Citation: Ma Siyue, Li Linyang, She Mengyao, Mo Yan, Zhang Shengyong, Liu Ping, Li Jianli. Synthesis and application of highly sensitive fluorescent probe for Hg²⁺ regulated by sulfur[J]. Chinese Chemical Letters, ;2017, 28(10): 2014-2018. doi: 10.1016/j.cclet.2017.09.027 shu

Synthesis and application of highly sensitive fluorescent probe for Hg²⁺ regulated by sulfur

Ministry of Education Key Laboratory of Synthetic and Natural Functional Molecule Chemistry, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China

Corresponding author: Li Jianli, lijianli@nwu.edu.cn

Received Date: 1 July 2017
Revised Date: 3 September 2017
Accepted Date: 7 September 2017
Available Online: 9 October 2017

Figures(6)

Rhodamine-based fluorescent probe is widely used in chemical analysis, environmental analysis and life sciences area due to their excellent optical properties. Based on the thiophilic property of Hg²⁺, using C=S structural motif as the core segment, our group have designed and synthesized three novel probes containing cinnamyl aldehyde with different substituents, exhibiting high selectivity and excellent sensitivity. The structure-property relationships of these probes have been investigated that the optical change caused by electron withdrawing effect and heavy atom effect. Furthermore, these Hg²⁺ probes could be applied in living mice imaging, which provide a promising tool for quantitative mercury (Ⅱ) ion imaging in living organism.
- Fluorescent probe,
- Rhodamine 6G,
- Mercury (Ⅱ) ion,
- Electronic effect,
- Biological application
1. [1]
  K.P. Carter, A.M. Young, A.E. Palmer, Chem. Rev. 114(2014) 4564-4601. doi: 10.1021/cr400546e
2. [2]
  X. Chen, T. Pradhan, F. Wang, J.S. Kim, J. Yoon, Chem. Rev.112(2012) 1910-1956. doi: 10.1021/cr200201z
3. [3]
  J.A. Cotruvo Jr., A.T. Aron, K.M. Ramos-Torres, C.J. Chang, Chem. Soc. Rev. 44(2015) 4400-4414. doi: 10.1039/C4CS00346B
4. [4]
  M.H. Lee, J.S. Kim, J.L. Sessler, Chem. Soc. Rev. 44(2015) 4185-4191. doi: 10.1039/C4CS00280F
5. [5]
  Z. Liu, W. He, Z. Guo, Chem. Soc. Rev. 42(2013) 1568-1600. doi: 10.1039/c2cs35363f
6. [6]
  X. Qian, Z. Xu, Chem. Soc. Rev. 44(2015) 4487-4493. doi: 10.1039/C4CS00292J
7. [7]
  K.D. Bhatt, D.J. Vyas, B.A. Makwana, et al., Chin. Chem. Lett. 27(2016) 731-737. doi: 10.1016/j.cclet.2016.01.012
8. [8]
  L. Yuan, W. Lin, K. Zheng, L. He, W. Huang, Chem. Soc. Rev. 42(2013) 622-661. doi: 10.1039/C2CS35313J
9. [9]
  H. Wang, P. Zhang, J. Chen, et al., Sens. Actuators B:Chem. 242(2017) 818-824. doi: 10.1016/j.snb.2016.09.177
10. [10]
  H. Wang, Y. Wang, J. Jin, R. Yang, Anal. Chem. 80(2008) 9021-9028. doi: 10.1021/ac801382k
11. [11]
  Z. Gu, M. Zhao, Y. Sheng, L.A. Bentolila, Y. Tang, Anal. Chem. 83(2011) 2324-2329 Washington DC, U.S.. doi: 10.1021/ac103236g
12. [12]
  L. Yu, W. Lan, H. Xu, et al., Sens. Actuators B:Chem. 248(2017) 411-418. doi: 10.1016/j.snb.2017.03.153
13. [13]
