Citation: Zhou Xiaoqin, Cui Mengyuan, Jia Chengli, Yang Min, Ji Min, Wang Peng. Novel Ratio-Based Fluorescent Probe for Intracellular Cys Detection[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2502-2507. doi: 10.6023/cjoc202003007 shu

Novel Ratio-Based Fluorescent Probe for Intracellular Cys Detection

Zhou Xiaoqin ^a ,
Cui Mengyuan ^b ,
Jia Chengli ^a ,
Yang Min ^a ,
Ji Min ^a,, ,
Wang Peng ^b,,

a.
School of Biological Sciences and Medical Engineering, Southeast University, Nanjing 210009
b.
School of Biomedical Engineering, China Pharmaceutical University, Nanjing 211198

Corresponding author: Ji Min, 101010516@seu.edu.cn Wang Peng, wangpeng159seu@hotmail.com
Received Date: 3 March 2020
Revised Date: 4 May 2020
Available Online: 19 May 2020
Fund Project: The National Natural Science Foundation of China 81671745Project supported by the National Natural Science Foundation of China (No. 81671745)

Figures(6)

Cysteine is an important biological component of the human body, its levels are related to many diseases. It is especially important to respond quickly and accurately to cysteine concentrations. This study is based on the classical cysteine response mechanism. The thiol group of cysteine undergoes Michael addition to acrylate, and then undergoes intramolecular cyclization to specifically recognize cysteine. A novel ratio-based fluorescent probe was designed and synthesized in this study. The research results found that the probe can specifically recognize cysteine, the detection limit can reach 75 nmol·L^-1, can fully respond within 30 min, and has good stability. It exists in cells and has little cytotoxic effects. Therefore, on the basis of solving the problem of poor water solubility, the probe can quickly and accurately analyze the concentration of cysteine in cells, which provides a new means for the study of various diseases and new ideas for the development of chemical materials.
- cysteine,
- ratio-based,
- fluorescent probe,
- michael addition,
- indocyanines
1. [1]
  (a) Dai, C. G.; Du, X. J.; Song, Q. H. J. Org. Chem. 2015, 80, 12088.
  (b) Ganganboina, A. B.; Dutta Chowdhury, A.; Doong, R. A. ACS Appl. Mater. Interfaces 2018, 10, 614.
2. [2]
  Chen, W.; Luo, H.; Liu, X.; Foley, J. W.; Song, X. Anal. Chem. 2016, 88, 3638. doi: 10.1021/acs.analchem.5b04333
3. [3]
  (a) He, L.; Yang, X.; Xu, K.; Lin, W. Anal. Chem. 2017, 89, 9567.
  (b) Tian, Q.; Chen, S.; Chen, J.; Liu, R.; Wang, Y.; Yang, X.; Ye, Y. Chin. J. Org. Chem. 2019, 39, 2089(in Chinese).
  (田庆, 陈双虎, 陈景龙, 刘蕊, 汪雨诗, 杨晓朋, 叶勇, 有机化学, 2019, 39, 2089.)
4. [4]
  (a) Dong, B.; Lu, Y.; Zhang, N.; Song, W.; Lin, W. Anal. Chem. 2019, 91, 5513.
  (b) Li, S.; Song, D.; Huang, W.; Li, Z.; Liu, Z. Anal. Chem. 2020, 92, 2802.
5. [5]
  (a) Cao, X.; Lin, W.; Yu, Q. J. Org. Chem. 2011, 76, 7423.
  (b) Chang, M. J.; Joo, J. H.; Lee, M. H. Bull. Korean Chem. Soc. 2019, 40, 539.
  (c) Chen, C.; Zhou, L.; Liu, W.; Liu, W. Anal. Chem. 2018, 90, 6138.
6. [6]
  Deng, L.; Wu, W.; Guo, H.; Zhao, J.; Ji, S.; Zhang, X.; Yuan, X.; Zhang, C. J. Org. Chem. 2011, 76, 9294. doi: 10.1021/jo201487m
7. [7]
  (a) He, L.; Xu, Q.; Liu, Y.; Wei, H.; Tang, Y.; Lin, W. ACS Appl. Mater. Interfaces 2015, 7, 12809.
  (b) Ding, Y.; Pan, Y.; Han, Y. Ind. Eng. Chem. Res. 2019, 58, 7786.
8. [8]
