Abstract
A sensitive and accurate chemiluminescence (CL) method was developed for one-step determination of diphenyl ether herbicides at trace level with nitrofen (2,4-dichlorophenyl-p-nitrophenyl ether) as a model analyte. Candida rugosa lipase (CRL) was immobilized on a nanocarrier of amine-linked covalent organic framework (named as COF-300-AR) through a self-assembly strategy. The formed nanocomposite of COF-300-AR@CRL owns dual enzymatic catalytic activities. It can directly catalyze luminol-dissolved oxygen reaction to produce an intense CL emission by virtue of oxidase mimic activity of COF-300-AR but also effectively decompose nitrofen to release phenolic compounds by the immobilized CRL. The released phenolic compounds own strong reducing capacity and in turn decrease the CL signal sharply. Under the optimal conditions, the decreased CL intensity presents a good linear response to nitrofen concentration in the 0.02–50.0 μM range. The limit of detection (LOD, 3sb/S) is 11 nM and the precision is 2.0% for replicate measurements of 50.0 nM nitrofen solution (n = 11). This method has the advantages of rapid analytical efficiency, good selectivity, satisfactory stability, and recyclability. Recovery experiments were conducted on spiked vegetable and fruit samples with the recoveries falling in the range 90.0–107.0%.
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References
Peillex C, Pelletier M (2020) The impact and toxicity of glyphosate and glyphosate-based herbicides on health and immunity. J Immunotoxicol 17:163–174. https://doi.org/10.1080/1547691X.2020.1804492
Ribeiro YM, Moreira DP, Weber AA, Sales CF, Melo RMC, Bazzoli N, Rizzo E, Paschoalini AL (2022) Adverse effects of herbicides in freshwater Neotropical fish: a review. Aquat Toxicol 252:106293. https://doi.org/10.1016/j.aquatox.2022.106293
Tsai WT (2013) A review on environmental exposure and health risks of herbicide. paraquat. Toxicol Environ Chem 95:197–206. https://doi.org/10.1080/02772248.2012.761999
Huang DC, You MS, Hou YM, Li ZS (2005) Effects of chemical herbicides on bio-communities in agroecosystems. Acta Ecologica Sinica 25:1451–1458
Triantafyllidis V, Mavroeidis A, Kosma C, Karabagias IK, Zotos A, Kehayias G, Beslemes D, Roussis I, Bilalis D, Economou G (2023) Herbicide use in the era of farm to fork: strengths, weaknesses, and future implications. Water Air Soil Poll 234:94. https://doi.org/10.1007/s11270-023-06125-x
Romero-Lopez M, Oria M, Ferrer-Marquez F, Varela MF, Lampe K, Watanabe-Chailland M, Martinez L, Peiro JL (2023) Fetal lung hypoxia and energetic cell failure in the nitrofen–induced congenital diaphragmatic hernia rat model. Pediatr Surg Int 39:180. https://doi.org/10.1007/s00383-023-05452-8
http://www.moa.gov.cn/ztzl/ncpzxzz/flfg/200709/t20070919_893058.htm. Accessed 5 July 2023
Wang MT, Zhou X, Zang XH, Pang YC, Chang Q, Wang C, Wang Z (2018) Determination of pesticides residues in vegetable and fruit samples by solid-phase microextraction with a covalent organic framework as the fiber coating coupled with gas chromatography and electron capture detection. J Sep Sci 41:4038–4046. https://doi.org/10.1002/jssc.201800644
Pang YC, Zang XH, Wang MT, Chang QY, Zhang SH, Wang C, Wang Z (2018) Fibrous boron nitride nanocomposite for magnetic solid phase extraction of ten pesticides prior to the quantitation by gas chromatography. Microchim Acta 185:561. https://doi.org/10.1007/s00604-018-3103-0
Bodur S, Balurdere EG (2019) Simultaneous determination of selected herbicides in dam lake, river and well water samples by gas chromatography mass spectrometry after vortex assisted binary solvent liquid phase microextraction. Microchem J 145:168–172. https://doi.org/10.1016/j.microc.2018.10.033
Turan NB, Bakirdere S (2021) A miniaturized spray-assisted fine-droplet-formation-based liquid-phase microextraction method for the simultaneous determination of fenpiclonil, nitrofen and fenoxaprop-ethyl as pesticides in soil samples. Rapid Commun Mass Spectrom 35:e8943. https://doi.org/10.1002/rcm.8943
