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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 5: 1239 - 1245

DOI: https://doi.org/10.6023/cjoc201911015

A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging

  • Guo Zhenbo ,
  • Zheng Xueyang ,
  • Li Xueyan ,
  • Jia Qingfei ,
  • Zhang Pingzhu ,
  • Wei Chao ,
  • Li Xiaoliu
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  • Key Laboratory of Chemical Biology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002

Received date: 2019-11-08

  Revised date: 2019-12-04

  Online published: 2020-01-03

Supported by

Project supported by the National Natural Science Foundation of China (No. 21572044), the Natural Science Foundation of Hebei Province (No. B2018201234) and the Colleges and Universities Science Technology Research Project of Hebei Province (No. QN2017015).

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Abstract

Intracellular small-molecule thiols, such as cysteine (Cys), homocysteine (Hcy) and glutathione (GSH), play pivotal roles in several physiological and pathological processes. A bodipy-nitroolefin-conjugated fluorescent probe based on photoinduced electron transfer (PET) mechanism was designed and successfully constructed. The probe selectively responds to biothiols by Michael addition reaction of the sulfhydryl group to the double bond activated by Nitroolefin moiety and gives an off-on fluorescent response. The fluorescence detection limit for GSH was calculated to be 11×10-9 mol/L. The results of fluorescence confocal imaging indicated that the probe has appreciable cell permeability and can serve as a fluorescent probe for detecting biothiols in living cells and zebrafish.

Key words： thiol; nitroolefin; fluorescent probe; bioimaging

Cite this article

Guo Zhenbo , Zheng Xueyang , Li Xueyan , Jia Qingfei , Zhang Pingzhu , Wei Chao , Li Xiaoliu . A Nitroolefin Based Thiol Fluorescent Probe: Synthesis and Application in Bioimaging[J]. Chinese Journal of Organic Chemistry, 2020 , 40(5) : 1239 -1245 . DOI: 10.6023/cjoc201911015

References

[1] Wood, Z. A.; Schröder, E.; Robin Harris, J.; Poole, L. B. Trends Biochem. Sci. 2003, 28, 32.
[2] Townsend, D. M.; Tew, K. D.; Tapiero, H. Biomed. Pharmacother. 2003, 57, 145.
[3] Reddie, K. G.; Carroll, K. S. Curr. Opin. Chem. Biol. 2008, 12, 746.
[4] Rusin, O.; St Luce, N. N.; Agbaria, R. A.; Escobedo, J. O.; Jiang, S.; Warner, I. M.; Dawan, F. B.; Lian, K.; Strongin, R. M. J. Am. Chem. Soc. 2004, 126, 438.
[5] Paulsen, C. E.; Carroll, K. S. Chem. Rev. 2013, 113, 4633.
[6] Seshadri, S.; Beiser, A.; Selhub, J.; Jacques, P. F.; Rosenberg, I. H.; D'Agostino, R. B.; Wilson, P. W. F.; Wolf, P. A. New Engl. J. Med. 2002, 346, 476.
[7] Kaluzna-Czaplinska, J.; Zurawicz, E.; Michalska, M.; Rynkowski, J. Acta Biochim. Pol. 2013, 60, 137.
[8] Estrela, J. M.; Ortega, A.; Obrador, E. Crit. Rev. Clin. Lab. Sci. 2006, 43, 143.
[9] Holmström, K. M.; Finkel, T. Nat. Rev. Mol. Cell Biol. 2014, 15, 411.
[10] Sippel, T. O. J. Histochem. Cytochem. 1981, 29, 314.
[11] Jung, H. S.; Chen, X.; Kim, J. S.; Yoon, J. Chem. Soc. Rev. 2013, 42, 6019.
[12] Wang, S. Q.; Shen, S. L.; Zhang, Y. R.; Dai, X.; Zhao, B. X. Chin. J. Org. Chem. 2014, 34, 1717(in Chinese). (王胜清, 申世立, 张延如, 戴溪, 赵宝祥, 有机化学, 2014, 34, 1717.)
[13] Niu, L.-Y.; Chen, Y.-Z.; Zheng, H.-R.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Chem. Soc. Rev. 2015, 44, 6143.
[14] Yan, P. P.; Wang, T.; Zhang, D.; Ma, X. X. Chin. J. Org. Chem. 2019, 39, 916(in Chinese). (闫沛沛, 王婷, 张丹, 马晓雪, 有机化学, 2019, 37, 916.)
[15] Hui, X. P.; Yin, C.; Ma, J.; Xu, P. F. Synth. Commun. 2009, 39, 676.
[16] Sun, Y.-Q.; Chen, M.; Liu, J.; Lv, X.; Li, J.-F.; Guo, W. Chem. Commun. 2011, 47, 11029.
[17] Zhang, M.; Wu, Y.; Zhang, S.; Zhu, H.; Wu, Q.; Jiao, L.; Hao, E. Chem. Commun. 2012, 48, 8925.
[18] Kang, J.; Huo, F.; Chao, J.; Yin, C. Spectrochim. Acta A 2018, 195, 16.
[19] Wang, L. Y.; Chen, X. G.; Cao, D. R. Sens. Actuators, B 2017, 244, 531.
[20] Jung, H. S.; Ko, K. C.; Kim, G. H.; Lee, A. R.; Na, Y. C.; Kang, C.; Lee, J. Y.; Kim, J. S. Org. Lett. 2011, 13, 1498.
[21] Ma, C.; Wei, C.; Li, X.; Zheng, X.; Chen, B.; Wang, M.; Zhang, P.; Li, X. Dyes Pigm. 2019, 162, 624.
[22] Matsumoto, T.; Urano, Y.; Takahashi, Y.; Mori, Y.; Terai, T.; Nagano, T. J. Org. Chem. 2011, 76, 3616.
[23] Kálai, T.; Hideg, K. Tetrahedron 2006, 62, 10352.
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