Abstract
In this work, simple, cost efficient, highly selective and sensitive assay methods for dopamine (DA) concentration and tyrosinase (TYR) activity were established based on a benzoyl peroxide (BPO) facilitated in situ “turn-on” fluorogenic reaction between resorcinol (RS) and DA, in which BPO was introduced in the system to accelerate DA oxidation, thereby realizing a faster reaction with RS to form the fluorescent substance, azamonardine, which was verified by HPLC, 1H NMR, 13C NMR and high resolution mass spectrometry. The introduction of BPO remarkably improved the sensitivity, linearity range and response speed for assay of DA and TYR. For the determination of DA concentration, the concentration has a good linear relationship in the range of 4.0–1.2 μM, and the detection limit is as low as 0.8 nM, and it was successfully applied to measuring DA in human urine and serum samples. In addition, a fluorescent method for determining the TYR activity was further established based on the enzymatic oxidation of tyramine to DA, the detection limit is 0.0013 U mL−1. And the method was used to determine TYR in human serum and screening of TYR inhibitors.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Acuna AU, Alvarez-Perez M, Liras M, Coto PB, Amat-Guerri F (2013) Synthesis and photophysics of novel biocompatible fluorescent oxocines and azocines in aqueous solution. Phys Chem Chem Phys 15:16704–16712. https://doi.org/10.1039/C3CP52228H
Ao H, Qian ZS, Zhu YY, Zhao MZ, Tang C, Huang YY, Feng H, Wang AJ (2016) A fluorometric biosensor based on functional Au/Ag nanoclusters for real-time monitoring of tyrosinase activity. Biosens Bioelectron 86:542–547. https://doi.org/10.1016/j.bios.2016.07.051
Benedetto GED, Fico D, Pennetta A, Malitesta C, Nicolardi G, Lofrumento DD, Nuccio FD, Pesa VL (2014) A rapid and simple method for the determination of 3, 4-dihydroxyphenylacetic acid, norepinephrine, dopamine, and serotonin in mouse brain homogenate by HPLC with fluorimetric detection. J Pharm Biomed Anal 98:266–270. https://doi.org/10.1016/j.jpba.2014.05.039
Chen C, Pang LH, Wang R, Zou CP, Ruan GT, Sun YJ, Zhang CW, Yu HD, Li L, Liu JH (2021) Fluorescence copolymer-based dual-signal monitoring tyrosinase activity and its inhibitor screening via blue-green emission transformation. Spectrochim Acta A Mol Biomol Spectrosc 246:119028. https://doi.org/10.1016/j.saa.2020.119028
Cheng XM, Zhang RY, Cai XL, Liu B (2017) A reusable and naked-eye molecular probe with aggregation-induced emission (AIE) characteristics for hydrazine detection. J Mater Chem B 5:3565–3571. https://doi.org/10.1039/C7TB00436B
Cheng X, Chai YY, Xu J, Wang L, Wei FD, Xu GH, Sun Y, Hu Q, Cen Y (2020) Enzyme cascade reaction-based ratiometric fluorescence probe for visual monitoring the activity of alkaline phosphatase. Sens Actuators B Chem 309:127765. https://doi.org/10.1016/j.snb.2020.127765
Crescenzi O, Napolitano A, Prota G, Peter MG (1991) Oxidative coupling of dopa with resorcinol and phloroglucinol: Isolation of adducts with an unusual tetrahydromethanobenzofuro(2,3-d)azocine skeleton. Tetrahedron 47:6243–6250. https://doi.org/10.1016/S0040-4020(01)86556-X
