Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(10): 109838. doi: 10.1016/j.cclet.2024.109838 shu

A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging

Chuanfeng Fan ^a ,
Jian Gao ^a ,
Yingkai Gao ^a ,
Xintong Yang ^a ,
Gaoning Li ^a ,
Xiaochun Wang ^{a, b, *,} ,
Fei Li ^{c, *,} ,
Jin Zhou ^d ,
Haifeng Yu ^e ,
Yi Huang ^c ,
Jin Chen ^a ,
Yingying Shan ^a ,
Li Chen ^a

a.
Key Laboratory of Optic-electric Sensing and Analytical Chemistry for Life Science, MOE, Shandong Provincial Key Laboratory of Biochemical Engineering, Qingdao Nucleic Acid Rapid Detection Engineering Research Center, College of Marine Science and Biological Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
b.
School of Chemistry and Life Science, Anshan Normal University, Liaoning Key Laboratory of Development and Utilization for Natural Products Active Molecules, Anshan 114007, China
c.
Biomedical Analysis Center, Army Medical University, Chongqing 400038, China
d.
School of Pharmacy, Weifang Medical University, Weifang 261053, China
e.
College of Chemistry, Baicheng Normal University, Baicheng 137000, China

wangwxc1120@163.com

lf112.2004@163.com

Received Date: 1 January 2024
Revised Date: 1 March 2024
Accepted Date: 27 March 2024
Available Online: 28 March 2024

Figures(9)

