Abstract
Detection of carbendazim (CZ) fungicide residues in food has received increasing attention in recent years. However, most reported methods are sophisticated, high cost, and low throughput. In this study, we designed a label-free fluorescent aptasensor for detecting CZ by using a G-quadruplex-specific probe. The anti-CZ aptamer could be partially complementary to the guanine (G)-rich sequence PW17 and block the formation of G-quadruplex structures, while not in the presence of CZ. The formed G-quadruplex structure in the presence of CZ could non-covalently bind to the fluorescent probe N-methyl mesoporphyrin IX (NMM) and activate its fluorescence. A linear relationship between fluorescence and CZ was obtained in the concentration range of 0.05–0.4 μM with a detection limit of 24.28 nM. This study provides a new perspective for designing label-free aptasensors.
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References
Alkhamis O, Canoura J, Bukhryakov KV, Tarifa A, DeCaprio AP, Xiao Y (2022) DNA aptamer-cyanine complexes as generic colorimetric small-molecule sensors. Angew Chem Int Ed 61(3):e202112305. https://doi.org/10.1002/anie.202112305
Cao Q, Li Y, Freisinger E, Qin PZ, Sigel RKO, Mao Z-W (2017) G-quadruplex DNA targeted metal complexes acting as potential anticancer drugs. Inorg Chem Front 4(1):10–32. https://doi.org/10.1039/C6QI00300A
Chen B, Huang Q, Qu Z, Li C, Li Q, Shi J, Fan C, Wang L, Zuo X, Shen J, Li J (2020) Probing transient DNA conformation changes with an intercalative fluorescent excimer. Angew Chem Int Ed 60(12):6624–6630. https://doi.org/10.1002/anie.202014466
Deore PS, Gray MD, Chung AJ, Manderville RA (2019) Ligand-induced G-quadruplex polymorphism: a DNA nanodevice for label-free aptasensor platforms. J Am Chem Soc 141(36):14288–14297. https://doi.org/10.1021/jacs.9b06533
Dong YY, Yang LJ, Zhang L (2017a) Simultaneous electrochemical detection of benzimidazole fungicides carbendazim and thiabendazole using a novel nanohybrid material-modified electrode. J Agric Food Chem 65(4):727–736. https://doi.org/10.1021/acs.jafc.6b04675
Dong Z-Z, Lu L, Wang W, Li G, Kang T-S, Han Q, Leung C-H, Ma D-L (2017b) Luminescent detection of nicking endonuclease Nb.BsmI activity by using a G-quadruplex-selective iridium(III) complex in aqueous solution. Sens Actuators B 246:826–832. https://doi.org/10.1016/j.snb.2017.02.156
Dunn MR, Jimenez RM, Chaput JC (2017) Analysis of aptamer discovery and technology. Nat Rev Chem 1(10):16. https://doi.org/10.1038/s41570017-0076
Eissa S, Zourob M (2017) Selection and characterization of DNA aptamers for electrochemical biosensing of carbendazim. Anal Chem 89(5):3138–3145. https://doi.org/10.1021/acs.analchem.6b04914
Feng G, Luo X, Lu X, Xie S, Deng L, Kang W, He F, Zhang J, Lei C, Lin B, Huang Y, Nie Z, Yao S (2019a) Engineering of nucleic acids and synthetic cofactors as holo sensors for probing signaling molecules in the cellular membrane microenvironment. Angew Chem Int Ed 58(20):6590–6594. https://doi.org/10.1002/anie.201901320
Feng SX, Li YG, Zhang RY, Li YC (2019b) A novel electrochemical sensor based on molecularly imprinted polymer modified hollow N, S-Mo2C/C spheres for highly sensitive and selective carbendazim determination. Biosens Bioelectron 142:111491. https://doi.org/10.1016/j.bios.2019.111491
Fu RJ, Zhou J, Liu YL, Wang YW, Liu HR, Pang JX, Cui YL, Zhao QY, Wang CQ, Li ZX, Jiao BN, He Y (2021) Portable and quantitative detection of carbendazim based on the readout of a thermometer. Food Chem 351:129292. https://doi.org/10.1016/j.foodchem.2021.129292
