Citation: Wang Jun, Wu Yinglong, Sun Lihe, Zeng Fang, Wu Shuizhu. NIR AIE System for Tracking Release of Taurine and ROS Scavenging[J]. Acta Chimica Sinica, ;2016, 74(11): 910-916. doi: 10.6023/A16070342 shu

NIR AIE System for Tracking Release of Taurine and ROS Scavenging

Wang Jun ^† ,
Wu Yinglong ^† ,
Sun Lihe ,
Zeng Fang ,
Wu Shuizhu ^*,,

1.
South China University of Technology, State Key Laboratory of Luminescent Materials & Devices, College of Material Science and Engineering, GuangZhou 510640

Corresponding author: Wu Shuizhu, shzhwu@scut.edu.cn
Received Date: 14 July 2016

Fund Project: National Key Basic Research Program of China 2013CB834702and the National Natural Science Foundation of China 21474031and the National Natural Science Foundation of China 21574044

Figures(5)

Fluorophores with aggregation-induced emission (AIE) feature are favorable tools for both chemical sensing and bioimaging. Inflammatory cells excessively express hydrolytic enzymes (esterase, protease and phosphatase) and are usually exposed to elevated levels of reactive oxygen species (ROS). Overexpression of ROS and the insufficient neutralization by antioxidants may give rise to the development of oxidative stress and chronic inflammation. Taurine (2-aminoethanesulfonic acid), as an effective antioxidant, can protect tissues from oxidative stress associated with various inflammatory diseases. Moreover, it has been recently reported that the incorporation of taurine can amazingly boost the cellular uptake for intracellular accumulation. Herein, we designed and synthesized a new near-infrared (NIR) AIE fluorophore DTPE. We anticipate that, the combination of the hydrophilic taurine with the NIR AIE fluorophore through an ester bond could be a remarkable method for extending the applications of AIE-active fluorophores e.g. as a trackable visualized therapeutic system featuring both imaging esterase-activated taurine release and ROS scavenging. Then we obtained the AIE probe system DTPE-Tau by incorporating taurine with the fluorophore through carbamate bond. The hydrophilic taurine moiety endows the system with enhanced water solubility and cellular uptake ability. The system is characterized by several advantages, such as large Stokes shift (225 nm), low cytotoxicity, and good photostability. The ester bond can be hydrolysed by the overexpressed esterase in inflammatory cells, thereby releasing a taurine moiety for ROS scavenging and in the meantime the AIE fluorophore moiety acts as a reporter for tracking esterase-activated taurine release. The enhancement of emission could serve as the reporting signal. The release rate is determined to be 75% for esterase at 0.05 mg/mL, calculated based on the fluorescence-intensity working curve. Also, the probe has been successfully utilized for tracking esterase-activated release of taurine and scavenging intracellular ROS in RAW264.7 cell line, which shows great potential for trackable visualized therapy.
- aggregation induced emission,