Dai HX, Chen D, Li Y, Cao PF, Wang N, Lin M (2018) Voltammetric sensing of dopamine based on a nanoneedle array consisting of NiCO2S4 hollow core-shells on a nickel foam. Microchim Acta 185:157. https://doi.org/10.1007/s00604-018-2718-5
Ding YZ, Wang WF, Chai T, Qiang Y, Shi YP, Yang JL (2019) Ratiometric target-triggered fluorescent silicon nanoparticles probe for quantitative visualization of tyrosinase activity. Talanta 197:113–121. https://doi.org/10.1016/j.talanta.2019.01.002
Du X, Li LX, Li JS, Yang CW, Frenkel N, Welle A, Heissler S, Nefedov A, Grunze M, Levkin P (2014) UV-triggered dopamine polymerization: control of polymerization, surface coating, and photopatterning. Adv Mater 26:8029–8033. https://doi.org/10.1002/adma.201403709
Garcia-Jimenez A, Teruel-Puche JA, Garcia-Ruiz PA, Berna J, Rodríguez-López JN, Tudela J, Garcia-Canovas F (2017) Action of 2,2′,4,4′-tetrahydroxybenzophenone in the biosynthesis pathway of melanin. Int J Biol Macromol 98:622–629. https://doi.org/10.1016/j.ijbiomac.2017.02.032
Garcia-Molina F, Munoz JL, Varon R (2007) A review on spectrophotometric methods for measuring the monophenolase and diphenolase activities of tyrosinase. J Agric Food Chem 55:9739–9749. https://doi.org/10.1021/jf0712301
He XJ, Dai LX, Wen H, Xu CC, Xu W, Ye LS, Sun XS, Song W, Shen JL (2021) Reaction-based chemosensor as dual-channel indicator for visualizing and bioimaging of exogenous hypochlorite concentrations in living cells, Pseudomonas aeruginosa, and zebrafish. Anal Chim Acta 1157:338391. https://doi.org/10.1016/j.aca.2021.338391
Iacomino M, Alfieri ML, Crescenzi O, d’Ischia M, Napolitano A (2019) Unimolecular variant of the fluorescence turn-on oxidative coupling of catecholamines with resorcinols. ACS Omega 4:1541–1548. https://doi.org/10.1021/acsomega.8b02778
Lee JH, Ryu JS, Kang YK, Lee H, Chung HJ (2021) Polydopamine sensors of bacterial hypoxia via fluorescence coupling. Adv Funct Mater 31:2007993. https://doi.org/10.1002/adfm.202007993
Li Z, Xia XF, You Y, Lu CF, Yang GC, Ma C, Nie JQ, Sun Q, Wu SL, Ren J, Wang FY (2021) Fast-response fluorescent probe with favorable water solubility for highly sensitive imaging of endogenous tyrosinase in living cells and zebrafish model. Chin Chem Lett 32:1785–1789. https://doi.org/10.1016/j.cclet.2020.12.053
Lin J, Fisher D (2007) Melanocyte biology and skin pigmentation. Nature 445:843–850. https://doi.org/10.1038/nature05660
Liu SY, Shi FP, Zhao XJ, Chen L, Su XG (2013) 3-Aminophenyl boronic acid-functionalized CuInS2 quantum dots as a near-infrared fluorescence probe for the determination of dopamine. Biosens Bioelectron 47:379–384. https://doi.org/10.1016/j.bios.2013.03.055
Liu Y, Wu LQ, Dai YX, Li YP, Qi SL, Du JS (2021a) A novel dibenzimidazole-based fluorescent probe with high sensitivity and selectivity for copper ions. J Photochem Photobiol A 406:113018. https://doi.org/10.1016/j.jphotochem.2020.113018
Liu YB, Zhang Y, Zhang XL, Zhang W, Wang XH, Sun Y, Ma PY, Huang YB, Song DQ (2021b) Near-infrared fluorescent probe based on Ag&Mn:ZnInS QDs for tyrosinase activity detection and inhibitor screening. Sens Actuators B Chem 344:130234. https://doi.org/10.1016/j.snb.2021.130234
