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

  • 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.
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    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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