  C. Wu, J. Wang, J. Shen, C. Bi, H. Zhou, Sens. Actuators B:Chem. 243(2017) 678-683. doi: 10.1016/j.snb.2016.12.046
14. [14]
  X. Wen, Z. Fan, Sens. Actuators B:Chem. 247(2017) 655-663. doi: 10.1016/j.snb.2017.03.062
15. [15]
  Y. Li, N. Liu, H. Liu, et al., Sci. Rep. 7(2017) 45974. doi: 10.1038/srep45974
16. [16]
  S.Y. Ding, M. Dong, Y.W. Wang, et al., J. Am. Chem. Soc. 138(2016) 3031-3037. doi: 10.1021/jacs.5b10754
17. [17]
  A. Kumar, J.D. Singh, Inorg. Chem. 51(2012) 772-774. doi: 10.1021/ic2023902
18. [18]
  S. Saha, P. Mahato, U. Reddy, et al., Inorg. Chem. 51(2012) 336-345. doi: 10.1021/ic2017243
19. [19]
  S. Ando, K. Koide, J. Am. Chem. Soc. 133(2011) 2556-2566. doi: 10.1021/ja108028m
20. [20]
  F. Loe-Mie, G. Marchand, J. Berthier, et al., Angew. Chem. Int. Ed. 49(2010) 424-427.
21. [21]
  E. Detsri, Chin. Chem. Lett. 27(2016) 1635-1640. doi: 10.1016/j.cclet.2016.05.008
22. [22]
  X.M. Li, R.R. Zhao, Y.L. Wei, et al., Chin. Chem. Lett. 27(2016) 813-816. doi: 10.1016/j.cclet.2016.04.001
23. [23]
  X.D. Jiang, H.F. Yu, J.L. Zhao, et al., Chin. Chem. Lett. 26(2015) 1241-1245. doi: 10.1016/j.cclet.2015.07.002
24. [24]
  B. Bag, A. Pal, Org. Biomol. Chem. 9(2011) 4467-4480. doi: 10.1039/c0ob01179g
25. [25]
  N. Dave, M.Y. Chan, P.J.J. Huang, B.D. Smith, J. Liu, J. Am. Chem. Soc. 132(2010) 12668-12673. doi: 10.1021/ja106098j
26. [26]
  E.U. Akkaya, M.E. Huston, A.W. Czarnik, J. Am. Chem. Soc. 112(1990) 3590-3593. doi: 10.1021/ja00165a051
27. [27]
  G. Hennrich, H. Sonnenschein, U. Resch-Genger, J. Am. Chem. Soc. 121(1999) 5073-5074. doi: 10.1021/ja983802r
28. [28]
  K. Rurack, M. Kollmannsberger, U. Resch-Genger, J. Daub, J. Am. Chem. Soc.122(2000) 968-969. doi: 10.1021/ja992630a
29. [29]
  E.M. Nolan, S.J. Lippard, J. Am. Chem. Soc. 129(2007) 5910-5918. doi: 10.1021/ja068879r
30. [30]
  L. Yuan, W. Lin, K. Zheng, S. Zhu, Acc Chem. Res. 46(2013) 1462-1473. doi: 10.1021/ar300273v
31. [31]
  W. Xu, Z. Zeng, J.H. Jiang, et al., Angew. Chem. Int. Ed. Engl. 55(2016) 13658-13699. doi: 10.1002/anie.201510721
32. [32]
  H. Yu, Y. Xiao, H. Guo, X. Qian, Chem.-Eur. J. 17(2011) 3179-3191. doi: 10.1002/chem.v17.11
33. [33]
  Y. Yue, F. Huo, P. Ning, et al., J. Am. Chem. Soc. 139(2017) 3181-3185. doi: 10.1021/jacs.6b12845
34. [34]
  X. Chen, G. Zhou, X. Peng, J. Yoon, Chem. Soc. Rev. 41(2012) 4610-4630. doi: 10.1039/c2cs35055f
35. [35]
  X. Chen, F. Wang, J.Y. Hyun, et al., Chem. Soc. Rev. 45(2016) 2976-3016. doi: 10.1039/C6CS00192K
36. [36]
  H.S. Jung, X. Chen, J.S. Kim, J. Yoon, Chem. Soc. Rev. 42(2013) 6019-6031. doi: 10.1039/c3cs60024f
37. [37]
  J. Li, D. Yim, W.D. Jang, J. Yoon, Chem. Soc. Rev. 46(2017) 2437-2458. doi: 10.1039/C6CS00619A
38. [38]
  M. She, Z. Yang, L. Hao, et al., Sci. Rep. 6(2016) 28972. doi: 10.1038/srep28972
39. [39]
  S. Ma, Y. Wang, M. She, et al., Rev. Anal. Chem. (2017), doi:http://dx.doi.org/10.1515/revac-2016-0024. doi: 10.1515/revac-2016-0024
40. [40]
