Abstract
A photo-induced metal–organic framework-enzyme hybrid nanosystem was developed via a controllable physical embedding method that displays dual enzymatic and photo-non-enzymatic strategy which cause high stability and cascade catalytic performance to oxidation of o-phenylenediamine and generate a UV–Vis signal at 450 nm for the tracing and sensitive detection of putrescine (Put). Under optimal conditions, the present bioassay provides a wide detection range from 0.02 to 10 µM and 20–80 µM with a detection limit of 5.5 nM, which is more desirable than numerous previous reports. In addition, the established colorimetric photo-bioassay can selectively and accurately identify Put in the presence of other distributing species. The present work provides an elegant strategy to merged photo-nanozymes’ and enzyme capabilities and also broadened the sensing strategies of photo-nanozymes with promising potential in the realm of cancer diagnosis and food quality monitoring as well as its potential in various bioassays and heterogeneous catalysis fields.
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Singh H, Singh G, Kaur N, Singh N (2022) Pattern-based colorimetric sensor array to monitor food spoilage using automated high-throughput analysis. Biosens Bioelectron 196:113687
Kim H, Trinh BT, Kim KH, Moon J, Kang H, Jo K, Akter R, Jeong J, Lim E-K, Jung J (2021) Au@ ZIF-8 SERS paper for food spoilage detection. Biosens Bioelectron 179:113063
Andre RS, Ngo QP, Fugikawa-Santos L, Correa DS, Swager TM (2021) Wireless tags with hybrid nanomaterials for volatile amine detection. ACS Sensors 6(6):2457–2464
Gao J-X, Qin L, Wen S-Y, Huang X-H, Dong X-P, Zhou D-Y, Zhu B-W (2021) Simultaneous determination of acrylamide, 5-hydroxymethylfurfural, and heterocyclic aromatic amines in thermally processed foods by ultrahigh-performance liquid chromatography coupled with a Q exactive HF-X mass spectrometer. J Agric Food Chem 69(7):2325–2336
Świder O, Roszko MŁ, Wójcicki M, Szymczyk K (2019) Biogenic amines and free amino acids in traditional fermented vegetables—dietary risk evaluation. J Agric Food Chem 68(3):856–868
Watanabe M, Ohta Y, Licang S, Motoyama N, Kikuchi J (2015) Profiling contents of water-soluble metabolites and mineral nutrients to evaluate the effects of pesticides and organic and chemical fertilizers on tomato fruit quality. Food Chem 169:387–395
Kim KH, Park CS, Park SJ, Kim J, Seo SE, An JE, Ha S, Bae J, Phyo S, Lee J (2022) In-situ food spoilage monitoring using a wireless chemical receptor-conjugated graphene electronic nose. Biosens Bioelectron 200:113908
Orouji A, Ghasemi F, Bigdeli A, Hormozi-Nezhad MR (2021) Providing multicolor plasmonic patterns with Au@ Ag core–shell nanostructures for visual discrimination of biogenic amines. ACS Appl Mater Interfaces 13(17):20865–20874
Qi X-N, Che Y-X, Qu W-J, Zhang Y-M, Yao H, Lin Q, Wei T-B (2021) Design and Fabricating biogenic amine-responsive platform based on self-assembly property of phenazine derivative for visual monitoring of meat spoilage. Sens Actuators, B Chem 333:129430
Draz ME, Darwish HW, Darwish IA, Saad AS (2021) Solid-state potentiometric sensor for the rapid assay of the biologically active biogenic amine (tyramine) as a marker of food spoilage. Food Chem 346:128911
Mairal Lerga T, Jauset-Rubio M, Skouridou V, Bashammakh AS, El-Shahawi MS, Alyoubi AO, O’Sullivan CK (2019) High affinity aptamer for the detection of the biogenic amine histamine. Anal Chem 91(11):7104–7111
