Skip to main content
SpringerLink
Log in

Designing anticancer combretastatin A-4 analogues with aggregation-induced emission characteristics

  • Communications
  • Published:
Science China Chemistry Aims and scope Submit manuscript

Abstract

Herein a series of combretastatin A-4 (CA-4) analogues with aggregation-induced emission characteristics (compounds a1–a19) were rationally designed and synthesized. The research results showed that the mechanism of AIE of a1–a19 could be attributed to the dual function of the restriction of intramolecular motion (RIM) and J-aggregate formation. Furthermore, the detailed investigation on the action mechanisms revealed that a19 diffused from lysosomes into the cytoplasm, and then targeted the colchicine binding site to induce cell cycle arrest and apoptosis in cancer cells. These results provide new ideas and impetus for the rational design of CA-4 analogues.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Hou L, Huang W, Cheng J, Deng X, Lai H, Chen Z, Zhan Z, Feng P, Li Y, Yang F, Chen T. Chem Commun, 2020, 56: 14495–14498

    Article  CAS  Google Scholar 

  2. Yadykov AV, Scherbakov AM, Trofimova VV, Lvov AG, Markosyan AI, Zavarzin IV, Shirinian VZ. Org Lett, 2019, 21: 9608–9612

    Article  CAS  Google Scholar 

  3. Hua S, Chen F, Gou S. Eur J Med Chem, 2020, 187: 111949

    Article  CAS  Google Scholar 

  4. Cui YJ, Liu C, Ma CC, Ji YT, Yao YL, Tang LQ, Zhang CM, Wu JD, Liu ZP. J Med Chem, 2020, 63: 14840–14866

    Article  CAS  Google Scholar 

  5. Pang Y, An B, Lou L, Zhang J, Yan J, Huang L, Li X, Yin S. J Med Chem, 2017, 60: 7300–7314

    Article  CAS  Google Scholar 

  6. Liu Y, Wu Y, Sun L, Gu Y, Hu L. Eur J Med Chem, 2020, 191: 112181

    Article  CAS  Google Scholar 

  7. Pecnard S, Hamze A, Bignon J, Prost B, Deroussent A, Gallego-Yerga L, Peláez R, Paik JY, Diederich M, Alami M, Provot O. Eur J Med Chem, 2021, 223: 113656

    Article  CAS  Google Scholar 

  8. Pettit GR, Toki B, Herald DL, Verdier-Pinard P, Boyd MR, Hamel E, Pettit RK. J Med Chem, 1998, 41: 1688–1695

    Article  CAS  Google Scholar 

  9. Fareed MR, Shoman ME, Hamed MIA, Badr M, Bogari HA, Elhady SS, Ibrahim TS, Abuo-Rahma GEDA, Ali TFS. Pharmaceuticals, 2021, 14: 1114

    Article  CAS  Google Scholar 

  10. Luo J, Xie Z, Lam JWY, Cheng L, Tang BZ, Chen H, Qiu C, Kwok HS, Zhan X, Liu Y, Zhu D. Chem Commun, 2001, 1740–1741

  11. Wang H, Liu G. J Mater Chem B, 2018, 6: 4029–4042

    Article  CAS  Google Scholar 

  12. Liu Q, Chen X, Zhou Z, Huang T, Wang Y, Xie S, Zeng Z, Tang BZ. Sci China Chem, 2021, 64: 1976–1984

    Article  CAS  Google Scholar 

  13. Xiao Q, Zhao X, Xiong H. Chin Chem Lett, 2021, 32: 1687–1690

    Article  CAS  Google Scholar 

  14. Li J, Gao H, Liu R, Chen C, Zeng S, Liu Q, Ding D. Sci China Chem, 2020, 63: 1428–1434

    Article  CAS  Google Scholar 

  15. Yao H, Dai J, Zhuang Z, Yao J, Wu Z, Wang S, Xia F, Zhou J, Lou X, Zhao Z. Sci China Chem, 2020, 63: 1815–1824

    Article  CAS  Google Scholar 

  16. Dey S, Kumari S, Kalainayakan SP, Campbell Iii J, Ghosh P, Zhou H, FitzGerald KE, Li M, Mason RP, Zhang L, Liu L. Oncotarget, 2018, 9: 4090–4101

