Citation: Kang Yan-Fei, Niu Li-Ya, Yang Qing-Zheng. Fluorescent probes for detection of biothiols based on "aromatic nucleophilic substitution-rearrangement" mechanism[J]. Chinese Chemical Letters, ;2019, 30(10): 1791-1798. doi: 10.1016/j.cclet.2019.08.013 shu

Fluorescent probes for detection of biothiols based on "aromatic nucleophilic substitution-rearrangement" mechanism

Kang Yan-Fei ^a,b ,
Niu Li-Ya ^b,*, ,
Yang Qing-Zheng ^b,*,

a.
Hebei Key Laboratory of Quality & Safety Analysis-Testing for Agro-Products and Food, and College of Laboratory Medicine, Hebei North University, Zhangjiakou 075000, China
b.
Key Laboratory of Radiopharmaceuticals, Ministry of Education, College of Chemistry, Beijing Normal University, Beijing 100875, China

Author Bio: Yan-Fei Kang received his Ph.D. degree in State Key Laboratory of Applied Organic Chemistry of Lanzhou University in 2014. Subsequently, he joined the Hebei North University as an assistant professor. He carried out a visiting scholar research (2017–2019) at the Beijing Normal University (BNU) with Prof. Qing-Zheng Yang. His research interests focus on fluorescent probes for bioimaging and photodynamic therapy
Li-Ya Niu received both her B.S. and M.S. degrees from Beihang University (BUAA), and obtained her Ph.D. degree in organic chemistry from the Technical Institute of Physics and Chemistry, Chinese Academy of Sciences (TIPC, CAS) in 2013 under supervision of Prof. Qing-Zheng Yang. She had worked as an assistant professor at TIPC (2013–2016). In 2016, she moved to BNU as a lecturer and was promoted to associate professor in 2019. Her research interests include the fluorescent probes, functional optical materials and their biological applications
Qing-Zheng Yang received his Ph.D. in 2003 from the TIPC, CAS, under the supervision of professor Chen-Ho Tung and Li-Zhu Wu. After completing postdoctoral research at the University Louis Pasteur and University of Illinois, Urbana, he returned to TIPC in 2009 as a full professor. He moved to BNU in 2014, where he is a professor of chemistry. His research interests cover photochemistry of supramolecular assemblies and fluorescent probes for bioimaging

niuly@bnu.edu.cn

qzyang@bnu.edu.cn

Received Date: 5 July 2019
Revised Date: 11 August 2019
Accepted Date: 12 August 2019
Available Online: 14 October 2019

Figures(16)

