Design, Synthesis, and Anti-Breast Cancer Activity of Novel Fluorinated 7- O -Modified Genistein Derivatives

• Published in: Medicinal chemistry (Shp-sariqah, United Arab Emirates) Vol. 19; no. 1; p. 64
• Main Authors: Yang, Zhifang, Liu, Yi, Liu, Zhuo, Xu, Qinfang, Liu, Shun, Jiang, Kailin, Shi, Yuanlong, Xu, Wenyu, Yang, Zehua, Mi, Pengbing, Xiang, Yijun, Yao, Xu, Zheng, Xing
• Format: Journal Article
• Language: English
• Published: Netherlands 01.01.2023
• Subjects: Antineoplastic Agents; Breast Neoplasms - pathology; Cell Line; Cell Line, Tumor; Cell Proliferation; Drug Screening Assays, Antitumor; Female; Genistein - pharmacology; Genistein - therapeutic use; Humans; Molecular Structure; Tamoxifen - pharmacology; Tamoxifen - therapeutic use; fluorinated-genistein derivatives; baker-venkataraman reaction; genistein; MTT assay; structure-activity relationship; Anti-breast cancer activities
• ISSN: 1875-6638
• DOI: 10.2174/1573406418666220607140651

Genistein has been limited in clinical application due to its low bioavailability, extremely poor liposolubility, and fast glycosylation rate, though it possesses anti-breast cancer activity. Therefore, the discovery of novel genistein derivatives is an urgency. To enhance the anti-breast cancer activity of genistein, a series of novel fluorinated genistein derivatives were synthesized. Their in vitro antitumor activity was investigated by the MTT assay against three cancer cell lines, via, MDA-MB-231, MCF-7, and MDA-MB-435, respectively. Analogs 1d, 2b, and 3b showed remarkable anticancer activities compared to tamoxifen, a clinical anti-breast cancer drug on the market. The activities against breast cancer of genistein were enhanced by introducing the 7- alkoxyl group and fluorine atom into the B-ring. Therefore, these compounds may be potential candidates for treating breast cancer.