A novel flavonol-based colorimetric and turn-on fluorescent probe for rapid determination of hydrazine in real water samples and its bioimaging in vivo andin vitro
Ahui Qin, Yan Zhang, Shuai Gong, Mingxin Li, Yu Gao, Xu Xu, Jie Song, Zhonglong Wang, Shifa Wang
A novel flavonol-based colorimetric and turn-on fluorescent probe for rapid determination of hydrazine in real water samples and its bioimaging in vivo andin vitro
Hydrazine is extremely toxic and causes severe harm to human body. Herein, a novel fluorescent probe 4-oxo-2-styryl-4H-chromen-3-yl thiophene-2-carboxylate (FHT) was synthesized for detecting hydrazine by using natural cinnamaldehyde as starting material. This probe exhibited significantly enhanced fluorescence response towards hydrazine over various common metal ions, anions, and amine compounds. The detection limit of probe FHT for hydrazine was as low as 0.14 μmol·L–1, significantly lower than that of the threshold value of 0.312 μmol·L–1, imposed by the Environmental Protection Agency. Moreover, the proposed probe was able to detect hydrazine within wide pH (5–10) and linear detection ranges (0–110 μmol·L–1). This probe was employed for determining trace hydrazine in different environmental water samples. The probe FHT-loaded filter paper strips were able to conveniently detect hydrazine of low concentration through distinct naked-eye and fluorescent color changes. Importantly, the probe FHT with low cytotoxicity was successfully applied to visualize hydrazine in living Hela cells and zebrafish.
cinnamaldehyde / 3-hydroxychromone derivative / hydrazine / fluorescent probe
[1] |
Serov A, Kwak C. Direct hydrazine fuel cells: a review. Applied Catalysis B: Environmental, 2010, 98( 1-2): 1– 9
CrossRef
Google scholar
|
[2] |
Zhang J Y, Wang H, Tian Y, Yan Y, Xue Q, He T, Liu H, Wang C, Chen Y, Xia B Y. Anodic hydrazine oxidation assists energy-efficient hydrogen evolution over a bifunctional cobalt perselenide nanosheet electrode. Angewandte Chemie International Edition, 2018, 57( 26): 7649– 7653
CrossRef
Google scholar
|
[3] |
Zhang T, Zhu L, Lin W. A near infrared ratiometric fluorescent probe with aggregation induced emission (AIE) characteristics for hydrazine detection in vitro and in vivo. Dyes and Pigments, 2021, 188 : 109177
CrossRef
Google scholar
|
[4] |
Feng Z, Wang E, Huang S, Liu J. A bifunctional nanoporous Ni–Co–Se electrocatalyst with a superaerophobic surface for water and hydrazine oxidation. Nanoscale, 2020, 12( 7): 4426– 4434
CrossRef
Google scholar
|
[5] |
Wang G, Zhang C, He X, Li Z, Zhang X, Wang L, Fang B. Detection of hydrazine based on nano-Au deposited on porous-TiO2 film. Electrochimica Acta, 2010, 55( 24): 7204– 7210
CrossRef
Google scholar
|
[6] |
Shi X, Yin C, Zhang Y, Wen Y, Huo F. A novel ratiometric and colorimetric fluorescent probe for hydrazine based on ring-opening reaction and its applications. Sensors and Actuators B: Chemical, 2019, 285 : 368– 374
CrossRef
Google scholar
|
[7] |
Cui L, Peng Z, Ji C, Huang J, Huang D, Ma J, Zhang S, Qian X, Xu Y. Hydrazine detection in the gas state and aqueous solution based on the Gabriel mechanism and its imaging in living cells. Chemical Communications (Cambridge), 2014, 50( 12): 1485– 1487
CrossRef
Google scholar
|
[8] |
Shyamaprosad G, Sangita D, Krishnendu A, Bholanath P, Sukanya P, Subhra Kanti M, Sabyasachi S. A chemodosimeter for the ratiometric detection of hydrazine based on return of ESIPT and its application in live-cell imaging. Organic Letters, 2013, 15( 21): 5412– 5415
CrossRef
Google scholar
|
[9] |