Biothiols, including cysteine (Cys), homocysteine (Hcy), and glutathione (GSH) play important roles in physiological processes, and the detection of thiol using fluorescent probes has attracted attention due to their high sensitivity and selectively and invasive on-time imaging. However, the similar structures and reactivity of these biothiols present great challenges for selective detection. This review focused on the the "aromatic nucleophilic substitution-rearrangement (S_NAr-rearrangement) mechanism", which provided a powerful tool to design fluorescent probes for the discrimination between biothiols. We classify the fluorescent probes according to types of fluorophores, such as difluoroboron dipyrromethene (BODIPY), nitrobenzoxadiazole (NBD), cyanine, pyronin, naphthalimide, coumarin, and so on. We hope this review will inspire exploration of new fluorescent probes for biothiols and other relevant analytes.
- Biothiols,
- Fluorescent probes,
- Aromatic nucleophilic substitution,
- Rearrangement,
- Fluorophores,
- Bioapplication
1. [1]
  T.V. Mishanina, M. Libiad, R. Banerjee, Nat. Chem. Biol. 11(2015) 457-464. doi: 10.1038/nchembio.1834
2. [2]
  B. Debreceni, L. Debreceni, Cardiovasc. Ther. 32(2014) 130-138. doi: 10.1111/1755-5922.12064
3. [3]
  C. Harris, J.M. Hansen, Methods Mol. Biol. 889(2012) 325-346.
4. [4]
  B.D. Paul, S.H. Snyder, Nat. Rev. Mol. Cell Biol. 13(2012) 499-507. doi: 10.1038/nrm3391
5. [5]
  B.D. Paul, J.I. Sbodio, S.H. Snyder, Trends Pharmacol. Sci. 39(2018) 513-524. doi: 10.1016/j.tips.2018.02.007
6. [6]
  Z. Xu, X. Huang, X. Han, et al., Chem 4(2018) 1609-1628. doi: 10.1016/j.chempr.2018.04.003
7. [7]
  K. Umezawa, M. Yoshida, M. Kamiya1, et al., Nat. Chem. 9(2017) 279-286. doi: 10.1038/nchem.2648
8. [8]
  Y. Yue, F. Huo, P. Ning, et al., J. Am. Chem. Soc. 139(2017) 3181-3185. doi: 10.1021/jacs.6b12845
9. [9]
  M. She, Z. Wang, T. Luo, et al., Chem. Sci. 9(2018) 8065-8070. doi: 10.1039/C8SC03421D
10. [10]
  H. Chen, Y. Tang, M. Ren, et al., Chem. Sci. 7(2016) 1896-1903. doi: 10.1039/C5SC03591K
11. [11]
  H. Nie, L. Qiao, W. Yang, et al., J. Mater. Chem. B 4(2016) 4826-4831. doi: 10.1039/C6TB00938G
12. [12]
  L. Song, X.D. Sun, Y. Ge, et al., Chin. Chem. Lett. 27(2016) 1776-1780. doi: 10.1016/j.cclet.2016.05.007
13. [13]
  X. Chen, Y. Zhou, X. Peng, et al., Chem. Soc. Rev. 39(2010) 2120-2135. doi: 10.1039/b925092a
14. [14]
  H.S. Jung, X. Chen, J.S. Kim, et al., Chem. Soc. Rev. 42(2013) 6019-6031. doi: 10.1039/c3cs60024f
15. [15]
  L.Y. Niu, Y.Z. Chen, H.R. Zheng, et al., Chem. Soc. Rev. 44(2015) 6143-6160. doi: 10.1039/C5CS00152H
16. [16]
  O. Rusin, N.N. St. Luce, R.A. Agbaria, et al., J. Am. Chem. Soc. 126(2004) 438-439. doi: 10.1021/ja036297t
17. [17]
  X. Yang, Y. Guo, R.M. Strongin, Angew. Chem. Int. Ed. 50(2011) 10690-10693. doi: 10.1002/anie.201103759
18. [18]
  Q. Liu, C. Zhang, X. Wang, et al., Chem.-Asian J. 11(2016) 202-206. doi: 10.1002/asia.201501013
19. [19]
  H. Zhang, R. Liu, J. Liu, et al., Chem. Sci. 7(2016) 256-260. doi: 10.1039/C5SC02431E
20. [20]
  L.Y. Niu, Y.S. Guan, Y.Z. Chen, et al., J. Am. Chem. Soc. 134(2012) 18928-18931. doi: 10.1021/ja309079f
21. [21]
