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Synthesis and Antitumor Activity Study of Novel Formononetin Derivatives

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Abstract

Objective: In order to enrich the library of anti-tumor small molecule compounds, 8 compounds, with highly effective antitumor, have been designed and synthesized. Methods: MTT assay was used to detect the antiproliferation activity of 8 compounds on four human tumor cell lines (HCT-116, HeLa, DU-145, and SGC-7901). Cell cycle experiment, cell migration experiment, cell clone experiment and cell apoptosis experiment were used to study the antitumor mechanism of compound (V). Results: The compound (V) showed the strongest antitumor activity against the above four human tumor cells, especially against HCT-116 cells, with an IC50 value of 4.21 ± 0.39 μM, which was significantly lower than that of cyclophosphamide. The results of a variety of cell experiments showed that the compound (V) significant antitumor activity, such as inhibiting the proliferation and migration of HCT-116 cells, arresting HCT-116 cells at S phase, and inducing apoptosis in HCT-116 cells. Discussion: Slight changes in the R group can cause significant changes in the in vitro antitumor activity, and when R is a strong electron donor group of ethyl L-tyrosinate, compound (V) exhibits the strongest inhibitory effect, with an IC50 value of 4.21 ± 0.39 μM on HCT-116 cells. Conclusions: 8 compounds showed significant anti-tumor activity, and the compound (V), with a strong electron donor group of ethyl L-tyrosinate, showed the most significant effect, and the antiproliferation and antimigration effects of compound (V) was further investigated.

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DATA AVAILABILITY

The data that support the findings of this study are available from the corresponding author upon reasonable request.

REFERENCES

  1. Ghaly, G., Tallima, H., Dabbish, E., Badr El-Din, N., Abd El-Rahman, M.K., Ibrahim, M.A.A., and Shoeib, T., Molecules, 2023, vol. 3, p. 1148. https://doi.org/10.3390/molecules28031148

    Article  CAS  Google Scholar 

  2. Lafta, H.A., AbdulHussein, A.H., Al-Shalah, S.A.J., Alnassar, Y.S., Mohammed, N.M., Akram, S.M., Qasim, M.T., and Najafi, M., Curr. Top Med. Chem., 2023, vol. 12, pp. 1104–1122. https://doi.org/10.2174/1568026623666230201145909

    Article  CAS  Google Scholar 

  3. Farhan, M., El-Oirdi, M., Aatif, M., Nahvi, I., Muteeb, G., Alam, M.W., Molecules, 2023, vol. 7, p. 2925. https://doi.org/10.3390/molecules28072925

    Article  CAS  Google Scholar 

  4. Al-Shami, A.S., Essawy, A.E., and Elkader, H.A.E.A., Phytother Res., 2023, vol. 6, pp. 2693–2737. https://doi.org/10.1002/ptr.7870

    Article  CAS  Google Scholar 

  5. Agarwal, A., Wahajuddin, M., Chaturvedi, S., Singh, S.K., Rashid, M., Garg, R., Chauhan, D., Sultana, N., and Gayen, J.R., Curr. Drug Deliv., 2023, vol. 24, pp. 261–270. https://doi.org/10.2174/1567201820666230124114906

    Article  CAS  Google Scholar 

  6. Lu, X.Q., Qin, S., and Li, J., Molecules, 2023, vol. 13, p. 5039. https://doi.org/10.3390/molecules28135039

    Article  CAS  Google Scholar 

  7. Zhou, H., Wang, P., Qin, X., Zhang, X., Lai, K.P., and Chen, J., Food Funct., 2023, vol. 12, pp. 5787–5804. https://doi.org/10.1039/d2fo03962a

    Article  CAS  Google Scholar 

  8. Zhang, L.F., Zhang, X.Y., Wang, A.C., Feng, Y.J., Qi, X.M., Zhang, Y.L., Li, Q.F., Qiao, Y.B., and Li, Q.S., Toxicol. Appl. Pharmacol., 2023, vol. 472, p. 116571. https://doi.org/10.1016/j.taap.2023.116571

    Article  CAS  PubMed  Google Scholar 

  9. Bhardwaj, V.K. and Purohit, R., Carbohydr. Polym., 2023, vol. 310, p. 120729. https://doi.org/10.1016/j.carbpol.2023.120729

    Article  CAS  PubMed  Google Scholar 

  10. Yang, K., Jin, M.J., Quan, Z.S., and Piao, H.R., Molecules, 2019, vol. 5, p. 884. https://doi.org/10.3390/molecules24050884

    Article  CAS  Google Scholar 

  11. Zhao, W., Zheng, X.D., Tang, P.Y., Li, H.M., Liu, X., Zhong, J.J., and Tang, Y.J., Med. Res. Rev., 2023, vol. 14, pp. 1778–1808. https://doi.org/10.1002/med.21963

