Citation: Bi Keying, Tan Rui, Hao Ruiting, Miao Lanxi, He Yanqi, Wu Xianghua, Zhang Junfeng, Xu Rui. A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO₃^-) in cells and C. elegans[J]. Chinese Chemical Letters, ;2019, 30(3): 545-548. doi: 10.1016/j.cclet.2018.11.020 shu

A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO₃^-) in cells and C. elegans

Bi Keying ^a,1 ,
Tan Rui ^a,1 ,
Hao Ruiting ^b ,
Miao Lanxi ^c ,
He Yanqi ^c ,
Wu Xianghua ^a ,
Zhang Junfeng ^a,*, ,
Xu Rui ^b,*,

a.
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China
b.
College of Energy and Environment Science, Yunnan Normal University, Kunming 650500, China
c.
College of Chemical Science and Technology, Yunnan University, Kunming 650091, China

junfengzhang78@126.com

ecowatch_xr@163.com

Received Date: 27 September 2018
Revised Date: 14 November 2018
Accepted Date: 16 November 2018
Available Online: 17 March 2018

Figures(5)

Bisulfite (HSO₃^-) is an important sulfur dioxide (SO₂) derivative, which plays a major role in many physiological processes and is also closely associated with a variety of diseases. Thus the development of highly selective and sensitive fluorescent probes is essential to detect HSO₃^- in living cells. In this work, we report the synthesis and analysis of a ratiometric fluorescent probe for selective detection of HSO₃^- based on the 1, 4-nucleophilic addition reaction with the carbazole as an electron donor (D) and aldehyde group as an electron acceptor (A). The addition of HSO₃^- and other ions to our probe can be observed by UV vis and fluorescence spectrometry. Our investigation proved that the probe is highly selective and sensitive for HSO₃^- and ratiometric changes. Moreover, the probe has good cell permeability and was successfully applied to the detection of exogenous HSO₃^- in Hela cells and C. elegans.
- Bisulfite,
- Fluorescent probe,
- Ratiometric,
- Colorimetric,
- Fluorescence imaging
1. [1]
  H. Mana, U. Spohn, Anal. Chem. 73(2001) 3187-3192. doi: 10.1021/ac001049q
2. [2]
  G.J. Mohr, Chem. Commun. 22(2002) 2646-2647.
3. [3]
  M. Zhao, D.B. Hibbert, J.J. Gooding, Anal. Chim. Acta 556(2006) 195-200. doi: 10.1016/j.aca.2005.05.083
4. [4]
  S. Iwasawa, Y. Kikuchi, Y. Nishiwaki, et al., J. Occup. Health 51(2009) 38-47. doi: 10.1539/joh.L8075
5. [5]
  N. Sang, Y. Yun, H. Li, et al., Toxicol. Sci. 114(2010) 226-236. doi: 10.1093/toxsci/kfq010
6. [6]
  D.P. Li, X.J. Han, Z.Q. Yan, et al., Dyes Pigm. 151(2018) 95-101. doi: 10.1016/j.dyepig.2017.12.056
7. [7]
  A. Isaac, J. Davis, C. Livingstone, et al., Trends Analyt. Chem. 25(2006) 589-598. doi: 10.1016/j.trac.2006.04.001
8. [8]
  J.B. Chao, H.J. Wang, Y.B. Zhang, et al., New J. Chem. 42(2018) 3322-3333. doi: 10.1039/C7NJ03903D
9. [9]
  T. Fazio, C.R. Warner, Food Addit. Contam. 7(1990) 433-454. doi: 10.1080/02652039009373907
10. [10]
  R.C. Claudia, J.C. Francisco, Food Control 21(2010) 1331-1337. doi: 10.1016/j.foodcont.2010.04.005
11. [11]
  D. Yang, H.Y. Tian, T.N. Zang, et al., Sci. Rep. 7(2017) 9174. doi: 10.1038/s41598-017-09525-2
12. [12]
  L. Song, X.D. Sun, Y.H. Yao, et al., Chin. Chem. Lett. 27(2016) 1776-1780. doi: 10.1016/j.cclet.2016.05.007
13. [13]
  L. Yu, Y.M. Qiao, L.X. Miao, et al., Chin. Chem. Lett. 29(2018) 1545-1559. doi: 10.1016/j.cclet.2018.09.005
14. [14]
  P.A. Gale, G.S.E. Garcia, J. Garric, Chem. Soc. Rev. 37(2008) 151-190. doi: 10.1039/B715825D
15. [15]
  M.R. Martinez, F. Sancenon, Chem. Rev. 103(2003) 4419-4476. doi: 10.1021/cr010421e
16. [16]
  M.Y. Wu, K. Li, C.Y. Li, et al., Chem. Commun. (Camb.) 50(2014) 183-185. doi: 10.1039/C3CC46468G
17. [17]
  J.C. Xu, J. Pan, X.M. Jiang, et al., Biosens. Bioelectron. 77(2016) 725-732. doi: 10.1016/j.bios.2015.10.049
18. [18]
  W.J. Ma, J.J. Du, J. Yin, et al., Sens. Actuators B-Chem. 267(2018) 104-110. doi: 10.1016/j.snb.2018.03.184
19. [19]
  Y. Liu, M.Y. Wu, Y.H. Liu, et al., Chem. Commun. 51(2015) 10236-10239. doi: 10.1039/C5CC03055B
20. [20]
  Y. Liu, K. Li, K.X. Xie, et al., Chem. Commun. 52(2016) 3430-3433. doi: 10.1039/C5CC10505F
21. [21]
  H. Wang, D. Yang, R. Tan, et al., Sens. Actuators B-Chem. 247(2017) 883-888. doi: 10.1016/j.snb.2017.03.030
22. [22]
  B. Jin, X. Zhang, W. Zheng, et al., Anal. Chem. 86(2014) 943-952. doi: 10.1021/ac403676x
23. [23]
  Y. Zhang, Y.Y. Fu, D.F. Zhu, et al., Chin. Chem. Lett. 27(2016) 1429-1436. doi: 10.1016/j.cclet.2016.05.019
24. [24]
  L. Feng, M. Chhabra, W.H. So, et al., Chin. Chem. Lett. 29(2018) 1147-1150. doi: 10.1016/j.cclet.2018.05.031
25. [25]
  J.C. Xu, H.Q. Yuan, L.T. Zeng, et al., Chin. Chem. Lett. 29(2018) 1456-1464. doi: 10.1016/j.cclet.2018.08.012
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沈阳化工大学材料科学与工程学院沈阳 110142

A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO3-) in cells and C. elegans

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通讯作者: 陈斌, bchen63@163.com

A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO₃^-) in cells and C. elegans