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| A novel resorufin based fluorescent “turn-on” probe for the selective detection of hydrazine and application in living cells |
| Tun Tang, Yu-Qi Chen, Bo-Shi Fu, Zhi-Yong He, Heng Xiao, Fan Wu, Jia-Qi Wang, Shao-Ru Wang, Xiang Zhou |
| College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Wuhan 430072, China |
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Abstract In this study, a resorufin derivative RTP-1, which is a novel fluorescent "turn-on" probe for sensitive detection of hydrazine within 30 min, is designed and synthesized. The selective deprotection of the ester group of the probe by hydrazine led to a prominent enhancement of fluorescent intensity, aswell as a remarkable color change from colorless to pink, which could be distinguished by naked eye. The fluorescence enhancement showed decent linear relationship with hydrazine concentration ranging from 0 to 50 μmol/L, with a detection limit of 0.84 μmol/L. The specificity of RTP-1 for hydrazine to a number of metal ions, anions and amines is satisfactory. The sensing mechanism of RTP-1 and hydrazine was evaluated by HPLC, ESI mass spectrometry and density functional theory (DFT). Moreover, we have utilized this fluorescent probe for imaging hydrazine in living cells, and the fluorescence was clearly observed when the cells were incubated with hydrazine (100 μmol/L) for 30 min.
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Received: 29 October 2015
Published: 22 January 2016
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| Fund:This work was supported by the National Basic Research Program of China (973 Program, Nos. 2012CB720600, 2012CB720603), the National Science Foundation of China (Nos. 91413109, 21202126) and East Lake High-tech Zone 3551 Talents Scheme. |
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Corresponding Authors:
Xiang Zhou
E-mail: xzhou@whu.edu.cn
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| [1] |
S.S. Narayanan, F. Scholz, A comparative study of the electrocatalytic activities of some metal hexacyanoferrates for the oxidation of hydrazine, Electroanalysis 11(1999) 465-469.
|
| [2] |
U. Ragnarsson, Synthetic methodology for alkyl substituted hydrazines, Chem. Soc. Rev. 30(2001) 205-213.
|
| [3] |
K. Yamada, K. Yasuda, N. Fujiwara, et al., Potential application of anion-exchange membrane for hydrazine fuel cell electrolyte, Electrochem. Commun. 5(2003) 892-896.
|
| [4] |
S. Garrod, M.E. Bollard, A.W. Nicholls, et al., Integrated metabonomic analysis of the multiorgan effects of hydrazine toxicity in the rat, Chem. Res. Toxicol. 18(2005) 115-122.
|
| [5] |
H.W. Schiessl, Hydrazine and its derivatives, in:Kirk-Othmer (Ed.), Encyclopedia of Chemical Technology, John Wiley & Sons, New York, 2000, pp. 562-607.
|
| [6] |
J.W. Mo, B. Ogorevc, X.J. Zhang, B. Pihlar, Cobalt and copper hexacyanoferrate modified carbon fiber microelectrode as an all-solid potentiometric microsensor for hydrazine, Electroanalysis 12(2000) 48-54.
|
| [7] |
E.H. Vernot, J.D. MacEwen, R.H. Bruner, et al., Long-term inhalation toxicity of hydrazine, Fundam. Appl. Toxicol. 5(1985) 1050-1064.
|
| [8] |
S.M. Sanins, J.A. Timbrell, C. Elcombe, J.K. Nicholson, Proton NMR spectroscopic studies on the metabolism and biochemical effects of hydrazine in vivo, Arch. Toxicol. 66(1992) 489-495.
|
| [9] |
C.A. Reilly, S.D. Aust, Peroxidase substrates stimulate the oxidation of hydralazine to metabolites which cause single-strand breaks in DNA, Chem. Res. Toxicol. 10(1997) 328-334.
|
| [10] |
J.A. Oh, J.H. Park, H.S. Shin, Sensitive determination of hydrazine in water by gas chromatography-mass spectrometry after derivatization with ortho-phthalaldehyde, Anal. Chim. Acta 769(2013) 79-83.
