Fluorescent Detection of 2,4-Dichlorophenoxyacetic Acid in Food Samples Based on Covalent Organic Frameworks and MnO2 Nanosheets
Tóm tắt
2,4-Dichlorophenoxyacetic acid (2,4-D) is a typical chlorinated aromatic herbicide which is widely used because of its low cost. Herein, a new fluorescent assay for 2,4-D is developed based on covalent organic frameworks (COFs) and MnO2 nanosheets. The fluorescence of COFs is quenched effectively by MnO2 nanosheets. Ascorbic acid 2-phosphate (AAP) is hydrolyzed by alkaline phosphatase (ALP) to produce ascorbic acid (AA), which reduces MnO2 nanosheets into Mn2+, so the quenched fluorescence recovers. Additionally, 2,4-D can inhibit the catalytic activity of ALP. Therefore, the addition of 2,4-D quenches the fluorescence of COF-MnO2 system again. Under the optimum conditions, this assay displays a wide linear range of 2,4-D from 1 to 150,000 ng/mL with a limit of detection of 0.36 ng/mL. Then, this method is successfully used to measure 2,4-D in rice, millet, and cucumber samples with satisfactory recoveries. Compared with other probes for 2,4-D detection, both of COFs and MnO2 nanosheets are stable, cost-effective, and easily prepared. The sensitivity and linear range of 2,4-D in this strategy are superior to most reported works. This is the first time that a novel sensing platform using fluorescent COFs and MnO2 nanosheets is developed for 2,4-D.
Tài liệu tham khảo
Bollella P, Fusco G, Tortolini C, Sanzò G, Antiochia R, Favero G, Mazzei F (2016) Inhibition-based first-generation electrochemical biosensors: theoretical aspects and application to 2,4-dichlorophenoxy acetic acid detection. Anal Bioanal Chem 408(12):3203–3211
Boro RC, Kaushal J, Nangia Y et al (2011) Gold nanoparticles catalyzed chemiluminescence immunoassay for detection of herbicide 2,4-dichlorophenoxyacetic acid. Analyst 136(10):2125–2130
Chamkasem N, Morris C (2016) Direct determination of 2,4-dichlorophenoxyacetic acid in soybean and corn by liquid chromatography/tandem mass spectrometry. J Reg Sci 4(2):9–18
Chen H, Zhang ZX, Zhang GM, Guo XF, Zhang HS, Wang H (2010) Liquid chromatographic determination of endogenous phytohormones in vegetable samples based on chemical derivatization with 6-oxy (acetylpiperazine) fluorescein. J Agric Food Chem 58(8):4560–4564
Chen X, Zhang H, Wan Y, Chen X, Li Y (2018) Determination of 2,4-dichlorophenoxyacetic acid (2,4-D) in rat serum for pharmacokinetic studies with a simple HPLC method. PLoS One 13(1):e0191149
Cote AP, Benin AI, Ockwig NW et al (2005) Porous, crystalline, covalent organic frameworks. Science 310(5751):1166–1170
Ding JH, Lu Z, Wang RZ, Shen G, Xiao L (2014) Piezoelectric immunosensor with gold nanoparticles enhanced competitive immunoreaction technique for 2,4-dichlorophenoxyacetic acid quantification. Sensors Actuators B Chem 193:568–573
Ding SY, Dong M, Wang YW, Chen YT, Wang HZ, Su CY, Wang W (2016) Thioether-based fluorescent covalent organic framework for selective detection and facile removal of mercury (II). J Am Chem Soc 138(9):3031–3037
Galvão AC, Robazza WS, Bianchi AD, Matiello JA, Paludo AR, Thomas R (2018) Solubility and thermodynamics of vitamin C in binary liquid mixtures involving water, methanol, ethanol and isopropanol at different temperatures. J Chem Thermodyn 121:8–16
Habila MA, Alothman ZA, Al-tamrah SA et al (2015) Activated carbon from waste as an efficient adsorbent for malathion for detection and removal purposes. J Ind Eng Chem 32:336–344