Fujii T, Podbevšek P, Plavec J, Sugimoto N (2017) Effects of metal ions and cosolutes on G-quadruplex topology. J Inorg Biochem 166:190–198. https://doi.org/10.1016/j.jinorgbio.2016.09.001
Gao T, Luo Y, Li W, Cao Y, Pei R (2020) Progress in the isolation of aptamers to light-up the dyes and the applications. Analyst 145(3):701–718. https://doi.org/10.1039/C9AN01825E
Georgiades SN, Abd Karim NH, Suntharalingam K, Vilar R (2010) Interaction of metal complexes with G-quadruplex DNA. Angew Chem Int Ed 49(24):4020–4034. https://doi.org/10.1002/anie.200906363
Guan M, Guo Y, Yan X, Si X, Peng X, Lei Y, Shen X, Luo L, He H (2022) Silver ions involved fluorescence “on–off” responses of gold nanoclusters system for determination of carbendazim residues in fruit samples. Food Chem 386:132836. https://doi.org/10.1016/j.foodchem.2022.132836
Guo Y, Xu L, Hong S, Sun Q, Yao W, Pei R (2016) Label-free DNA-based biosensors using structure-selective light-up dyes. Analyst 141(24):6481–6489. https://doi.org/10.1039/c6an01958g
Han Y, He X, Yang WX, Luo XL, Yu Y, Tang WZ, Yue TL, Li ZH (2021) Ratiometric fluorescent sensing carbendazim in fruits and vegetables via its innate fluorescence coupling with UiO-67. Food Chem 345:128839. https://doi.org/10.1016/j.foodchem.2020.128839
Jin W, Ruiyi L, Nana L, Xiulan S, Haiyan Z, Guangli W, Zaijun L (2021) Electrochemical detection of carbendazim with mulberry fruit-like gold nanocrystal/multiple graphene aerogel and DNA cycle amplification. Microchim Acta 188(8):1–12. https://doi.org/10.1007/s00604-021-04886-y
Ko C-N, Cheng S, Leung C-H, Ma D-L (2020) A long-lived phosphorescence amplification system integrated with graphene oxide and a stable split G-quadruplex protector as an isothermal “off–on” biosensor for the HBV gene. ACS Appl Bio Mater 3(7):4556–4565. https://doi.org/10.1021/acsabm.0c00481
Li T, Wang E, Dong S (2009) Potassium-lead-switched G-quadruplexes: a new class of DNA logic gates. J Am Chem Soc 131(42):15082–15083. https://doi.org/10.1021/ja9051075
Li L, Xu S, Yan H, Li X, Yazd HS, Li X, Huang T, Cui C, Jiang J, Tan W (2021) Nucleic acid aptamers for molecular diagnostics and therapeutics: advances and perspectives. Angew Chem Int Ed 60(5):2221–2231. https://doi.org/10.1002/anie.202003563
Liu J, Cao Z, Lu Y (2009) Functional nucleic acid sensors. Chem Rev 109(5):1948–1998. https://doi.org/10.1021/cr030183i
Liu X, He F, Zhang F, Zhang Z, Huang Z, Liu J (2020) Dopamine and melamine binding to gold nanoparticles dominates their aptamer-based label-free colorimetric sensing. Anal Chem 92(13):9370–9378. https://doi.org/10.1021/acs.analchem.0c01773
Lv M, Guo Y, Ren J, Wang E (2019) Exploration of intramolecular split G-quadruplex and its analytical applications. Nucleic Acids Res 47(18):9502–9510. https://doi.org/10.1093/nar/gkz749
Ma DL, He HZ, Leung KH, Zhong HJ, Chan DSH, Leung CH (2013) Label-free luminescent oligonucleotide-based probes. Chem Soc Rev 42(8):3427–3440. https://doi.org/10.1039/C2CS35472A
Mergny J-L, Sen D (2019) DNA quadruple helices in nanotechnology. Chem Rev 119(10):6290–6325. https://doi.org/10.1021/acs.chemrev.8b00629
Monchaud D, Yang P, Lacroix L, Teulade-Fichou M-P, Mergny J-L (2008) A metal-mediated conformational switch controls G-quadruplex binding affinity. Angew Chem Int Ed 47(26):4858–4861. https://doi.org/10.1002/anie.200800468
Oliveira ACM, Araujo DAG, Pradela LA, Takeuchi RM, Santos AL (2021) A robust and versatile micropipette tip-based miniaturized electrochemical cell for determination of carbendazim. Sens Actuators B 327:128880. https://doi.org/10.1016/j.snb.2020.128880