Zhao X X, Zhang J F, Liu W, Zhou S, Zhou Z Q, Xiao Y H, Xi G, Miao J Y, Zhao B X. A unique dansyl-based chromogenic chemosensor for rapid and ultrasensitive hydrazine detection. Journal of Materials Chemistry B, 2014, 2( 42): 7344– 7350
CrossRef
Google scholar
|
[10] |
Ma J, Fan J, Li H, Yao Q, Xia J, Wang J, Peng X. Probing hydrazine with a near-infrared fluorescent chemodosimeter. Dyes and Pigments, 2017, 138 : 39– 46
CrossRef
Google scholar
|
[11] |
Choudhary G, Hansen H. Human health perspective on environmental exposure to hydrazines: a review. Chemosphere, 1998, 37( 5): 801– 843
CrossRef
Google scholar
|
[12] |
Liu J, Zhou W H, You T Y, Li F L, Wang E K, Dong S J. Detection of hydrazine, methylhydrazine, and isoniazid by capillary electrophoresis with a palladium-modified microdisk array electrode. Analytical Chemistry, 1996, 68( 19): 3350– 3353
CrossRef
Google scholar
|
[13] |
Liu J, Li Y, Jiang J, Huang X. C@ZnO nanorod array-based hydrazine electrochemical sensor with improved sensitivity and stability. Dalton Transactions (Cambridge, England), 2010, 39( 37): 8693– 8697
CrossRef
Google scholar
|
[14] |
Bhutani H, Singh S, Vir S, Bhutani K K, Kumar R, Chakraborti A K, Jindal K C. LC and LC-MS study of stress decomposition behaviour of isoniazid and establishment of validated stability-indicating assay method. Journal of Pharmaceutical and Biomedical Analysis, 2007, 43( 4): 1213– 1220
CrossRef
Google scholar
|
[15] |
Zhou J, Shi R, Liu J, Wang R, Xu Y, Qian X. An ESIPT-based fluorescent probe for sensitive detection of hydrazine in aqueous solution. Organic & Biomolecular Chemistry, 2015, 13( 19): 5344– 5348
CrossRef
Google scholar
|
[16] |
Mahapatra A K, Karmakar P, Manna S, Maiti K, Mandal D. Benzthiazole-derived chromogenic, fluorogenic and ratiometric probes for detection of hydrazine in environmental samples and living cells. Journal of Photochemistry and Photobiology A: Chemistry, 2017, 334 : 1– 12
CrossRef
Google scholar
|
[17] |
Shi X, Huo F, Chao J, Yin C. A ratiometric fluorescent probe for hydrazine based on novel cyclization mechanism and its application in living cells. Sensors and Actuators B: Chemical, 2018, 260 : 609– 616
CrossRef
Google scholar
|
[18] |
Choi M G, Hwang J, Moon J O, Sung J, Chang S K. Hydrazine-selective chromogenic and fluorogenic probe based on levulinated coumarin. Organic Letters, 2011, 13( 19): 5260– 5263
CrossRef
Google scholar
|
[19] |
Wu W N, Wu H, Wang Y, Mao X J, Zhao X L, Xu Z Q, Fan Y C, Xu Z H. A highly sensitive and selective off−on fluorescent chemosensor for hydrazine based on coumarin beta-diketone. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, 188 : 80– 84
CrossRef
Google scholar
|
[20] |
Tiensomjitr K, Noorat R, Wechakorn K, Prabpai S, Suksen K, Kanjanasirirat P, Pewkliang Y, Borwornpinyo S, Kongsaeree P. A rhodol-based fluorescent chemosensor for hydrazine and its application in live cell bioimaging. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2017, 185 : 228– 233
CrossRef
Google scholar
|
[21] |
Nandi S, Sahana A, Mandal S, Sengupta A, Chatterjee A, Safin D A, Babashkina M G, Tumanov N A, Filinchuk Y, Das D. Hydrazine selective dual signaling chemodosimetric probe in physiological conditions and its application in live cells. Analytica Chimica Acta, 2015, 893 : 84– 90
CrossRef
Google scholar
|
[22] |
Zheng X X, Wang S Q, Wang H Y, Zhang R R, Liu J T, Zhao B X. Novel pyrazoline-based selective fluorescent probe for the detection of hydrazine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 138 : 247– 251
CrossRef
Google scholar
|
[23] |
Wang L, Liu F Y, Liu H Y, Dong Y S, Liu T Q, Liu J F, Yao Y W, Wan X J. A novel pyrazoline-based fluorescent probe for detection of hydrazine in aqueous solution and gas state and its imaging in living cells. Sensors and Actuators B: Chemical, 2016, 229 : 441– 452
