Citation: Xiwei Li, Caiyun Liu, Na Gao, Wenlong Sheng, Baocun Zhu. A melatonin-based targetable fluorescent probe for screening of tumor cells and real-time imaging of glutathione fluctuations in tumor cells[J]. Chinese Chemical Letters, ;2022, 33(5): 2527-2531. doi: 10.1016/j.cclet.2021.11.080 shu

A melatonin-based targetable fluorescent probe for screening of tumor cells and real-time imaging of glutathione fluctuations in tumor cells

Xiwei Li ^a ,
Caiyun Liu ^{a, *,} ,
Na Gao ^a ,
Wenlong Sheng ^b ,
Baocun Zhu ^{a, *,}

a.
School of Water Conservancy and Environment, University of Jinan, Ji'nan 250022, China
b.
Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Ji'nan 250103, China

liucaiyun1982072@163.com

lcyzbc@163.com

Received Date: 20 September 2021
Revised Date: 23 November 2021
Accepted Date: 26 November 2021
Available Online: 1 December 2021
Fund Project: the National Natural Science Foundation of China 21777053the National Natural Science Foundation of China 22176070Shandong Province Higher Educational Youth Innovation Science and Technology Program 2019KJD005

Figures(3)

Glutathione (GSH) is a key maintainer of cellular redox balance and plays an important role in many physiological effects. For example, GSH has been widely implicated in cancer initiation, progression and metastasis. Moreover, the concentrations of GSH in tumor cells can influence drug resistance. Given the serious harmfulness of cancer and the important roles of GSH in cancer, it has great significance to development probes for screening of tumor cells and real-time monitoring of GSH fluctuations in tumor cells. However, no targetable probe for reversible imaging of GSH in tumor cells has been reported. Herein, we constructed a melatonin-based targetable and reversible fluorescent probe (GR-MT) for screening of tumor cells and real-time imaging of GSH fluctuations in tumor cells. The probe uses coumarin as the skeleton, Michael addition reaction as the reaction mechanism, and melatonin as the targeted groups of tumor cells. The experimental results demonstrate this probe has many advantages including high selectivity, satisfactory sensitivity, excellent reversible ability, rapid reaction speed, and outstanding targetability of tumor cells. Therefore, this study provides a promising tool for tumor cells screening and real-time detection of GSH fluctuations in specific tumor cells.
- Glutathione,
- Reversible detection,
- Fluorescent probe,
- Tumor cells screening,
- Melatonin
1. [1]
  Z. Liu, X. Zhou, Y. Miao, et al., Angew. Chem. Int. Ed. 56(2017) 5812-5816. doi: 10.1002/anie.201702114
2. [2]
  J.M. Estrela, A. Ortega, S. Mena, J.A. Sirerol, E. Obrador, Rev. Clin. Lab. Sci. 53(2016) 253-267. doi: 10.3109/10408363.2015.1136259
3. [3]
  R. Banerjee, J. Biol. Chem. 287(2012) 4397-4402. doi: 10.1074/jbc.R111.287995
4. [4]
  X. Guo, Y. Cheng, X. Zhao, et al., J. Nanobiotechnol. 16(2018) 74. doi: 10.1186/s12951-018-0398-2
5. [5]
  B.A. Arrick, C.F. Nathan, O.W. Griffith, Z.A. Cohn, J. Biol. Chem. 257(1982) 1231-1237. doi: 10.1016/S0021-9258(19)68180-9