Yan M, Jia YQ, Qi PR, Wang YH, Ji QQ, Wang MM, Wang Q, Hao YL (2021) Determination of three diphenyl ether herbicides in rice by magnetic solid phase extraction using Fe3O4@MOF-808 coupled with high performance liquid chromatography. Chin J Chromatogr 39:316–323. https://doi.org/10.3724/SP.J.1123.2020.06007
Wang P, Xu XX, Guo LL, Liu LQ, Kuang H, Xiao J, Xu CL (2023) Hapten synthesis and a colloidal gold immunochromatographic strip assay to detect nitrofen and bifenox in fruits. Analyst 148:2449–2458. https://doi.org/10.1039/d3an00358b
Mandal W, Fajal S, Samanta P, Dutta S, Shirolkar MM, More YD, Ghosh SK (2022) Selective and sensitive recognition of specific types of toxic organic pollutants with a chemically stable highly luminescent porous organic polymer (POP). ACS Appl Polym Mater 4:8633–8644. https://doi.org/10.1021/acsapm.2c01538
Cheng YF, Ma BK, Tan CP, Lai OM, Panpipat W, Cheong LZ, Shen C (2020) Hierarchical macro-microporous ZIF-8 nanostructures as efficient nano-lipase carriers for rapid and direct electrochemical detection of nitrogenous diphenyl ether pesticides. Sensor Actuat B-Chem 321:128477. https://doi.org/10.1016/j.snb.2020.128477
Cheng YF, Lai OM, Tan CP, Panpipat W, Cheong LZ, Shen C (2021) Proline-modified UIO-66 as nanocarriers to enhance Candida rugosa lipase catalytic activity and stability for electrochemical detection of nitrofen. ACS Appl Mater Inter 13:4146–4155. https://doi.org/10.1021/acsami.0c17134
Chen YX, Yuan GS, Tan LC, Wang P, Lu RW, Wang CJ (2022) Hollow hierarchical Cu-BTC as nanocarriers to immobilize lipase for electrochemical biosensor. J Inorg Organomet Polym Mater 32:4401–4411. https://doi.org/10.1007/s10904-022-02434-6
Sharma R, Chisti Y, Banerjee UC (2001) Production, purification, characterization, and applications of lipases. Biotechnol Adv 19:627–662. https://doi.org/10.1016/S0734-9750(01)00086-6
Ismail AR, Baek KH (2020) Lipase immobilization with support materials, preparation techniques, and applications: present and future aspects. Int J Biol Macromol 163:1624–1639. https://doi.org/10.1016/j.ijbiomac.2020.09.021
Zhao G, Dong X, Du Y, Zhang N, Bai G, Wu D, Ma H, Wang Y, Cao W, Wei Q (2022) Enhancing electrochemiluminescence efficiency through introducing atomically dispersed ruthenium in nickel-based metal-organic frameworks. Anal Chem 94:10557–10566. https://doi.org/10.1021/acs.analchem.2c02334
Gan JS, Bagheri AR, Aramesh N, Gul I, Franco M, Almulaiky YQ, Bilal M (2021) Covalent organic frameworks as emerging host platforms for enzyme immobilization and robust biocatalysis-a review. Int J Biol Macromol 167:502515. https://doi.org/10.1016/j.ijbiomac.2020.12.002
Wang SZ, Xia XC, Chen FE (2022) Engineering of covalent organic framework–based advanced platforms for enzyme immobilization: strategies, research progress, and prospects. Adv Mater Interfaces 9:2200874. https://doi.org/10.1002/admi.202200874
Oliveira FL, França AD, de Castro AM, de Souza ROMA, Esteves PM, Gonçalves RSB (2020) Enzyme immobilization in covalent organic frameworks: strategies and applications in biocatalysis. ChemPlusChem 85:2051–2066. https://doi.org/10.1002/cplu.202000549
Uribe-Romo FJ, Hunt JR, Furukawa H, Klock C, O’Keeffe M, Yaghi OM (2009) A crystalline imine–linked 3-D porous covalent organic framework. J Am Chem Soc 131:4570–4571. https://doi.org/10.1021/ja8096256
Jin P, Niu X, Zhang F, Dong K, Dai H, Zhang H, Wang W, Chen H, Chen X (2020) Stable and reusable light-responsive reduced covalent organic framework (COF-300-AR) as an oxidase-mimicking catalyst for GSH detection in cell lysate. ACS Appl Mater Inter 12:20414–20422. https://doi.org/10.1021/acsami.0c01763
Kong M, Jin P, Wei W, Wang W, Qin H, Chen H, He J (2021) Covalent organic frameworks (COF-300-AR) with unique catalytic performance in luminol chemiluminescence for sensitive detection of serotonin. Microchem J 160A:105650. https://doi.org/10.1016/j.microc.2020.105650
