Citation: Yan Peipei, Wang Ting, Zhang Dan, Ma Xiaoxue. Progress in Fluorescence Sensors for Detection of Thiols[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 916-928. doi: 10.6023/cjoc201807055 shu

Progress in Fluorescence Sensors for Detection of Thiols

Yan Peipei ^a,, ,
Wang Ting ^b ,
Zhang Dan ^b ,
Ma Xiaoxue ^a

a.
Shandong Medical Technician College, Taian 271000
b.
School of Chemistry and Chemical Engineering, Guizhou University, Guiyang 550000

Corresponding author: Yan Peipei, 1458851831@qq.com
Received Date: 31 July 2018
Revised Date: 11 October 2018
Available Online: 28 April 2018

Figures(38)

Sulfhydryl compounds, such as cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and so on, play an important role in the normal human physiological processes. Molecular fluorescent probes have attracted much attention of scholar in the detection of sulfhydryl compounds, since it has the advantage of good selectivity, high sensitivity, good biocompatibility and real-time in situ monitoring. At present, the design of thiol-based fluorescent probes is mainly based on the strong nucleophilicity of sulfhydryl groups. In this paper, the synthesis of fluorescent probes for detecting sulfhydryl compounds, which was reported from 2013 to 2018, is reviewed based on the different mechanism of the reaction between fluorescence probe and sulfhydryl, including Michael addition, cyclization of aldehyde groups, sulfonamides or sulfonates of the lysis, natural chemical linkage and so on. The detection limit of the probe, response time, equivalence ratio were elaborated.
- thiols,
- fluorescent probe,
- biological thiols,
- research progress
1. [1]
  Schulz, J. B.; Lindenau, J.; Seyfried, J.; Dichgans, J. Eur. J. Biochem. 2000, 267(16), 4904. doi: 10.1046/j.1432-1327.2000.01595.x
2. [2]
  Haugaard, N. Ann. N. Y. Acad. Sci. 2000, 899(1), 148.
3. [3]
  Khoo, H. E.; Chen D. S.; Yuen, R. Toxicon 1998, 36(3), 469.
4. [4]
  Benathan, M.; Virador, V.; Furumura, M.; Kobayashi, N.; Panizzon, R. G.; Hearing, V. J. Cell. Mol. Biol. 1999, 45(7), 981.
5. [5]
  Zhang, Z. X.; Geng, D. Y.; Han, Q.; Liang, S. D.; Guo, H. R. J. Fish Biol. 2013, 83(5), 1287. doi: 10.1111/jfb.2013.83.issue-5
6. [6]
  Uchida, E.; Uemura, H.; Tanaka, T.; Nishikawa, S.; Uesugi, S.; Tanaka, A.; Morikawa, M.; Hayakawa, T.; Ikehara, M. Chem. Pharm. Bull. 1991, 39(1), 150. doi: 10.1248/cpb.39.150
7. [7]
  Kulwin, M. H. J. Invest. Dermatol. 1953, 20(3), 237. doi: 10.1038/jid.1953.26
8. [8]
  Sawamoto, O.; Kurisu, K.; Kuwamura, M.; Kotani, T.; Yamate, J.; Yamate, J. Exp. Toxicol. Pathol. 2003, 55(2~3), 121.
9. [9]
  Badawy, A. H.; Abdel.; Aal, S. F.; Samour, S. A. J. Egypt. Soc. Parasitol. 1989, 19(2), 563.
10. [10]
  Shahrokhian, S.; Lead Am. J. Anal. Chem. 2001, 73(24), 5972.
11. [11]
  Tan, B.; Venketasubramanian, N.; Vrooman, H.; Cheng, C. Y.; Wong, T. Y.; Ikram, M. K.; Chen, C.; Hilal, S. Alzheimera Dis. 2018, 62(2), 877. doi: 10.3233/JAD-170796
12. [12]
  Doody, R. S.; Demirovic, J.; Ballantyne, C. M.; Chan, W.; Barber, R.; Powell, S.; Pavlik, V. Alzheimers Dement. (Amst.) 2015, 1(4), 464.