6. [6]
  J.M. Estrela, A. Ortega, S. Mena, J.A. Sirerol, E. Obrador, Crit. Rev. Clin. Lab. Sci. 53(2016) 253-267. doi: 10.3109/10408363.2015.1136259
7. [7]
  L.H. Fu, Y.L. Wan, C. Qi, et al., Adv. Mater. 33(2021) 2006892. doi: 10.1002/adma.202006892
8. [8]
  A.K. Godwin, A. Meister, P.J. Dwyer, et al., Natl. Acad. Sci. U. S. A. 89(1992) 3070-3074. doi: 10.1073/pnas.89.7.3070
9. [9]
  M. Gao, F.B. Yu, C. Lv, J. Choo, L. Chen, Chem. Soc. Rev. 46(2017) 2237-2271. doi: 10.1039/C6CS00908E
10. [10]
  Y. Wang, L.X. Chen, J. Med. Chem. 64(2021) 2967-2970. doi: 10.1021/acs.jmedchem.1c00433
11. [11]
  M. Rafii, R. Elango, G.C. Martin, et al., Anal. Biochem. 371(2007) 71-81. doi: 10.1016/j.ab.2007.07.026
12. [12]
  N. Burford, M.D. Eelman, D.E. Mahony, M. Morash, Chem. Commun. (2003) 146-147.
13. [13]
  W. Chen, Y. Zhao, T. Seefeldt, X. Guan, J. Pharm. Biomed. Anal. 48(2008) 1375-1380. doi: 10.1016/j.jpba.2008.08.033
14. [14]
  Z.W. Ye, W. Yang, C. Wang, et al., J. Am. Chem. Soc. 141(2019) 14491-14495. doi: 10.1021/jacs.9b04893
15. [15]
  X.Y. Song, S. Bai, N. He, et al., ACS Sens. 6(2021) 1228-1239. doi: 10.1021/acssensors.0c02519
16. [16]
  X.Z. Luo, Z.Y. Cheng, R. Wang, F.B. Yu, Anal. Chem. 93(2021) 2490-2499. doi: 10.1021/acs.analchem.0c04529
17. [17]
  L. Jia, L.Y. Niu, Q.Z. Yang, Anal. Chem. 92(2020) 10800-10806. doi: 10.1021/acs.analchem.0c02255
18. [18]
  X.Y. Song, R. Wang, J.F. Gao, et al., Chin. Chem. Lett. 33(2022) 1567-1571. doi: 10.1016/j.cclet.2021.08.111
19. [19]
  X.Y. Song, X.Y. Han, F.B. Yu, et al., Theranostics 8(2018) 2217-2228. doi: 10.7150/thno.24041
20. [20]
  H.C. Zhu, C.Y. Liu, M.J. Su, et al., Coordin. Chem. Rev. 488(2021) 214153.
21. [21]
  H. Zhang, X.X. Yue, W.X. Li, et al., Sens. Actuators B: Chem. 331(2021) 129394. doi: 10.1016/j.snb.2020.129394
22. [22]
  Y. Yang, Y. Feng, H. Li, et al., Sens. Actuators B: Chem. 333(2021) 129189. doi: 10.1016/j.snb.2020.129189
23. [23]
  H.M. Yan, F.J. Huo, Y.K. Yue, J.B. Chao, C.X. Yin, J. Am. Chem. Soc. 143(2021) 318-325. doi: 10.1021/jacs.0c10840
24. [24]
  T.T. Niu, G.X. Yin, T. Yu, et al., Anal. Chim. Acta 1115(2020) 52-60. doi: 10.1016/j.aca.2020.02.059
25. [25]
  Y.X. Zou, M.S. Li, Y.L. Xing, et al., ACS Sens. 5(2020) 242-249. doi: 10.1021/acssensors.9b02118
26. [26]
  H. Li, Y.Z. Yang, X.Y. Qi, et al., Anal. Chim. Acta 1117(2020) 18-24. doi: 10.1016/j.aca.2020.03.040
27. [27]
  N.Y. She, Z.H. Wang, T.Y. Luo, et al., Chem. Sci. 9(2018) 8065-8070. doi: 10.1039/C8SC03421D
28. [28]
  Z.W. Yuan, L.J. Gui, J.R. Zheng, et al., ACS Appl. Mater. Interfaces 10(2018) 30994-31007. doi: 10.1021/acsami.8b09841
29. [29]
  S. Khatun, S. Yang, Y.Q. Zhao, et al., Anal. Chem. 92(2020) 10989-10995. doi: 10.1021/acs.analchem.9b05175
30. [30]
  W.J. Wu, X.X. Liao, Y. Chen, L.N. Ji, H. Chao, Anal. Chem. 93(2021) 8062-8070. doi: 10.1021/acs.analchem.1c01409
31. [31]
  B.B. Zhang, X.P. Yang, R. Zhang, et al., Anal. Chem. 89(2017) 10384-10390. doi: 10.1021/acs.analchem.7b02361
32. [32]