  B. Liu, X. Hu, J. Chai, B. Yang, Sens. Actuators B:Chem. 228(2016) 94-100. doi: 10.1016/j.snb.2016.01.005
41. [41]
  H. Ye, F. Ge, X.C. Chen, et al., Sens. Actuators B:Chem. 182(2013) 273-279. doi: 10.1016/j.snb.2013.03.015
42. [42]
  C. Zhang, B. Gao, Q. Zhang, et al., Talanta 154(2016) 278-283. doi: 10.1016/j.talanta.2016.03.067
43. [43]
  Q.Q. Rui, Y. Zhou, Y. Fang, C. Yao, Spectrochim. Acta Part A:Mol. Biomol. Spectrosc. 159(2016) 209-218. doi: 10.1016/j.saa.2016.01.024
44. [44]
  X. Zhang, Y. Xiao, X. Qian, Angew. Chem. Int. Ed. Engl. 47(2008) 8025-8029. doi: 10.1002/anie.v47:42
45. [45]
  M. She, S. Wu, Z. Wang, et al., Sens. Actuators B:Chem. 247(2017) 129-138. doi: 10.1016/j.snb.2017.03.015
1. [1]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
2. [2]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
3. [3]
  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
4. [4]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
5. [5]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
6. [6]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
7. [7]
  Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
8. [8]
  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
9. [9]
  Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
10. [10]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
11. [11]
  Quan Zhang , Shunjie Xing , Jingqian Han , Li Feng , Jianchun Li , Zhaosheng Qian , Jin Zhou . Organic pollutant sensing for human health based on carbon dots. Chinese Chemical Letters, 2025, 36(1): 110117-. doi: 10.1016/j.cclet.2024.110117
12. [12]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
13. [13]
  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
14. [14]
  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
15. [15]
  Xiaoning Li , Quanyu Shi , Meng Li , Ningxin Song , Yumeng Xiao , Huining Xiao , Tony D. James , Lei Feng . Functionalization of cellulose carbon dots with different elements (N, B and S) for mercury ion detection and anti-counterfeit applications. Chinese Chemical Letters, 2024, 35(7): 109021-. doi: 10.1016/j.cclet.2023.109021
16. [16]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
17. [17]
  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
18. [18]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778
19. [19]
  Lanyun Zhang , Weisi Wang , Yu-Qiang Zhao , Rui Huang , Yuxun Lu , Ying Chen , Liping Duan , Ying Zhou . Mechanism study of the molluscicide candidate PBQ on Pomacea canaliculata using a viscosity-sensitive fluorescent probe. Chinese Chemical Letters, 2025, 36(1): 109798-. doi: 10.1016/j.cclet.2024.109798
20. [20]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(743)
HTML views(5)

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

Synthesis and application of highly sensitive fluorescent probe for Hg2+ regulated by sulfur

Metrics

通讯作者: 陈斌, bchen63@163.com

Synthesis and application of highly sensitive fluorescent probe for Hg²⁺ regulated by sulfur