Roy R, Sajeev NR, Sharma V, Koner AL (2019) Aggregation induced emission switching based ultrasensitive ratiometric detection of biogenic diamines using a perylenediimide-based smart fluoroprobe. ACS Appl Mater Interfaces 11(50):47207–47217
Sudalaimani S, Kumar KS, Esokkiya A, Suresh C, Giribabu K (2021) Electrified liquid–liquid interface as an electrochemical tool for the sensing of putrescine and cadaverine. Analyst 146(10):3208–3215
Vargas AJ, Wertheim BC, Gerner EW, Thomson CA, Rock CL, Thompson PA (2012) Dietary polyamine intake and risk of colorectal adenomatous polyps. Am J Clin Nutr 96(1):133–141
Leelasree T, Aggarwal H (2022) MOF sensors for food safety: ultralow detection of putrescine and cadaverine in protein rich foods. J Mater Chem C 10(6):2121
Del Rio B, Redruello B, Linares DM, Ladero V, Ruas-Madiedo P, Fernandez M, Martin MC, Alvarez MA (2019) The biogenic amines putrescine and cadaverine show in vitro cytotoxicity at concentrations that can be found in foods. Sci Rep 9(1):1–7
Lin X, Tang Y, Hu Y, Lu Y, Sun Q, Lv Y, Zhang Q, Wu C, Zhu M, He Q (2021) Sodium reduction in traditional fermented foods: challenges, strategies, and perspectives. J Agric Food Chem 69(29):8065–8080
Betancourt L, Rada P, Hernandez L, Araujo H, Ceballos G, Hernandez L, Tucci P, Mari Z, De Pasquale M, Paredes D (2018) Micellar electrokinetic chromatography with laser induced fluorescence detection shows increase of putrescine in erythrocytes of Parkinson’s disease patients. J Chromatogr B 1081:51–57
Leonardo S, Campàs M (2016) Electrochemical enzyme sensor arrays for the detection of the biogenic amines histamine, putrescine and cadaverine using magnetic beads as immobilisation supports. Microchim Acta 183(6):1881–1890
Noreldeen HA, Yang L, Guo X-Y, He S-B, Peng H-P, Deng H-H, Chen W (2022) A peroxidase-like activity-based colorimetric sensor array of noble metal nanozymes to discriminate heavy metal ions. Analyst 147(1):101–108
Jain R, Thakur A, Kaur P, Kim K-H, Devi P (2020) Advances in imaging-assisted sensing techniques for heavy metals in water: trends, challenges, and opportunities. TrAC, Trends Anal Chem 123:115758
Li Z-M, Zhong X-L, Wen S-H, Zhang L, Liang R-P, Qiu J-D (2019) Colorimetric detection of methyltransferase activity based on the enhancement of CoOOH nanozyme activity by ssDNA. Sens Actuators, B Chem 281:1073–1079
Li M, Chen J, Wu W, Fang Y, Dong S (2020) Oxidase-like MOF-818 nanozyme with high specificity for catalysis of catechol oxidation. J Am Chem Soc 142(36):15569–15574
Zhang J, Liu J (2020) Light-activated nanozymes: catalytic mechanisms and applications. Nanoscale 12(5):2914–2923
Wu S, Zhang J, Wu P (2019) Photo-modulated nanozymes for biosensing and biomedical applications. Anal Methods 11(40):5081–5088
Li S, Shang L, Xu B, Wang S, Gu K, Wu Q, Sun Y, Zhang Q, Yang H, Zhang F (2019) A nanozyme with photo-enhanced dual enzyme-like activities for deep pancreatic cancer therapy. Angew Chem 131(36):12754–12761
Yu S, Jang D, Maji SK, Chung K, Lee JS, Mota FM, Wang J, Kim S, Kim DH (2021) Sophisticated plasmon-enhanced photo-nanozyme for anti-angiogenic and tumor-microenvironment-responsive combinatorial photodynamic and photothermal cancer therapy. J Ind Eng Chem 104:106–116
