Citation: Rui Chen, Wenxiu Li, Rong Li, Sixin Ai, Huayong Zhu, Weiying Lin. Cysteine-activated fluorescence/photoacoustic integrated probe for non-invasive diagnosis of drug-induced liver injury[J]. Chinese Chemical Letters, ;2023, 34(5): 107845. doi: 10.1016/j.cclet.2022.107845 shu

Cysteine-activated fluorescence/photoacoustic integrated probe for non-invasive diagnosis of drug-induced liver injury

Guangxi Key Laboratory of Electrochemical Energy Materials, Institute of Optical Materials and Chemical Biology, School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China

weiyinglin2013@163.com

Received Date: 26 May 2022
Revised Date: 15 September 2022
Accepted Date: 21 September 2022
Available Online: 24 September 2022

Figures(4)

Hepatotoxicity is a serious problem faced by clinical drugs, and long-term administration or overdose may lead to liver failure and even death of patients. Therefore, developing a reliable detection method for the early diagnosis and therapy of drug-induced liver injury (DILI) has significant meaning. Near-infrared fluorescence (NIRF) and photoacoustic (PA) dual-modality tomography probes can be used for imaging with high sensitivity and high-resolution of disease-related markers in deep tissues. Here, we developed a novel Cys-activated NIRF and PA dual-modality imaging probe (CDR) for early diagnosis of DILI, for the first time. The organic molecular probe CDR could respond rapidly to Cys, resulting in the absorption peak red-shifted from 560 nm to 725 nm, which also leads to the activation of the PA₇₂₅ signal and NIRF₇₆₅ signal. In addition, the new probe CDR could be used for NIRF/PA imaging of exogenous and endogenous Cys level in live cells and mice. More importantly, CDR has also been successfully used for in situ detection of Cys in early DILI mice and evaluate the therapeutic effect of NAC. Therefore, the CDR might become a powerful tool to research the physiological effect of Cys and evaluate the degree of DILI.
- Near-infrared fluorescence,
- Photoacoustic imaging,
- Fluorescence imaging,
- Cysteine
1. [1]
  K. Ray, Nat. Rev. Gastro. Hepat. 15 (2018) 130–131. doi: 10.1038/nrgastro.2018.13
2. [2]
  T. Akaike, T. Ida, F.Y. Wei, et al., Nat. Commun. 8 (2017) 1177. doi: 10.1038/s41467-017-01311-y
3. [3]
  M. Fellner, E. Siakkou, A.-.S. Faponle, et al., J. Biol. Inorg. Chem. 21 (2016) 501–510. doi: 10.1007/s00775-016-1360-0
4. [4]
  Y. Zhou, J. Wang, D. Zhang, et al., Chin. Med. UK 16 (2021) 135. doi: 10.1186/s13020-021-00543-x
5. [5]
  R.J. Andrade, N. Chalasani, E.S. Björnsson, et al., Nat. Rev. Dis. Primers. 5 (2019) 58. doi: 10.1038/s41572-019-0105-0
6. [6]
  J.S. Au, V.J. Navarro, S. Rossi, Aliment. Pharm. Ther. 34 (2011) 11–20. doi: 10.1111/j.1365-2036.2011.04674.x
7. [7]
  R.A. Nathwani, S. Pais, T.B. Reynolds, N. Kaplowitz, Hepatology 41 (2005) 380–382. doi: 10.1002/hep.20548
8. [8]
  J. Ozer, M. Ratner, M. Shaw, W. Bailey, S. Schomaker, Toxicology 245 (2008) 194–205. doi: 10.1016/j.tox.2007.11.021
9. [9]
  X. Chen, Y. Zhou, X. Peng, J. Yoon, Chem. Soc. Rev. 39 (2010) 2120–2135. doi: 10.1039/b925092a
10. [10]
  G.B. Steventon, S. Khan, S.C. Mitchell, J. Pharm. Pharmacol. 70 (2018) 1069–1077. doi: 10.1111/jphp.12944
11. [11]
  T. Rehman, M.A. Shabbir, M. Inam-Ur-Raheem, et al., Food. Sci. Nutr. 8 (2020) 4696–4707. doi: 10.1002/fsn3.1818
12. [12]
  C.M. Hunt, J.I. Papay, V. Stanulovic, A. Regev, Hepatology 66 (2017) 646–654. doi: 10.1002/hep.29152
13. [13]
  S.A. Seifert, D. Kovnat, V.E. Anderson, et al., Toxicol. Lett. 54 (2016) 282–285. doi: 10.3109/15563650.2015.1134798
14. [14]
