77316-86-0Relevant academic research and scientific papers
Effects of 7-O substitutions on estrogenic and anti-estrogenic activities of daidzein analogues in MCF-7 breast cancer cells
Jiang, Quan,Payton-Stewart, Florastina,Elliott, Steven,Driver, Jennifer,Rhodes, Lyndsay V.,Zhang, Qiang,Zheng, Shilong,Bhatnagar, Deepak,Boue, Stephen M.,Collins-Burow, Bridgette M.,Sridhar, Jayalakshmi,Stevens, Cheryl,McLachlan, John A.,Wiese, Thomas E.,Burow, Matthew E.,Wang, Guangdi
, p. 6153 - 6163 (2010)
Daidzein (1) is a natural estrogenic isoflavone. We report here that 1 can be transformed into anti-estrogenic ligands by simple alkyl substitutions of the 7-hydroxyl hydrogen. To test the effect of such structural modifications on the hormonal activities of the resulting compounds, a series of daidzein analogues have been designed and synthesized. When MCF-7 cells were treated with the analogues, those resulting from hydrogen substitution by isopropyl (3d), isobutyl (3f), cyclopentyl (3g), and pyrano- (2) inhibited cell proliferation, estrogen-induced transcriptional activity, and estrogen receptor (ER) regulated progesterone receptor (PgR) gene expression. However, methyl (3a) and ethyl (3b) substitutions of the hydroxyl proton only led to moderate reduction of the estrogenic activities. These results demonstrated the structural requirements for the transformation of daidzein from an ER agonist to an antagonist. The most effective analogue, 2, was found to reduce in vivo estrogen stimulated MCF-7 cell tumorigenesis using a xenograft mouse model.
Daidzein analogs as treatment for cancer
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Page/Page column 6, (2017/08/26)
Provided are compositions for treatment of cancers, including breast cancer, comprising at least one novel daidzein analog, as well as methods of using the same for preventing or treating cancer or tumor growth.
Design, synthesis, and osteogenic activity of daidzein analogs on human mesenchymal stem cells
Strong, Amy L.,Jiang, Quan,Zhang, Qiang,Zheng, Shilong,Boue, Stephen M.,Elliott, Steven,Burow, Matthew E.,Bunnell, Bruce A.,Wang, Guangdi
, p. 143 - 148 (2014/03/21)
Osteoporosis is caused by an overstimulation of osteoclast activity and the destruction of the bone extracellular matrix. Without the normal architecture, osteoblast cells are unable to rebuild phenotypically normal bone. Hormone replacement therapy with estrogen has been effective in increasing osteoblast activity but also has resulted in the increased incidence of breast and uterine cancer. In this study we designed and synthesized a series of daidzein analogs to investigate their osteogenic induction potentials. Human bone marrow derived mesenchymal stem cells (MSCs) from three different donors were treated with daidzein analogs and demonstrated enhanced osteogenesis when compared to daidzein treatment. The enhanced osteogenic potential of these daidzein analogs resulted in increased osterix (Sp7), alkaline phosphatase (ALP), osteopontin (OPN), and insulin-like growth factor 1 (IGF-1), which are osteogenic transcription factors that regulate the maturation of osteogenic progenitor cells into mature osteoblast cells.
