Citation: Tian Qing, Chen Shuanghu, Chen Jinglong, Liu Rui, Wang Yushi, Yang Xiaopeng, Ye Yong. A Novel Rhodamine Analogues-Based Near-Infrared Fluorescent Probe for Cys[J]. Chinese Journal of Organic Chemistry, ;2019, 39(7): 2089-2093. doi: 10.6023/cjoc201812047 shu

A Novel Rhodamine Analogues-Based Near-Infrared Fluorescent Probe for Cys

College of Chemistry and Molecular Engineering of Zhengzhou University, Zhengzhou 450001

Corresponding author: Ye Yong, yeyong03@tsinghua.org.cn
Received Date: 26 December 2018
Revised Date: 25 February 2019
Available Online: 8 July 2019
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21572209), the Program for Innovative Research Team (in Science and Technology) at University of Henan Province (No. 17IRTSTHN002) and Innovation and Entrepreneurship Training Plan for College Students of Zhengzhou University (No. 2018cxcy012)Innovation and Entrepreneurship Training Plan for College Students of Zhengzhou University 2018cxcy012the National Natural Science Foundation of China 21572209the Program for Innovative Research Team (in Science and Technology) at University of Henan Province 17IRTSTHN002

Figures(2)

A near-infrared fluorescence probe CS-Cys was synthesized using rhodamine analoguse as near-infrared fluorescent group. The probe can specifically response to Cys, not to other sulfhydryl amino acids. The response mechanism is that Cys reacts with the acrylic ester of CS-Cys and the conjugated addition-cyclization reaction occurs, then the hydroxyl groups are exposed and fluorescence is released. Through studying the fluorescence changes of CS-Cys and Cys in different pH environments, it was found that the donor ability of the electron-donor group and the process of the ICT could be monitored by changing the pH of probe solution, and the fluorescence excitation wavelength and the emission wavelength could be adjusted to the near infrared region.
- fluorescent probe,
- cysteine,
- near-infrared,
- rhodamine analogues,
- ICT
1. [1]
  Ubuka, T.; Ohta, J.; Yao, W. B.; Abe, T.; Teraoka, T.; Kurozumi, Y. Amino Acids 1992, 2, 143. doi: 10.1007/BF00806085
2. [2]
  Wang, X. B.; Jin, H. F.; Tang, C. S.; Du, J. B. Clin. Exp. Pharmacol. Physiol. 2010, 37, 745.
3. [3]
  Yue, Y.; Huo, F.; Yin, C. Sci. Sin. Chim. 2016, 47, 249(in Chinese).
4. [4]
  Reddie, K. G.; Carroll, K. S. Curr. Opin. Chem. Biol. 2008, 12, 746. doi: 10.1016/j.cbpa.2008.07.028
5. [5]
  Weerapana, E.; Wang, C.; Simon, G. M.; Richter, F.; Khare, S.; Dillon, M. B.; Cravatt, B. F. Nature 2010, 468, 790. doi: 10.1038/nature09472
6. [6]
  Liu, C.; Li, Y.; Qi, F.; Long, L.; Yang, R. Sci. Sin. Chim. 2017, 47, 1015(in Chinese).
7. [7]
  Yang, X.; Liu, W.; Tang, J.; Li, P.; Weng, H.; Ye, Y.; Xian, M.; Tang, B.; Zhao, Y. Chem. Commun. 2018, 54, 11387. doi: 10.1039/C8CC05418E
8. [8]
  Elshorbagy, A. K.; Kozich, V.; Smith, A. D. Curr. Opin. Clin. Nutr. 2012, 15, 49. doi: 10.1097/MCO.0b013e32834d199f
9. [9]
  Niu, L. Y.; Guan, Y. S.; Chen, Y. Z.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z. Chem. Cummun. 2013, 49, 1294. doi: 10.1039/c2cc38429a
10. [10]
  Yang, T.; Guo, Z.; Shao, A.; Zhao, P.; Zhu, W. Chin. J. Appl. Chem. 2016, 33, 397(in Chinese). doi: 10.11944/j.issn.1000-0518.2016.04.160053
11. [11]
  Hou, J. T.; Yang, J.; Li, K.; Yu, K. K.; Yu, X. Q. Sens. Actuators, B Chem. 2015, 214, 92. doi: 10.1016/j.snb.2015.02.112
12. [12]
  Liu, S. R.; Chang, C. Y.; Wu, S. P. Anal. Chim. Acta 2014, 849, 64. doi: 10.1016/j.aca.2014.08.024
13. [13]
  Yang, Y.; Huo, F.; Yin, C.; Zheng, A.; Chao, J.; Li, Y.; Liu, D. Biosens. Bioelectron 2013, 47, 300. doi: 10.1016/j.bios.2013.03.007
14. [14]
  Wang, S.; Shen, S.; Zhang, Y.; Dai, X.; Zhao, B. Chin. J. Org. Chem. 2014, 34, 1717(in Chinese).
15. [15]
  Zhou, X.; Jin, X.; Sun, G.; Wu, X. Chem. Eur.-J. 2013, 19, 7817. doi: 10.1002/chem.201300078
16. [16]
  Niu, L. Y.; Guan, Y. S.; Chen, Y. Z.; Wu, L. ZTung, C. H.; Yang, Q. Z. J. Am. Chem. Soc. 2012, 134, 18928. doi: 10.1021/ja309079f
17. [17]
  Gong, J.; Wei, P.; Su, Y.; Li, Y.; Feng, X.; Lam, J. W. Y.; Zhang, D.; Song, X.; Tang, B. Z. Chin. Chem. Lett. 2018, 29, 1493 doi: 10.1016/j.cclet.2018.05.043
18. [18]
  Xie, Z.; Fu, M.; Yin, B.; Zhu, Q. Chin. J. Org. Chem. 2018, 38, 1364(in Chinese).
19. [19]
  Liu, K.; Shang, H.; Kong, X.; Ren, M.; Wang, J. Y.; Liu, Y.; Lin, W. Biomaterials 2016, 100, 162. doi: 10.1016/j.biomaterials.2016.05.029
20. [20]
  Yuan, L.; Lin, W.; Chen, H. Biomaterials 2013, 34, 9566. doi: 10.1016/j.biomaterials.2013.08.081
21. [21]
  Yuan, L.; Lin, W.; Yang, Y.; Chen, H. J. Am. Chem. Soc. 2012, 134, 1200. doi: 10.1021/ja209292b
22. [22]
  Wang, C.; Wong, K. M. C. Inorg. Chem. 2013, 52, 13432. doi: 10.1021/ic401810x
23. [23]
  Jia, X.; Chen, Q.; Yang, Y.; Tang, Y.; Wang, R.; Xu, Y.; Zhu, W.; Qian, X. J. Am. Chem. Soc. 2016, 138, 10778. doi: 10.1021/jacs.6b06398
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