    Article  Google Scholar 

  17. Eikesdal HP, Bjerkvig R, Mella O, Dahl O. Radiother Oncol, 2001, 60: 147–154

    Article  CAS  Google Scholar 

  18. Nkepang G, Bio M, Rajaputra P, Awuah SG, You Y. Bioconj Chem, 2014, 25: 2175–2188

    Article  CAS  Google Scholar 

  19. Zhao Z, Zhang H, Lam JWY, Tang BZ. Angew Chem Int Ed, 2020, 59: 9888–9907

    Article  CAS  Google Scholar 

  20. Wright HJ, Hou J, Xu B, Cortez M, Potma EO, Tromberg BJ, Razorenova OV. Proc Natl Acad Sci USA, 2017, 114: E6556–E6565

    CAS  PubMed  PubMed Central  Google Scholar 

  21. Wang M, Wu Y, Xu C, Zhao R, Huang Y, Zeng X, Chen T. Chem Asian J, 2019, 14: 2648–2655

    Article  CAS  Google Scholar 

  22. Zhao Z, Gao P, You Y, Chen T. Chem Eur J, 2018, 24: 3289–3298

    Article  CAS  Google Scholar 

  23. Fu DJ, Fu L, Liu YC, Wang JW, Wang YQ, Han BK, Li XR, Zhang C, Li F, Song J. Sci Rep, 2017, 7: 12788

    Article  Google Scholar 

  24. Jiménez C, Ellahioui Y, Álvarez R, Aramburu L, Riesco A, González M, Vicente A, Dahdouh A, Ibn Mansour A, Jiménez C, Martín D, Sarmiento RG, Medarde M, Caballero E, Peláez R. Eur J Med Chem, 2015, 100: 210–222

    Article  Google Scholar 

  25. Hao SY, Qi ZY, Wang S, Wang XR, Chen SW. Bioorg Med Chem, 2021, 31: 115985

    Article  CAS  Google Scholar 

  26. Chen Z, Lai H, Hou L, Chen T. Chem Commun, 2020, 56: 179–196

    Article  CAS  Google Scholar 

  27. Albassam H, Mehta CH, Nayak UY. J Biomol Struct Dyn, 2021, 1–15

  28. Sun M, Qian Q, Shi L, Xu L, Liu Q, Zhou L, Zhu X, Yue JM, Yan D. Sci China Chem, 2020, 63: 35–41

    Article  CAS  Google Scholar 

  29. Yang Y, Wang Y, Xu L, Chen T. Chin Chem Lett, 2020, 31: 1801–1806

    Article  CAS  Google Scholar 

  30. Chen M, Huang X, Lai J, Ma L, Chen T. Chin Chem Lett, 2021, 32: 158–161

    Article  CAS  Google Scholar 

  31. Li H, Yao Q, Pu Z, Chung J, Ge H, Shi C, Xu N, Xu F, Sun W, Du J, Fan J, Wang J, Yoon J, Peng X. Sci China Chem, 2021, 64: 499–508

    Article  CAS  Google Scholar 

  32. Li J, Luo H, Zhu X, Zhao J, Chen T. Chin Chem Lett, 2021, 32: 1799–1802

    Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Key R&D Programs of China (2017YFC1103603), the National Natural Science Foundation of China (21877049, 32171296), Guangdong Natural Science Foundation (2020B1515120043), the Innovation Team Project in Guangdong Colleges and Universities (2019KCXTD008) and K. C. Wong Education Foundation.

Author information

Author notes

  1. These authors contributed equally to this work.

Authors and Affiliations

  1. College of Chemistry and Materials Science, Guangdong Provincial Key Laboratory of Functional Supramolecular Coordination Materials and Applications, Jinan University, Guangzhou, 510632, China

    Rucheng Zhao, Yusheng Wu, Yuequn Zhang, Jiabao Ling, Xinxin Liu, Jiaqi Xiang, Xiangchao Zeng & Tianfeng Chen

Authors
  1. Rucheng Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yusheng Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yuequn Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jiabao Ling
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xinxin Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jiaqi Xiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Xiangchao Zeng
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Tianfeng Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Xiangchao Zeng or Tianfeng Chen.

Ethics declarations

Conflict of interest The authors declare no conflict of interest.

Additional information

Supporting information The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

Supporting Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhao, R., Wu, Y., Zhang, Y. et al. Designing anticancer combretastatin A-4 analogues with aggregation-induced emission characteristics. Sci. China Chem. 65, 694–698 (2022). https://doi.org/10.1007/s11426-021-1197-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11426-021-1197-4

Keywords

Search

Navigation