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Design, Synthesis and Study of a Novel Antitumor Active Sinomeninylethylenesulfamide

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Abstract

We developed an antitumor compound through a clever one-pot design. Firstly, one end of ethylenediamine was connected to the carbonyl group of sinomenine, then the sulfonamide group was reintroduced and a new sinomeninylethylenesulfamide compound was synthesized. The cell viability of HeLa, HCT-116, McF-7 and L-02 cell lines was determined by sinocine, sinomeninylethylenesulfamide, 5-F and sinomeninylethylenesulfamide+5-F, respectively. The results showed that sinocine sulfa-5-F had better inhibitory effect on HeLa and HCT-116 cell lines, 23.16 ± 4.52 and 21.93 ± 1.07, respectively. Finally, the high binding energy of sinomeninylethylenesulfamide compound and target protein was predicted by molecular simulation docking.

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REFERENCES

  1. Sebastien, R., Sinaeda, A., Aymeric, N., and Gilles, P.V.W., Biochem. Pharmacol., 2018, vol. 153, pp. 24–34.

    Article  Google Scholar 

  2. Muraro, D.S., Abrantes, F.L., Pozebon, H., Gabriel, M., and Marco, E., Aust. J. Crop Sci., 2021, vol. 15, pp. 9–15. https://doi.org/10.21475/ajcs.21.15.01.1942

    Article  CAS  Google Scholar 

  3. Moatasem, A.-S., Syakirah, S., and Rashid, A.R., Eur. Asian J. Biol. Sci., 2020, vol. 14, pp. 3607–3616.

    Google Scholar 

  4. Yang, Z.S., Sun, A.P., Zhao, X.S., Chen, Z.G., and Tian, Z.W., Int. J. Biol. Macromol., 2020, vol. 151, pp. 878–884. https://doi.org/10.1016/j.ijbiomac.2020.02.165

    Article  CAS  PubMed  Google Scholar 

  5. Rana, R., Sharma, R., and Kumar, A., Infect. Disord.: Drug Targ., 2019, vol. 19, pp. 224–237. https://doi.org/10.2174/1871526518666180806123230

    Article  CAS  Google Scholar 

  6. Fu, K., Wang, C., Ma, C., Zhou, H. Li, Y.X., Front. Pharmacol., 2021, vol. 12, p. 771459.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Yang, Z.S., Sun, A.P., Zhao, T.S., Chen, Z.G., Xie, Y.F., Int. J. Biol. Macromol., 2020, vol. 15, pp. 878–884.

    Article  CAS  Google Scholar 

  8. Flanz, J. and Smith, A., Cancer J., 2009, vol. 15, pp. 292–297.

    Article  PubMed  Google Scholar 

  9. Hui, Y.Z., Int. Conf. Tradit. Chin. Med.: Sci., Regul., Globalization, 2001, vol. 2000, pp. 1–12.

  10. Geng, P.B., Xu, X.H., and Gao, Z., J. Oleo Sci., 2021, vol. 70, pp. 1815–1828. https://doi.org/10.5650/jos.ess21255

    Article  CAS  PubMed  Google Scholar 

  11. Yi, L., Ke, J.Y., Liu, J.Y., Lai, H.L., Liu, L., and Wang, P.X., J. Leukocyte Biol., 2021, vol. 110, pp. 1113–1120. https://doi.org/10.1002/jlb.3ma0121-024rrrr

    Article  CAS  PubMed  Google Scholar 

  12. Chen, X., Li, D., Zhang, H., Duan, Y., and Huang, Y., Int. J. Pharm., 2021, vol. 606, p. 120894. https://doi.org/10.1016/j.ijpharm.2021.120894

    Article  CAS  PubMed  Google Scholar 

  13. Liao, K., Su, X., Lei, K., Liu, Z., and Wang, M.M., Biomed. Pharmacother., 2021, vol. 135, p. 111195. https://doi.org/10.1016/j.biopha.2020.111195

    Article  CAS  PubMed  Google Scholar 

  14. Shu, Z., Cao, Y., Tao, Y., and Gui, S., Drug Delivery, 2020, vol. 27, pp. 642–651. https://doi.org/10.1080/10717544.2020.1754524

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Wang, Y., Yu, C., and Zhang, H., Phytother. Res., 2019, vol. 33, pp. 1827–1836. https://doi.org/10.1002/ptr.6372

    Article  CAS  PubMed  Google Scholar 

  16. Zhang, Y.-S., Han, J.-Y., Iqbal, O., and Liang, A.-H., Int. J. Mol. Sci., 2019, vol. 20, pp. 70/1–70/15. https://doi.org/10.3390/ijms20010070

