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

Figures(11)

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
1. [1]
  Lei ZHANG , Cheng HE , Yang JIAO . An azo-based fluorescent probe for the detection of hypoxic tumor cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1162-1172. doi: 10.11862/CJIC.20250081
2. [2]
  Linfang ZHANG , Wenzhu YIN , Gui YIN . A 2-dicyanomethylene-3-cyano-4,5,5-trimethyl-2,5-dihydrofuran-based near-infrared fluorescence probe for the detection of hydrogen sulfide and imaging of living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 540-548. doi: 10.11862/CJIC.20240405
3. [3]
  Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112
4. [4]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
5. [5]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
6. [6]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
7. [7]
  Zhoupeng Zheng , Shengyi Gong , Qianhua Li , Shiya Zhang , Guoqiang Feng . Lipid droplets and gallbladder targeted fluorescence probe for ratiometric NO imaging in gallstones disease models. Chinese Chemical Letters, 2025, 36(5): 110191-. doi: 10.1016/j.cclet.2024.110191
8. [8]
  Baoli Yin , Xinlin Liu , Zhe Li , Zhifei Ye , Youjuan Wang , Xia Yin , Sulai Liu , Guosheng Song , Shuangyan Huan , Xiao-Bing Zhang . Ratiometric NIR-Ⅱ fluorescent organic nanoprobe for imaging and monitoring tumor-activated photodynamic therapy. Chinese Chemical Letters, 2025, 36(5): 110119-. doi: 10.1016/j.cclet.2024.110119
9. [9]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
10. [10]
  Sixin Ai , Wenxiu Li , Huayong Zhu , Yang Wan , Weiying Lin . Viscosity-responsive signal amplification dual-modal probe triggered by cysteine/homocysteine for monitoring diabetic liver damages and repair processes. Chinese Chemical Letters, 2025, 36(3): 109904-. doi: 10.1016/j.cclet.2024.109904
11. [11]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
12. [12]
  Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
13. [13]
  Yijian Zhao , Jvzhe Li , Yunyi Shi , Jie Hu , Meiyi Liu , Yao Shen , Xinglin Hou , Qiuyue Wang , Qi Wang , Zhiyi Yao . A label-free and ratiometric fluorescent sensor based on porphyrin-metal-organic frameworks for sensitive detection of ochratoxin A in cereal. Chinese Chemical Letters, 2025, 36(4): 110132-. doi: 10.1016/j.cclet.2024.110132
14. [14]
  Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
15. [15]
  Tiancong Shi , Xi Chen , Xiao Zhou , Hongyi Zhang , Fuping Han , Lihan Cai , Wen Sun , Jianjun Du , Jiangli Fan , Xiaojun Peng . Azaindole-based asymmetric pentamethine cyanine dye for mitochondrial pH detection and near-infrared ratiometric fluorescence imaging of mitophagy. Chinese Chemical Letters, 2025, 36(6): 110408-. doi: 10.1016/j.cclet.2024.110408
16. [16]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
17. [17]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
18. [18]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
19. [19]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
20. [20]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1386)
HTML views(241)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142