  L.Y. Niu, Y.S. Guan, Y.Z. Chen, et al., Chem. Commun. 49(2013) 1294-1296. doi: 10.1039/c2cc38429a
22. [22]
  L.Y. Niu, Q.Q. Yang, H.R. Zheng, et al., RSC Adv. 5(2015) 3959-3964. doi: 10.1039/C4RA13526A
23. [23]
  X.L. Liu, L.Y. Niu, Y.Z. Chen, et al., Biosens. Bioelectron. 90(2017) 403-409. doi: 10.1016/j.bios.2016.06.076
24. [24]
  M.Y. Jia, L.Y. Niu, Y. Zhang, et al., ACS Appl. Mater. Interfaces 7(2015) 5907-5914. doi: 10.1021/acsami.5b00122
25. [25]
  L.Y. Niu, M.Y. Jia, P.Z. Chen, et al., RSC Adv. 5(2015) 13042-13045. doi: 10.1039/C4RA16601A
26. [26]
  Y. Liu, L.Y. Niu, Y.Z. Chen, et al., J. Photochem. Photobiol. A 355(2018) 311-317. doi: 10.1016/j.jphotochem.2017.08.042
27. [27]
  X.L. Liu, L.Y. Niu, Y.Z. Chen, et al., Org. Biomol. Chem. 15(2017) 1072-1075. doi: 10.1039/C6OB02407F
28. [28]
  F. Wang, Z. Guo, X. Li, et al., Chem.-Eur. J. 20(2014) 11471-11478. doi: 10.1002/chem.201403450
29. [29]
  D.H. Ma, D. Kim, E. Seo, et al., Analyst 140(2015) 422-427. doi: 10.1039/C4AN01791A
30. [30]
  L.Y. Niu, H.R. Zheng, Y.Z. Chen, et al., Analyst 139(2014) 1389-1395. doi: 10.1039/c3an01849k
31. [31]
  L. Song, L.M. Ma, Q. Sun, et al., Chin. Chem. Lett. 27(2016) 330-334. doi: 10.1016/j.cclet.2015.12.012
32. [32]
  Y.H. Chen, J.C. Tsai, T.H. Cheng, et al., Biosens. Bioelectron. 56(2014) 117-123. doi: 10.1016/j.bios.2014.01.009
33. [33]
  D. Lee, G. Kim, J. Yin, et al., Chem. Commun. 51(2015) 6518-6520. doi: 10.1039/C5CC01071C
34. [34]
  Q. Hu, C. Yu, X. Xia, et al., Biosens. Bioelectron. 81(2016) 341-348. doi: 10.1016/j.bios.2016.03.011
35. [35]
  X. Yang, L. He, K. Xu, et al., Anal. Chem. Acta 981(2017) 86-93. doi: 10.1016/j.aca.2017.05.016
36. [36]
  P. Wang, Y. Wang, N. Li, et al., Sens. Actuators B-Chem. 245(2017) 297-304. doi: 10.1016/j.snb.2017.01.127
37. [37]
  X. Qiu, X. Jiao, C. Liu, et al., Dye. Pigments 140(2017) 212-221. doi: 10.1016/j.dyepig.2017.01.047
38. [38]
  Z. Ye, C. Duan, Q. Hu, et al., J. Mater. Chem. B 5(2017) 3600-3606. doi: 10.1039/C7TB00489C
39. [39]
  J. Zhang, X. Ji, J. Zhou, et al., Sens. Actuators B-Chem. 257(2018) 1076-1082. doi: 10.1016/j.snb.2017.10.133
40. [40]
  M.D. Hammers, M.D. Pluth, Anal. Chem. 86(2014) 7135-7140. doi: 10.1021/ac501680d
41. [41]
  X. Gao, X. Li, L. Li, et al., Chem. Commun. 51(2015) 9388-9390. doi: 10.1039/C5CC02788H
42. [42]
  J. Xu, J. Pan, Y. Zhang, et al., Sens. Actuators B-Chem. 238(2017) 58-65. doi: 10.1016/j.snb.2016.07.038
43. [43]
  L. He, X. Yang, K. Xu, et al., Chem. Sci. 8(2017) 6257-6265. doi: 10.1039/C7SC00423K
44. [44]
  H. Zhang, L. Xu, W. Chen, et al., Anal. Chem. 91(2019) 1904-1911. doi: 10.1021/acs.analchem.8b03869
45. [45]
  J. Pan, Y. Zhang, J. Xu, et al., RSC Adv. 5(2015) 97781-97787. doi: 10.1039/C5RA21025A
46. [46]
  Y.S. Guan, L.Y. Niu, Y.Z. Chen, et al., RSC Adv. 4(2014) 8360-8364. doi: 10.1039/c3ra47116k
47. [47]
  X. Wang, J. Lv, X. Yao, et al., Chem. Commun. 50(2014) 15439-15442. doi: 10.1039/C4CC06637E
48. [48]
  S.Y. Lim, K.H. Hong, D.I. Kim, et al., J. Am. Chem. Soc. 136(2014) 7018-7025. doi: 10.1021/ja500962u
49. [49]
  J. Liu, Y.Q. Sun, H. Zhang, et al., Chem. Sci. 5(2014) 3183-3188. doi: 10.1039/c4sc00838c
50. [50]
  L. Ma, J. Qian, H. Tian, et al., Analyst 137(2012) 5046-5050. doi: 10.1039/c2an35624d