13. [13]
  Dietrichmuszalska, A.; Malinowska, J.; Olas, B.; Głowacki, R.; Bald, E.; Wachoeicz, B.; Rabe-Jabłońska, J. Neurochem. Res. 2012, 37(5), 1057. doi: 10.1007/s11064-012-0707-3
14. [14]
  Elkhairy, L. Ueland, P. M.; Refsum, H.; Graham, I. M.; Vollset, S. E. Circulation 2001, 103(21), 2544. doi: 10.1161/01.CIR.103.21.2544
15. [15]
  Stamler, J. S.; Slivka, A. Homocysteine Metabolism: From Basic Science to Clinical Medicine, Springer, US, 1997, pp. 211～222.
16. [16]
  Fraternale, A.; Casabianca, A.; Orlandi, C.; Cerasi, A.; Chiarantini, L.; Brandi, G.; Magnani, M. Antiviral Res.2002, 56(3), 263. doi: 10.1016/S0166-3542(02)00128-6
17. [17]
  Morgenstern, I.; Raijmakers, M. T. M.; Peters, W. H. M.; Hoensch, H.; Kirch, W. Dig. Dis. Sci. 2003, 48(10), 2083. doi: 10.1023/A:1026338812708
18. [18]
  Lv, Z.; Sun, Z.; Song, C.; Lu, S. M.; Chen, G.; You, G. M. Talanta 2016, 161, 228-237. doi: 10.1016/j.talanta.2016.08.040
19. [19]
  Kawanishi, S. Biochim. Biophys. Acta, Gen. Subj. 2002, 1570(1), 47.
20. [20]
  Ercal, N.; Le, K.; Treeratphan, P.; Matthews, R. Biomed. Chromatogr. 2015, 10(1), 15.
21. [21]
  Baron, M.; Sochor, J. Int. J. Electrochem. Sci. 2013, 8(9), 11072.
22. [22]
  Sippel, T. O. Histochem. J. 1978, 10(5), 597. doi: 10.1007/BF01003140
23. [23]
  Chen, J.; Jiang, X.; Carroll, S. L.; Huang, J.; Wang, J. Org. Lett. 2015, 17(24), 5978. doi: 10.1021/acs.orglett.5b02910
24. [24]
  Ren, W. X.; Han, J.; Pradhan, T.; Lim, J. Y.; Lee, J. H.; Lee, J.; Kim, J. H.; Kim, J. S. Biomaterials 2014, 35(13), 4157. doi: 10.1016/j.biomaterials.2014.01.055
25. [25]
  Niu, L. Y.; Chen, Y. Z.; Zheng, H. R.; Wu, L. Z.; Tung, C. H.; Yang, Q. Z. Chem. Soc. Rev. 2015, 44(17), 6143. doi: 10.1039/C5CS00152H
26. [26]
  Fan, W.; Huang, X.; Shi, X.; Wang, Z.; Lu, Z. L.; Fan, C. H.; Bo, Q. B. Spectrochim. Acta, Part A 2017, 173, 918. doi: 10.1016/j.saa.2016.10.060
27. [27]
  Dai, X.; Zhang, T.; Liu, Y. Z.; Yan, T.; Li, Y.; Miao, J. Y.; Zhao, B. X. Sens. Actuators, B 2015, 207, 872. doi: 10.1016/j.snb.2014.10.082
28. [28]
  Lim, S. Y.; Yoon, D. H.; Ha, D. Y.; Ahn, J. M.; Kim, D.; Kown, H.; Ha, H. J.; Kim, H. J. Sens. Actuators, B 2013, 188(11), 111.
29. [29]
  Huo, F.; Kang, J.; Yin, C.; Yue, Y. K.; Hao, J. S.; Chao, J. B.; Liu, D. S. Sens. Actuators, B 2015, 207(7), 139.
30. [30]
  Qu, L.; Yin, C.; Huo, F.; Li, J.; Chao, J.; Zhang, Y. Sens. Actuators, B 2014, 195(5), 246.