- taurine,
- near-infrared fluorescence imaging,
- esterase,
- tetraphenylethylene
1. [1]
  Li, P.; Xiao, H.; Tang, B. Chin. J. Chem. 2012, 30, 1992. doi: 10.1002/cjoc.201200652
2. [2]
  Xia, Z.; Shao, A.; Li, Q.; Zhu, S.; Zhu, W. Acta Chim. Sinica 2016, 74, 351. doi: 10.6023/A16010001
3. [3]
  Fan, J. L.; Xu, Q. L.; Zhu, H.; Peng, X. J. Chin. J. Org. Chem. 2014, 34(8), 1623. doi: 10.6023/cjoc201403024
4. [4]
  Chen, Y.; Qiu, T.; Zhao, W.; Fan, L. Polym. Chem. 2015, 6, 1576. doi: 10.1039/C4PY01615G
5. [5]
  Guo, S.; Zheng, F.; Zeng, F.; Wu, S. Z. Chinese J. Polym. Sci. 2016, 34, 830. doi: 10.1007/s10118-016-1793-5
6. [6]
  Yu, C.; Li, X.; Zeng, F.; Zheng, F.; Wu, S. Z. Chem. Commun. 2013, 49, 403. doi: 10.1039/C2CC37329G
7. [7]
  Yu, C.; Wu, Y.; Zeng, F.; Li, X.; Shi, J.; Wu, S. Z. Biomacromolecules 2013, 14, 4507. doi: 10.1021/bm401548u
8. [8]
  Pan, L.; Luo, W.; Chen, M.; Liu, J.; Xu, L.; Hu, R.; Zhao, Z.; Qin, A.; Tang, B. Z. Chin. J. Org. Chem. 2016, 36(6), 1316. doi: 10.6023/cjoc201602020
9. [9]
  Chan, J.; Dodani, S. C.; Chang, C. J. Nat. Chem. 2012, 4, 973. doi: 10.1038/nchem.1500
10. [10]
  Du, F. K.; Xu, J. S.; Zeng, F.; Wu, S. Z. Acta Chim. Sinica 2016, 74, 241. doi: 10.6023/A15120780
11. [11]
  Akdeniz, A.; Mosca, L.; Minami, T.; Anzenbacher Jr., P. Chem. Commun. 2015, 51, 5770. doi: 10.1039/C5CC00376H
12. [12]
  Sun, J. B.; Zhang, G. H.; Jia, X. Y.; Xue, P. C.; Jia, J. H.; Lu, R. Acta Chim. Sinica 2016, 74(2), 165. doi: 10.6023/A15090628
13. [13]
  Shi, D. T.; Zhou, D.; Zang, Y.; Li, J.; Chen, G. R.; James, T. D.; He, X. P.; Tian, H. Chem. Commun. 2015, 51, 3653. doi: 10.1039/C4CC09771H
14. [14]
  Wu, B. Y.; Yan, X. P. Chem. Commun. 2015, 51, 3903. doi: 10.1039/C5CC00286A
15. [15]
  Zhang, Z.; Huang, J.; Dong, B.; Yuan, Q.; He, Y.; Wolfbeis, O. S. Nanoscale 2015, 7, 4149. doi: 10.1039/C4NR07559E
16. [16]
  Hou, X.; Yu, Q.; Zeng, F.; Ye, J.; Wu, S. J. Mater. Chem. B 2015, 3, 1042.
17. [17]
  Ding, J.; Li, H.; Wang, C.; Yang, J.; Xie, Y.; Peng, Q.; Li, Q.; Li, Z. ACS Appl. Mater. Interfaces 2015, 7, 11369. doi: 10.1021/acsami.5b01800
18. [18]
  Xu, S. Y.; Sun, X.; Ge, H.; Arrowsmith, R. L.; Fossey, J. S.; Pascu, S. I.; Jiang, Y. B.; James, T. D. Org. Biomol. Chem. 2015, 13, 4143. doi: 10.1039/C4OB02267J
19. [19]
  Au-Yeung, H. Y.; Chan, J.; Chantarojsiri, T.; Chang, C. J. J. Am. Chem. Soc. 2013, 135, 15165. doi: 10.1021/ja4072964
20. [20]
  He, X. P.; Tian, H. Small 2016, 12, 144. doi: 10.1002/smll.v12.2
21. [21]
  Hettiarachchi, S. U.; Prasai, B.; McCarley, R. L. J. Am. Chem. Soc. 2014, 136, 7575. doi: 10.1021/ja5030707
22. [22]
  Mei, J.; Leung, N. L.; Kwok, R. T.; Lam, J. W.; Tang, B. Z. Chem. Rev. 2015, 115, 11718. doi: 10.1021/acs.chemrev.5b00263
23. [23]
  Gao, M.; Hu, Q.; Feng, G.; Tang, B. Z.; Liu, B. J. Mater. Chem. B 2014, 2, 3438. doi: 10.1039/c4tb00345d
24. [24]
  Tang, X.; Bai, Q.; Peng, Q.; Gao, Y.; Li, J.; Liu, Y.; Yao, L.; Lu, P.; Yang, B.; Ma, Y. Chem. Mater. 2015, 27, 7050. doi: 10.1021/acs.chemmater.5b02685
25. [25]