CrossRef
Google scholar
|
[24] |
Lin Y D, Chow T J. A pyridomethene-BF2 complex-based chemosensor for detection of hydrazine. RSC Advances, 2013, 3( 39): 17924– 17929
CrossRef
Google scholar
|
[25] |
Goswami S, Paul S, Manna A. A highly reactive (< 1 min) ratiometric chemodosimeter for selective “naked eye” and fluorogenic detection of hydrazine. RSC Advances, 2013, 3( 41): 18872– 18877
CrossRef
Google scholar
|
[26] |
Goswami S, Aich K, Das S, Basu Roy S, Pakhira B, Sarkar S. A reaction based colorimetric as well as fluorescence ‘turn on’ probe for the rapid detection of hydrazine. RSC Advances, 2014, 4( 27): 14210– 14214
CrossRef
Google scholar
|
[27] |
Qu D Y, Chen J L, Di B. A fluorescence “switch-on” approach to detect hydrazine in aqueous solution at neutral pH. Analytical Methods, 2014, 6( 13): 4705– 4709
CrossRef
Google scholar
|
[28] |
Qin T, Liu B, Xu Z, Yao G, Xu H, Zhao C. Flavonol-based small-molecule fluorescent probes. Sensors and Actuators B: Chemical, 2021, 336 : 129718
CrossRef
Google scholar
|
[29] |
Deng S, Wu J, Zhang K, Li Y, Yang L, Hu D, Jin Y, Hao Y, Wang X, Liu Y, Liu H, Chen Y, Xie M. Fluorescence resonance energy transfer-mediated immunosensor based on design and synthesis of the substrate of amp cephalosporinase for biosensing. Analytical Chemistry, 2019, 91( 17): 11316– 11323
CrossRef
Google scholar
|
[30] |
Nguyen K H, Hao Y, Chen W, Zhang Y, Xu M, Yang M, Liu Y N. Recent progress in the development of fluorescent probes for hydrazine. Luminescence, 2018, 33( 5): 816– 836
CrossRef
Google scholar
|
[31] |
Carrillo J T, Borthakur D. Do uncommon plant phenolic compounds have uncommon properties? A mini review on novel flavonoids. Journal of Bioresources and Bioproducts, 2021, 6 : 279– 291
|
[32] |
Wang D, Fan X, Sun S, Du S, Li H, Zhu J, Tang Y, Chang M, Xu Y. Substituent effect: a new strategy to construct a ratiometric fluorescent probe for detection of Al3+ and imaging in vivo. Sensors and Actuators B: Chemical, 2018, 264 : 304– 311
CrossRef
Google scholar
|
[33] |
Dong L Y, Wang L Y, Wang X F, Liu Y, Liu H L, Xie M X. Development of fluorescent FRET probe for determination of glucose based on β-cyclodextrin modified ZnS-quantum dots and natural pigment 3-hydroxyflavone. Dyes and Pigments, 2016, 128 : 170– 178
CrossRef
Google scholar
|
[34] |
Ghosh D, Batuta S, Das S, Begum N A, Mandal D. Proton transfer dynamics of 4′-N,N-dimethylamino-3-hydroxyflavone observed in hydrogen-bonding solvents and aqueous micelles. Journal of Physical Chemistry B, 2015, 119( 17): 5650– 5661
CrossRef
Google scholar
|
[35] |
Jin X, Liu C, Wang X, Huang H, Zhang X, Zhu H. A flavone-based ESIPT fluorescent sensor for detection of N2H4 in aqueous solution and gas state and its imaging in living cells. Sensors and Actuators B: Chemical, 2015, 216 : 141– 149
CrossRef
Google scholar
|
[36] |
Zhang X, Shi C, Ji P, Jin X, Liu J, Zhu H. A red-emitting fluorescent probe based on flavone for hydrazine detection and its application in aqueous solution. Analytical Methods, 2016, 8( 10): 2267– 2273
CrossRef
Google scholar
|
[37] |
Xavier J C, de Almeida-Neto F W Q, Rocha J E, Freitas T S, Freitas P R, de Araújo A C J, da Silva P T, Nogueira C E S, Bandeira P N, Marinho M M.
CrossRef
Google scholar
|
[38] |
Sedgwick A C, Wu L, Han H H, Bull S D, He X P, James T D, Sessler J L, Tang B Z, Tian H, Yoon J. Excited-state intramolecular proton-transfer (ESIPT) based fluorescence sensors and imaging agents. Chemical Society Reviews, 2018, 47( 23): 8842– 8880
CrossRef
Google scholar
|
/
〈 | 〉 |