51. [51]
  L. Song, T. Jia, W. Lu, et al., Org. Biomol. Chem. 12(2014) 8422-8427. doi: 10.1039/C4OB01219D
52. [52]
  K. Xiong, F. Huo, J. Chao, et al., Anal. Chem. 91(2019) 1472-1478. doi: 10.1021/acs.analchem.8b04485
53. [53]
  Y. Lia, W. Liu, P. Zhang, et al., Biosens. Bioelectron. 90(2017) 117-124. doi: 10.1016/j.bios.2016.11.021
54. [54]
  S.V. Mulay, Y. Kim, M. Choi, et al., Anal. Chem. 90(2018) 2648-2654. doi: 10.1021/acs.analchem.7b04375
55. [55]
  Y. Yang, H. Wang, Y.L. Wei, et al., Chin. Chem. Lett. 28(2017) 2023-2026. doi: 10.1016/j.cclet.2017.08.051
56. [56]
  Y. Kim, S.V. Mulay, M. Choi, et al., Chem. Sci. 6(2015) 5435-5439. doi: 10.1039/C5SC02090E
57. [57]
  J. Liu, Y.Q. Sun, Y. Huo, et al., J. Am. Chem. Soc. 136(2014) 574-577. doi: 10.1021/ja409578w
58. [58]
  G.X. Yin, T.T. Niu, Y.B. Gan, et al., Angew. Chem. Int. Ed. 57(2018) 4991-4994. doi: 10.1002/anie.201800485
59. [59]
  G. Yin, T. Niu, T. Yu, et al., Angew. Chem. Int. Ed. 58(2019) 4557-4561. doi: 10.1002/anie.201813935
60. [60]
  C.X. Yin, K.M. Xiong, F.J. Huo, et al., Angew. Chem. Int. Ed. 56(2017) 13188-13198. doi: 10.1002/anie.201704084
61. [61]
  Y. Yue, F. Huo, F. Cheng, et al., Chem. Soc. Rev. 48(2019) 4155-4177. doi: 10.1039/C8CS01006D
62. [62]
  Y. Liu, J. Tan, Y. Zhang, et al., Biomaterials 173(2018) 1-10. doi: 10.1016/j.biomaterials.2018.04.053
63. [63]
  B. Shi, Z. Zhang, Q. Jin, et al., J. Mater. Chem. B 6(2018) 7439-7443.
64. [64]
  F. Wang, Y. Zhu, L. Zhou, et al., Angew. Chem. Int. Ed. 54(2015) 7349-7353. doi: 10.1002/anie.201502899
65. [65]
  Y.Q. Sun, J. Liu, H. Zhang, et al., J. Am. Chem. Soc. 136(2014) 12520-12523. doi: 10.1021/ja504156a
66. [66]
  H. Zhang, J. Liu, B. Hu, et al., Chem. Sci. 9(2018) 3209-3214. doi: 10.1039/C7SC05407F
67. [67]
  X.X. Chen, L.Y. Niu, N. Shao, et al., Anal. Chem. 91(2019) 4301-4306. doi: 10.1021/acs.analchem.9b00169
1. [1]
  Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
2. [2]
  Xu Qu , Pengzhao Wu , Kaixuan Duan , Guangwei Wang , Liang-Liang Gao , Yuan Guo , Jianjian Zhang , Donglei Shi . Self-calibrating probes constructed on a unique dual-emissive fluorescence platform for the precise tracking of cellular senescence. Chinese Chemical Letters, 2024, 35(12): 109681-. doi: 10.1016/j.cclet.2024.109681
3. [3]
  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
4. [4]
  Yuting Zhang , Zhiqian Wang . Methods and Case Studies for In-Depth Learning of the Aldol Reaction Based on Its Reversible Nature. University Chemistry, 2024, 39(7): 377-380. doi: 10.3866/PKU.DXHX202311037
5. [5]
  Xiaoyu Chen , Jiahao Hu , Jingyi Lin , Haiyang Huang , Changqing Ye , Hongli Bao . Biisoindolylidene solvatochromic fluorophores: Synthesis and photophysical properties. Chinese Chemical Letters, 2025, 36(2): 109923-. doi: 10.1016/j.cclet.2024.109923
6. [6]
  Haixian Ren , Yuting Du , Xiaojing Yang , Fangjun Huo , Le Zhang , Caixia Yin . Development of ESIPT-based specific fluorescent probes for bioactive species based on the protection-deprotection of the hydroxyl. Chinese Chemical Letters, 2025, 36(2): 109867-. doi: 10.1016/j.cclet.2024.109867
7. [7]
