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Probing the human estrogen receptor-α binding requirements for phenolic mono- and di-hydroxyl compounds: a combined synthesis, binding and docking study.

Abstract：

:Various estrogen analogs were synthesized and tested for binding to human ERα using a fluorescence polarization displacement assay. Binding affinity and orientation were also predicted using docking calculations. Docking was able to accurately predict relative binding affinity and orientation for estradiol, but only if a tightly bound water molecule bridging Arg394/Glu353 is present. Di-hydroxyl compounds sometimes bind in two orientations, which are flipped in terms of relative positioning of their hydroxyl groups. Di-hydroxyl compounds were predicted to bind with their aliphatic hydroxyl group interacting with His524 in ERα. One nonsteroid-based dihdroxyl compound was 1000-fold specific for ERβ over ERα, and was also 25-fold specific for agonist ERβ versus antagonist activity. Docking predictions suggest this specificity may be due to interaction of the aliphatic hydroxyl with His475 in the agonist form of ERβ, versus with Thr299 in the antagonist form. But, the presence of this aliphatic hydroxyl is not required in all compounds, since mono-hydroxyl (phenolic) compounds bind ERα with high affinity, via hydroxyl hydrogen bonding interactions with the ERα Arg394/Glu353/water triad, and van der Waals interactions with the rest of the molecule.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

McCullough C,Neumann TS,Gone JR,He Z,Herrild C,Wondergem Nee Lukesh J,Pandey RK,Donaldson WA,Sem DS

doi

10.1016/j.bmc.2013.11.024

subject

Has Abstract

pub_date

2014-01-01 00:00:00

pages

303-10

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00955-3

journal_volume

22

pub_type

杂志文章

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