ARTICLES

Application and Cell Imaging of Turn-On Fluorescent Probe for Hydrogen Sulfide Based on Benzopyran in Food Samples

  • Lin Liu ,
  • Lin Chen ,
  • Xiaoling Hu ,
  • Keli Zhong ,
  • Jinglin Zhang ,
  • Lijun Tang
Expand
  • a College of Chemistry and Material Engineering, Bohai University, Jinzhou, Liaoning 121013
    b Liaoning Inspection, Examination & Certification Centre, Shenyang 110000
    c Key Laboratory of Brewing Molecular Engineering of China Light Industry, Beijing Technology and Business University, Beijing 100048
These authors contributed equally to this work.

Received date: 2023-11-14

  Revised date: 2024-01-14

  Online published: 2024-02-20

Supported by

Scientific Research Fund of Liaoning Provincial Education Department(LJKMZ20221480); Open Project Program of the Key Laboratory of Brewing Molecular Engineering of China Light Industry(BME-202202); Open Project of Institute of Ocean of Bohai University(BDHYYJY2023008)

Abstract

Hydrogen sulfide (H2S) is not only involved in the physiological regulation of human body, but also has an impact on the flavor and taste of wine. Therefore, a benzopyran derivative modified by 2,4-dinitrobenzene (DCM-dip) was synthesized, which had no fluorescence in dimethyl sulfoxide (DMSO)/phosphate buffered saline (PBS) (V:V=8:2, pH=8) solution. DCM-dip underwent a thiolysis reaction with H2S to release the intermediate with fluorescence, which showed a fluorescence turn-on response for recognition of H2S. DCM-dip recognized H2S with a response time of 20 min, a detection limit of 2.82 μmol/L, pH application range of 8~11 and a large Stokes shift (123 nm), avoiding background interference. The application research indicates that DCM-dip can be used to detect H2S in red wine and beer samples, and image for H2S in living cells.

Cite this article

Lin Liu , Lin Chen , Xiaoling Hu , Keli Zhong , Jinglin Zhang , Lijun Tang . Application and Cell Imaging of Turn-On Fluorescent Probe for Hydrogen Sulfide Based on Benzopyran in Food Samples[J]. Chinese Journal of Organic Chemistry, 2024 , 44(6) : 2027 -2032 . DOI: 10.6023/cjoc202311014