|
| [11] |
Z.K. He, B. Fuhrmann, U. Spohn, Coulometric microflow titrations with chemiluminescent andamperometricequivalencepoint detection:bromimetric titrationof low concentrations of hydrazine and ammonium, Anal. Chim. Acta 409(2000) 83-91.
|
| [12] |
A. Benvidi, P. Kakoolaki, H.R. Zare, R. Vafazadeh, Electrocatalytic oxidation of hydrazine at a Co(II) complex multi-wall carbon nanotube modified carbon paste electrode, Electrochim. Acta 56(2011) 2045-2050.
|
| [13] |
X.X. Zhao, J.F. Zhang, W. Liu, et al., A unique dansyl-based chromogenic chemosensor for rapid and ultrasensitive hydrazine detection, J. Mater. Chem. B 2(2014) 7344-7350.
|
| [14] |
S. Goswami, S. Das, K. Aich, et al., A chemodosimeter for the ratiometric detection of hydrazine based on return of ESIPT and its application in live-cell imaging, Org. Lett. 15(2013) 5412-5415.
|
| [15] |
B. Chen, X. Sun, X. Li, H. Ågren, Y.S. Xie, TICT based fluorescence "turn-on" hydrazine probes, Sens. Actuators B 199(2014) 93-100.
|
| [16] |
Y. Sun, D. Zhao, S.W. Fan, L. Duan, A 4-hydroxynaphthalimide-derived ratiometric fluorescent probe for hydrazine and its in vivo applications, Sens. Actuators B 208(2015) 512-517.
|
| [17] |
Y.Q. Tan, J.C. Yu, J.K. Gao, et al., A new fluorescent and colorimetric probe for trace hydrazine with a wide detection range in aqueous solution, Dyes Pigments 99(2013) 966-971.
|
| [18] |
S. Goswami, S. Das, K. Aich, D. Sarkar, T.K. Mondal, A coumarin based chemodosimetric probe for ratiometric detection of hydrazine, Tetrahedron Lett. 55(2014) 2695-2699.
|
| [19] |
J. Zhao, Y.Q. Xu, H.J. Li, A.P. Lu, S.Q. Sun, A facile intracellular fluorescent probe for detection of hydrazine and its application, New J. Chem. 37(2013) 3849-3852.
|
| [20] |
L.L. Xiao, J. Tu, S.Q. Sun, et al., A fluorescent probe for hydrazine and its in vivo applications, RSC Adv. 4(2014) 41807-41811.
|
| [21] |
M.H. Lee, B. Yoon, J.S. Kim, J.L. Sessler, Naphthalimide trifluoroacetyl acetonate:a hydrazine-selective chemodosimetric sensor, Chem. Sci. 4(2013) 4121-4126.
|
| [22] |
Y. Qian, J. Lin, L.J. Han, L. Lin, H.L. Zhu, A resorufin-based colorimetric and fluorescent probe for live-cell monitoring of hydrazine, Biosens. Bioelectron. 58(2014) 282-286.
|
| [23] |
S. Goswami, K. Aich, S. Das, et al., A reaction based colorimetric as well as fluorescence 'turn on' probe for the rapid detection of hydrazine, RSC Adv. 4(2014) 14210-14214.
|
| [24] |
M. Sun, D.H. Shangguan, H.M. Ma, et al., Simple PbII fluorescent probe based on PbII-catalyzed hydrolysis of phosphodiester, Biopolymers 72(2003) 413-420.
|
| [25] |
W.Z. Gao, B.G. Xing, R.Y. Tsien, J.H. Rao, Novel fluorogenic substrates for imaging b-lactamase gene expression, J. Am. Chem. Soc. 125(2003) 11146-11147.
|
| [26] |
S.Y. Kim, J.I. Hong, Chromogenic and fluorescent chemodosimeter for detection of fluoride in aqueous solution, Org. Lett. 9(2007) 3109-3212.
|
| [27] |
M.G. Choi, S.Y. Cha, J.E. Park, et al., Selective perborate signaling by deprotection of fluorescein and resorufin acetates, Org. Lett. 12(2010) 1468-1471.
|
| [28] |
M.G. Choi, J. Hwang, S. Eor, S.K. Chang, Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufin levulinate, Org. Lett. 12(2010) 5624-5627.
|
|
|
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