Citation: He Ping, Tang Lijun, Zhong Keli, Hou Shuhua, Yan Xiaomei. Fluorescence Recognition of H₂S by a Benzothiazole Derivative and Its Live Cell Imaging[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 423-428. doi: 10.6023/cjoc201608003 shu

Fluorescence Recognition of H₂S by a Benzothiazole Derivative and Its Live Cell Imaging

He Ping ^a ,
Tang Lijun ^a,*,, ,
Zhong Keli ^a ,
Hou Shuhua ^a ,
Yan Xiaomei ^b,*,,

a.
College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121013
b.
College of Laboratory Medicine, Dalian Medical University, Dalian 116044

Corresponding author: Tang Lijun, ljtang@bhu.edu.cn Yan Xiaomei, xmyan1978@sina.com
Received Date: 4 August 2016
Revised Date: 19 September 2016

Fund Project: the National Natural Science Foundation of China U1608222the Liaoning Excellent Talents in University LR2015001the National Natural Science Foundation of China 21476029

Figures(10)

A new benzothiazole-derived fluorescence probe 2-(4-azidobenzyl) oxy-3-(benzo[d]thiazol-2-yl)-5-methylben-zaldehyde (HBTA) was synthesized from 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methylbenzaldehyde, and the structure of HBTA was characterized. The recognition behaviors of HBTA to H₂S were investigated and the results show that HBTA exhibits good selectivity and sensitivity to H₂S with fast response and good anti-interference ability. The probe can be applied to detect H₂S in a broad pH range, and the detection limit of HBTA for H₂S was estimated to be 9.09×10^-7 mol·L^-1. Cell imaging studies reveal that HBTA is capable of detect H₂S in live cells.
- hydrogen sulfide,
- fluorescent probe,
- benzothiazole,
- cells imaging
1. [1]
  Li, L.; Rose, P.; Moore, P. K. Annu. Rev. Pharmacol. Toxicol. 2011, 51, 169. doi: 10.1146/annurev-pharmtox-010510-100505
2. [2]
  Lovatt, E. C. Q. J. Exp. Physiol. Cogn. Med. Sci. 1967, 52, 231. doi: 10.1113/expphysiol.1967.sp001909
3. [3]
  (a) Eto, K.; Asada, T.; Arima, K.; Makifuchi, T.; Kimura, H. Biochem. Biophys. Res. Commun. 2002, 293, 1485.
  (b) Kamoun, P.; Belardinelli, M. C.; Chabli, A.; Lallouchi, K.; Chadefaux-Vekemans, B. Am. J. Med. Genet., Part A 2003, 116A, 310.
  (c) Yang, W.; Yang, G.; Jia, X.; Wu, L.; Wang, R. J. Physiol. 2005, 569, 519.
  (d) Fiorucci, S.; Antonelli, E.; Mencarelli, A.; Orlandi, S.; Renga, B.; Rizzo, G.; Distrutti, E.; Shah, V.; Morelli, A. Hepatology 2005, 42, 539.
4. [4]
  (a) Qian, L.; Lancaster, J. R. Nitric Oxide 2013, 35, 21.
  (b) Yang, C.; Yang, Z.; Zhang, M.; Dong, Q.; Wang, X.; Lan, A.; Zeng, F.; Chen, P.; Wang, C.; Feng, J. PLoS One 2011, 6, e21971.
5. [5]
  (a) Qandil, A. M. Int. J. Mol. Sci. 2012, 13, 17244.
  (b) Lefer, D. J. Br. J. Pharmacol. 2008, 155, 617.
6. [6]
  (a) Choi, M. G.; Cha, S.; Lee, H.; Jeon, H. L.; Chang, S. K. Chem. Commun. 2009, 47, 7390.
  (b) Lawrence, N. S.; Davis, J.; Compton, R. G. Talanta 2000, 52, 771.
  (c) Hannestad, U.; Margheri, S.; Bo, S. Anal. Biochem. 1989, 178, 394.
7. [7]
  (a) Yu, F.; Han, X.; Chen, L. Chem. Commun. 2014, 50, 12234.
  (b) Guo, Z.; Chen, G.; Zeng, G.; Li, Z.; Chen, A.; Wang, J.; Jiang, L. Analyst 2015, 140, 1772.
  (c) Lin, V. S.; Chen, W.; Xian, M.; Chang, C. J. Chem. Soc. Rev. 2014, 44, 4596.
8. [8]
  Liu, C.; Pan, J.; Li, S.; Zhao, Y.; Wu, L. Y.; Berkman, C. E.; Whorton, A. R.; Xian, M. Angew. Chem., Int. Ed. 2011, 50, 10327. doi: 10.1002/anie.201104305
9. [9]
  Fang, F.-L.; Jing, J. Q.; Chen, X. M. Chin. J. Org. Chem. 2014, 34, 2178 (in Chinese). doi: 10.6023/cjoc201404015
10. [10]
  Hou, F.; Huang, L.; Xi, P.; Cheng, J.; Zhao, X.; Xie, G.; Shi, Y.; Cheng, F.; Yao, X.; Bai, D.; Zeng, Z. Inorg. Chem. 2012, 51, 2454. doi: 10.1021/ic2024082
11. [11]
  Tian, H.; Qian, J.; Bai, H.; Qian, S.; Zhang, L.; Zhang, W. Anal. Chim. Acta 2013, 768, 136. doi: 10.1016/j.aca.2013.01.030
12. [12]
  (a) Kabil, O.; Banerjee, R. J. Biol. Chem. 2010, 285, 21903.
  (b) Chegaev, K.; Rolando, B.; Cortese, D.; Gazzano, E.; Buondonno, I.; Lazzarato, L.; Fanelli, M.; Hattinger, C. M.; Serra, M.; Riganti, C.; Fruttero, R.; Ghigo, D.; Gasco, A. J. Med. Chem. 2016, 59, 4881.
13. [13]
  (a) Zhang, J.; Guo, W. Chem. Commun. 2014, 50, 4214.
  (b) Zheng, Y.; Zhao, M.; Qiao, Q.; Liu, H.; Lang, H.; Xu, Z. Dyes Pigm. 2013, 98, 367.
  (c) Paul, S.; Goswami, S.; Mukhopadhyay, C. D. New J. Chem. 2015, 39, 8940.
14. [14]
  Yin, J.; Wu, Q.; Chang, X. Talanta 2014, 121, 122-126. doi: 10.1016/j.talanta.2014.01.001
15. [15]
  Jian, X.; Yan, Z.; Hui, Y.; Gao, X.; Shao, S. Anal. Chem. 2015, 88.
16. [16]
  (a) And, T. J. D.; Julius Rebek, J. J. Am. Chem. Soc. 2006, 128, 4500.
  (b) Huang, Z.; Ding, S.; Yu, D.; Huang, F.; Feng, G. Chem. Commun. 2014, 50, 9185.
  (c) Roy, A.; Kand, D.; Saha, T.; Talukdar, P. Chem. Commun. 2014, 50, 5510.
17. [17]
  Tang, L.; Dai, X.; Wen, X.; Wu, D.; Zhang, Q. Spectrochim. Acta, Part A 2015, 139, 329. doi: 10.1016/j.saa.2014.12.055
18. [18]
  Belkheira, M.; Abed, D. E.; Pons, J.-M.; Bressy, C. Chem.-Eur. J. 2011, 17, 12917. doi: 10.1002/chem.v17.46
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Fluorescence Recognition of H₂S by a Benzothiazole Derivative and Its Live Cell Imaging