  (a) Guo, L.; Chan, M. S.; Xu, D.; Tam, D. Y.; Bolze, F.; Lo, P. K.; Wong, M. S. ACS Chem. Biol. 2015, 10, 1171-5.
  (b) He, L.; Yang, Y.; Lin, W. Anal. Chem. 2019, 91, 15220.
  (c) Ji, Y.; Wang, Y.; Zhang, N.; Xu, S.; Zhang, L.; Wang, Q.; Zhang, Q.; Hu, H. Y. J. Org. Chem. 2019, 84, 1299.
9. [9]
  Fu, Z. H.; Han, X.; Shao, Y.; Fang, J.; Zhang, Z. H.; Wang, Y. W.; Peng, Y. Anal. Chem. 2017, 89, 1937. doi: 10.1021/acs.analchem.6b04431
10. [10]
  (a) Sun, S.; Qiao, B.; Jiang, N.; Wang, J.; Zhang, S.; Peng, X. Org. Lett. 2014, 16, 1132.
  (b) Yang, L. L.; Zou, S. Y.; Fu, Y. H.; Li, W.; Wen, X. P.; Wang, P. Y.; Wang, Z. C.; Ouyang, G. P.; Li, Z.; Yang, S. J. Agric. Food Chem. 2020, 68, 4285.
11. [11]
  (a) Chen, Y.; Zhao, J.; Guo, H.; Xie, L. J. Org Chem. 2012, 77, 2192.
  (b) Gong, D.; Han, S. C.; Iqbal, A.; Qian, J.; Cao, T.; Liu, W.; Liu, W.; Qin, W.; Guo, H. Anal. Chem. 2017, 89, 13112.
  (c) Zhang, D.; Xu, N.; Li, H.; Yao, Q.; Xu, F.; Fan, J.; Du, J.; Peng, X. Ind. Eng. Chem. Res. 2017, 56, 9303.
12. [12]
  (a) Jia, T.; Fu, C.; Huang, C.; Yang, H.; Jia, N. ACS Appl. Mater. Interfaces 2015, 7, 10013.
  (b) Sarkar, A.; Fouzder, C.; Chakraborty, S.; Ahmmed, E.; Kundu, R.; Dam, S.; Chattopadhyay, P.; Dhara, K. Chem. Res. Toxicol. 2020, 33, 651.
13. [13]
  Luo, Z.; Huang, Z.; Li, K.; Sun, Y.; Lin, J.; Ye, D.; Chen, H.-Y. Anal. Chem. 2018, 90, 2875. doi: 10.1021/acs.analchem.7b05022
14. [14]
  Wang, W. H.; Rusin, O.; Xu, X. Y.; Kim, k. k.; Escobedo, J. O.; Fakayode, S. O.; Fletcher, K. A.; Lowry, M.; Schowalter, C. M.; Lawrence, C. M.; Froczek, F. R.; Warner, I. M.; Strongin, R. M. J. AM. CHEM. SOC. 2005, 127, 15949-15958 doi: 10.1021/ja054962n
15. [15]
  (a) Chen, J.; Jiang, X.; Carroll, S.; Huang, J.; Wang, J. Org. Lett. 2015, 17, 5978.
  (b) Cheng, T.; Huang, W.; Gao, D.; Yang, Z.; Zhang, C.; Zhang, H.; Zhang, J.; Li, H.; Yang, X. F. Anal. Chem. 2019, 91, 10894.
16. [16]
  Sinha, S. H.; Owens, E. A.; Feng, Y.; Yang, Y.; Xie, Y.; Tu, Y.; Henary, M.; Zheng, Y. G. Eur. J. Med. Chem. 2012, 54, 647. doi: 10.1016/j.ejmech.2012.06.017
17. [17]
  Liu, B.; Wang, J.; Zhang, G.; Bai, R.; Pang, Y. ACS Appl. Mater. Interfaces 2014, 6, 4402. doi: 10.1021/am500102s
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]
  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
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]
  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
5. [5]
  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
6. [6]
  Zhixiao Xiong , Shanni Qiu , Yuyu Wang , Houna Duan , Yi Xiao , Yufang Xu , Weiping Zhu , Xuhong Qian . Photocalibrated NO release from the zinc ion fluorescent probe based on naphthalimide and its application in living cells. Chinese Chemical Letters, 2025, 36(4): 110002-. doi: 10.1016/j.cclet.2024.110002
7. [7]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
8. [8]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
16. [16]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
17. [17]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
18. [18]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
19. [19]
  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
20. [20]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1349)
HTML views(168)

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