Genistein is a phytoestrogen compound which possesses multiple biological activities such as anti-cancer, while its application is limited by poor pharmacokinetic properties. Structural modification is an effective approach to get genistein derivatives with better activities and approved pharmacokinetic properties. Based on previous research work, we synthesized two series of genistein derivatives bearing halogen substituents, and evaluated their inhibitory effects on the cancer cell lines MCF-7, MDA-MB-231, and MDA-MB-435. Among these derivatives, compound XI displayed the best inhibitory activity against MCF-7, MDA-MB-231 and MDA-MB-435 cell lines in vitro, which is worth further studies.
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References
F. Bray, J. Ferlay, I. Soerjomataram, et al., CA Cancer J. Clin., 68(6), 394 – 424 (2018).
K. Sak, Asian Pac. J. Cancer Prev., 18(9), 2309 – 2328 (2017).
S. Thota, D. A. Rodrigues, and E. J. Barreiro, Mini Rev. Med. Chem., 18(15), 1265 – 1269 (2018).
S. R. Lepri, R. C. Luiz, L. C. Zanelatto, et al., Cytotechnology, 65(2), 213 – 22 (2013).
A. Antosiak, K. Milowska, K. Maczynska, et al., Med. Chem. Res., 26(1), 64 – 73 (2017).
V. Mukund, D. Mukund, V. Sharma, et al., Crit. Rev. Oncol. Hematol., 119(13 – 22 (2017).
C. Spagnuolo, G. L. Russo, I. E. Orhan, et al., Adv. Nutr., 6(4), 408 – 19 (2015).
Y. Mizushina, K. Shiomi, I. Kuriyama, et al., Int. J. Oncol., 43(4), 1117 – 24 (2013).
C. K. Taylor, R. M. Levy, J. C. Elliott, et al., Nutr. Rev., 67(7), 398 – 415 (2009).
S. Poschner, A. Maier-Salamon, M. Zehl, et al., Front. Pharmacol., 8, 699 (2017).
D. G. Pons, J. Vilanova-Llompart, A. Gaya-Bover, et al., Int. J. Food Sci. Nutr., No. 2, 1 – 9 (2019).
M. Ono, K. Ejima, T. Higuchi, et al., Nutr. Cancer, 69(8), 1300 – 1307 (2017).
E. M. Shehata, Y. S. Elnaggar, S. Galal, et al., Int. J. Pharm., 511(2), 745 – 56 (2016).
Y. Ning, M. Xu, X. Cao, et al., Oncol. Rep., 38(2), 949 – 958 (2017).
P. Zhou, C. Wang, Z. Hu, et al., BMC Cancer, 17(1), 813 (2017).
F. Ardito, M. R. Pellegrino, D. Perrone, et al., Oncol. Targets Ther., 10, 5405 – 5415 (2017).
Z. Wang, X. Deng, S. Xiong, et al., Nat. Prod. Res., 32(24), 2900 – 2909 (2018).
Y. Guo, L. Shen, X. Yao, et al., Luminescence, 32(8), 1368 – 1384 (2017).
Y. Wei, Q. Zheng, G. Tang, et al., Med. Chem., 12(5), 441 – 7 (2016).
X. Qiang, Z. Sang, W. Yuan, et al., Eur. J. Med. Chem., 76, 314 – 331 (2014).
Acknowledgements
This research was supported by the National Natural Science Foundation of China (No. 81273537); the Key Project of Hunan Province Science and Technology Department (No.2016DK2001), the Key Project of Hengyang Science and Technology Department (No. 2017KJ166), the Key Disciplines of Hunan Province and Zhengxiang Scholar Program of the University of South China, Joint Funds of Hunan Province and Hengyang City (2017JJ4050), Hunan Provincial Natural Science Foundation of China(2018JJ3456), and the Project of Education Department of Hunan Province (17C1398).
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Ren, Y., Chen, H., Yao, X. et al. Design, Synthesis and Anticancer Evaluation of New 7-O-Alkylation Genistein Derivatives. Pharm Chem J 54, 924–931 (2020). https://doi.org/10.1007/s11094-020-02298-5
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DOI: https://doi.org/10.1007/s11094-020-02298-5