    Article  CAS  Google Scholar 

  12. Yang, C., Li, D., Ko, C.N., Wang, K., and Wang, H., Front Immunol., 2023, vol. 14, p. 1133050. https://doi.org/10.3389/fimmu.2023.1133050

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. Li, J., Li, F., and Jin, D., Am. J. Chin. Med., 2023, vol. 4, pp. 883–908. https://doi.org/10.1142/S0192415X23500416

    Article  Google Scholar 

  14. Amini, P., Moazamiyanfar, R., Dakkali, M.S., Khani, A., Jafarzadeh, E., Mouludi, K., Khodamoradi, E., Johari, R., Taeb, S., and Najafi, M., Curr. Top Med. Chem., 2023, vol. 8, pp. 629–648. https://doi.org/10.2174/1568026623666221014152759

    Article  CAS  Google Scholar 

  15. Zhou, X., Li, Y., Yang, C., Chen, D., Wang, T., Liu, T., Yan, W., Su, Z., Peng, B., and Ren, X., Life Sci., 2023, vol. 327, p. 121698. https://doi.org/10.1016/j.lfs.2023.121698

    Article  CAS  PubMed  Google Scholar 

  16. Hu, Y., Zhai, W., Tan, D., Chen, H., Zhang, G., Tan, X., Zheng, Y., Gao, W., Wei, Y., Wu, J., and Yang, X., Front Pharmacol., 2023, vol. 14, p. 1111912. https://doi.org/10.3389/fphar.2023.1111912

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Chen, L., Xing, D., Guo, L.R., Jin, J., and Li, S., Clin Lab., 2023, vol. 3. https://doi.org/10.7754/Clin.Lab.2022.220403

  18. Han, N.R., Park, H.J., Ko, S.G., and Moon, P.D., Nutrients, 2023, vol. 12, p. 2790. https://doi.org/10.3390/nu15122790

    Article  CAS  Google Scholar 

  19. Meng, H., Li, J., Sun, H., Lin, Y., Xu, H., and Zhang, N., Drug Dev. Res., 2023, vol. 8, pp. 1325–1334. https://doi.org/10.1002/ddr.22092

    Article  CAS  Google Scholar 

  20. Chen, Z., He, S., Lian, S., Shen, Y., Jiang, W., Zhou, L., Zhou, L., Zhang, X., Biosci. Rep., 2023, vol. 3, p. 20222429. https://doi.org/10.1042/BSR20222429

    Article  Google Scholar 

  21. Zhang, L., Liu, Y., Lei, X., Liu, X., Sun, H., and Liu, S., Cell Biol. Int., 2023, vol. 15, pp. 1600–1613. https://doi.org/10.1002/cbin.12055

    Article  CAS  Google Scholar 

  22. Matsumoto, Y., Fukui, T., Horitani, S., Tanimura, Y., Suzuki, R., Tomiyama, T., Honzawa, Y., Tahara, T., Okazaki, K., and Naganuma, M., Int. J. Mol. Sci., 2023, vol. 14, p. 11697. https://doi.org/10.3390/ijms241411697

    Article  CAS  Google Scholar 

  23. Li, J., Dong, T., Wu, Z., Zhu, D., and Gu, H., Cell Death Discov., 2023, vol. 1, p. 103. https://doi.org/10.1038/s41420-023-01403-3

    Article  Google Scholar 

  24. Xu, L., Che, S., Chen, H., Liu, Q., Shi, J., Jin, J., and Hou, Y., J. Cell Biochem., 2023, vol. 2, pp. 1145–1154. https://doi.org/10.1002/jcb.30437

    Article  CAS  Google Scholar 

  25. Zhang, W., Zhuang, S., Guan, H., Li, F., Zou, H., and Li, D., J. Biomol. Struct. Dyn., 2023, vol. 15, pp. 1–13. https://doi.org/10.1080/07391102.2023.2212066

    Article  CAS  Google Scholar 

  26. Lan, Y., Yang, Y., Das, A., Bhattacharya, B., and Roy, S., Indian J. Pharmacol., 2023, vol. 2, pp. 97–107. https://doi.org/10.4103/ijp.ijp_168_22

    Article  CAS  Google Scholar 

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Funding

This work was financially supported by Guangxi Collaborative Innovation Center of Modern Sericulture and Silk (Grant no. 2022GXCSSC10) and High-level Talents Scientific Research Startup Fund of Hechi University (Grant no. 2019GCC008).

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Correspondence to Liwei Pan.

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Luo, Z., Pan, L., Yin, X. et al. Synthesis and Antitumor Activity Study of Novel Formononetin Derivatives. Russ J Bioorg Chem 50, 313–327 (2024). https://doi.org/10.1134/S1068162024020110

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