Haeri SA, Abbasi S (2016) Biocoacervation extraction combined with dispersive solid phase extraction using a reversed-phase core–shell magnetic molecularly imprinted sorbent for 2,4-dichlorophenoxyacetic acid prior to its determination by HPLC. J Iran Chem Soc 13(11):1993–1999
Hu XL, Wu XM, Fang X et al (2016) Switchable fluorescence of gold nanoclusters for probing the activity of alkaline phosphatase and its application in immunoassay. Biosens Bioelectron 77:666–672
Huang M, Zhang YX, Li F et al (2014) Self-assembly of mesoporous nanotubes assembled from interwoven ultrathin birnessite-type MnO2 nanosheets for asymmetric supercapacitors. Sci Rep 4:3878
Kandambeth S, Biswal BP, Chaudhari HD et al (2017) Selective molecular sieving in self-standing porous covalent-organic-framework membranes. Adv Mater 29(2):1603945
Kim SJ, Gobi KV, Tanaka H et al (2008) A simple and versatile self-assembled monolayer based surface plasmon resonance immunosensor for highly sensitive detection of 2,4-D from natural water resources. Sensors Actuators B Chem 130(1):281–289
Lescano MR, Pizzul L, Castillo MP, Zalazar CS (2018) Glyphosate and aminomethylphosphonic acid degradation in biomixtures based on alfalfa straw, wheat stubble and river waste. J Environ Manag 228:451–457
Li ZP, Zhang YW, Xia H, Mu Y, Liu X (2016) A robust and luminescent covalent organic framework as a highly sensitive and selective sensor for the detection of Cu2+ ions. Chem Commun 52(39):6613–6616
Lin YH, Lu F, Wang J (2004) Disposable carbon nanotube modified screen-printed biosensor for amperometric detection of organophosphorus pesticides and nerve agents. Electroanalysis 16(1-2):145–149
Liu J, Yang SH, Li FY, Dong L, Liu J, Wang X, Pu Q (2015) Highly fluorescent polymeric nanoparticles based on melamine for facile detection of TNT in soil. J Mater Chem A 3(18):10069–10076
Liu ZG, Cai XH, Lin XF, Zheng Y, Wu Y, Chen P, Weng S, Lin L, Lin X (2016a) Signal-on fluorescent sensor based on GQDs–MnO2 composite for glutathione. Anal Methods 8(11):2366–2374
Liu L, Xia L, Guo C, Wu C, Chen G, Li G, Sun Z, You J (2016b) A sensitive and efficient method for the determination of 8 chlorophenoxy acid herbicides in crops by dispersive liquid–liquid microextraction and HPLC with fluorescence detection and identification by MS. Anal Methods 8(17):3536–3544
Liu J, Nan Y, Chang X, Li X, Fang Y, Liu Y, Tang Y, Wang X, Li R, Ma J (2017) Hierarchical nitrogen-enriched porous carbon materials derived from Schiff-base networks supported FeCo2O4 nanoparticles for efficient water oxidation. Int J Hydrog Energy 42(16):10802–10812
Lv B, Wei M, Liu Y, Liu X, Wei W, Liu S (2016) Ultrasensitive photometric and visual determination of organophosphorus pesticides based on the inhibition of enzyme-triggered formation of core-shell gold-silver nanoparticles. Microchim Acta 183(11):2941–2948
Maleki N, Safavi A, Hasanpour F et al (2008) Determination of traces of 2,4-dichlorophenoxy acetic acid in environmental samples. Sci Iran:430–434
Pang S, Yang TX, He LL (2016) Review of surface enhanced Raman spectroscopic (SERS) detection of synthetic chemical pesticides. TrAC Trends Anal Chem 85:73–82
Park JY, Choi JH, Abd El-Aty AM et al (2011) Development and validation of an analytical method for determination of endocrine disruptor, 2,4-D, in paddy field water. Biomed Chromatogr 25(9):1018–1024
Peng YW, Huang Y, Zhu YH, Chen B, Wang L, Lai Z, Zhang Z, Zhao M, Tan C, Yang N, Shao F, Han Y, Zhang H (2017) Ultrathin two-dimensional covalent organic framework nanosheets: preparation and application in highly sensitive and selective DNA detection. J Am Chem Soc 139(25):8698–8704