As a hydrolase, chymotrypsin (CHT) is involved in many physiological activities, and its abnormal activity is closely related to diabetes, pancreatic fibrosis, chronic pancreatitis and pancreatic cancer. In this work, an innovative long-wavelength emission fluorescent probe TCF-CHT was designed and synthesized for the high specificity detection of CHT, which utilized TCF-OH and a mimetic peptide substrate 4-bromobutyryl as chromogenic group and recognition group, respectively. TCF-CHT exhibited excellent selectivity and eye-catching sensitivity (8.91 ng/mL) towards CHT, "off-on" long-wavelength emission at 670 nm and large Stokes shift (140 nm). Furthermore, the successful fulfillment and perfect performance in imaging endogenous CHT in complex organisms (P815 cells, HepG2 cells, zebrafish and tumor-bearing mice) verified its potential as a powerful tool for the recognition of CHT in complicated biological environments.
- Chymotrypsin,
- Fluorescent probe,
- Long-wavelength emission,
- Large Stokes shift,
- Bioimaging
1. [1]
  G.J.C. Vreeke, J.P. Vincken, P.A. Wierenga, Food Res. Int. 165 (2023) 112485. doi: 10.1016/j.foodres.2023.112485
2. [2]
  T.S. Corrigan, L.M. Lotti Diaz, S.E. Border, et al., J. Enzym. Inhib. Med. Chem. 35 (2020) 1387–1402. doi: 10.1080/14756366.2020.1781107
3. [3]
  J. Carrere, C. Figarella, O. Guy, et al., Biochim. Biophys. Acta 883 (1986) 46–53. doi: 10.1016/0304-4165(86)90133-9
4. [4]
  A. Karlund, I. Paukkonen, C. Gomez-Gallego, M. Kolehmainen, Healthcare 9 (2021) 1002. doi: 10.3390/healthcare9081002
5. [5]
  H. Filali, O.M.E. Yaagoubi, A. Lahmadi, et al., Clin. Proteom. 19 (2022) 41. doi: 10.1186/s12014-022-09375-9
6. [6]
  S.V. Lucena, F.P. Rufino, G.E.D. De Dantas Moura, et al., 3 Biotech 12 (2022) 19.
7. [7]
  H.J. Sun, J.Q. Xiao, Q.H. Qiao, et al., Int. J. Oral Maxillofac. Surg. 46 (2017) 877–882. doi: 10.1016/j.ijom.2017.02.1267
8. [8]
  D. Shah, K. Mital, Adv. Ther. 35 (2018) 31–42. doi: 10.1007/s12325-017-0648-y
9. [9]
  J.Q. Li, L.L. Wang, G.T. Zeng, et al., Immunopharm. Immunot. 44 (2022) 959–969. doi: 10.1080/08923973.2022.2093743
10. [10]
  J. Ko, L. Skudder-Hill, J. Cho, S.H. Bharmal, M.S. Petrov, World J. Gastroenterol. 27 (2021) 3357–3371.
11. [11]
  S. Trapp, A.A. Aghdassi, J. Glaubitz, et al., J. Cell. Mol. Med. 25 (2021) 4658–4670. doi: 10.1111/jcmm.16404
12. [12]
  G. Sanchez, S. Chalmers, X. Ahumada, et al., PLoS One 15 (2020) e0233591. doi: 10.1371/journal.pone.0233591
13. [13]
  V. Carmona, S.M. Aragon, J. Goldberg, et al., Nutr. Neurosci. 23 (2020) 575–590. doi: 10.1080/1028415X.2018.1534793
14. [14]
  A. Toth, A. Demcsak, F. Zankl, et al., Pancreatology 22 (2022) 713–718. doi: 10.1016/j.pan.2022.06.258
15. [15]
  A. Jermusyk, J. Zhong, K.E. Connelly, et al., Am. J. Hum. Genet. 108 (2021) 1852–1865. doi: 10.1016/j.ajhg.2021.09.002
16. [16]
  A. Hedstrom, C. Steiner, R. Valente, et al., Minerva Gastroenterol. Dietol. 66 (2020) 17–22.
17. [17]
  V.I. Fedchenko, A.V. Veselovsky, A.T. Kopylov, S.A. Kaloshina, A.E. Medvedev, Med. Hypotheses 165 (2022) 110895. doi: 10.1016/j.mehy.2022.110895
18. [18]
  A.V. Braun, V.F. Taranchenko, L.A. Tikhomirov, A.P. Grechukhin, I.V. Rybal'chenko, J. Anal. Chem. 73 (2018) 622–631.