Teng X, Qi L, Liu T, Li LH, Lu C (2023) Nanomaterial-based chemiluminescence systems for tracing of reactive oxygen species in biosensors. TRAC-Trend Anal Chem 162:117020. https://doi.org/10.1016/j.trac.2023.117020
Wang Y, Zhao G, Chi H, Yang S, Niu Q, Wu D, Cao W, Li T, Ma H, Wei Q (2021) Self-luminescent lanthanide metal-organic frameworks as signal probes in electrochemiluminescence immunoassay. J Am Chem Soc 143:504–512. https://doi.org/10.1021/jacs.0c12449
Tiwari A, Dhoble SJ (2018) Recent advances and developments on integrating nanotechnology with chemiluminescence assays. Talanta 180:1–11. https://doi.org/10.1016/j.talanta.2017.12.031
Al Yahyai I, AI-Lawati HA (2021) A review of recent developments based on chemiluminescence detection systems for pesticides analysis. Luminescence 36:266–277. https://doi.org/10.1002/bio.3947
Chang JF, Yu L, Hou T, Hu RX, Li F (2023) Direct and specific detection of glyphosate using a phosphatase-like nanozyme-mediated chemiluminescence strategy. Anal Chem 95:4479–4485. https://doi.org/10.1021/acs.analchem.2c05198
Ma YY, Zhao YX, Xu XT, Ding SJ, Li YH (2021) Magnetic covalent organic framework immobilized gold nanoparticles with high-efficiency catalytic performance for chemiluminescent detection of pesticide triazophos. Talanta 235:122798. https://doi.org/10.1016/j.talanta.2021.122798
Chen Y, Shi ZL, Wei L, Zhou B, Tan J, Zhou HL, Zhang YB (2019) Guest-dependent dynamics in a 3D covalent organic framework. J Am Chem Soc 141:3298–3303. https://doi.org/10.1021/jacs.8b13691
Liu H, Chu J, Yin Z, Cai X, Zhuang L, Deng H (2018) Covalent organic frameworks linked by amine bonding for concerted electrochemical reduction of CO2. Chem 4:1696–1709. https://doi.org/10.1016/j.chempr.2018.05.003
Feng JB, Li YY, Zhang Y, Xu YY, Cheng XW (2022) Adsorptive removal of indomethacin and diclofenac from water by polypyrrole doped-GO/COF-300 nanocomposites. Chem Eng J 429:132499. https://doi.org/10.1016/j.cej.2021.132499
Yuan MY, Xiao SJ, Wu YN, Qiu AT, Guo J, Zhong ZQ, Zhang L (2022) Visual detection of captopril based on the light activated oxidase-mimic activity of covalent organic framework. Microchem J 175:107080. https://doi.org/10.1016/j.microc.2021.107080
Tan H, Zhao Y, Xu X, Sun Y, Li Y, Du J (2019) A covalent triazine framework as an oxidase mimetic in the luminol chemiluminescence system: application to the determination of the antioxidant rutin. Microchim Acta 187:42. https://doi.org/10.1007/s00604-019-4058-5
Jin P, Niu X, Gao Z, Xue X, Zhang F, Cheng W, Ren C, Du H, Manyande A, Chen H (2021) Ultrafine platinum nanoparticles supported on covalent organic frameworks as stable and reusable oxidase-like catalysts for cellular glutathione detection. ACS Appl Nano Mater 4:5834–5841. https://doi.org/10.1021/acsanm.1c00752
Cheng C, Shen C, Lai OM, Tan CP, Cheong LZ (2021) Biomimetic self–assembly of lipase-zeolitic imidazolate frameworks with enhanced biosensing of protox inhibiting herbicides. Anal Methods UK 13:4974–4984. https://doi.org/10.1039/d1ay01307f
Ministry of Agriculture of the People’s Republic of China Announcement No. 199. National Health and Family Planning Commission of People’s Republic of China and Ministry of Agriculture of People’s Republic of China (2002). https://www.sdtdata.com/fx/fmoa/tsLibCard/122748.html. Accessed 5 July 2023
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The authors really appreciate the financial support from Natural Science Foundation of Shaanxi Province (Grant No. 2020JM-035).
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Ma, Y., Li, Y. COF-300-AR@CRL as a two-in-one nanocatalyst for one-step chemiluminescent detection of diphenyl ether herbicide residues in vegetable and fruit samples. Microchim Acta 190, 492 (2023). https://doi.org/10.1007/s00604-023-06077-3
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DOI: https://doi.org/10.1007/s00604-023-06077-3