Zhang J, Wu S, Lu X, Wu P, Liu J (2019) Manganese as a catalytic mediator for photo-oxidation and breaking the pH limitation of nanozymes. Nano Lett 19(5):3214–3220
Lin Y, Liu X, Liu Z, Xu Y (2021) Visible-light-driven photocatalysis-enhanced nanozyme of TiO2 nanotubes@ MoS2 nanoflowers for efficient wound healing infected with multidrug-resistant bacteria. Small 17(39):2103348
Liu C, Zhang M, Geng H, Zhang P, Zheng Z, Zhou Y, He W (2021) NIR enhanced peroxidase-like activity of Au@ CeO2 hybrid nanozyme by plasmon-induced hot electrons and photothermal effect for bacteria killing. Appl Catal B 295:120317
Liu Y, Zhou M, Cao W, Wang X, Wang Q, Li S, Wei H (2019) Light-responsive metal–organic framework as an oxidase mimic for cellular glutathione detection. Anal Chem 91(13):8170–8175
Niu X, Li X, Lyu Z, Pan J, Ding S, Ruan X, Zhu W, Du D, Lin Y (2020) Metal–organic framework based nanozymes: promising materials for biochemical analysis. Chem Commun 56(77):11338–11353
Wang D, Jana D, Zhao Y (2020) Metal–organic framework derived nanozymes in biomedicine. Acc Chem Res 53(7):1389–1400
Wang X, Jiang X, Wei H (2020) Phosphate-responsive 2d-metal–organic-framework-nanozymes for colorimetric detection of alkaline phosphatase. J Mater Chem B 8(31):6905–6911
Wu J, Yu Y, Cheng Y, Cheng C, Zhang Y, Jiang B, Zhao X, Miao L, Wei H (2021) Ligand-dependent activity engineering of glutathione peroxidase-mimicking MIL-47 (V) metal–organic framework nanozyme for therapy. Angew Chem 133(3):1247–1254
Mandal S, Prasad SR, Mandal D, Das P (2019) Bovine serum albumin amplified reactive oxygen species generation from anthrarufin-derived carbon dot and concomitant nanoassembly for combination antibiotic–photodynamic therapy application. ACS Appl Mater Interfaces 11(36):33273–33284
Deng Q, Wang R, Wang Y, Yang Z, Gou B, Li J, Yan Y, Yang R (2022) Exploration of bifunctional vanadium-based metal-organic framework with double active centers for potassium-ion batteries. J Colloid Interface Sci 628:556–565
He B, Zhang Q, Man P, Zhou Z, Li C, Li Q, Xie L, Wang X, Pang H, Yao Y (2019) Self-sacrificed synthesis of conductive vanadium-based metal–organic framework nanowire-bundle arrays as binder-free cathodes for high-rate and high-energy-density wearable Zn-ion batteries. Nano Energy 64:103935
Ishimaru M, Muto Y, Nakayama A, Hatate H, Tanaka R (2019) Determination of biogenic amines in fish meat and fermented foods using column-switching high-performance liquid chromatography with fluorescence detection. Food Anal Methods 12(1):166–175
Liu J, Lin C, Zhang W, Yang Q, Meng J, He L, Deng L, Zeng X (2021) Exploring the bacterial community for starters in traditional high-salt fermented Chinese fish (Suanyu). Food Chem 358:129863
Šimat V, Dalgaard P (2011) Use of small diameter column particles to enhance HPLC determination of histamine and other biogenic amines in seafood. LWT-Food Sci Technol 44(2):399–406
Li H, Wu J, Wang L, Liao Q, Niu X, Zhang D, Wang K (2022) A zinc ion hybrid capacitor based on sharpened pencil-like hierarchically porous carbon derived from metal–organic framework. Chem Eng J 428:131071
Niu B, Yao B, Zhu M, Guo H, Ying S, Chen Z (2021) Carbon paste electrode modified with fern leave-like MIL-47 (as) for electrochemical simultaneous detection of Pb (II), Cu (II) and Hg (II). J Electroanal Chem 886:115121
Feng W, Zhao T, Zhou Y, Li F, Zou Y, Bai S, Wang W, Yang L, Wu X (2013) Optimization of enzyme-assisted extraction and characterization of collagen from Chinese sturgeon (Acipenser sturio Linnaeus) skin. Pharmacogn Mag 9(Suppl 1):S32
