Citation: Jian-Chao SHI, Yu-Man TIAN, Wei-Na WU, Yuan WANG, Xiao-Xia LI. A quinoxaline-containing Schiff base probe for the selective and sensitive detection of Zn2+ and imaging application in living cells[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(7): 1295-1302. doi: 10.11862/CJIC.2023.110 shu

A quinoxaline-containing Schiff base probe for the selective and sensitive detection of Zn2+ and imaging application in living cells

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  • A Schiff base probe, namely N′ -(quinoxaline-2-ylmethylene) pyridinyl hydrazide (1) was produced by a simple condensation reaction and was fully characterized through 1H NMR, 13C NMR, and ESI-MS. Probe 1 was nonemissive while displaying a strong emission at 500 nm in the presence of Zn2+. This fluorescence enhancement was highly selective and sensitive toward Zn2+ over other common cations, with a detection limit of 0.16 μmol·L-1. The coordination mode of 1 with Zn2+ was proposed by means of ESI-MS, 1H NMR, and UV-Vis. The crystal structure of the 1-Zn2+ complex was characterized by X- ray single- crystal diffraction, further confirming the coordination behavior of the probe. The results showed that the probe can coordinate two independent Zn2+ ions via ONN and NN donor sets, which are connected by bridged CH3O- and Cl- to form a 1D chain. Finally, the probe was used to trace Zn2+ in HeLa cells.
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    1. [1]

      Yoon S A, Lee J, Lee M H. A ratiometric fluorescent probe for Zn2+ based on pyrene-appended naphthalimide - dipicolylamine[J]. Sens. Actuator B-Chem., 2018,258:50-55. doi: 10.1016/j.snb.2017.11.126

    2. [2]

      Liu R, Kowada T, Du Y Y, Amagai Y, Matsui T, Inaba K, Mizukami S. Organelle-level labile Zn2+ mapping based on targetable fluorescent sensors[J]. ACS Sens., 2022,7:748-757. doi: 10.1021/acssensors.1c02153

    3. [3]

      Zhang C B, Gao R K, Zhang L L, Liu C B, Yang Z M, Zhao S L. Design and synthesis of a ratiometric photoacoustic probe for in situ imaging of zinc ions in deep tissue in vivo[J]. Anal. Chem., 2020,92:6382-6390. doi: 10.1021/acs.analchem.9b05431

    4. [4]

      Li C R, Li S L, Yang Z Y. Development of a coumarin-furan conjugate as Zn2+ ratiometric fluorescent probe in ethanol-water system[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2017,174:214-222. doi: 10.1016/j.saa.2016.11.034

    5. [5]

      Lu X M, Wu M Y, Wang S W, Qin J C, Li P Y. An AIE/PET -based fluorescent probe for Zn2+/Al3+ detection and its application in fluores-cence - assisted diagnosis for prostate cancer[J]. Dyes Pigment., 2022,203110372. doi: 10.1016/j.dyepig.2022.110372

    6. [6]

      Zhou X Y, Li P X, Shi Z H, Tang X L, Chen C Y, Liu W S. A highly selective fluorescent sensor for distinguishing cadmium from zinc ions based on a quinoline platform[J]. Inorg. Chem., 2012,51:9226-9231. doi: 10.1021/ic300661c

    7. [7]

      Han Y, Goldberg J M, Lippard S J, Palmer A E. Superiority of Spiro-Zin2 versus FluoZin-3 for monitoring vesicular Zn2+ allows tracking of lysosomal Zn2+ pools[J]. Sci. Rep., 2018,815034. doi: 10.1038/s41598-018-33102-w

    8. [8]

      Zastrow M L, Huang Z, Lippard S J. Halotag-based hybrid targetable and ratiometric sensors for intracellular zinc[J]. ACS Chem. Biol., 2020,15:396-406. doi: 10.1021/acschembio.9b00872

    9. [9]

      Shin I-S, Bae S W, Kim H, Hong J-I. Electrogenerated chemiluminescent anion sensing: Selective recognition and sensing of pyrophosphate[J]. Anal. Chem., 2010,82:8259-8265. doi: 10.1021/ac1017293

    10. [10]

      Liu Z, Zhang C, Li Y, Wu Z, Qian F, Yang X, He W, Gao X, Guo Z. A Zn2+ fluorescent sensor derived from 2 - (pyridin - 2 - yl)benzoimidazole with ratiometric sensing potential[J]. Org. Lett., 2009,11:795-798. doi: 10.1021/ol802537c

    11. [11]

      Qian F, Zhang C, Zhang Y M, He W J, Gao X, Hu P, Guo Z J. Visible light excitable Zn2+ fluorescent sensor derived from an intramolecular charge transfer fluorophore and its in vitro and in vivo application[J]. J. Am. Chem. Soc., 2009,131:1460-1468. doi: 10.1021/ja806489y

    12. [12]

      Fang L, Crespo-Otero R, Jones C R, Watkinson M. Protect to detect: A Golgi apparatus targeted probe to image mobile zinc through the use of a lipophilic cell-labile protecting group strategy[J]. Sens. Actuator B-Chem., 2021,338129850. doi: 10.1016/j.snb.2021.129850

    13. [13]