Ma ZY, Xu YF, Li PP, Cheng D, Zhu XH, Liu ML, Zhang YY, Liu Y (2021) Self-catalyzed surface reaction-induced fluorescence resonance energy transfer on cysteine-stabilized MnO2 quantum dots for selective detection of dopamine. Anal Chem 93:3586–3593. https://doi.org/10.1021/acs.analchem.0c05102
Mao GB, Du MY, Wang XX, Jia XH, He ZK (2018) Simple construction of ratiometric fluorescent probe for the detection of dopamine and tyrosinase by the naked eye. Analyst 143:5295–5301. https://doi.org/10.1039/C8AN01640B
Mi GH, Yang M, Wang CJ, Zhang B, Hu XY, Hao H, Fan J (2021) A simple “turn off-on” ratio fluorescent probe for sensitive detection of dopamine and lysine/arginine. Spectrochim Acta A Mol Biomol Spectrosc 253:119555. https://doi.org/10.1016/j.saa.2021.119555
Mirica LM, Vance M, Rudd DJ, Hedman B, Hodgson KO, Solomon EI, Stack TDP (2005) Tyrosinase reactivity in a model complex: an alternative hydroxylation mechanism. Science 308:1890–1892. https://doi.org/10.1126/science.1112081
Niu C, Yin L, Nie LF, Dou J, Zhao JY, Li G, Aisa HA (2016) Synthesis and bioactivity of novel isoxazole chalcone derivatives on tyrosinase and melanin synthesis in murine B16 cells for the treatment of vitiligo. Bioorg Med Chem Lett 24:5440–5448. https://doi.org/10.1016/j.bmc.2016.08.066
Ortiz-Gomez I, Ortega-Muñoz M, Marín-Sánchez A, Orbe-Payá I, Hernandez-Mateo F, Capitan-Vallvey L (2020) A vinyl sulfone clicked carbon dot-engineered microfluidic paper-based analytical device for fluorometric determination of biothiols. Microchim Acta 187:421. https://doi.org/10.1007/s00604-020-04382-9
Perry M, Li Q, Kennedy RT (2009) Review of recent advances in analytical techniques for the determination of neurotransmitter. Anal Chim Acta 653:1–22. https://doi.org/10.1016/j.aca.2009.08.038
Qian CG, Zhu S, Feng PJ, Chen YL, Yu JC, Tang X, Liu Y, Shen QD (2015) Conjugated polymer nanoparticles for fluorescence imaging and sensing of neurotransmitter dopamine in living cells and the brains of zebrafish larvae. ACS Appl Mater Interfaces 7:18581–18589. https://doi.org/10.1021/acsami.5b04987
Qu F, Huang W, You JM (2018) A fluorescent sensor for detecting dopamine and tyrosinase activity by dual-emission carbon dots and gold nanoparticles. Colloids Surf B 162:212–219. https://doi.org/10.1016/j.colsurfb.2017.11.055
Qu ZY, Yu T, Bi LH (2019) A dual-channel ratiometric fluorescent probe for determination of the activity of tyrosinase using nitrogen-doped graphene quantum dots and dopamine-modified CdTe quantum dots. Microchim Acta 186:635. https://doi.org/10.1007/s00604-019-3733-x
Ren W, Zhang Y, Liang WY, Yang XP, Jiang WD, Liu XH, Zhang W (2021) A facile and sensitive ratiometric fluorescence sensor for rapid visual monitoring of trace resorcinol. Sens Actuators B Chem 330:129390. https://doi.org/10.1016/j.snb.2020.129390
Rolff M, Schottenheim J, Decker H, Tuczek F (2011) Copper-O2 reactivity of tyrosinase models towards external monophenolic substrates: molecular mechanism and comparison with the enzyme. Chem Soc Rev 40:4077–4098. https://doi.org/10.1039/C0CS00202J
Shen BX, Qian Y (2019) Red emission cysteine probe with high selectivity based on fluorescent protein chromophores and turn-on fluorescence in cell cultures. Dyes Pigm 166:350–356. https://doi.org/10.1007/10.1016/j.dyepig.2019.03.034
