P (2019) Determination of norepinephrine using a glassy carbon electrode modified with graphene quantum dots and gold nanoparticles by square wave stripping voltammetry. J Appl Electrochem 49:423–432. https://doi.org/10.1007/s10800-019-01288-0
Gan T, Lv Z, Sun YY, Shi ZX, Sun JY, Zhao AX (2016) Highly sensitive and molecular selective electrochemical sensing of 6-benzylaminopurine with multiwall carbon nanotube@SnS2-assisted signal amplification. J Appl Electrochem 46:389–401. https://doi.org/10.1007/s10800-016-0923-7
Hu YQ, Xu Z, Zhang S, Wu X, Ding JW, Lv ZS, Feng LS (2017) Recent developments of coumarin-containing derivatives and their anti-tubercular activity. Eur J Med Chem 136:122–130. https://doi.org/10.1016/j.ejmech.2017.05.004
Huang J, Zhang X, Liu S, Lin Q, He X, Xing X, Lian W (2011) Electrochemical sensor for bisphenol a detection based on molecularly imprinted polymers and gold nanoparticles. J Appl Electrochem 41:1323–1328. https://doi.org/10.1007/s10800-011-0350-8
Iskierko Z, Sharma PS, Bartold K, Pietrzyk-Le A, Noworyta K, Kutner W (2016) Molecularly imprinted polymers for separating and sensing of macromolecular compounds and microorganisms. Biotechnol Adv 34:30–46. https://doi.org/10.1016/j.biotechadv.2015.12.002
Jafarpour F, Darvishmolla M (2018) Peroxy mediated Csp 2–Csp 3 dehydrogenative coupling: regioselective functionalization of coumarins and coumarin-3-carboxylic acids. Org Biomol Chem 16:3396–3401. https://doi.org/10.1039/C7OB02771
Jameel E, Umar T, Kumar J, Hoda N (2016) Coumarin: a privileged scaffold for the design and development of antineurodegenerative agents. Chem Biol Drug Des 87:21–38. https://doi.org/10.1111/cbdd.1262
Ji Q, Ge Z, Ge Z, Chen K, Wu H, Liu X, Huang Y, Yuan L, Yang X, Liao F (2016) Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents. Eur J Med Chem 108:166–176. https://doi.org/10.1016/j.ejmech.2015.11.027
Kubrak T, Dresler S, Szymczak G, Bogucka-Kocka A (2015) Rapid determination of coumarins in plants by capillary electrophoresis. Anal Lett 48:2819–2832. https://doi.org/10.1016/j.chroma.2006.09.070
Li GJ, Wu HJ, Wang Y, Hung WL, Rouseff RL (2019) Determination of citrus juice coumarins, furanocoumarins and methoxylated flavones using solid phase extraction and HPLC with photodiode array and fluorescence detection. Food Chem 271:29–38. https://doi.org/10.1016/j.foodchem.2018.07.130
McAdam K, Enos T, Goss C, Kimpton H, Faizi A, Edwards S, Wright C, Porter A, Rodu B (2018) Analysis of coumarin and angelica lactones in smokeless tobacco products. Cent J 12:142. https://doi.org/10.1186/s13065-018-0506-2
Nowak PM, Woźniakiewicz M, Piwowarska M, Kościelniak P (2016) Determination of acid dissociation constant of 20 coumarin derivatives by capillary electrophoresis using the amine capillary and two different methodologies. J Chromatogr A 1446:149–157. https://doi.org/10.1016/j.chroma.2016.03.084
Qian T, Yu C, Zhou X, Ma P, Wu S, Xu L, Shen J (2014) Ultrasensitive dopamine sensor based on novel molecularly imprinted polypyrrole coated carbon nanotubes. Biosens Bioelectron 58:237–241. https://doi.org/10.1016/j.bios.2014.02.081
Ren Z, Nie B, Liu T, Yuan F, Feng F, Zhang Y, Zhou W, Xu X, Yao M, Zhang F (2016) Simultaneous determination of coumarin and its derivatives in tobacco products by liquid chromatography-tandem mass spectrometry. Molecules 21:1511. https://doi.org/10.3390/molecules21111511
Salvador JP, Tassies D, Reverter JC, Marco MP (2018) Enzyme-linked immunosorbent assays for therapeutic drug monitoring coumarin oral anticoagulants in plasma. Anal Chim Acta 1028:59–65. https://doi.org/10.1016/j.aca.2018.04.042
Sandhu S, Bansal Y, Silakari O, Bansal G (2014) Coumarin hybrids as novel therapeutic agents. Bioorgan Med Chem 22:3806–3814. https://doi.org/10.1016/j.bmc.2014.05.032