19. [19]
  X. Jin, L.M. Yang, X.W. Yan, Q.Q. Wang, ACS Chem. Neurosci. 12 (2021) 1093–1099. doi: 10.1021/acschemneuro.0c00816
20. [20]
  B. Ramesh, S. Abnouf, S. Mali, et al., ACS Chem. Biol. 14 (2019) 2616–2628. doi: 10.1021/acschembio.9b00506
21. [21]
  T.B. Ren, Z.Y. Wang, Z. Xiang, et al., Angew. Chem. Int. Ed. 60 (2020) 800–805.
22. [22]
  K.H. Gebremedhin, Y.M. Li, Q.C. Yao, et al., J. Mater. Chem. B 7 (2019) 408–414. doi: 10.1039/C8TB02635A
23. [23]
  W.J. Zhang, F.J. Huo, Y.K. Yue, et al., J. Am. Chem. Soc. 142 (2020) 3262–3268. doi: 10.1021/jacs.9b13936
24. [24]
  H.B. Xiao, P. Li, B. Tang, Coord. Chem. Rev. 427 (2021) 213582. doi: 10.1016/j.ccr.2020.213582
25. [25]
  Y. Gao, Y.L. Hu, Q.M. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 10756–10765. doi: 10.1002/anie.202101278
26. [26]
  X. Luo, L.Y. Gu, X.H. Qian, Y.J. Yang, Chem. Commun. 56 (2020) 9067–9078. doi: 10.1039/D0CC00542H
27. [27]
  X.Y. Li, X.H. Li, H.M. Ma, Chem. Sci. 11 (2020) 1617–1622. doi: 10.1039/C9SC05505C
28. [28]
  Q.Q. Yang, N. Ji, Y. Zhan, et al., Anal. Chim. Acta 1186 (2021) 339116. doi: 10.1016/j.aca.2021.339116
29. [29]
  J. Xing, Q.Y. Gong, R.F. Zou, et al., J. Mater. Chem. B 6 (2018) 1449–1451. doi: 10.1039/C7TB03303F
30. [30]
  J. Liu, Z.Q. Wang, G.J. Mao, et al., Anal. Chim. Acta 1171 (2021) 338655. doi: 10.1016/j.aca.2021.338655
31. [31]
  H.Y. Zhang, X.Y. Yin, J.X. Hong, Y.Z. Deng, G.Q. Feng, Talanta 223 (2021) 121768. doi: 10.1016/j.talanta.2020.121768
32. [32]
  W.X. Yao, Y.J. Cao, M.Y. She, et al., ACS Sens. 6 (2021) 54–62. doi: 10.1021/acssensors.0c01707
33. [33]
  Y.P. Chen, J. Cao, X.X. Jiang, Z.Z. Pan, N.Y. Fu, Sens. Actuator. B: Chem. 273 (2018) 204–210. doi: 10.1016/j.snb.2018.06.021
34. [34]
  L. Wu, S.H. Yang, H. Xiong, et al., Anal. Chem. 89 (2017) 3687–3693. doi: 10.1021/acs.analchem.6b05115
35. [35]
  H. Xiong, R.R. Li, S.Y. Liu, et al., ACS Appl. Bio Mater. 1 (2018) 310–317. doi: 10.1021/acsabm.8b00072
36. [36]
  S. Mu, Y.X. Xu, Y.T. Zhang, et al., J. Mater. Chem. B 7 (2019) 2974–2980. doi: 10.1039/C9TB00085B
37. [37]
  Y. Okorochenkova, M. Porubsky, S. Benicka, J. Hlavac, Chem. Commun. 54 (2018) 7589–7592. doi: 10.1039/C8CC01731J
38. [38]
  J.M. Wang, Z.D. Teng, T. Cao, et al., Sens. Actuator. B: Chem. 306 (2020) 127567. doi: 10.1016/j.snb.2019.127567
39. [39]
  Y. Qu, Z.S. Xu, J.M. Wang, et al., Sens. Actuator. B: Chem. 382 (2023) 133552. doi: 10.1016/j.snb.2023.133552
40. [40]
  H.Y. Sun, R.C. Panicker, S.Q. Yao, Biopolymers 88 (2010) 141–149.
41. [41]
  S.Y. Liu, X.T. Zou, X. Gao, Y.Y. Zhang, Anal. Chem. 94 (2022) 17922–17929. doi: 10.1021/acs.analchem.2c03933
42. [42]
  D. Sondag, J. Merx, E. Rossing, et al., ChemBioChem 23 (2022) e202200190. doi: 10.1002/cbic.202200190
43. [43]
  B.D. Vieira, H. Niero, R. de Felicio, et al., Front. Microbiol. 13 (2022) 786008. doi: 10.3389/fmicb.2022.786008
44. [44]
  Y.Q. Zi, D.W. Xu, C. Li, F. Qu, X.E. Zhao, Sens. Actuator. B: Chem. 345 (2021) 130243. doi: 10.1016/j.snb.2021.130243
45. [45]
  L.P. Yang, Z.G. Li, T.H. Wei, et al., Front. Chem. 8 (2020) 522974. doi: 10.3389/fchem.2020.522974
46. [46]