31. [31]
  Shen, Y.; Liu, C.; Zhang, Y.; Zhang, X.; Zhang, C.; Jin, J.; Liu, X.; Li, H.; Yao, S. J. Anal. Methods Chem. 2015, 7(15), 6419.
32. [32]
  Liu, T.; Huo, F.; Yin, C.; Li, J.; Chao, J.; Zhang, Y. Dyes Pigm. 2016, 128, 209. doi: 10.1016/j.dyepig.2015.12.031
33. [33]
  Zhao, Y.; Xue, Y.; Li, H.; Zhu, R.; Ren, Y.; Shi, Q.; Wang, S.; Guo, W. Spectrochim. Acta, Part A 2017, 175, 215. doi: 10.1016/j.saa.2016.12.031
34. [34]
  Yue, Y.; Huo, F.; Peng, N.; Zhang, Y.; Chao, J.; Meng, X.; Yin, C. J. Am. Chem. Soc. 2017, 139(8), 3181. doi: 10.1021/jacs.6b12845
35. [35]
  Sok, N.; Nikolantonaki, M.; Guyot, S.; Nguyen, T. D.; Viaux, A. S.; Bagala, F.; Rousselin, Y.; Husson, F.; Gougeon, R.; Saurel, R. Sens. Actuators, B 2016, 242, 865.
36. [36]
  Long, L.; Zhou, L.; Wang, L.; Meng, S.; Gong, A.; Du, F.; Zhang, C. Org. Biomol. Chem. 2013, 11(47), 8214. doi: 10.1039/c3ob41741g
37. [37]
  Dai, C. G.; Du, X. J.; Song, Q. H. J. Org. Chem. 2015, 80(24), 12088. doi: 10.1021/acs.joc.5b02041
38. [38]
  Ou-Yang, J.; Li, C. Y.; Li, Y. F.; Fei, J.; Xu, F.; Li, S. J.; Nie, S. X. Sens. Actuators, B 2017, 240, 1165. doi: 10.1016/j.snb.2016.09.074
39. [39]
  Meng, X.; Ye, W.; Wang, S.; Feng, Y; Chen, M.; Zhu, M.; Guo, Q. Sens. Actuators, B 2014, 201(4), 520.
40. [40]
  Chen, C.; Liu, W.; Xu, C.; Liu, W. Biosens. Bioelectron. 2016, 85, 46. doi: 10.1016/j.bios.2016.04.098
41. [41]
  Zhang, J.; Lv, Y.; Zhang, W.; Ding, H.; Liu, R.; Zhao, Y.; Zhang, G.; Tian, Z. Talanta 2016, 146, 41. doi: 10.1016/j.talanta.2015.08.025
42. [42]
  Kong, F.; Liu, R.; Chu, R.; Wang, X.; Xu, K.; Tang, B. Chem. Commun. 2013, 49(80), 9176. doi: 10.1039/c3cc45519j
43. [43]
  Gong, D.; Tian, Y.; Yang, C.; Iqbal, A.; Wang, Z.; Liu, W.; Qin, W.; Zhu, X.; Guo, H. Biosens. Bioelectron. 2016, 85, 178. doi: 10.1016/j.bios.2016.05.013
44. [44]
  Gao, H.; Li, Z.; Zhao, Y.; Qi, H.; Zhang, C. Sens. Actuators, B 2017, 245, 853. doi: 10.1016/j.snb.2017.01.190
45. [45]
  Kim, S. K.; Gupta, M.; Lee, H. I. Sens. Actuators, B 2017, 257, 728.
