Citation: Nannan Wang, Han Wang, Jian Zhang, Xin Ji, Huihui Su, Jinying Liu, Jiamin Wang, Weili Zhao. Endogenous peroxynitrite activated fluorescent probe for revealing anti‐tuberculosis drug induced hepatotoxicity[J]. Chinese Chemical Letters, ;2022, 33(3): 1584-1588. doi: 10.1016/j.cclet.2021.09.046 shu

Endogenous peroxynitrite activated fluorescent probe for revealing anti‐tuberculosis drug induced hepatotoxicity

Nannan Wang ^{a, 1} ,
Han Wang ^{a, 1} ,
Jian Zhang ^{a, *,} ,
Xin Ji ^b ,
Huihui Su ^a ,
Jinying Liu ^a ,
Jiamin Wang ^{c, *,} ,
Weili Zhao ^{a, b, *,}

a.
Key Laboratory for Special Functional Materials of Ministry of Education, School of Materials Science and Engineering, Henan University, Kaifeng 475004, China
b.
School of Pharmacy, Institutes of Integrative Medicine, Fudan University, Shanghai 201203, China
c.
Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng 475004, China

jianzhang@henu.edu.cn

jmwang@henu.edu.cn

zhaoweili@fudan.edu.cn

Received Date: 27 June 2021
Revised Date: 12 September 2021
Accepted Date: 13 September 2021
Available Online: 17 September 2021

Figures(5)

