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Structure Database (LMSD)

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Common Name

Daidzein

Systematic Name

4',7-Dihydroxyisoflavone

Synonyms

7-Hydroxy-3-(4-hydroxyphenyl)chromen-4-one
Daidzeol
Isoaurostatin

LM ID

LMPK12050038

Formula

C₁₅H₁₀O₄

Exact Mass

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254.05791

Status

Curated

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Classification

Biological Context

Daidzein is an isoflavone phytoestrogenic compound that has been found in soybeans and other legumes.¹ It binds to estrogen receptor β (ERβ; Ki = 2.8 µM) but not ERα at concentrations up to 1 mM.² It is estrogenic in vitro, increasing gene transcription mediated by the estrogen response element (ERE) in a reporter assay in an ERβ-dependent manner (EC50 = 2.8 µM for MCF-7 cells expressing ERβ).¹ Daidzein is an inhibitor of carbonic anhydrase (CA) that is selective for carbonic CAVII and CAXII (Kis = 4.2 and 56 nM, respectively) over CAI, II, and IV (Kis = >10,000, >10,000, and 718.7 nM, respectively).³ It reduces tumor growth in a PC3 prostate cancer mouse orthotopic model when administered at a dose of 50 mg/kg per day and potentiates the effects of radiation therapy.⁴

This information has been provided by Cayman Chemical

References

1. Zhao, L., and Brinton, R.D. Structure-based virtual screening for plant-based ERβ-selective ligands as potential preventative therapy against age-related neurodegenerative diseases. J. Med. Chem. 48(10), 3463-3466 (2005).

2. Harris, D.M., Besselink, E., Henning, S.M., et al. Phytoestrogens induce differential estrogen receptor alpha- or beta-mediated responses in transfected breast cancer cells. Exp. Biol. Med. (Maywood) 230(8), 558-568 (2005).

3. Karioti, A., Ceruso, M., Carta, F., et al. New natural product carbonic anhydrase inhibitors incorporating phenol moieties. Bioorg. Med. Chem. 23(22), 7219-7225 (2015).

4. Singh-Gupta, V., Zhang, H., Yunker, C.K., et al. Daidzein effect on hormone refractory prostate cancer in vitro and in vivo compared to genistein and soy extract: Potentiation of radiotherapy. Pharm. Res. 27(6), 1115-1127 (2010).