Qu FL, Pei HM, Kong RM, Zhu S, Xia L (2017) Novel turn-on fluorescent detection of alkaline phosphatase based on green synthesized carbon dots and MnO2 nanosheets. Talanta 165:136–142
Qu F, Meng LX, Zi YQ, You J (2019) Ratiometric detection of alkaline phosphatase based on aggregation-induced emission enhancement. Anal Bioanal Chem 411(28):7431–7440
Qu F, Wang H, You JM (2020) Dual lanthanide-probe based on coordination polymer networks for ratiometric detection of glyphosate in food samples. Food Chem 323:126815
Reddy KS, Gambrell RP (1987) Factors affecting the adsorption of 2,4-D and methyl parathion in soils and sediments. Agric., Ecosyst. Environ 18(3):231–241
Roshan S, Asgharinezhad AA et al (2011) Determination of 2,4-D in environmental samples by three phases directly suspended LPME combined with HPLC-UV. Anal Methods 3(10):2261–2267
Stegbauer L, Schwinghammer K, Lotsch BV (2014) A hydrazone-based covalent organic framework for photocatalytic hydrogen production. Chem Sci 5(7):2789–2793
Sun ZJ, Shu D, Lv CJ, Zhang Q, He C, Tian S (2013) Fabrication and supercapacitive behavior of tetramethylammonium ion-intercalated MnO2 prepared by an exfoliation and self-assembly process. J Alloys Compd 569:136–143
Vinayaka AC, Basheer S, Thakur MS (2009) Bioconjugation of CdTe quantum dot for the detection of 2, 4-dichlorophenoxyacetic acid by competitive fluoroimmunoassay based biosensor. Biosens. Bioelectron 24(6):1615–1620
Wang XY, Yu JL, Wu XQ, Fu J, Kang Q, Shen D, Li J, Chen L (2016) A molecular imprinting-based turn-on ratiometric fluorescence sensor for highly selective and sensitive detection of 2,4-dichlorophenoxyacetic acid (2,4-D). Biosens Bioelectron 81:438–444
Wang QL, Li J, Li XD, Ding LS, Xie J, Qing LS (2017) A simple nano-SiO2-based ELISA method for residue detection of 2,4-dichlorophenoxyacetic acid in bean sprouts. Food Anal Methods 10(5):1500–1506
Wu MX, Yang YW (2017) Applications of covalent organic frameworks (COFs): from gas storage and separation to drug delivery. Chin Chem Lett 28(6):1135–1143
Xiao T, Sun J, Zhao JH, Wang S, Liu G, Yang X (2018) FRET effect between fluorescent polydopamine nanoparticles and MnO2 nanosheets and its application for sensitive sensing of alkaline phosphatase. ACS Appl Mater Interfaces 10(7):6560–6569
Yan X, Li HX, Han XS, Su X (2015) A ratiometric fluorescent quantum dots based biosensor for organophosphorus pesticides detection by inner-filter effect. Biosens Bioelectron 74:277–283
Yang YJ, Yuan WT, Li SB, Yang X, Xu J, Jiang Y (2015) Manganese dioxide nanoparticle enrichment in porous conducting polymer as high performance supercapacitor electrode materials. Electrochim Acta 165:323–329
Zhang CL, Zhang SM, Yan YH, Xia F, Huang A, Xian Y (2017) Highly fluorescent polyimide covalent organic nanosheets as sensing probes for the detection of 2,4,6-trinitrophenol. ACS Appl Mater Interfaces 9(15):13415–13421
Zhang XJ, He MQ, He P, Li C, Liu H, Zhang X, Ma Y (2018) Ultrafine nano-network structured bacterial cellulose as reductant and bridging ligands to fabricate ultrathin K-birnessite type MnO2 nanosheets for supercapacitors. Appl Surf Sci 433:419–427
Zhao X, Yan N (2015) One-pot synthesis and assembly of melamine-based nanoparticles for microporous polymer organic frameworks and their application as a support for a silver nanoparticle catalyst. RSC Adv 5(86):69955–69961
Zhao ZL, Fan HH, Zhou GF, Bai H, Liang H, Wang R, Zhang X, Tan W (2014) Activatable fluorescence/MRI bimodal platform for tumor cell imaging via MnO2 nanosheet–aptamer nanoprobe. J Am Chem Soc 136(32):11220–11223