  A. Pastore, A. Alisi, G. Di Giovamberardino, et al., Int. J. Mol. Sci. 15 (2014) 21202–21214. doi: 10.3390/ijms151121202
15. [15]
  L. Yue, H. Huang, W. Song, W. Lin, Chem. Eng. J. 441 (2022) 135981. doi: 10.1016/j.cej.2022.135981
16. [16]
  W. Li, R. Li, R. Chen, et al., Anal. Chem. 93 (2021) 8978–8985. doi: 10.1021/acs.analchem.1c01568
17. [17]
  J. Xu, J. Pan, Y. Zhang, et al., Sens. Actuators B 238 (2017) 58–65. doi: 10.1016/j.snb.2016.07.038
18. [18]
  R. Zhang, J. Yong, J. Yuan, Z. Xu, Coordin. Chem. Rev. 408 (2020) 213182. doi: 10.1016/j.ccr.2020.213182
19. [19]
  L. Yuan, W. Lin, K. Zheng, L. He, W. Huang, Chem. Soc. Rev. 42 (2013) 622–661. doi: 10.1039/C2CS35313J
20. [20]
  S. Cai, C. Liu, X. Jiao, L. Zhao, X. Zeng, J. Mater. Chem. B 8 (2020) 2269–2274. doi: 10.1039/c9tb02609f
21. [21]
  H. Ren, F. Huo, Y. Zhang, S. Zhao, C. Yin, Sens. Actuators B 319 (2020) 128248. doi: 10.1016/j.snb.2020.128248
22. [22]
  Y. Yang, T. Zhou, M. Jin, et al., J. Am. Chem. Soc. 142 (2020) 1614–1620. doi: 10.1021/jacs.9b12629
23. [23]
  A. Tarai, Y. Li, B. Liu, et al., Coordin. Chem. Rev. 445 (2021) 214070. doi: 10.1016/j.ccr.2021.214070
24. [24]
  X. Wu, W. Shi, X. Li, H. Ma, Acc. Chem. Res. 52 (2019) 1892–1904. doi: 10.1021/acs.accounts.9b00214
25. [25]
  X. Li, X. Liang, J. Yin, W. Lin, Chem. Soc. Rev. 50 (2021) 102–119. doi: 10.1039/D0CS00896F
26. [26]
  T. Li, F. Huo, J. Chao, C. Yin, Chem. Commun. 56 (2020) 11453–11456. doi: 10.1039/d0cc04839a
27. [27]
  R. Li, W. Li, R. Chen, W. Lin, Sens. Actuators B 347 (2021) 130616. doi: 10.1016/j.snb.2021.130616
28. [28]
  X.P. Fan, W. Yang, T.B. Ren, et al., Anal. Chem. 94 (2022) 1474–1481. doi: 10.1021/acs.analchem.1c05026
29. [29]
  C. Zhang, Z. Qiu, L. Zhang, et al., Chem. Sci. 12 (2021) 4883–4888. doi: 10.1039/d0sc06573k
30. [30]
  W. Li, R. Li, R. Chen, et al., Anal. Chem. 94 (2022) 7996–8004. doi: 10.1021/acs.analchem.2c01048
31. [31]
  H. Yan, F. Huo, Y. Yue, J. Chao, C. Yin, J. Am. Chem. Soc. 143 (2021) 318–325. doi: 10.1021/jacs.0c10840
32. [32]
  D. Chen, H. -. M. Ni, L. Wang, et al., Hepatology 69 (2019) 2164–2179. doi: 10.1002/hep.30422
33. [33]
  X. Shi, H. Bai, M. Zhao, et al., Transl. Res. 196 (2018) 31–41. doi: 10.1016/j.trsl.2018.02.003
34. [34]
  Y. Ntamo, K. Ziqubu, N. Chellan, et al., Oxid. Med. Cell. Longev. 2021 (2021) 3320325.
35. [35]
  G.P. Sreekanth, J. Panaampon, A. Suttitheptumrong, et al., Antiviral. Res. 166 (2019) 42–55.
36. [36]
  H. Jaeschke, J.Y. Akakpo, D.S. Umbaugh, A. Ramachandran, Toxicol. Sci. 174 (2020) 159–167. doi: 10.1093/toxsci/kfaa002
1. [1]
  Yiling Li , Zekun Gao , Xiuxiu Yue , Minhuan Lan , Xiuli Zheng , Benhua Wang , Shuang Zhao , Xiangzhi Song . FRET-based two-photon benzo[a] phenothiazinium photosensitizer for fluorescence imaging-guided photodynamic therapy. Chinese Chemical Letters, 2024, 35(7): 109133-. doi: 10.1016/j.cclet.2023.109133
2. [2]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
3. [3]
  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
4. [4]
  Jinyu Guo , Yandai Lin , Shaohua He , Yueqing Chen , Fenglu Li , Renjie Ruan , Gaoxing Pan , Hexin Nan , Jibin Song , Jin Zhang . Utilizing dual-responsive iridium(Ⅲ) complex for hepatocellular carcinoma: Integrating photoacoustic imaging with chemotherapy and photodynamic therapy. Chinese Chemical Letters, 2024, 35(9): 109537-. doi: 10.1016/j.cclet.2024.109537
5. [5]
  Lijia Xu , Tong Zhong , Wei Zhao , Bing Yao , Lin Ding , Huangxian Ju . Chemoselective labeling-based spermatozoa glycan imaging reveals abnormal glycosylation in oligoasthenotspermia. Chinese Chemical Letters, 2024, 35(4): 108760-. doi: 10.1016/j.cclet.2023.108760
6. [6]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
7. [7]