46. [46]
  Wang, J.; Cheng, Z.; Zhang, J.; Zhu, X.; Liu, X.; Wang, Q.; Zhang, H. Spectrochim. Acta, Part A 2016, 166, 31. doi: 10.1016/j.saa.2016.05.004
47. [47]
  Chen, S.; Li, H.; Hou, P. Tetrahedron 2017, 73(5), 589. doi: 10.1016/j.tet.2016.12.049
48. [48]
  Wei, M.; Yin, P.; Shen, Y.; Zhang, L.; Deng, J.; Xue, S.; Li, H.; Guo, B.; Zhang, Y.; Yao, S. Chem. Commun. 2013, 49(41), 4640. doi: 10.1039/c3cc39045d
49. [49]
  Liu, Y.; Xiang, K.; Guo, M; Tian, B.; Zhang, J. L. Tetrahedron Lett. 2016, 57(23), 2478. doi: 10.1016/j.tetlet.2016.04.068
50. [50]
  Fan, J.; Han, Z.; Yao, K.; Peng, X. J. Sci. Rep. 2016, 6, 19562. doi: 10.1038/srep19562
51. [51]
  Yoshida, M.; Kamiya, M.; Yamasoba, T.; Urano, Y. Bioorg. Med. Chem. Lett. 2014, 24(18), 4363. doi: 10.1016/j.bmcl.2014.08.033
52. [52]
  Wang, K.; Leng, T.; Liu, Y.; Wang, C.; Shi, P.; Shen, Y.; Zhu, W. H. Sens. Actuators, B 2017, 248, 338. doi: 10.1016/j.snb.2017.03.127
53. [53]
  Xu, K.; Qiang, M.; Gao, W.; Su, R. Chem. Sci. 2013, 4(3), 1079. doi: 10.1039/c2sc22076h
54. [54]
  Zheng, L. Q.; Li, Y.; Yu, X. D.; Xu, J. J.; Chen, H. Y. Anal. Chim. Acta 2014, 850, 71. doi: 10.1016/j.aca.2014.09.004
55. [55]
  Lim, S. Y.; Na, M. J.; Kim, H. J. Sens. Actuators, B 2013, 185(8), 720.
56. [56]
  Shen, W.; Ge, J.; He, S.; Zhang, R.; Zhao, C.; Fan, Y.; Yu, S.; Liu, B.; Zhu, Q. Chem. Asian J. 2017, 12(13), 1532. doi: 10.1002/asia.v12.13
57. [57]
  Song, L.; Ma, L. M.; Qian, S.; Zhang, W. B.; Lan, M. B.; Qian, J. H. Chin. Chem. Lett. 2016, 27(3), 330. doi: 10.1016/j.cclet.2015.12.012
58. [58]
  Dai, X.; Wang, Z. Y.; Du, Z. F.; Cui, J.; Miao, J. Y.; Zhao, B. X. Anal. Chim. Acta 2015, 900, 103. doi: 10.1016/j.aca.2015.10.023
59. [59]
  Hou, X.; Li, Z.; Li, B.; Liu, C.; Xu, Z. Sens. Actuators, B 2018, 260, 295.. doi: 10.1016/j.snb.2018.01.013
60. [60]
  Vigneaud, V. D.; Ressler, C.; Swan, C. J. M. J. Am. Chem. Soc. 1953, 75(19), 4879. doi: 10.1021/ja01115a553
61. [61]
  Lv, H.; Yang, X. F.; Zhong, Y.; Guo, Y.; Li, Z.; Li, H. Anal. Chem. 2014, 86(3), 1800. doi: 10.1021/ac4038027
62. [62]
  He, G.; Li, J.; Yang, L.; Hou, C.; Ni, T.; Yang, Z.; Qian, X.; Li, C. Plos One. 2016, 11(2), e0148026. doi: 10.1371/journal.pone.0148026
63. [63]
  Sun, Q.; Sheng, J. Chem. Ind. Eng. Prog. 1997, 10(1), 48.
64. [64]
  Zhang, L.; Wang, E. Nano Today 2014, 9(1), 132. doi: 10.1016/j.nantod.2014.02.010
65. [65]
  T Tian, D.; Qian, Z.; Xia, Y.; Zhu, C. Langmuir 2012, 28(8), 3945. doi: 10.1021/la204380a
66. [66]
  Xu, X.; Qiao, J.; Li, N.; Qi, L.; Zhang, S. Anal. Chim. Acta 2015, 879, 97. doi: 10.1016/j.aca.2015.03.036
67. [67]
  Zhang, S.; Qin, W.; Liu, X.; Zhang, J. mBio 2017, 8(6), e01620.
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