References

[1]
Ding, H. C.; Yue, L. S.; Ai, Y.; Zhu, Z. F.; Fan, C. B.; Liu, G.; Pu, S. Z. Spectrochim. Acta, Part A 2024, 304, 123348.
[2]
Lau, N.; Pluth, M. D. Curr. Opin. Chem. Biol. 2019, 49, 1.
[3]
Zhang, N.; Zheng, Y.; Chen, W.-G.; Li, R.; Song, L.-X.; Xu, L.-H.; Xu, K.-S. J. Huazhong Univ. Sci. Technol. (Med. Sci.) 2017, 37, 705.
[4]
Panagaki, T.; Randi, E. B.; Augsburger, F.; Szabo, C. Proc. Natl. Acad. Sci. U. S. A. 2019, 116, 18769.
[5]
Wu, K.; Wang, X. M.; Gong, L. L.; Zhai, X. Y.; Wang, K.; Qiu, X.; Zhang, H.; Tang, Z. X.; Jiang, H. Q.; Wang, X. M. Biosens. Bioelectron. 2023, 237, 115521.
[6]
Lee, K.-W.; Chen, H.; Wan, Y. P.; Zhang, Z.; Huang, Z. M.; Li, S. L.; Lee, C.-S. Biomaterials 2022, 289, 121753.
[7]
Ferreira, V.; Franco-Luesma, E.; Vela, E.; Lopez, R.; Hernández-Orte, P. J. Agric. Food Chem. 2017, 66, 2237.
[8]
Li, Y.; Zhang, Y. J.; Ye, D. Q.; Song, Y. Y.; Shi, J. L.; Qin, Y.; Liu, Y. L. Food Microbiol. 2022, 103, 103961.
[9]
Huang, Y.; Li, Y.; Huang, X.; Tang, L.; Yan, X. Dyes Pigm. 2024, 222, 111901.
[10]
Li, Y.; Huang, Y.; Huang, X.; Tang, L. J. Mol. Struct. 2024, 1299, 137168.
[11]
Li, H. N.; Fang, Y. X.; Yan, J. J.; Ren, X. Y.; Zheng, C.; Wu, B.; Wang, S. Y.; Li, Z. L.; Hua, H. M.; Wang, P.; Li, D. H. TrAC, Trends Anal. Chem. 2021, 134, 116117.
[12]
Wang, K.; Guo, R.; Chen, X.-Y.; Li, X.-L.; Hu, Z.-G.; Wang, X.; Wang, C.-Y.; Qin, Y.-J.; Yao, K.; Yang, Y.-S. Chem. Eng. J. 2023, 468, 143611.
[13]
Jiang, L. R.; Chen, T. H.; Song, E. W.; Fan, Y.; Min, D. Y.; Zeng, L. T.; Bao, G.-M. Chem. Eng. J. 2022, 427, 131563.
[14]
Tian, L.; Sun, X. F.; Zhou, L. L.; Zhong, K. L.; Li, S. D.; Yan, X. M.; Tang, L. J. Food Chem. 2023, 407, 135031.
[15]
Zhong, K. L.; Li, Y.; Hu, X. L.; Li, Y. Y.; Tang, L. J.; Sun, X. F.; Li, X. P.; Zhang, J. L.; Meng, Y. Q.; Ma, R.; Wang, S. L.; Li, J. R. Food Chem. 2024, 438, 137987.
[16]
Yang, Y.; Yan, X.; Liang, T.; Tian, M.; Wu, C.; Tang, L.; Sun, X.; Zhang, J.; Li, Y.; Zhong, K. J. Hazard. Mater. 2024, 469, 134003.
[17]
Yang, Y.; Chen, L.; Hu, X.; Zhong, K.; Li, S.; Yan, X.; Zhang, J.; Tang, L. Chin. J. Org. Chem. 2023, 43, 308. (in Chinese)
[17]
(杨雅馨, 陈琳, 胡晓玲, 钟克利, 李世迪, 燕小梅, 张璟琳, 汤立军, 有机化学, 2023, 43, 308.)
[18]
Chen, G.; Xu, J.; Zhan, Z. H.; Gao, X. Y.; Jiao, M. Q.; Ren, M. Z.; Lv, L. H.; Chen, T.; Li, Y. L.; Liu, Y. X. Dyes Pigm. 2020, 172, 107850.
[19]
Gong, S. Y.; Zheng, Z. P.; Guan, X. G.; Feng, S. M.; Feng, G. Q. Anal. Chem. 2021, 93, 5700.
[20]
Ou, L. Y.; Guo, R.; Lin, W. Y. Anal. Methods 2021, 13, 1511.
[21]
Wang, J. P.; Wen, Y.; Huo, F. J.; Yin, C. X. Sens. Actuators, B 2019, 297, 126773.
[22]
Liang, T. Y.; Qiang, T. T.; Ren, L. F.; Cheng, F.; Wang, B. S.; Li, M. L.; Hu, W.; James, T. D. Chem. Sci. 2022, 13, 2992.
[23]
Ding, D. H.; Li, J. F.; Xu, L. Z.; Wang, J. Y.; Tan, D.; Lin, W. Y. J. Mater. Chem. B 2022, 10, 4568.
[24]
Guo, Z.; Chen, G. Q.; Zeng, G. M.; Li, Z. W.; Chen, A. W.; Wang, J. J.; Jiang, L. B. Analyst 2015, 140, 1772.
[25]
Wang, J. L.; Chen, Y.; Yang, C. Y.; Wei, T.; Han, Y. F.; Xia, M. RSC Adv. 2016, 6, 33031.
[26]
He, L. W.; Yang, X. L.; Xu, K. X.; Kong, X. Q.; Lin, W. Y. Chem. Sci. 2017, 8, 6257.
[27]
Mu, S.; Zhang, J. L.; Gao, H.; Wang, Y. Y.; Rizvi, S. F. A.; Ding, N. N.; Liu, X. Y.; Wu, L.; Zhang, H. X. J. Hazard. Mater. 2022, 422, 126898.
[28]
Li, S.; Huo, F. J.; Yin, C. X. Dyes Pigm. 2022, 197, 109825.
[29]
Zhang, C. L.; Zhang, Y. P.; Wang, H. Y.; Zhao, H. Y.; Shang, M. T.; Zhang, L.; Li, X. L.; Wang, Y. Chin. J. Org. Chem. 2021, 41, 2384. (in Chinese)
[29]
(张成路, 张彦朋, 王华玉, 赵洹影, 尚美彤, 张璐, 李香玲, 王一鸣, 有机化学, 2021, 41, 2384.)
[30]
Xie, Q.-L.; Liu, W.; Liu, X.-J.; Ouyang, F.; Kuang, Y.-Q.; Jiang, J.-H. Anal. Methods 2017, 9, 2859.
[31]
Shang, Z. Y.; Meng, Q. T.; Tian, D. H.; Wang, Y.; Zhang, Z. X.; Zhang, Z. Q.; Zhang, R. Food Chem. 2023, 427, 136701.
[32]
Su, W. T.; Huang, L.; Zhu, L.; Lin, W. Y. Sensors Actuators B: Chem. 2022, 369, 132297.
[33]
Zhang, W. J.; Lv, Y. X.; Huo, F. J.; Zhang, Y. B.; Yin, C. X. Dyes Pigm. 2022, 204, 110442.
[34]
Ma, B.; Tian, D.-H.; Yan, S.; Li, X.-C.; Dai, F.; Zhou, B. Sens. Actuators, B 2021, 327, 128937.
Outlines

/