Barthelet K, Marrot J, Riou D, Férey G (2002) A breathing hybrid organic–inorganic solid with very large pores and high magnetic characteristics. Angew Chem Int Ed 41(2):281–284
Zhao C, He Y, Wang X, Sun W (2021) Photoelectrochemical determination of oxidase activity based on photoinduced direct electron transfer of protein by using a convenient photoelectrochemical detector. Sens Actuators, B Chem 328:128992
Mishra A, Kumar A, Hodges D, Misra R (2017) Tunable TiO2–pepsin thin film as a low-temperature electron transport layer for photoelectrochemical cells. Mater Technol 32(13):829–837
Mansingh S, Subudhi S, Sultana S, Swain G, Parida K (2021) Cerium-based metal–organic framework nanorods nucleated on CeO2 nanosheets for photocatalytic N2 fixation and water oxidation. ACS Applied Nano Mater 4(9):9635–9652
Karimi R, Yousefi F, Ghaedi M, Dashtian K, Yasin G (2022) Unveiling charge dynamics of Co3S4 nanowalls/CdS nanospheres nn heterojunction for efficient photoelectrochemical Cr (VI) detoxification and N2 fixation. J Environ Chem Eng 10:108549
Kröger J, Jiménez-Solano A, Savasci G, Lau VWh, Duppel V, Moudrakovski I, Küster K, Scholz T, Gouder A, Schreiber ML (2021) Morphology control in 2D carbon nitrides: Impact of particle size on optoelectronic properties and photocatalysis. Adv Func Mater 31(28):2102468
Denisov N, Zhou X, Cha G, Schmuki P (2021) Photocurrent conversion efficiency of TiO2 nanotube photoanodes in dependence of illumination intensity. Electrochim Acta 377:137988
Liu G-Q, Yang Y, Li Y, Zhuang T, Li X-F, Wicks J, Tian J, Gao M-R, Peng J-L, Ju H-X (2021) Boosting photoelectrochemical efficiency by near-infrared-active lattice-matched morphological heterojunctions. Nat Commun 12(1):1–9
Dashtian K, Shahbazi S, Tayebi M, Masoumi Z (2021) A review on metal-organic frameworks photoelectrochemistry: a headlight for future applications. Coord Chem Rev 445:214097
Ning P, Liang J, Li L, Chen D, Qin L, Yao X, Chen H, Huang Y (2021) In situ growth of Z-scheme CuS/CuSCN heterojunction to passivate surface defects and enhance charge transport. J Colloid Interface Sci 590:407–414
Dashtian K, Ghaedi M, Hajati S (2019) Photo-sensitive Pb5S2I6 crystal incorporated polydopamine biointerface coated on nanoporous TiO2 as an efficient signal-on photoelectrochemical bioassay for ultrasensitive detection of Cr (VI) ions. Biosens Bioelectron 132:105–114
Dashtian K, Hajati S, Ghaedi M (2020) L-phenylalanine-imprinted polydopamine-coated CdS/CdSe nn type II heterojunction as an ultrasensitive photoelectrochemical biosensor for the PKU monitoring. Biosens Bioelectron 165:112346
Huai X, Girardi L, Lu R, Gao S, Zhao Y, Ling Y, Rizzi GA, Granozzi G, Zhang Z (2019) The mechanism of concentric HfO2/Co3O4/TiO2 nanotubes investigated by intensity modulated photocurrent spectroscopy (IMPS) and electrochemical impedance spectroscopy (EIS) for photoelectrochemical activity. Nano Energy 65:104020
Li F, Yang H, Zhuo Q, Zhou D, Wu X, Zhang P, Yao Z, Sun L (2021) A cobalt@ cucurbit [5] uril complex as a highly efficient supramolecular catalyst for electrochemical and photoelectrochemical water splitting. Angew Chem 133(4):2004–2013
Dashtian K, Hajati S, Ghaedi M (2021) Ti-based solid-state imprinted-Cu2O/CuInSe2 heterojunction photoelectrochemical platform for highly selective dopamine monitoring. Sensors and Actuators B: Chemical 326:128824
