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

  • 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.
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    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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