Shu W, Wu YL, Zang SP, Su S, Kang H, Jing J, Zhang XL (2020) A mitochondria-targeting highly specific fluorescent probe for fast sensing of endogenous peroxynitrite in living cells. Sens Actuators B Chem 303:127284. https://doi.org/10.1016/j.snb.2019.127284
Sun Y, Lin TR, Zeng CH, Jiang GY, Zhang XH, Ye FG, Zhao SL (2021) A self-correcting fluorescent assay of tyrosinase based on Fe-MIL-88B-NH2 nanozyme. Microchim Acta 188:158. https://doi.org/10.1007/s00604-021-04808-y
Suzuki Y (2017) Design and synthesis of fluorescent reagents for selective detection of dopamine. Sens Actuators B Chem 239:383–389. https://doi.org/10.1016/j.snb.2016.08.019
Suzuki Y (2019) Development of fluorescent reagent based on ligand exchange reaction for the highly sensitive and selective detection of dopamine in the serum. Sensors 19:3928. https://doi.org/10.3390/s19183928
Teng Y, Li J, Jia XF, Wang EK (2015) Ratiometric fluorescence detection of tyrosinase activity and dopamine using thiolate-protected gold nanoclusters. Anal Chem 87:4897–4902. https://doi.org/10.1021/acs.analchem.5b00468
Tessari I, Bisaglia M, Velle F, Samori B, Bergantino E, Mammi S, Bubacco L (2008) The reaction of alpha-synuclein with tyrosinase: possible implications for Parkinson disease. J Biol Chem 283:16808–16817. https://doi.org/10.1074/jbc.M709014200
Varodi C, Pogacean F, Gheorghe M, Mirel V, Coros M, Barbu-Tudoran L, Stefan-van Staden R-I, Pruneanu S (2020) Stone paper as a new substrate to fabricate flexible screen-printed electrodes for the electrochemical detection of dopamine. Sensors 20:3609. https://doi.org/10.3390/s20123609
Wang L, Gan ZF, Guo D, Xia HL, Patrice FT, Hafez ME, Li DW (2019) Electrochemistry-regulated recyclable SERS sensor for sensitive and selective detection of tyrosinase activity. Anal Chem 91:6507–6513. https://doi.org/10.1021/acs.analchem.8b05341
Wang CJ, Shi HX, Yang M, Yan YJ, Liu EZ, Ji Z, Fan J (2020a) A novel nitrogen-doped carbon quantum dots as effective fluorescent probes for detecting dopamine. J Photochem Photobiol A 391:112374. https://doi.org/10.1016/j.jphotochem.2020.112374
Wang M, Xie JL, Li J, Fan YY, Deng X, Duan HL, Zhang ZQ (2020b) 3-Aminophenyl boronic acid functionalized quantum-dot-based ratiometric fluorescence sensor for the highly sensitive detection of tyrosinase activity. ACS Sens 5:1634–1640. https://doi.org/10.1021/acssensors.0c00122
Wang CJ, Shi HX, Yang M, Yao Z, Zhang B, Liu EZ, Hu XY, Xue WM, Fan J (2021a) Biocompatible sulfur nitrogen co-doped carbon quantum dots for highly sensitive and selective detection of dopamine. Colloids Surf B 205:111874. https://doi.org/10.1016/j.colsurfb.2021.111874
Wang ZQ, Zhang XD, Zhang H, Tang Y, Pan H, Wang H, Ji T, Guo YF, Gao QS, Song T, Zhang ZC (2021b) Discovery of a fluorogenic probe for in situ pyruvate kinase M2 Isoform (PKM2) labeling through chemoselective SNAr with a binding site lysine residue. Anal Chem 93:9669–9676. https://doi.org/10.1021/acs.analchem.1c00208
Wei MX, Wei N, Pang LF, Guo XF, Wang H (2021) Determination of dopamine in human serum based on green-emitting fluorescence carbon dots. Opt Mater 118:111257. https://doi.org/10.1016/j.optmat.2021.111257
