Citation: Shen Youming, Gu Biao, Liu Xin, Tang Yucai, Li Haitao. A Benzothiazole-Based Ratiometric Fluorescent Probe for Highly Selective Detection of Homocysteine and Its Bioimaging Application[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2442-2449. doi: 10.6023/cjoc202004009 shu

A Benzothiazole-Based Ratiometric Fluorescent Probe for Highly Selective Detection of Homocysteine and Its Bioimaging Application

Shen Youming ^a,, ,
Gu Biao ^b,, ,
Liu Xin ^a ,
Tang Yucai ^a ,
Li Haitao ^c

a.
Hunan Provincial Key Laboratory of Water Treatment Functional Materials, Hunan University of Arts and Science, Changde, Hunan 415000
b.
College of Chemistry and Materials Science, Hengyang Normal University, Hengyang, Hunan 421008
c.
College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081

Corresponding author: Shen Youming, ymshen79@163.com Gu Biao, biaogu@hynu.edu.cn
Received Date: 6 April 2020
Revised Date: 7 May 2020
Available Online: 25 May 2020
Fund Project: the Environmental Monitoring and Evaluation Center of Hengyang Normal University KYJG1803the National Natural Science Foundation of China 21907026Project supported by the National Natural Science Foundation of China (No. 21907026), the Hunan Provincial Natural Science Foundation of China (No. 2019JJ50009), the Scientific Research Fund of Hunan Provincial Education Department (No. 18B369) and the Environmental Monitoring and Evaluation Center of Hengyang Normal University (No. KYJG1803)the Scientific Research Fund of Hunan Provincial Education Department 18B369the Hunan Provincial Natural Science Foundation of China 2019JJ50009

