Citation: Yunlong Lu, Yuanhao Liu, Zhenlin Liang, Xiaoyan Ma, Lijuan Liu, Zhenfan Wen, Iogann Tolbatov, Alessandro Marrone, Wukun Liu. NHC-gold(I)-alkyne complexes induced hepatocellular carcinoma cell death through bioorthogonal activation by palladium complex in living system[J]. Chinese Chemical Letters, ;2023, 34(9): 108413. doi: 10.1016/j.cclet.2023.108413 shu

NHC-gold(I)-alkyne complexes induced hepatocellular carcinoma cell death through bioorthogonal activation by palladium complex in living system

Yunlong Lu ^{a, d, 1} ,
Yuanhao Liu ^{a, 1} ,
Zhenlin Liang ^a ,
Xiaoyan Ma ^a ,
Lijuan Liu ^a ,
Zhenfan Wen ^a ,
Iogann Tolbatov ^b ,
Alessandro Marrone ^c ,
Wukun Liu ^{a, d, *,}

a.
Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, School of Medicine & Holistic Integrative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, China
b.
Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, Tarragona 43007, Spain
c.
Dipartimento di Farmacia, Università degli Studi "G. D'Annunzio" Chieti-Pescara, Via dei Vestini, Chieti 66100, Italy
d.
State key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210023, China

liuwukun0000@njucm.edu.cn

liuwukun0000@hotmail.com

Received Date: 2 February 2023
Revised Date: 23 March 2023
Accepted Date: 30 March 2023
Available Online: 31 March 2023

Figures(5)

Bioorthogonal reactions can take place in biological environments without interfering with biochemical processes. In this study, Pd(PPh₃)₂Cl₂ was used as a bioorthogonal catalyst to in situ transform the stable N-heterocyclic carbene (NHC)-gold(I)-alkyne complex 5 to its active species which can effectively inhibit thioredoxin reductase (TrxR) and exhibit significant anticancer bioactivity in hepatocellular carcinoma (HCC).
- Hepatocellular carcinoma,
- N-Heterocyclic carbene,
- Gold complex,
- Alkyne,
- Bioorthogonal activation
1. [1]
  J.M. Llovet, J. Zucman-Rossi, E. Pikarsky, et al., Nat. Rev. Dis. Primers 2 (2016) 16018.
2. [2]
  J.M. Llovet, R.K. Kelley, A. Villanueva, et al., Nat. Rev. Dis. Primers 7 (2021) 6.
3. [3]
  R.L. Siegel, K.D. Miller, A. Jemal, CA Cancer J. Clin. 70 (2020) 7-30. doi: 10.3322/caac.21590
4. [4]
  R.M. Feng, Y.N. Zong, S.M. Cao, R.H. Xu, Cancer Commun. 39 (2019) 22. doi: 10.1186/s40880-019-0368-6
5. [5]
  S. Mancarella, S. Krol, A. Crovace, et al., Cancers (Basel) 11 (2019) 1510. doi: 10.3390/cancers11101510
6. [6]
  M. Bian, R. Fan, Z. Yang, et al., J. Med. Chem. 65 (2022) 1848-1866. doi: 10.1021/acs.jmedchem.1c01248
7. [7]
  C. Kole, N. Charalampakis, S. Tsakatikas, et al., Cancers (Basel) 12 (2020) 2859. doi: 10.3390/cancers12102859
8. [8]
  D. Liu, K.F. Staveley-O'Carroll, G. Li, J. Clin. Cell. Immunol. 6 (2015) 376.
9. [9]
  E. Breous, R. Thimme, J. Hepatol. 54 (2011) 830-834.
10. [10]
  S. Jia, S. Yang, H. Ji, et al., Chin. Chem. Lett. 31 (2020) 1104-1108.
11. [11]
  G. Zou, K. Zhang, W. Yang, et al., Chin. Chem. Lett. 32 (2021) 3252-3256.
12. [12]
  Z. Shao, C. Zhang, X. Zhu, et al., Chin. Chem. Lett. 30 (2019) 2169-2172.
13. [13]
  R.E. Bird, S.A. Lemmel, X. Yu, Q.A. Zhou, Bioconjugate Chem. 32 (2021) 2457-2479. doi: 10.1021/acs.bioconjchem.1c00461
14. [14]
  Y. Long, B. Cao, X. Xiong, et al., Angew. Chem. Int. Ed. 60 (2021) 4133-4141. doi: 10.1002/anie.202013366
15. [15]
  J.J. Hirner, Y. Shi, S.A. Blum, Acc. Chem. Res. 44 (2011) 603-613. doi: 10.1021/ar200055y
16. [16]
  M. Bian, R. Fan, S. Zhao, W. Liu, J. Med. Chem. 62 (2019) 7309-7321. doi: 10.1021/acs.jmedchem.8b01595
17. [17]
  Z. Xu, J. Xu, S. Sun, et al., Redox Biol. 54 (2022) 102351.
18. [18]
  M. Bian, R. Fan, G. Jiang, et al., J. Med. Chem. 63 (2020) 9197-9211. doi: 10.1021/acs.jmedchem.0c00257
19. [19]
  Y. Lu, X. Ma, X. Chang, et al., Chem. Soc. Rev. 51 (2022) 5518-5556. doi: 10.1039/d1cs00933h
20. [20]
  T. Zou, C.T. Lum, C.N. Lok, et al., Chem. Soc. Rev. 44 (2015) 8786-8801.
21. [21]
  B. Bertrand, A. Casini, Dalton Trans. 43 (2014) 4209-4219.
22. [22]
  A.S.K. Hashmi, C. Lothschütz, R. Döpp, et al., Angew. Chem. Int. Ed. 48 (2009) 8243-8246. doi: 10.1002/anie.200902942
23. [23]
  W. Liu, K. Bensdorf, M. Proetto, et al., J. Med. Chem. 54 (2011) 8605-8615. doi: 10.1021/jm201156x
24. [24]
  W. Liu, K. Bensdorf, M. Proetto, et al., J. Med. Chem. 55 (2012) 3713-3724. doi: 10.1021/jm3000196
25. [25]
  M. Bian, Y. Sun, Y. Liu, et al., Chem. Eur. J. 26 (2020) 7092-7108. doi: 10.1002/chem.202000045
26. [26]
  I. Ott, X. Qian, Y. Xu, et al., J. Med. Chem. 52 (2009) 763-770. doi: 10.1021/jm8012135
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