  Kai An , Qinglong Qiao , Lovelesh , Syed Ali Abbas Abedi , Xiaogang Liu , Zhaochao Xu . "Superimposed" spectral characteristics of fluorophores arising from cross-conjugation hybridization. Chinese Chemical Letters, 2025, 36(1): 109786-. doi: 10.1016/j.cclet.2024.109786
8. [8]
  Ying-Di Hao , Zhi-Qian Lin , Xiao-Yu Guo , Jiao Liang , Can-Kun Luo , Qian-Tao Wang , Li Guo , Yong Wu . Rhodium-catalyzed Doyle-Kirmse rearrangement reactions of sulfoxoniun ylides. Chinese Chemical Letters, 2024, 35(4): 108834-. doi: 10.1016/j.cclet.2023.108834
9. [9]
  Wenyu Gao , Liming Zhang , Chuang Zhao , Lixiang Liu , Xingran Yang , Jinbo Zhao . Controlled semi-Pinacol rearrangement on a strained ring: Efficient access to multi-substituted cyclopropanes by group migration strategy. Chinese Chemical Letters, 2024, 35(9): 109447-. doi: 10.1016/j.cclet.2023.109447
10. [10]
  Ruru Li , Qian Liu , Hui Li , Fengbin Sun , Zhurui Shen . Rational design of dual sites induced local electron rearrangement for enhanced photocatalytic oxygen activation. Chinese Chemical Letters, 2024, 35(11): 109679-. doi: 10.1016/j.cclet.2024.109679
11. [11]
  Huashan Huang , Jingze Chen , Luyun Zhang , Hong Yan , Siqi Li , Fen-Er Chen . Oscillatory flow reactor facilitates fast photochemical Wolff rearrangement toward synthesis of α-substituted amides in flow. Chinese Chemical Letters, 2025, 36(2): 109992-. doi: 10.1016/j.cclet.2024.109992
12. [12]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
13. [13]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
14. [14]
  Ling-Ling Wu , Xiangchuan Meng , Qingyang Zhang , Xiaowan Han , Feiya Yang , Qinghua Wang , Hai-Yu Hu , Nianzeng Xing . Heavy-atom engineered hypoxia-responsive probes for precisive photoacoustic imaging and cancer therapy. Chinese Chemical Letters, 2024, 35(4): 108663-. doi: 10.1016/j.cclet.2023.108663
15. [15]
  Fukui Shen , Yuqing Zhang , Guoqing Luan , Kaixue Zhang , Zhenzhen Wang , Yunhao Luo , Yuanyuan Hou , Gang Bai . Revealing drug targets with multimodal bioorthogonal AMPD probes through visual metabolic labeling. Chinese Chemical Letters, 2024, 35(12): 109646-. doi: 10.1016/j.cclet.2024.109646
16. [16]
  Kun Zou , Yihang Xiao , Jinyu Yang , Mingxuan Wu . Facile semisynthesis of histone H3 enables nucleosome probes for investigation of histone H3K79 modifications. Chinese Chemical Letters, 2024, 35(10): 109497-. doi: 10.1016/j.cclet.2024.109497
17. [17]
  Xiao-Tong Sun , Hao-Fei Ni , Yi Zhang , Da-Wei Fu . Hybrid perovskite shows temperature-dependent photoluminescence and dielectric response triggered by halogen substitution. Chinese Journal of Structural Chemistry, 2024, 43(6): 100212-100212. doi: 10.1016/j.cjsc.2024.100212
18. [18]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
19. [19]
  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
20. [20]
  Ya-Ping Liu , Zhi-Rong Gui , Zhen-Wen Zhang , Sai-Kang Wang , Wei Lang , Yanzhu Liu , Qian-Yong Cao . A phenylphenthiazide anchored Tb(Ⅲ)-cyclen complex for fluorescent turn-on sensing of ClO⁻. Chinese Chemical Letters, 2025, 36(2): 109769-. doi: 10.1016/j.cclet.2024.109769

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(1610)
HTML views(15)

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