  F.B. Yu, P. Li, G.Y. Li, et al., J. Am. Chem. Soc. 133(2011) 11030-11033. doi: 10.1021/ja202582x
33. [33]
  K.H. Xu, M.M. Qiang, W. Gao, et al., Chem. Sci. 4(2013) 1079-1086. doi: 10.1039/c2sc22076h
34. [34]
  X. Jiang, Y. Yu, J. Chen, et al., ACS Chem. Biol. 10(2015) 864-874. doi: 10.1021/cb500986w
35. [35]
  M. Tian, X.Y. Liu, H. He, et al., Anal. Chem. 92(2020) 10068-10075. doi: 10.1021/acs.analchem.0c01881
36. [36]
  M. Tian, M. Yang, Y. Liu, F.L. Jiang, ACS Appl. Bio. Mater. 2(2019) 4503-4514. doi: 10.1021/acsabm.9b00642
37. [37]
  X.Q. Jiang, J.W. Chen, A. Bajic, et al., Nat. Commun. 8(2017) 16087. doi: 10.1038/ncomms16087
38. [38]
  J.W. Chen, X.Q. Jiang, S.L. Carroll, J. Huang, J. Wang, Org. Lett. 17(2015) 5978-5981. doi: 10.1021/acs.orglett.5b02910
39. [39]
  C.J. Liang, X.H. Chen, Q. Tang, et al., Chem. Commun. 56(2020) 6368-6371. doi: 10.1039/D0CC01747G
40. [40]
  J.W. Chen, X.Q. Jiang, C.W. Zhang, et al., ACS Sens. 2(2017) 1257-1261. doi: 10.1021/acssensors.7b00425
41. [41]
  E.M. Jeong, J.H. Yoon, J.S. Lim, et al., Stem Cell Rep. 13(2018) 600-614.
42. [42]
  X.Q. Jiang, C.W. Zhang, J.W. Chen, et al., Antioxid. Redox Signal. 30(2019) 1900-1910. doi: 10.1089/ars.2018.7605
43. [43]
  M. Tian, Y. Liu, F.L. Jiang, Anal. Chem. 92(2020) 14285-14291. doi: 10.1021/acs.analchem.0c03418
44. [44]
  K. Umezawa, M. Yoshida, M. Kamiya, T. Yamasoba, Y. Urano, Nat. Chem. 9(2017) 279-286. doi: 10.1038/nchem.2648
45. [45]
  Y.C. Yang, P.C. Chiou, P.C. Chen, et al., Environ. Toxicol. 34(2019) 203-209. doi: 10.1002/tox.22674
46. [46]
  E.K. Elmahallawy, Y. Mohamed, W. Abdo, T. Yanai, Int. J. Mol. Sci. 21(2020) 4521. doi: 10.3390/ijms21124521
47. [47]
  J. Karolina, N. Katarzyna, P. Aleksandra, et al., Cancers (Basel) 11(2019) 1001. doi: 10.3390/cancers11071001
1. [1]
  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
2. [2]
  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
3. [3]
  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
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]
  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
7. [7]
  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
8. [8]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  Beitong Zhu , Xiaorui Yang , Lirong Jiang , Tianhong Chen , Shuangfei Wang , Lintao Zeng . A portable and versatile fluorescent platform for high-throughput screening of toxic phosgene, diethyl chlorophosphate and volatile acyl chlorides. Chinese Chemical Letters, 2025, 36(1): 110222-. doi: 10.1016/j.cclet.2024.110222
16. [16]
  Zhihui Zhang , Ru Sun , Chong Bian , Hongbo Wang , Zhen Zhao , Panpan Lv , Jianzhong Lu , Haixin Zhang , Hulie Zeng , Yuanyuan Chen , Zhijuan Cao . A dual-protease-triggered chemiluminescent probe for precise tumor imaging. Chinese Chemical Letters, 2025, 36(2): 109784-. doi: 10.1016/j.cclet.2024.109784
17. [17]
  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
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(2)
Abstract views(777)
HTML views(55)

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