Articles

A Flavone-Based Fluorescent Probe for Hydrazine and Its Bioimaging in Live Cells

  • Ju Zhiyu ,
  • Shu Penghua ,
  • Xie Zhiyu ,
  • Jiang Yuqing ,
  • Tao Weijie ,
  • Xu Zhihong
Expand
  • a Xuchang Municipality Key Laboratory of Chemo/Biosensing and Detection, School of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000;
    b College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450052

Received date: 2018-08-28

  Revised date: 2018-11-03

  Online published: 2018-11-26

Supported by

Project supported by the Science and Technology Project of Henan Province (Nos. 182102311108, 182102310066), the Program for Science and Technology Innovation Talents in Universities of Henan Province (No. 15HASTIT002), and the National Natural Science Foundation of China (Nos. 21702178, U1304202).

Abstract

A 3-hydroxyflavonoid esters HFBA was synthesized by the reaction of 2-hydroxyacetophenone with p-methyl benzaldehyde, and its structure was characterized by NMR and high resolution mass spectrometer. The recognition behaviors of HFBA to hydrazine were investigated and the results show that HFBA exhibits good selectivity and sensitivity to N2H4 with fast response and good anti-interference ability in DMSO/PBS buffer (pH=7.4). Furthermore, the detection limit of HFBA for hydrazine was estimated to be 0.11 μmol/L, and the probe HFBA was successfully applied for the imaging of hydrazine in living cells.

Cite this article

Ju Zhiyu , Shu Penghua , Xie Zhiyu , Jiang Yuqing , Tao Weijie , Xu Zhihong . A Flavone-Based Fluorescent Probe for Hydrazine and Its Bioimaging in Live Cells[J]. Chinese Journal of Organic Chemistry, 2019 , 39(3) : 697 -702 . DOI: 10.6023/cjoc201808035