Omar I, O’Neill TM, Rossall S (2006) Biological control of fusarium crown and root rot of tomato with antagonistic bacteria and integrated control when combined with the fungicide carbendazim. Plant Pathol 55(1):92–99. https://doi.org/10.1111/j.1365-3059.2005.01315.x
Ouyang Q, Wang L, Ahmad W, Rong YW, Li HH, Hu YQ, Chen QS (2021) A highly sensitive detection of carbendazim pesticide in food based on the upconversion-MnO2 luminescent resonance energy transfer biosensor. Food Chem 349:129157. https://doi.org/10.1016/j.foodchem.2021.129157
Ruiyi L, Yanhong J, Qinsheng W, Yongqiang Y, Nana L, Xiulan S, Zaijun L (2021) Serine and histidine-functionalized graphene quantum dot with unique double fluorescence emission as a fluorescent probe for highly sensitive detection of carbendazim. Sens Actuators B 343:130099. https://doi.org/10.1016/j.snb.2021.130099
Singh S, Singh N, Kumar V, Datta S, Wani AB, Singh D, Singh K, Singh J (2016) Toxicity, monitoring and biodegradation of the fungicide carbendazim. Environ Chem Lett 14(3):317–329. https://doi.org/10.1007/s10311-016-0566-2
Su L, Wang S, Wang L, Yan Z, Yi H, Zhang D, Shen G, Ma Y (2020) Fluorescent aptasensor for carbendazim detection in aqueous samples based on gold nanoparticles quenching rhodamine B. Spectrochim Acta A Mol Biomol Spectrosc 225:117511. https://doi.org/10.1016/j.saa.2019.117511
Tu X, Gao F, Ma X, Zou J, Yu Y, Li M, Qu F, Huang X, Lu L (2020) Mxene/carbon nanohorn/β-cyclodextrin-metal-organic frameworks as high-performance electrochemical sensing platform for sensitive detection of carbendazim pesticide. J Hazard Mater 396:122776. https://doi.org/10.1016/j.jhazmat.2020.122776
Wang J, Zhang Y, Wang H, Chen Y, Xu L, Gao T, Pei R (2016) Selection and analysis of DNA aptamers to berberine to develop a label-free light-up fluorescent probe. New J Chem 40(11):9768–9773. https://doi.org/10.1039/c6nj02290a
Wang J, Wang Q, Luo Y, Gao T, Zhao Y, Pei R (2019) In vitro selection of ssDNA aptamers that can specifically recognize and differentiate riboflavin and its derivative FAD. Talanta 204:424–430. https://doi.org/10.1016/j.talanta.2019.06.039
Wang SY, Shi XC, Liu FQ, Laborda P (2020) Chromatographic methods for detection and quantification of carbendazim in food. J Agric Food Chem 68(43):11880–11894. https://doi.org/10.1021/acs.jafc.0c04225
Wang P, Li W, Lu Z, Xiong W, Zhai K, Xiang D (2022) One-step simultaneous quantitative detection of three pesticides based on bimetallic organic framework nanomaterials and aptamers. Anal Sci 38(2):299–305. https://doi.org/10.2116/analsci.21P204
Xiao Y, Pavlov V, Niazov T, Dishon A, Kotler M, Willner I (2004) Catalytic beacons for the detection of DNA and telomerase activity. J Am Chem Soc 126(24):7430–7431. https://doi.org/10.1021/ja031875r
Xu L, Guo Y, Wang J, Zhou L, Zhang Y, Hong S, Wang Z, Zhang J, Pei R (2015a) A H+/Ag+ dual-target responsive label-free light-up probe based on a DNA triplex. Chem Asian J 10(5):1126–1129. https://doi.org/10.1002/asia.201500001
Xu L, Shen X, Hong S, Wang J, Zhang Y, Wang H, Zhang J, Pei R (2015b) Turn-on and label-free fluorescence detection of lead ions based on target-induced G-quadruplex formation. Chem Commun 51(38):8165–8168. https://doi.org/10.1039/c5cc01590a
Xu L, Shen X, Hong S, Wang J, Zhou L, Chen X, Pei R (2015c) Thiazole orange as a fluorescent light-up probe for the i-motif and its application to the development of a molecular logic system. Asian J Org Chem 4(12):1375–1378. https://doi.org/10.1002/ajoc.201500347
Xu L, Sun N, Zhou L, Chen X, Wang J, Wang Q, Wang K, Zhang J, Pei R (2015d) A label-free fluorescence assay for potassium ions using riboflavin as a G-quadruplex ligand. Analyst 140(10):3352–3355. https://doi.org/10.1039/c5an00242g