  17. Zhang, Y., Zou, B., Tan, Y., Su, J., Liu, L., and Li, X., Pharmacol. Res., 2019, vol. 142, pp. 140–150. https://doi.org/10.1016/j.phrs.2019.02.015

    Article  CAS  PubMed  Google Scholar 

  18. Yue, M.F., Zhang, X.Y., Dou, Y.N., Wei, Z.F., and Dai, Y., Front. Pharmacol., 2018, vol. 9, pp. 675/1–675/13. https://doi.org/10.3389/fphar.2018.00675

  19. Xu, W., Wang, X., Tu, Y., Sugiyama K., Yamada, H., and Hirano, T., Phytother. Res., 2019, vol. 33, pp. 187–196. https://doi.org/10.1002/ptr.6215

    Article  CAS  PubMed  Google Scholar 

  20. Qian, X., Zhao, Z., Shang, W., and Cai, H., Mol. Med. Rep., 2018, vol. 18, pp. 49–58. https://doi.org/10.3892/mmr.2018.8959

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Wang, Y., Jin, Y., Yun, X., and Xia, Y., Life Sci., 2018, vol. 209, pp. 228–235. https://doi.org/10.1016/j.lfs.2018.08.012

    Article  CAS  PubMed  Google Scholar 

  22. Zhao, F., Wang, Y., and Jin, G.F., Arabian J. Chem., 2021, vol. 14, p. 103395. https://doi.org/10.1016/j.arabjc.2021.103395

    Article  CAS  Google Scholar 

  23. Baskan, C., Erturk, A.G., Aydin, B., and Siriken, B., Bioorg. Chem., 2022, vol. 119, p. 105517. https://doi.org/10.1016/j.bioorg.2021.105517

    Article  CAS  PubMed  Google Scholar 

  24. Watson, D.J., Laing, L., Gibhard, L., and Wiesner, L., Antimicrob. Agent Chemother., 2021, vol. 65, p. e00990. https://doi.org/10.1128/aac.00990-21

    Article  CAS  Google Scholar 

  25. Shaki, H. and Color, F., Fibers Polym., 2020, vol. 21, pp. 2530–2538. https://doi.org/10.1007/s12221-020-1148-2

    Article  CAS  Google Scholar 

  26. Suthagar, K., Jiao, W., Munier-Lehmann, H., and Fairbanks, A.J., Carbohyd. Res., 2018, vol. 457, pp. 32–40. https://doi.org/10.1016/j.carres.2018.01.001

    Article  CAS  Google Scholar 

  27. Becheker, I., Berredjem, H., Boufas, W., and Berredjem, M., Int. J. Pharm. Sci. Rev. Res., 2016, vol. 39, pp. 125–133.

    CAS  Google Scholar 

  28. Suthagar, K. and Fairbanks, A.J., Org. Biomol. Chem., 2016, vol. 14, pp. 1748–1754. https://doi.org/10.1039/C5OB02317C

    Article  CAS  PubMed  Google Scholar 

  29. Bhatt, N., Vyas, K., Joshi, K., and Nimavat, K., Asian J. Biochem. Pharm. Res., 2011, vol. 1, pp. 464–469.

    CAS  Google Scholar 

  30. Gao, X., Sun, B., Hou, Y., Li, D., and Hua, H., J. Enzyme Inhib. Med. Chem., 2022, vol. 37, pp. 1870–1883.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. Zhu, Z., Zhou, H., Chen, F., Hu, Q., and Wang, T., ChemMedChem., 2022, Ahead of Print.

  32. Wei, C.-J., Xu, F., Shi, M.-J., Hu, J.-W., Wang, J.-J., Zhen, B., Wang, J.-H., and Du, G.-H., J. Asian Nat. Prod. Res., 2017, vol. 20, pp. 277–291.

    Article  PubMed  Google Scholar 

  33. Yukio, H., Hiroshi, I., Kunihiko, N., Koichi, T., and Hideji, I., J. Chem. Soc., Chem. Comm., 1994, vol. 23, pp. 2707–2708.

    Google Scholar 

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Funding

This research reported in this publication was supported by the scientific research foundation of Jiangsu University (Grant no. 17JDG002).

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Correspondence to T. Jin.

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The authors declare that they have no conflicts of interest.

This article does not contain any studies involving animals or human participants performed by any of the authors.

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Yue, H., Jin, T., Shao, S. et al. Design, Synthesis and Study of a Novel Antitumor Active Sinomeninylethylenesulfamide. Russ J Bioorg Chem 48 (Suppl 1), S96–S100 (2022). https://doi.org/10.1134/S1068162023010302

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