References

[1] Mao, C.-H.; Wang, Q.-M.; Ou, X.-M.; Huang, R.-Q.; Chen, L.; Sang, J.; Bi, F.-C. J. Org. Chem. 2006, 26, 60(in Chinese). (毛春晖, 汪清民, 欧晓明, 黄润秋, 陈莉, 尚坚, 毕富春, 有机化学, 2006, 26, 60.)
[2] Jing, X.; Wang, Q.; Bi, X.; Wu, L.; Yan, C. Chin. J. Org. Chem. 2010, 30, 904(in Chinese). (景崤壁, 汪清, 毕晓昕, 吴林韬, 颜朝国, 有机化学, 2010, 30, 904.)
[3] Wang, J.-T.; Xiong, J.-K.; Li, J.-J.; Wang, J.-L.; Wang, K.-.R.; Li, X.-L. Chin. J. Org. Chem. 2017, 37, 1407(in Chinese). (王金涛, 熊就凯, 李娟娟, 王佳利, 王克让, 李小六, 有机化学, 2017, 37, 1407.)
[4] Ma, X.-M.; Shen, W. Chin. J. Org. Chem. 2011, 31, 1668(in Chinese). (马学美, 沈威, 有机化学, 2011, 31, 1668.)
[5] Troyan, J. E. Ind. Eng. Chem. 1953, 45, 2608.
[6] Keller, W. C. Aviat., Space Environ. Med. 1988, 59, 100.
[7] Reilly, C. A.; Aust, S. D. Chem. Res. Toxicol. 1997, 10, 328.
[8] Zhu, S.; Lin, W.-Y.; Yuan, L. Anal. Chem. 2014, 86, 4611.
[9] Cui, L.; Peng, Z.; Ji, C.; Huang, J.; Huang, D.; Ma, J.; Zhang, S.; Qian, X.; Xu, Y. Chem. Commun. 2014, 50, 1485.
[10] Goswami, S.; Das, S.; Aich, K.; Pakhira, B.; Panja, S.; Mukherjee, S. K.; Sarkar, S. Org. Lett. 2013, 15, 5412.
[11] Hu, C.; Sun, W.; Cao, J.; Gao, P.; Wang, J.; Fan, J.; Song, F.; Sun, S.; Peng, X. Org. Lett. 2013, 15, 4022.
[12] Watt, G. W.; Chrisp, J. D. Anal. Chem. 1952, 24, 2006.
[13] Timbrell, J. A.; Wright, J. M.; Smith, C. M. J. Chromatogr. A 1997, 138, 165.
[14] Li, J.; Xie, H.; Chen, L. Sens. Actuators, B 2011, 153, 239.
[15] Xia, X.; Zeng, F.; Zhang, P.; Lyu, J.; Huang, Y.; Wu, S. Sens. Actuators, B 2016, 227, 411.
[16] Ju, Z.; Li, D.; Zhang, D.; Li, D.; Wu, C.; Xu, Z. J. Fluoresc. 2017, 27, 679.
[17] Qian, Y.; Lin, J.; Han, L.; Lin, L.; Zhu, H. Biosens. Bioelectron. 2014, 58, 282.
[18] Song, Z.; Kwok, R. T. K.; Zhao, E.; He, Z.; Hong, Y.; Lam, J. W. Y.; Liu, B.; Tang, B. ACS Appl. Mater. Interfaces 2014, 6, 17245.
[19] Dhiraj, P. M.; Hwajin, K.; Wan, S. C.; David, G. C. Org. Lett. 2013, 15, 3946.
[20] Zhang, X.; Liu, J.Y. Dyes Pigm. 2016, 125, 80.
[21] Li, X.; Hu, B.; Li, J.; Lu, P.; Wang, Y. Sens. Actuators, B 2014, 203, 635.
[22] Liu, B.; Wang, J.; Zhang, G.; Bai, R.; Pang, Y. ACS Appl. Mater. Interfaces 2014, 6, 4402.
[23] Liu, Y.; Yu, D.; Ding, S.; Xiao, Q.; Guo, J.; Feng, G. ACS Appl. Mater. Interfaces 2014, 6, 17543.
[24] Feng, L.; Liu, Z.; Hou, J.; Lv, X.; Ning, J.; Ge, G.; Cui, L.; Yang, J. Biosens. Bioelectron. 2015, 65, 9.
[25] Hu, Q. H.; Zeng, F.; Yu, C. M.; Wu, S. Z. Sens. Actuators, B 2015, 220, 720.
[26] Cui, Y.-Y.; Chen, Z.-P.; Yan, X.-F.; Yu, R.-Q. Chin. J. Anal. Chem. 2016, 47, 1250(in Chinese). (崔银银, 陈增萍, 严秀芳, 俞汝勤, 分析化学, 2016, 47, 1250.)
[27] Zhang, W.-J.; Hou, F.-J.; Yin, C.-X. Chin. J. Appl. Chem. 2017, 34, 1457(in Chinese). (张伟杰, 霍方俊, 阴彩霞, 应用化学, 2017, 34, 1457.)
[28] And, T. J. D.; Julius Rebek, J. J. Am. Chem. Soc. 2006, 128, 4500.
[29] Zhou, Y. M.; Zhang, J. L.; Zhang, L.; Zhang, Q. Y.; Ma, T. S.; Niu, J. Y. Dyes Pigm. 2013, 97, 148.
[30] Jin, X. D.; Liu, C. Z.; Wang, X. M.; Huang, H.; Zhang, X. Q.; Zhu, H. G. Sens. Actuators, B 2015, 216, 141.
[31] Tan,Y. Q.; Yu, J. C.; Gao, J. K.; Cui, Y. J.; Yang, Y.; Qian, G. D. Dyes Pigm. 2013, 99, 966.
[32] Qiu, Y.-F.; Zhang, Y.-R.; Zhang, W.-L.; Song, Z.-Y. J. Clin. Urology 2015, 30, 68(in Chinese). (邱永丰, 张永瑞, 张文岚, 宋志宇, 临床泌尿外科杂志, 2015, 30, 68.)

Outlines

/