      Fang L, Trigiante G, Crespo-Otero R, Hawes C S, Philpott M P, Jones C R, Watkinson M. Endoplasmic reticulum targeting fluorescent probes to image mobile Zn2+[J]. Chem. Sci., 2019,10:10881-10887. doi: 10.1039/C9SC04300D

    14. [14]

      Kiyose K, Kojima H, Urano Y, Nagano T. Development of a ratiometric fluorescent zinc ion probe in near-infrared region, based on tricarbocyanine chromophore[J]. J. Am. Chem. Soc., 2006,128:6548-6549. doi: 10.1021/ja060399c

    15. [15]

      LIU M, TAN H L, LIU Z G, WANG W, ZENG W B. Advances in fluorescent probes based on the small molecules for Zn2+[J]. Chin. J. Org. Chem., 2013,33:1655-1667.  

    16. [16]

      Wang F, Wang K J, Kong Q, Wang J, Xi D Z, Gu B W, Lu S, Wei T W, Chen X Q. Recent studies focusing on the development of fluorescence probes for zinc ion[J]. Coord. Chem. Rev., 2021,429213636. doi: 10.1016/j.ccr.2020.213636

    17. [17]

      Li J F, Yin C X, Huo F J. Development of fluorescent zinc chemosensors based on various fluorophores and their applications in zinc recognition[J]. Dyes Pigment., 2016,131:100-133. doi: 10.1016/j.dyepig.2016.03.043

    18. [18]

      Wu W N, Mao P D, Wang Y, Zhao X L, Xu Z Q, Xu Z H, Xue Y. Quinoline containing acetyl hydrazone: An easily accessible switch-on optical chemosensor for Zn2+[J]. Spectroc. Acta Pt. A -Molec. Biomolec. Spectr., 2018,188:324-331. doi: 10.1016/j.saa.2017.07.020

    19. [19]

      Tharmalingam B, Mathivanan M, Mani K S, Kaminsky W, Raghunath A, Jothi M, Perumal E, Murugesapandian B. Selective detection of pyrophosphate anion by zinc ensemble of C3-symmetric triaminoguanidine - pyrrole conjugate and its biosensing applications[J]. Anal. Chim. Acta, 2020,1103:192-201. doi: 10.1016/j.aca.2019.12.061

    20. [20]

      Jiang S J, Chen S B, Wang Z C, Guo H Y, Yang F F. First fluorescence sensor for simultaneously detecting three kinds of Ⅱ B elements (Zn2+, Cd2+ and Hg2+) based on aggregation-induced emission[J]. Sens. Actuator B-Chem., 2020,308127734. doi: 10.1016/j.snb.2020.127734

    21. [21]

      PENG S F, CHEN Z E. Synthesis of a new quinoxaline - triphenylamine derivative and its recognition property for Fe3+[J]. Chinese Journal of Synthetic Chemistry, 2022,30(5):393-399.  

    22. [22]

      Sheldrick G M. SADABS. University of Göttingen, Germany, 1996.

    23. [23]

      Sheldrick G M. SHELX-97, Program for the solution and the refinement of crystal structures. University of Göttingen, Germany, 1997.

    24. [24]

      Chang X C, Han X F, Liu B J, Jiang Z Y, Li S Z, Lv Y M, Li A L, Wang Y, Wu W N. A tosylhydrazone-based probe for the ratiometric fluorescent detection of hypochlorite in endoplasmic reticulum of living cells[J]. J. Mol. Struct., 2022,1255132382. doi: 10.1016/j.molstruc.2022.132382

    25. [25]

      Qin J C, Fan L, Yang Z Y. A small-molecule and resumable two-photon fluorescent probe for Zn2+ based on a coumarin Schiff-base[J]. Sens. Actuator B-Chem., 2016,228:156-161. doi: 10.1016/j.snb.2016.01.031

    26. [26]

      Tang Y Q, Sun J G, Yin B Z. A dual-response fluorescent probe for Zn2+ and Al3+ detection in aqueous media: pH-dependent selectivity and practical application[J]. Anal. Chim. Acta, 2016,942:104-111. doi: 10.1016/j.aca.2016.08.048

    27. [27]

      Mawai K, Nathani S, Roy P, Singh U P, Ghosh K. Combined experimental and theoretical studies on selective sensing of zinc and pyrophosphate ions by rational design of compartmental chemosensor probe: Dual sensing behaviour via secondary recognition approach and cell imaging studies[J]. Dalton Trans., 2018,47:6421-6434. doi: 10.1039/C8DT01016A

    28. [28]

      Wu W N, Mao P D, Jia L, Wang Y, Xu Z Q. Both visual and fluorescent sensors for Zn2+ based on bis(pyrrol-2-yl-methyleneamine) platform[J]. Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 2016,166:44-48. doi: 10.1016/j.saa.2016.05.014

    29. [29]

      Yuan C X, Liu X Y, Wu Y B, Lu L P, Zhu M L. A triazole Schiff basebased selective and sensitive fluorescent probe for Zn2+: A combined experimental and theoretical study[J]. Spectroc. Acta Pt. A - Molec. Biomolec. Spectr., 2016,154:215-219. doi: 10.1016/j.saa.2015.10.035

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