SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2949 - 2955

DOI: https://doi.org/10.6023/cjoc202004007

An “Off-On” Near-Infrared Fluorescent Probe for Cu2+ Detection in Living Cells

  • Fang Ru ,
  • Ding Xu ,
  • Luo Wen ,
  • Hong Chen
Expand
  • a Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan 475004;
    b Huaihe Hospital, Henan University, Kaifeng, Henan 475000

Received date: 2020-04-03

  Revised date: 2020-05-27

  Online published: 2020-06-28

Supported by

Project supported by the National Natural Science Foundation of China (No. U1704176), the Science and Technology Planning Project of Henan Province (No. 182102310504), the Science and Technology Administration of Kaifeng City (No. 1903004) and the Young Talents Program of Medical School of Henan University (No. 2019005).

Fold

Abstract

A near-infrared fluorescent probe (6) was designed and synthesized by using 2-(6-(dimethylamino)naphthalen-2-yl)-7-hydroxy-4H-chromen-4-one as report group and 2-picolinate as recognition group. The probe was identified by 1H NMR, 13C NMR, MS and elemental analysis. The probe could react specifically with Cu2+ and its fluorescence intensity increased obviously at 655 nm, at the meantime, the color change of the solution can be seen by naked eyes. A linear relationship was obtained between the fluorescence intensity and concentration of Cu2+ in the range of 0~2.0×10-5 mol/L, and the detection limit was 3.2×10-8 mol/L. The mechanism study showed that Cu2+ catalyzed the cleavage of the ester bond and strongly fluorescent 2-[6-(N,N-dimethylamino)naphthyl]-7-hydroxy-4H-chromen-4-one (5) was generated. In addition, the probe 6 could be used for fluorescence imaging of Cu2+ in living cells.

Key words： flavone; copper ion; near-infrared; fluorescent probe

Cite this article

Fang Ru , Ding Xu , Luo Wen , Hong Chen . An “Off-On” Near-Infrared Fluorescent Probe for Cu2+ Detection in Living Cells[J]. Chinese Journal of Organic Chemistry, 2020 , 40(9) : 2949 -2955 . DOI: 10.6023/cjoc202004007

References

[1] Zhang, H.; Qu, Y.; Zhao, K.; Wang, C.; Wu, Y.; Wu, H. J. Chin. Chem. Soc. 2019, 66, 1.
[2] Jung, H. S.; Kwon, P. S.; Lee, J. W.; Kim, J. I.; Hong, C. S.; Kim, J. W.; Yan, S.; Lee, J. Y.; Lee, J. H.; Joo, T.; Kim, J. S. J. Am. Chem. Soc. 2009, 131, 2008.
[3] (a) Hanif, M.; Rafiq, M.; Saleem, M.; Mustaqeem, M.; Jamil, S. J. Chin. Chem. Soc. 2018, 66, 500.
(b) Tang, M.; Zhu, B.; Qu, Y.; Jin, Z.; Bai, S.; Chai, F.; Chen, L.; Wang, C.; Qu, F. Mikrochim. Acta 2019, 187, 65.
(c) Lal, S.; Prakash, K.; Hooda, S.; Kumar, V.; Kumar, P. J. Mol. Struct. 2020, 1199, 127003.
[4] Xu, J.; Hou, Y.; Ma, Q.; Wu, X.; Feng, S.; Zhang, J.; Shen, Y. Spectrochim. Acta A 2014, 124, 416.
[5] Staderini, M.; Martin, M. A.; Bolognesi, M. L.; Menendez, J. C. Chem. Soc. Rev. 2015, 44, 1807.
[6] (a) Goswami, S.; Sen, D.; Das, A. K.; Das, N. K.; Aich, K.; Fun, H. K.; Quah, C. K.; Maity, A. K.; Saha, P. Sens. Actuators. B 2013, 183, 518.
(b) Yang, Y. S.; Cao, B. X.; Zhang, Y. P.; Dong, Y. Y. Chin. J. Org. Chem. 2017, 37, 3024(in Chinese) (杨云裳, 曹碧霞, 张应鹏, 董玉莹, 有机化学, 2017, 37, 3024.)
(c) Kaur, M.; Min J. C.; Choi, D. H. Dyes Pigm. 2016, 125, 1.
[7] (a) Xu, Z.; Yoon, J.; Spring, D. R. Chem. Commun. 2010, 46, 2563.
(b) Kaur, P.; Kaur, S.; Singh, K.; Sharma, P. R.; Kaur, T. Dalton Trans. 2011, 40, 10818.
(c) Chen, F.; Hou, F.; Huang, L.; Cheng, J.; Liu, H.; Xi, P.; Bai, D.; Zeng, Z. Dyes Pigm. 2013, 98, 146.
[8] Pronin, D.; Krishnakumar, S.; Rychlik, M.; Wu, H.; Huang, D. J. Agric. Food Chem. 2019, 67, 10726.
[9] (a) Liu, B.; Pang, Y.; Bouhenni, R.; Duah, E.; Paruchuri, S.; McDonald, L. Chem. Commun. 2015, 51, 11060.
(b) Qin, T.; Huang, Y.; Zhu, K.; Wang, J.; Pan, C.; Liu, B.; Wang, L. Anal. Chim. Acta 2019, 1076, 125.
(c) Zhu, K.; Lv, T.; Qin, T.; Huang, Y.; Wang, L.; Liu, B. Chem. Commun. 2019, 55, 13983.
(d) Qin, T.; Liu, B.; Huang, Y.; Yang, K.; Zhu, K.; Luo, Z.; Pan, C.; Wang, L. Sens. Actuators. B 2018, 277, 484.
[10] Yang, Y. C.; Zhao, Y. M.; Wang, Q. Z.; Ren, Q. L.; Shao, S. Y.; Luo, W. Fine Chem. 2018, 35, 4(in Chinese) (杨亚成, 赵永梅, 王清照, 任倩蕾, 邵双宇, 罗稳, 精细化工, 2018, 35, 4.)
[11] List, B.; Barbas III, C. F.; Lerner, R. A. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 15351.
[12] Chen, X.; Jia, J.; Ma, H.; Wang, S.; Wang, X. Anal. Chim. Acta 2009, 632, 9.
[13] Chen, S.; Hou, P.; Foley, J. W.; Song, X. Z. RSC Adv. 2013, 3, 5591.
Options
Outlines

/

〈 〉