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Elevated homocysteine (Hcy) has been considered as a risk factor for vascular and renal diseases. Therefore, the development of Hcy-specific fluorescent probes, especially ratiometric fluorescent probes is of great importance. In the present study, a highly Hcy selective ratiometric fluorescent probe 3-(benzo[d]thiazol-2-yl)-2-hydroxy-5-methyl-benzaldehyde (BA), based on an ortho-hydroxy aldehyde functionalized benzothiazole, is presented. The probe responded selectively to Hcy over other tested species including Cys and GSH with ratiometric fluorescence changes. The probe possessed itself green fluorescence (λ_em=544 nm). Addition of Hcy to the BA solution triggered remarkable blue fluorescence (λ_em=478 nm). The fluorescence intensity ratios (I_{478 nm}/I_{544 nm}) were linearly related to the amounts of Hcy from 0 to 1.0 mmol/L with a detection limit of 1.6 μmol/L. The probe BA possessed low cytotoxicity and desirable cell permeability, and could be employed for the ratiometric imaging of Hcy in living cells, suggesting its potential applications in biological systems. Moreover, the sensing mechanism of BA for Hcy was verified by NMR, HRMS and time-dependent density function theory calculations.
- homocysteine,
- ratiometric,
- fluorescent probe,
- cell imaging
1. [1]
  Bu, L.; Chen, J.; Wei, X.; Li, X.; Agren H.; Xie, Y. Dyes Pigm. 2017, 136, 724. doi: 10.1016/j.dyepig.2016.09.032
2. [2]
  Yang, X.; Guo, Y.; Strongin, R. M. Angew. Chem., Int. Ed. 2011, 50, 10690. doi: 10.1002/anie.201103759
3. [3]
  Lee, P. T.; Lowinsohn, D.; Compton, R. G. Analyst 2014, 139, 3755. doi: 10.1039/C4AN00372A
4. [4]
  Espina, J. G.; Montes-Bayón, M.; Blanco-González, E.; Sanz-Medel, A. Anal. Bioanal. Chem. 2015, 407, 7899. doi: 10.1007/s00216-015-8956-z
5. [5]
  Huo, F. J.; Sun, Y. Q.; Su, J.; Chao, J. B.; Zhi, H. J.; Yin, C. X. Org. Lett. 2009, 11, 4918. doi: 10.1021/ol901951h
6. [6]
  Inoue, T.; Kirchhoff, J. R. Anal. Chem. 2002, 74, 1349. doi: 10.1021/ac0108515
7. [7]
  Kamińska, A.; Olejarz, P.; Borowczyk, K.; Głowacki, R.; Chwatko, G. J. Sep. Sci. 2018, 41, 3241. doi: 10.1002/jssc.201800381
8. [8]
  Jiao, X.; Li, Y.; Niu, J.; Xie, X.; Wang, X.; Tang, B. Anal. Chem. 2018, 90, 533. doi: 10.1021/acs.analchem.7b04234
9. [9]
  Wang, R. X.; Lai, X. J.; Qiu, G. S.; Liu, J. B. Chin. J. Org. Chem. 2019, 39, 952(in Chinese).
10. [10]
  Yue, Y.; Huo, F.; Li, X.; Wen, Y.; Yi, T.; Salamanca, J.; Escobedo, J. O.; Strongin, R. M.; Yin, C. Org. Lett. 2017, 19, 82. doi: 10.1021/acs.orglett.6b03357
11. [11]
  Yue, P.; Yang, X.; Ning, P.; Xi, X.; Yu, H.; Feng, Y.; Shao, R.; Meng, X. Talanta 2018, 178, 24. doi: 10.1016/j.talanta.2017.08.085
12. [12]
  Liang, Q.; Zhang, Y. J.; Zeng, M.; Guan, L.; Xiao, Y. Y.; Xiao, F. Toxicol. Res. 2018, 7, 521. doi: 10.1039/C8TX00029H
13. [13]
  Cheng, T.; Huang, W.; Gao, D.; Yang, Z.; Zhang, C.; Zhang, H.; Zhang, J.; Li, H.; Yang, X. F. Anal. Chem. 2019, 91, 10894. doi: 10.1021/acs.analchem.9b02814
14. [14]
  Cheng, X. H.; Xu, K.; Qu, S. H.; Ruan, Z. J. Chin. J. Org. Chem. 2019, 39, 2835(in Chinese).
15. [15]
  Zhou, T. T.; Yang, Y. T.; Zhou, K. Y.; Xu, W. Z.; Li, W. Chin. J. Org. Chem. 2019, 39, 3498(in Chinese).
16. [16]
  Yan, P. P.; Wang, T.; Zhang, D.; Ma, X. X. Chin. J. Org. Chem. 2019, 39, 916(in Chinese).
17. [17]
  Qiu, X.; Jiao, X.; Liu, C.; Zheng, D.; Huang, K.; Wang, Q.; He, S.; Zhao, L.; Zeng, X. Dyes Pigm. 2017, 140, 212. doi: 10.1016/j.dyepig.2017.01.047
18. [18]
  Lee, H. Y.; Choi, Y. P.; Kim, S.; Yoon, T.; Guo, Z.; Lee, S.; Swamy, K. M. K.; Kim, G.; Lee, J. Y.; Shin, I.; Yoon, J. Chem. Commun. 2014, 50, 6967. doi: 10.1039/c4cc00243a
19. [19]
  Barve, A.; Lowry, M.; Escobedo, J. O.; Huynh, K. T.; Hakuna, L.; Strongin, R. M. Chem. Commun. 2014, 50, 8219. doi: 10.1039/C4CC03527E
20. [20]
  Zhang, Y. J.; Ma, Y.; Liang, N. J.; Liang, Y. H.; Lu, C.; Xiao, F. Ecotoxicol. Environ. Saf. 2019, 186, 109749. doi: 10.1016/j.ecoenv.2019.109749
21. [21]
  Zhao, N.; Gong, Q.; Zhang, R. X.; Yang, J.; Huang, Z. Y.; Li, N.; Tang, B. Z. J. Mater. Chem. C 2015, 3, 8397. doi: 10.1039/C5TC01159K
22. [22]
  Sedgwick, A. C.; Wu, L.; Han, H. H.; Bull, S. D.; He, X. P.; James, T. D.; Sessler, J. L.; Tang, B. Z.; Tian, H.; Yoon, J. Chem. Soc. Rev. 2018, 47, 8842. doi: 10.1039/C8CS00185E
23. [23]
  Meng, X.; Ye, W.; Wang, S.; Feng, Y.; Chen, M.; Zhu, M.; Guo, Q. Sens. Actuators, B 2014, 201, 520. doi: 10.1016/j.snb.2014.05.042
24. [24]
  Lee, K. S.; Kim, T. K.; Lee, J. H.; Kim, H. J.; Hong, J. I. Chem. Commun. 2008, 6173.
25. [25]
  Gu, B.; Huang, L.; Su, W.; Duan, X.; Li, H.; Yao, S. Anal. Chim. Acta 2017, 954, 97. doi: 10.1016/j.aca.2016.11.044
26. [26]
  Chang, I. J.; Hwang, K. S.; Chang, S. K. Dyes Pigm. 2017, 137, 69. doi: 10.1016/j.dyepig.2016.09.058
27. [27]
  Yang, L.; Su, Y.; Geng, Y.; Zhang, Y.; Ren, X.; He, L.; Song, X. ACS Sens. 2018, 3, 1863. doi: 10.1021/acssensors.8b00685
28. [28]
  Wang, Y. W.; Liu, S. B.; Ling, W. J.; Peng, Y. Chem. Commun. 2016, 52, 827. doi: 10.1039/C5CC07886E
29. [29]
  Huang, Z. J.; Ding, S. S.; Yu, D. H.; Huang, F. H.; Feng, G. Q. Chem. Commun. 2014, 50, 9185. doi: 10.1039/C4CC03818E
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