  Liu, Z.; Xue, W.; Cai, Z.; Zhang, G.; Zhang, D. J. Mater. Chem. 2011, 21, 14487. doi: 10.1039/c1jm12400e
26. [26]
  Zhang, Y.; Kong, L.; Shi, J.; Tong, B.; Zhi, J.; Feng, X.; Dong, Y. Chin. J. Chem. 2015, 33, 701. doi: 10.1002/cjoc.v33.7
27. [27]
  Hu, F.; Zhang, G.; Zhan, C.; Zhang, W.; Yan, Y.; Zhao, Y.; Fu, H.; Zhang, D. Small 2015, 11, 1335. doi: 10.1002/smll.201402051
28. [28]
  Yang, J.; Huang, J.; Sun, N.; Peng, Q.; Li, Q.; Ma, D.; Li, Z. Chemistry 2015, 21, 6862. doi: 10.1002/chem.201406190
29. [29]
  Gao, Y.; Qu, Y.; Jiang, T.; Zhang, H.; He, N.; Li, B.; Wu, J.; Hua, J. J. Mater. Chem. C 2014, 2, 6353.
30. [30]
  Ma, S.; Zhang, J.; Chen, J.; Wang, L.; Xu, B.; Tian, W. Chin. J. Chem. 2013, 31, 1418. doi: 10.1002/cjoc.v31.11
31. [31]
  Ewa, K.; Magdalena, P.; Barbara, L.; Malgorzata, O.; Pawel, M.; Wlodzimierz, M. Ann. Rheum. Dis. 2012, 71, 262. doi: 10.1136/annrheumdis-2011-200123
32. [32]
  Wu, Y.; Huang, S.; Zeng, F.; Wang, J.; Yu, C.; Huang, J.; Xie, H.; Wu, S. Chem. Commun. 2015, 51, 12791. doi: 10.1039/C5CC04771D
33. [33]
  Marcinkiewicz, J.; Kontny, E. Amino Acids 2014, 46, 7. doi: 10.1007/s00726-012-1361-4
34. [34]
  Hou, J. T.; Li, K.; Yang, J.; Yu, K. K.; Liao, Y. X.; Ran, Y. Z.; Liu, Y. H.; Zhou, X. D.; Yu, X. Q. Chem. Commun. 2015, 51, 6781. doi: 10.1039/C5CC01217A
35. [35]
  Long, L.; Wu, Y.; Wang, L.; Gong, A.; Hu, F.; Zhang, C. Chem. Commun. 2015, 51, 10435. doi: 10.1039/C5CC03972J
36. [36]
  Reja, S. I.; Bhalla, V.; Sharma, A.; Kaur, G.; Kumar, M. Chem. Commun. 2014, 50, 11911. doi: 10.1039/C4CC05356G
37. [37]
  Wu, Y.; Wang, J.; Zeng, F.; Huang, S.; Huang, J.; Xie, H.; Yu, C.; Wu, S. Z. ACS Appl. Mater. Interfaces 2016, 8, 1511. doi: 10.1021/acsami.5b11023
38. [38]
  Xiao, H.; Xin, K.; Dou, H.; Yin, G.; Quan, Y.; Wang, R. Chem. Commun. 2015, 51, 1442. doi: 10.1039/C4CC07411D
39. [39]
  Zhu, H.; Fan, J.; Wang, J.; Mu, H.; Peng, X. J. Am. Chem. Soc. 2014, 136, 12820. doi: 10.1021/ja505988g
40. [40]
  Sun, J. J.; Piao, S.; Cha, Y. N.; Kim, C. J. Clin. Biochem. Nutr. 2009, 45, 37. doi: 10.3164/jcbn.08-262
41. [41]
  Zhou, J.; Du, X.; Li, J.; Yamagata, N.; Xu, B. J. Am. Chem. Soc. 2015, 137, 10040. doi: 10.1021/jacs.5b06181
42. [42]
  Wang, J.; Wu, Y.; Zeng, F.; Huang, S.; Wu, S. Faraday Discuss. 2016, DOI:10. 1039/C6FD00118A. doi: 10.1039/C6FD00118A
43. [43]
  Pan, G.; Liu, S.; Zhao, X.; Zhao, J.; Fan, C.; Cui, W. Biomaterials 2015, 53, 202. doi: 10.1016/j.biomaterials.2015.02.078
44. [44]
  Yang, Y.-C.; Lu, H.-H.; Wang, W.-T.; Liau, I. Anal. Chem. 2011, 83, 8267. doi: 10.1021/ac202077x
45. [45]
  Salonen, T.; Sareila, O. U.; Kankaanranta, H.; Tuominen, R.; Moilanen, E. Br. J. Pharmacol. 2006, 147, 790. doi: 10.1038/sj.bjp.0706672
46. [46]
  Wang, B.; Yu, P. F.; Song, P.; Sun, X.; Yang, S.; Lou, Z.; Han, K. Chem. Commun. 2013, 49, 1014. doi: 10.1039/C2CC37803E
47. [47]
  Karlsson, M.; Kurz, T.; Brunk, U. T.; Nilsson, S. E.; Frennesson, C. I. Biochem. J. 2010, 428, 183. doi: 10.1042/BJ20100208
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