Pyrazinamide (PZA), isoniazid (INH) and rifampicin (RFP) are all commonly used anti-tuberculosis drugs in clinical practice, and long-term medication may cause severe liver damage and toxicity. The level of peroxynitrite (ONOO^–) generated in liver has long been regarded as a biomarker for the prediction and measurement of drug-induced liver injury (DILI). In this article, we constructed a BODIPY-based fluorescent probe (BDP-Py⁺) that enabled quickly and sensitively detect and image ONOO^– in vivo. Utilizing this probe, we demonstrated the change of ONOO^– content in cells and mice model of DILI induced by acetaminophen (APAP), and for the first time revealed the mechanism of liver injury induced by antituberculosis drug PZA. Moreover, BDP-Py⁺ could be applied to screen out and evaluate the hepatotoxicity of different anti-tuberculosis drugs. Comparing with the existing serum enzymes detection and H & E staining, the probe could achieve early diagnosis of DILI before solid lesions in liver via monitoring the up-regulation of ONOO^– levels. Collectively, this work will promote the understanding of the pathogenesis of anti-tuberculosis drug induced liver injury (ATB-DILI), and provide a powerful tool for the early diagnosis and treatment of DILI.
- Anti-tuberculosis drug induced liver injury,
- Peroxynitrite,
- Fluorescent probe,
- Drug-induced liver injury,
- Bioimaging
1. [1]
  W.M. Lee, Clin. Liver Dis. 17 (2013) 575-586. doi: 10.1016/j.cld.2013.07.001
2. [2]
  M. Pieroni, D. Machado, E. Azzali, et al., J. Med. Chem. 58 (2015) 5842-5853. doi: 10.1021/acs.jmedchem.5b00428
3. [3]
  J.Y. Wang, C.H. Tsai, Y.L. Lee, et al., Medicine 94 (2015) 982. doi: 10.1097/MD.0000000000000982
4. [4]
  T. Haque, E. Sasatomi, P.H. Hayashi, Gut Liver 10 (2016) 27-36. doi: 10.5009/gnl15114
5. [5]
  A.J. Shuhendler, K. Pu, L. Cui, J.P. Uetrecht, J. Rao, Nat. Biotechnol. 32 (2014) 373-380. doi: 10.1038/nbt.2838
6. [6]
  W.M. Lee, J. Hepatol. 67 (2017) 1324-1331. doi: 10.1016/j.jhep.2017.07.005
7. [7]
  C. Szabo, H. Ischiropoulos, R. Radi, Nat. Rev. Drug Discov. 6 (2007) 662-680. doi: 10.1038/nrd2222
8. [8]
  P. Pacher, J.S. Beckman, L. Liaudet, Physiol. Rev. 87 (2007) 315-424. doi: 10.1152/physrev.00029.2006
9. [9]
  G. Ferrer-Sueta, R. Radi, ACS Chem. Biol. 4 (2009) 161-177. doi: 10.1021/cb800279q
10. [10]
  R.J. Radi, Biol. Chem. 288 (2013) 26464-26472. doi: 10.1074/jbc.R113.472936
11. [11]
  N. Ieda, H. Nakagawa, T. Peng, et al., J. Am. Chem. Soc. 134 (2012) 2563-2568. doi: 10.1021/ja206744z
12. [12]
  C. Ducrocq, B. Blanchard, B. Pignatelli, H. Ohshima, Cell. Mol. Life Sci. 55 (1999) 1068-1077. doi: 10.1007/s000180050357
13. [13]
  G. Yin, T. Niu, T. Yu, et al., Angew. Chem. Int. Ed. 58 (2019) 4557-4561. doi: 10.1002/anie.201813935
14. [14]
  Y. Gan, G. Yin, T. Yu, et al., Talanta 210 (2020) 120612. doi: 10.1016/j.talanta.2019.120612
15. [15]
  H. Li, Q. Yao, F. Xu, et al., Angew. Chem. Int. Ed. 59 (2020) 10186-10195. doi: 10.1002/anie.202001675
16. [16]
  V. Nguyen, Y. Yim, S. Kim, et al., Angew. Chem. Int. Ed. 59 (2020) 8957-8962. doi: 10.1002/anie.202002843
17. [17]
  P. Chen, H. Zhang, L. Niu, et al., Adv. Funct. Mater. 27 (2017) 1700332. doi: 10.1002/adfm.201700332
18. [18]
  N. Liu, P. Chen, J. Wang, L. Niu, Q. Yang, Chin. Chem. Lett. 30 (2019) 1939-1941. doi: 10.1016/j.cclet.2019.04.058
19. [19]
  P. Lu, X. Zhang, T. Ren, L. Yuan, Chin. Chem. Lett. 31 (2020) 2980-2984. doi: 10.1016/j.cclet.2020.08.016
20. [20]
  K. Wang, W. Ma, Y. Xu, et al., Chin. Chem. Lett. 31 (2020) 3149-3152. doi: 10.1016/j.cclet.2020.08.039
21. [21]
  J. Han, X. Yue, J. Wang, et al., Chin. Chem. Lett. 31 (2020) 1508-1510. doi: 10.1016/j.cclet.2020.01.029
22. [22]
  X. Ren, L. Liao, Z. Yang, et al., Chin. Chem. Lett. 32 (2021) 1061-1065. doi: 10.1016/j.cclet.2020.09.024
23. [23]
