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High binding affinity for estrogen receptor and the appearance of estrogenic activity require a phenolic ring and an appropriate hydrophobic group adjacent to the phenolic ring.
These analogues were tested for their antiproliferative action on MCF-7 breast cancer cell lines as well as their binding affinity for estrogen receptor (ER) ER-α and ER-β receptors.
Isoflavones, such as genistein, apigenin, and kaempferol, have stronger binding affinity for estrogen receptor (ER) β than for ERα (Kuiper et al. 1998).
Due in part to its high binding affinity for estrogen receptor (ER) [ 13- 15], EE2 affects the HPG axis in FHM at environmentally relevant concentrations.
Although isoflavones have a weaker binding affinity for estrogen receptors than endogenous estrogens, circulating levels of isoflavones following consumption of soy will exceed endogenous estrogen levels by several orders of magnitude (Axelson et al., 1984; Cassidy et al., 1994; Adlercreutz and Mazur, 1997).
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A number of in vitro findings suggest interactions with other receptor systems involved in metabolic regulation (Wetherill et al. 2007), including anti-androgen effects at low concentrations and high binding affinity for estrogen-related receptor-γ (Takayanagi et al. 2006).
A study of the inhibitory potency with four other 17β-HSDs revealed they were selective, since they do not inhibit reductive types 1, 5 and 7, nor oxidative type 2. Interestingly, they did not show any binding affinity for steroid receptors (androgen, estrogen, glucocorticoid and progestin).
Equol is reported to bind to both estrogen receptors ERα and ERβ, with a higher binding affinity for ERβ, which has been implicated in the inhibition of proliferation and induction of apoptosis in breast cancer cells [ 8, 11- 13].
Using competitive ligand binding assays, it was found that the magnitude of vitellogenin/choriogenin induction by different estrogenic ligands correlated positively with preferential binding affinity for medaka ERβ subtypes, which are highly expressed in male medaka liver prior to estrogen exposure.
Tamoxifen, an antagonist of estrogen receptor (ER), has a high binding affinity for the microsomal antiestrogen binding site (AEBS), a hetero-oligomeric complex involved in cholesterol metabolism.
c Targets detected with no significant binding affinity for CIS22a.
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