Zhan Y, Yang S, Luo F, Guo L, Zeng Y, Qiu B, Lin Z (2020) Emission wavelength switchable carbon dots combined with biomimetic inorganic nanozymes for a two-photon fluorescence immunoassay. ACS Appl Mater Interfaces 12(27):30085–30094
Cui J, Pottosin I, Lamade E, Tcherkez G (2020) What is the role of putrescine accumulated under potassium deficiency? Plant Cell Environ 43(6):1331–1347
Munawar T, Yasmeen S, Hasan M, Mahmood K, Hussain A, Ali A, Arshad M, Iqbal F (2020) Novel tri-phase heterostructured ZnO–Yb2O3–Pr2O3 nanocomposite; structural, optical, photocatalytic and antibacterial studies. Ceram Int 46(8):11101–11114
Jana A, Kundu P, Paul S, Kondaiah P, Chakravarty AR (2022) Cobalt (III) complexes for light-activated delivery of acetylacetonate-BODIPY, cellular Imaging, and Photodynamic Therapy. Inorg Chem 61:6837
Zhang Y, Zeng X, Jiang X, Chen H, Long Z (2019) Ce-based UiO-66 metal-organic frameworks as a new redox catalyst for atomic spectrometric determination of Se (VI) and colorimetric sensing of Hg (II). Microchem J 149:103967
Jiao J, Yan X, Xing S, Zhang T, Han Q (2022) Design of a polyoxometalate-based metal–organic framework for photocatalytic C (sp3)–H oxidation of toluene. Inorg Chem 61(5):2421–2427
Zhao C, Jiang Z, Mu R, Li Y (2016) A novel sensor for dopamine based on the turn-on fluorescence of Fe-MIL-88 metal-organic frameworks–hydrogen peroxide–o-phenylenediamine system. Talanta 159:365–370
Ma X, Wen S, Xue X, Guo Y, Jin J, Song W, Zhao B (2018) Controllable synthesis of SERS-active magnetic metal–organic framework-based nanocatalysts and their application in photoinduced enhanced catalytic oxidation. ACS Appl Mater Interfaces 10(30):25726–25736
Yin Y, Gao C, Xiao Q, Lin G, Lin Z, Cai Z, Yang H (2016) Protein-metal organic framework hybrid composites with intrinsic peroxidase-like activity as a colorimetric biosensing platform. ACS Appl Mater Interfaces 8(42):29052–29061
Sardar R, Ahmed S, Yasin NA (2022) Role of exogenously applied putrescine in amelioration of cadmium stress in Coriandrum sativum by modulating antioxidant system. Int J Phytorem 24(9):955–962
Collado-González J, Piñero MC, Otálora G, López-Marín J, Amor FMd (2021) The effect of foliar putrescine application, ammonium exposure, and heat stress on antioxidant compounds in cauliflower waste. Antioxidants 10(5):707
Cai S, Fu Z, Xiao W, Xiong Y, Wang C, Yang R (2020) Zero-dimensional/two-dimensional Au x Pd100–x nanocomposites with enhanced nanozyme catalysis for sensitive glucose detection. ACS Appl Mater Interfaces 12(10):11616–11624
Nagvenkar AP, Gedanken A (2016) Cu0. 89Zn0. 11O, a new peroxidase-mimicking nanozyme with high sensitivity for glucose and antioxidant detection. ACS Appl Mater Inter 8(34):22301–22308
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The authors gratefully acknowledge the financial support from the Research Council of the Iran University of Science and Technology.
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Sharifnezhad, A.H., Dashtian, K., Zare-Dorabei, R. et al. Visible light-responsive vanadium-based metal–organic framework supported pepsin with high oxidase mimic activity for food spoilage monitoring. Microchim Acta 189, 448 (2022). https://doi.org/10.1007/s00604-022-05554-5
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DOI: https://doi.org/10.1007/s00604-022-05554-5