  J. Zhang, N. Wang, X. Ji, et al., Chem. Eur. J. 26 (2020) 4172-4192. doi: 10.1002/chem.201904470
24. [24]
  D. Shi, S. Chen, B. Dong, et al., Chem. Sci. 10 (2019) 3715-3722. doi: 10.1039/c9sc00180h
25. [25]
  Y. Zhang, Y.Gao H.Teng, et al., Chin. Chem. Lett. 31 (2020) 2917-2920. doi: 10.1016/j.cclet.2020.03.020
26. [26]
  H. Teng, J. Tian, D. Sun, et al., Sens. Actuat. B: Chem. 319 (2020) 128288. doi: 10.1016/j.snb.2020.128288
27. [27]
  B. Chen, S. Mao, Y. Sun, et al., Chem. Commun. 57 (2021) 4376-4379. doi: 10.1039/d1cc01104a
28. [28]
  J. Zhang, J. Kan, Y. Sun, et al., ACS Appl. Bio. Mater. 4 (2021) 2080-2088. doi: 10.1021/acsabm.0c01178
29. [29]
  J. Zhou, P. Jangili, S. Son, et al., Adv. Mater. 32 (2020) 2001945. doi: 10.1002/adma.202001945
30. [30]
  C. Zhang, H. Xie, T. Zhan, et al., Chem. Commun. 55 (2019) 9444-9447. doi: 10.1039/c9cc03909k
31. [31]
  B. Chen, C. Li, J. Zhang, et al., Chem. Commun. 55 (2019) 7410-7413. doi: 10.1039/c9cc03977e
32. [32]
  D. Cheng, W. Xu, X. Gong, L. Yuan, X. Zhang, Acc. Chem. Res. 54(2021) 403-415. doi: 10.1021/acs.accounts.0c00646
33. [33]
  Y. Huang, Y. Qi, C. Zhan, F. Zeng, S. Wu, Anal. Chem. 91 (2019) 8085-8092. doi: 10.1021/acs.analchem.9b00107
34. [34]
  D. Cheng, J. Peng, Y. Lv, et al., J. Am. Chem. Soc. 141 (2019) 6352-6361. doi: 10.1021/jacs.9b01374
35. [35]
  W. Jiang, Y. Li, W. Wang, et al., Chem. Commun. 55 (2019) 14307-14310. doi: 10.1039/c9cc07017f
36. [36]
  L. Wu, Q. Ding, X. Wang, et al., Anal. Chem. 92 (2020) 1245-1251. doi: 10.1021/acs.analchem.9b04411
37. [37]
  H. Wang, C. Liu, Z. He, et al., Anal. Chem. 93 (2021) 6551-6558. doi: 10.1021/acs.analchem.1c00742
38. [38]
  L. Wu, J. Liu, X. Tian, et al., Chem. Sci. 12 (2021) 3921-3928. doi: 10.1039/d0sc05937d
39. [39]
  B. Wang, Y. Wang, Y. Wang, et al., Anal. Chem. 92 (2020) 4154-4163. doi: 10.1021/acs.analchem.0c00329
40. [40]
  D. Cheng, Y. Pan, L. Wang, et al., J. Am. Chem. Soc. 139 (2017) 285-292. doi: 10.1021/jacs.6b10508
41. [41]
  D. Cheng, W. Xu, L. Yuan, X. Zhang, Anal. Chem. 89 (2017) 7693-7700. doi: 10.1021/acs.analchem.7b01671
42. [42]
  J. Chen, D. Huang, M. She, et al., ACS Sens. 6 (2021) 628-640. doi: 10.1021/acssensors.0c02343
43. [43]
  X. Ji, N. Wang, J. Zhang, et al., Dyes Pigments 187 (2021) 109089. doi: 10.1016/j.dyepig.2020.109089
44. [44]
  N. Wang, M. Chen, J. Gao, et al., Talanta 195 (2019) 281-289. doi: 10.1016/j.talanta.2018.11.066
45. [45]
  J. Zhang, X. Ji, J. Zhou, et al., Sens. Actuat. B: Chem. 257 (2018) 1076-1082. doi: 10.1016/j.snb.2017.10.133
46. [46]
  A.C. Sedgwick, H.H. Han, J. E. Gardiner, et al., Chem. Sci. 9 (2018) 3672-3676. doi: 10.1039/c8sc00733k
47. [47]
  S. Palanisamy, P.Y. Wu, S.C. Wu, et al., Biosens. Bioelectron. 91 (2017) 849-856. doi: 10.1016/j.bios.2017.01.027
48. [48]
  M. Weber, H.H. Han, B.H. Li, et al., Chem. Sci. 11 (2020) 8567-8571. doi: 10.1039/d0sc02438d
1. [1]
  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
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]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Yunlong Li , Xinyu Zhang , Shuang Liu , Chunsheng Li , Qiang Wang , Jin Ye , Yong Lu , Jiating Xu . Engineered iron-based metal-organic frameworks nanoplatforms for cancer theranostics: A mini review. Chinese Chemical Letters, 2025, 36(2): 110501-. doi: 10.1016/j.cclet.2024.110501
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]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  Qiang Li , Jiangbo Fan , Hongkai Mu , Lin Chen , Yongzhen Yang , Shiping Yu . Nucleus-targeting orange-emissive carbon dots delivery adriamycin for enhanced anti-liver cancer therapy. Chinese Chemical Letters, 2024, 35(6): 108947-. doi: 10.1016/j.cclet.2023.108947
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(447)
HTML views(14)

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