  J.T. Zhao, T. Ma, B.B. Chang, J.G. Fang, Molecules 27 (2022) 5922. doi: 10.3390/molecules27185922
47. [47]
  H. Li, Y.J. Kim, H. Jung, J.Y. Hyun, I.J. Shin, Chem. Soc. Rev. 51 (2022) 8957–9008. doi: 10.1039/D2CS00722C
48. [48]
  J. Zhou, C.M. Yu, Z. Li, et al., Anal. Methods 11 (2019) 1312–1316. doi: 10.1039/C9AY00041K
49. [49]
  Z.K. Wang, Z.Y. Zhao, C.Y. Liu, et al., Photochem. Photobiol. Sci. 18 (2019) 1851–1857. doi: 10.1039/c9pp00222g
50. [50]
  X.X. Teng, M.Y. Tian, J.W. Zhang, L.J. Tang, J.N. Xin, Tetrahedron Lett. 59 (2018) 2804–2808. doi: 10.1016/j.tetlet.2018.06.016
51. [51]
  H.Y. Xie, J. Gao, X.T. Sun, et al., Talanta 253 (2023) 123943. doi: 10.1016/j.talanta.2022.123943
52. [52]
  Y. Zhu, J.L. Han, Q. Zhang, et al., RSC Adv. 9 (2019) 26729–26733. doi: 10.1039/C9RA05650E
53. [53]
  W. Wang, Z.H. Peng, M. Ji, J.Q. Chen, P. Wang, Bioorg. Chem. 126 (2022) 105902. doi: 10.1016/j.bioorg.2022.105902
54. [54]
  M. Zhao, Y.J. Gao, S.Y. Ye, et al., Analyst 144 (2019) 6262–6269. doi: 10.1039/C9AN01505A
55. [55]
  Y. Wen, W.J. Zhang, T. Liu, F.J. Huo, C.X. Yin, Anal. Chem. 89 (2017) 11869–11874. doi: 10.1021/acs.analchem.7b03612
56. [56]
  T. Zhang, F.J. Huo, W.J. Zhang, J.B. Chao, C.X. Yin, Sens. Actuator. B: Chem. 345 (2021) 130393. doi: 10.1016/j.snb.2021.130393
57. [57]
  J.D. Wang, F.J. Huo, Y.B. Zhang, C.X. Yin, Chin. Chem. Lett. 34 (2023) 107818. doi: 10.1016/j.cclet.2022.107818
58. [58]
  Z.L. Qiu, J. Shu, D.P. Tang, Anal. Chem. 89 (2017) 5152–5160. doi: 10.1021/acs.analchem.7b00989
59. [59]
  S.Z. Lv, Y. Tang, K.Y. Zhang, D.P. Tang, Anal. Chem. 90 (2018) 14121–14125. doi: 10.1021/acs.analchem.8b04981
60. [60]
  S.Y. Shen, W.L. Xu, J.X. Lu, W.X. Qing, Y. Wang, Chin. Chem. Lett. 35 (2024) 108360. doi: 10.1016/j.cclet.2023.108360
61. [61]
  Y.Y. Sun, X.N. Zhou, L.Y. Sun, et al., Chin. Chem. Lett. 33 (2022) 4229–4232. doi: 10.1016/j.cclet.2022.01.087
62. [62]
  L.X. Fu, Y.Y. Tan, Y. Ding, et al., Chin. Chem. Lett. 35 (2024) 108886. doi: 10.1016/j.cclet.2023.108886
63. [63]
  S. Fatima, S. Gupta, A.B. Khan, S. ur Rehman, M.A. Jairajpuri, Biochem. Biophys. Res. Commun. 628 (2022) 25–31. doi: 10.1016/j.bbrc.2022.08.061
64. [64]
  Q. Miao, Y. Sun, T.T. Wei, et al., J. Biol. Chem. 283 (2008) 8218–8228. doi: 10.1074/jbc.M709789200
1. [1]
  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
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]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
4. [4]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
5. [5]
  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
6. [6]
  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
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]
  Zengchao Guo , Weiwei Liu , Tengfei Liu , Jinpeng Wang , Hui Jiang , Xiaohui Liu , Yossi Weizmann , Xuemei Wang . Engineered exosome hybrid copper nanoscale antibiotics facilitate simultaneous self-assembly imaging and elimination of intracellular multidrug-resistant superbugs. Chinese Chemical Letters, 2024, 35(7): 109060-. doi: 10.1016/j.cclet.2023.109060
9. [9]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(326)
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