Xu L, Hong S, Sun N, Wang K, Zhou L, Ji L, Pei R (2016a) Berberine as a novel light-up i-motif fluorescence ligand and its application in designing molecular logic systems. Chem Commun 52(1):179–182. https://doi.org/10.1039/c5cc08242k
Xu L, Wang J, Sun N, Liu M, Cao Y, Wang Z, Pei R (2016b) Neutral red as a specific light-up fluorescent probe for i-motif DNA. Chem Commun 52(99):14330–14333. https://doi.org/10.1039/c6cc07674b
Yan H, Liu L, Xu N, Kuang H, Xu C (2015) Development of an immunoassay for carbendazim based on a class-selective monoclonal antibody. Food Agric Immunol 26(5):659–670. https://doi.org/10.1080/09540105.2015.1007446
Yang YX, Huo DQ, Wu HX, Wang XF, Yang JS, Bian MH, Ma Y, Hou CJ (2018) N, P-doped carbon quantum dots as a fluorescent sensing platform for carbendazim detection based on fluorescence resonance energy transfer. Sens Actuators B 274:296–303. https://doi.org/10.1016/j.snb.2018.07.130
Yang Y, Xing XX, Zou T, Wang ZD, Zhao RJ, Hong P, Peng SJ, Zhang X, Wang YD (2020) A novel and sensitive ratiometric fluorescence assay for carbendazim based on N-doped carbon quantum dots and gold nanocluster nanohybrid. J Hazard Mater 386:121958. https://doi.org/10.1016/j.jhazmat.2019.121958
Zadeh JN, Steenberg CD, Bois JS, Wolfe BR, Pierce MB, Khan AR, Dirks RM, Pierce NA (2011) NUPACK: analysis and design of nucleic acid systems. J Comput Chem 32(1):170–173
Zhao XY, Zhang XM, Qin MW, Song YZ, Zhang JY, Xia XS, Cui XM, Gao K, Han QQ (2020) Determination of carbendazim by aptamer-based fluorescence resonance energy transfer (FRET). Anal Lett 54(13):2198–2210. https://doi.org/10.1080/00032719.2020.1849250
Zhou L, Shen X, Sun N, Wang K, Zhang Y, Pei R (2015) Label-free fluorescence light-up detection of T4 polynucleotide kinase activity using the split-to-intact G-quadruplex strategy by ligation-triggered and toehold-mediated strand displacement release. Analyst 140(16):5450–5453. https://doi.org/10.1039/C5AN01032B
Zhu CX, Liu D, Chen Z, Li LB, You TY (2019) An ultra-sensitive aptasensor based on carbon nanohorns/gold nanoparticles composites for impedimetric detection of carbendazim at picogram levels. J Colloid Interface Sci 546:92–100. https://doi.org/10.1016/j.jcis.2019.03.035
Zhu G-Y, Chen Y, Wang S-Y, Shi X-C, Herrera-Balandrano DD, Polo V, Laborda P (2022) Peel diffusion and antifungal efficacy of different fungicides in pear fruit: structure-diffusion-activity relationships. J Fungi 8(5):547
Zikos C, Evangelou A, Karachaliou C-E, Gourma G, Blouchos P, Moschopoulou G, Yialouris C, Griffiths J, Johnson G, Petrou P, Kakabakos S, Kintzios S, Livaniou E (2015) Commercially available chemicals as immunizing haptens for the development of a polyclonal antibody recognizing carbendazim and other benzimidazole-type fungicides. Chemosphere 119:S16–S20. https://doi.org/10.1016/j.chemosphere.2014.03.049
Acknowledgements
This work was supported by the Natural Science Foundation of Shandong Province, China (ZR2019BB047), Zhejiang Provincial Public Welfare Technology Application Research Program (LGF18H200007), and Zhejiang Provincial Medical and Health Science and Technology Plan (2018SKY).
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Jiang, L., Zhou, L., Sai, J. et al. A label-free aptasensor for fluorescent detection of carbendazim based on a G-quadruplex-specific probe. Chem. Pap. 77, 7475–7482 (2023). https://doi.org/10.1007/s11696-023-03020-x
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DOI: https://doi.org/10.1007/s11696-023-03020-x