Sarkar S, Santra M, Singha S, Jun YW, Reo YJ, Kim HR, Ahn KH (2018) Two-photon absorbing 8-hydroxy-benzo [g] coumarins with giant Stokes shifts: an environment-insensitive dye platform for probing biomolecules. J Mater Chem B 6:4446–4452. https://doi.org/10.1039/C8TB011
Sproll C, Ruge W, Andlauer C, Godelmann R, Lachenmeier DW (2008) HPLC analysis and safety assessment of coumarin in foods. Food Chem 109:462–469. https://doi.org/10.1016/j.foodchem.2007.12.068
Sun S, Wang H, Xie J, Su Y (2016) Simultaneous determination of rhamnose, xylitol, arabitol, fructose, glucose, inositol, sucrose, maltose in jujube (Zizyphus jujube Mill.) extract: comparison of HPLC–ELSD, LC–ESI–MS/MS and GC–MS. Chem Cent J. https://doi.org/10.1186/s13065-016-0171-2
Uzun L, Turner AP (2016) Molecularly-imprinted polymer sensors: realising their potential. Biosens Bioelectron 76:131–144. https://doi.org/10.1016/j.bios.2015.07.013
Vahabi V, Hatamjafari F (2014) Microwave assisted convenient one-pot synthesis of coumarin derivatives via Pechmann condensation catalyzed by FeF3 under solvent-free conditions and antimicrobial activities of the products. Molecules 19:13093–13103. https://doi.org/10.3390/molecules190913093
Vaiano F, Serpelloni G, Focardi M, Fioravanti A, Mari F, Bertol E (2015) LC–MS/MS and GC–MS methods in propofol detection: evaluation of the two analytical procedures. Forensic Sci Int 256:1–6. https://doi.org/10.1016/j.forsciint.2015.07.013
Vetter F, Müller C, Stöckelhuber M, Bracher F (2017) Determination of coumarin in seasonal bakery products using QuEChERS and GC-MS. J Pharm Sci 72:313–316. https://doi.org/10.1691/ph.2017.6215
Weigt S, Huebler N, Strecker R, Braunbeck T, Broschard TH (2012) Developmental effects of coumarin and the anticoagulant coumarin derivative warfarin on zebrafish (Danio rerio) embryos. Reprod Toxical 33:133–141. https://doi.org/10.1016/j.reprotox.2011.07.001
Woehrlin F, Fry H, Abraham K, Preiss-Weigert A (2010) Quantification of flavoring constituents in cinnamon: high variation of coumarin in cassia bark from the German retail market and in authentic samples from Indonesia. J Agric Food Chem 58:10568–10575. https://doi.org/10.1021/jf102112p
Woźniakiewicz M, Gładysz M, Nowak PM, Kędzior J, Kościelniak P (2017) Separation of 20 coumarin derivatives using the capillary electrophoresis method optimized by a series of Doehlert experimental designs. Talanta 167:714–724. https://doi.org/10.1016/j.talanta.2017.02.017
Zhang S, Yang J, Li H, Li Y, Liu Y, Zhang D, Zhang F, Zhou W, Chen X (2012) Skimmin, a coumarin, suppresses the streptozotocin-induced diabetic nephropathy in wistar rats. Eur J Pharmacol 692:78–83. https://doi.org/10.1016/j.ejphar.2012.05.017
Zhao A-H, Zhang Y-B, Yang X-W (2016) Simultaneous determination and pharmacokinetics of sixteen Angelicae dahurica coumarins in vivo by LC–ESI-MS/MS following oral delivery in rats. Phytomedicine 23:1029–1036. https://doi.org/10.1016/j.phymed.2016.06.015
Funding
This work was financially supported by the Natural Science Foundation of Tianjin Municipality (18JCYBJC21200), Tianjin Enterprise Technology Correspondent Project (18JCTPJC56300), the Foundation (No. BCERE202005) of Tianjin Key Laboratory of Brine Chemical Engineering and Resource Eco-utilization (Tianjin University of Science & Technology), P. R. China.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of interest
All authors declare no competing interests.
Ethical approval
There are no studies about human participants or animals in the article performed by any of the authors.
Informed consent
Informed consent is not applicable.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Zhao, X., Guo, Z., Hou, Y. et al. AuNP-/rGO-/GCE-based molecular imprinted electrochemical sensor for rapid and sensitive detection of coumarin. Chem. Pap. 76, 3679–3690 (2022). https://doi.org/10.1007/s11696-022-02139-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-022-02139-7