Wu CQ, Lin X, Wang QM (2021) Determination of hypochlorite via fluorescence change from blue to green based on 4-(1 H-imidazo (4,5-f) (1,10)-phenanthrolin-2-yl) benzaldehyde oxime. J Fluoresc 31:1125–1132. https://doi.org/10.1007/s10895-021-02740-1
Yang S, Jiang JX, Zhou AX, Zhou YB, Ye WL, Cao DS, Yang RH (2020) Substrate-photocaged enzymatic fluorogenic probe enabling sequential activation for light-controllable monitoring of intracellular tyrosinase activity. Anal Chem 92:7194–7199. https://doi.org/10.1021/acs.analchem.0c00746
Yildirim A, Bayindir M (2014) Turn-on fluorescent dopamine sensing based on in situ formation of visible light emitting polydopamine nanoparticles. Anal Chem 86:5508–5512. https://doi.org/10.1021/ac500771q
Yildiz HB, Freeman R, Gill R, Willner I (2008) Electrochemical, photoelectrochemical, and piezoelectric analysis of tyrosinase activity by functionalized nanoparticles. Anal Chem 80:2811–2816. https://doi.org/10.1021/ac702401v
Zhang RX, Fan ZF (2020) Nitrogen-doped carbon quantum dots as a “turn off-on” fluorescence sensor based on the redox reaction mechanism for the sensitive detection of dopamine and alpha lipoic acid. J Photochem Photobiol A 392:112438. https://doi.org/10.1016/j.jphotochem.2020.112438
Zhang XL, Zhu YG, Li X, Guo XH, Zhang B, Jia X, Dai B (2016) A simple, fast and low-cost turn-on fluorescence method for dopamine detection using in situ reaction. Anal Chim Acta 944:51–56. https://doi.org/10.1016/j.aca.2016.09.023
Zhang JZ, Chen YY, Zheng ZF, Wang ZZ, Zheng YJ, Lin XH, Weng SH (2019) Fluorescence sensing of tyrosinase activity based on amine rich carbon dots through direct interaction in a homogeneous system: detection mechanism and application. RSC Adv 9:20029–20034. https://doi.org/10.1039/C9RA03098K
Zhang YY, Xu HD, Yang YL, Zhu FM, Pu YX, You XS, Liao XL (2021) Efficient fluorescence resonance energy transfer-based ratiometric fluorescent probe for detection of dopamine using a dual-emission carbon dot-gold nanocluster nanohybrid. J Photochem 411:113195. https://doi.org/10.1016/j.jphotochem.2021.113195
Zhao JH, Bao XF, Wang S, Lu SS, Sun J, Yang XR (2017) In situ fluorogenic and chromogenic reactions for the sensitive dual-readout assay of tyrosinase activity. Anal Chem 89:10529–10536. https://doi.org/10.1021/acs.analchem.7b02739
Zhao JH, Liu GY, Sun J, Wang QF, Li ZJ, Yang XR (2020) Dual-readout tyrosinase activity assay facilitated by a chromo-fluorogenic reaction between catechols and naphthoresorcin. Anal Chem 92:2316–2322. https://doi.org/10.1021/acs.analchem.9b05204
Zolghadri S, Bahrami A, Khan MTH, Munoz-Munoz J, Garcia-Molina F, Garcia-Canovas F, Saboury AA (2019) A comprehensive review on tyrosinase inhibitors. J Enzyme Inhib Med Chem 34:279–309. https://doi.org/10.1080/14756366.2018.1545767
Acknowledgements
This work was supported by the National Natural Science Foundation of China (nos. 22074117 and 21974106).
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Ding, Y., Yang, LH., Shen, JW. et al. Highly sensitive assay of dopamine and tyrosinase using benzoyl peroxide facilitated in-situ fluorogenic reaction. Chem. Pap. 76, 4235–4244 (2022). https://doi.org/10.1007/s11696-022-02169-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-022-02169-1