Here, a series of ursolic acid (UA) derivatives were identified as potential protein tyrosine phosphatase 1B (PTP1B) enzyme inhibitors. All of the tested compounds showed potent PTP1B inhibitory activity (47.01–67.89%). Compound 2d (67.89%) exhibited the highest activity of all the synthesized compounds, which showed higher activity than observed for the positive control UA (51.13%). Molecular docking simulation and analysis suggested that compound 2d has a good binding interaction with the active pocket.
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References
X. Y. Xia and J. Xiao, Molecules, 26, 6934 (2021).
M. Teimouri, H. Hosseini, Z. ArabSadeghabadi, R. Babaei-Khorzoughi, S. Gorgani-Firuzjaee, and R. Meshkani, J. Physiol. Biochem., 78, 307 (2022).
G. Liu, Curr. Med. Chem., 10, 1407 (2003).
C. S. Li, T. Y. Zhang, Q. S. Zhang, X. Liu, J. X. Zou, and X. Q. Bai, Chem. Nat. Compd., 58, 882 (2022).
S. Fontanay, M. Grare, J. Mayer, C. Finance, and R. E. Duval, J. Ethnopharmacol., 120, 272 (2008).
S. L. Ullevig, Q. Zhao, D. Zamora, and R. Asmis, Atherosclerosis, 219, 409 (2011).
W. Zhang, D. Hong, Y. Zhou, Y. Zhang, Q. Shen, J. Y. Li, L. H. Hu, and J. Li, Biochim. Biophys. Acta, 1760, 1505 (2006).
J. Wu, Z. H. Zhang, L. H. Zhang, X. J. Jin, J. Ma, and H. R. Piao, Bioorg. Med. Chem. Lett., 29, 853 (2019).
T. Y. Zhang, C. S. Li, L. T. Cao, X. Q. Bai, D. H. Zhao, and S. M. Sun, Mol. Divers., 26, 1129 (2022).
J. Eberhardt, D. Santos-Martins, A. F. Tillack, and S. Forli, J. Chem. Inf. Model., 61, 3891 (2021).
O. Trott and A. J. Olson, J. Comp. Chem., 31, 455 (2010).
Z. H. Huang, L. Q. Yin, L. P. Guan, Z. H. Li, and C. Tan, Bioorg. Med. Chem. Lett., 30, 127173 (2020).
J. J. Ramirez-Espinosa, M. Y. Rios, P. Paoli, V. Flores-Morales, G. Camici, V. de la Rosa-Lugo, S. Hidalgo-Figueroa, G. Navarrete-Vazquez, and S. Estrada-Soto, Eur. J. Med. Chem., 87, 316 (2014).
W. Zhang, D. Hong, Y. Y. Zhou, Y. N. Zhang, Q. Shen, J. Y. Li, L. H. Hu, and J. Li, Biochim. Biophys. Acta, 1760, 1505 (2006).
Acknowledgment
This work was supported by the Natural Science Foundation of Jilin Province (No. YDZJ202201ZYTS277) and the Jilin Province Students′ Program for Innovation and Entrepreneurship Training (No. S202213706024).
In addition, Xueqian Bai and Zhe Liu contributed equally to this work.
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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2023, pp. 724–726.
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Bai, X., Liu, Z., Gao, J. et al. Discovery of Ursolic Acid Derivatives as Inhibitors of Protein Tyrosine Phosphatase 1B. Chem Nat Compd 59, 859–861 (2023). https://doi.org/10.1007/s10600-023-04135-z
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DOI: https://doi.org/10.1007/s10600-023-04135-z