  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
8. [8]
  Yiqiao Chen , Ao Liu , Biwen Yang , Zhenzhen Li , Binggang Ye , Zhouyi Guo , Zhiming Liu , Haolin Chen . Photoluminescence and photothermal conversion in boric acid derived carbon dots for targeted microbial theranostics. Chinese Chemical Letters, 2024, 35(9): 109295-. doi: 10.1016/j.cclet.2023.109295
9. [9]
  Fengkai Zou , Borui Su , Han Leng , Nini Xin , Shichao Jiang , Dan Wei , Mei Yang , Youhua Wang , Hongsong Fan . Red-emissive carbon quantum dots minimize phototoxicity for rapid and long-term lipid droplet monitoring. Chinese Chemical Letters, 2024, 35(10): 109523-. doi: 10.1016/j.cclet.2024.109523
10. [10]
  Peide Zhu , Yangjia Liu , Yaoyao Tang , Siqi Zhu , Xinyang Liu , Lei Yin , Quan Liu , Zhiqiang Yu , Quan Xu , Dixian Luo , Juncheng Wang . Bi-doped carbon quantum dots functionalized liposomes with fluorescence visualization imaging for tumor diagnosis and treatment. Chinese Chemical Letters, 2024, 35(4): 108689-. doi: 10.1016/j.cclet.2023.108689
11. [11]
  Kangmin Wang , Liqiu Wan , Jingyu Wang , Chunlin Zhou , Ke Yang , Liang Zhou , Bijin Li . Multifunctional 2-(2′-hydroxyphenyl)benzoxazoles: Ready synthesis, mechanochromism, fluorescence imaging, and OLEDs. Chinese Chemical Letters, 2024, 35(10): 109554-. doi: 10.1016/j.cclet.2024.109554
12. [12]
  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
13. [13]
  Botao QU , Qian WANG , Xiaogang NING , Yuxin ZHOU , Ruiping ZHANG . Deeply penetrating photoacoustic imaging in tumor tissues based on dual-targeted melanin nanoparticle. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1025-1032. doi: 10.11862/CJIC.20230416
14. [14]
  Leichen Wang , Anqing Mei , Na Li , Xiaohong Ruan , Xu Sun , Yu Cai , Jinjun Shao , Xiaochen Dong . Aza-BODIPY dye with unexpected bromination and high singlet oxygen quantum yield for photoacoustic imaging-guided synergetic photodynamic/photothermal therapy. Chinese Chemical Letters, 2024, 35(6): 108974-. doi: 10.1016/j.cclet.2023.108974
15. [15]
  Wenxiang Ma , Xinyu He , Tianyi Chen , De-Li Ma , Hongzheng Chen , Chang-Zhi Li . Near-infrared non-fused electron acceptors for efficient organic photovoltaics. Chinese Chemical Letters, 2024, 35(4): 109099-. doi: 10.1016/j.cclet.2023.109099
16. [16]
  Jing-Jing Zhang , Lujun Lou , Rui Lv , Jiahui Chen , Yinlong Li , Guangwei Wu , Lingchao Cai , Steven H. Liang , Zhen Chen . Recent advances in photochemistry for positron emission tomography imaging. Chinese Chemical Letters, 2024, 35(8): 109342-. doi: 10.1016/j.cclet.2023.109342
17. [17]
  Shihong Wu , Ronghui Zhou , Hang Zhao , Peng Wu . Sonoafterglow luminescence for in vivo deep-tissue imaging. Chinese Chemical Letters, 2024, 35(10): 110026-. doi: 10.1016/j.cclet.2024.110026
18. [18]
  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
19. [19]
  Lei Wang , Jun-Jie Wu , Chang-Cun Yan , Wan-Ying Yang , Zong-Lu Che , Xin-Yu Xia , Xue-Dong Wang , Liang-Sheng Liao . Near-infrared organic lasers with ultra-broad emission bands by simultaneously harnessing four-level and six-level systems. Chinese Chemical Letters, 2024, 35(8): 109365-. doi: 10.1016/j.cclet.2023.109365
20. [20]
  Ying Zhao , Yin-Hang Chai , Tian Chen , Jie Zheng , Ting-Ting Li , Francisco Aznarez , Li-Long Dang , Lu-Fang Ma . Size-controlled synthesis and near-infrared photothermal response of Cp* Rh-based metalla[2]catenanes and rectangular metallamacrocycles. Chinese Chemical Letters, 2024, 35(6): 109298-. doi: 10.1016/j.cclet.2023.109298

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(363)
HTML views(7)

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