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Understanding the Selectivity of Genistein for Human Estrogen Receptor-β Using X-Ray Crystallography and Computational Methods
Open accessAbstract
We present X-ray crystallographic and molecular modeling studies of estrogen receptors-alpha and -beta complexed with the estrogen receptor-beta-selective phytoestrogen genistein, and coactivator-derived NR box peptides containing an LXXLL motif. We demonstrate that the ligand binding mode is essentially identical when genistein is bound to both isoforms, despite the considerably weaker affinity of this ligand for estrogen receptor-alpha. In addition, we examine subtle differences between binding site residues, providing an explanation for why genistein is modestly selective for the beta isoform. To this end, we also present the results of quantum chemical studies and thermodynamic arguments that yield insight to the nature of the interactions leading to estrogen receptor-beta selectivity. The importance of our analysis to structure-based drug design is discussed.
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Cites
Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions
Krishnan, R., Binkley, J. S., Seeger, R., & Pople, J. A. (1980) · The Journal of Chemical Physics · doi:10.1063/1.438955 · Cited by 17,772
Harris, H. A., Katzenellenbogen, J. A., & Katzenellenbogen, B. S. (2002) · Endocrinology · doi:10.1210/en.2002-220403 · Cited by 357
Cited by
Estrogen receptors: how do they signal and what are their targets
Heldring, N., Pike, A., Andersson, S., Matthews, J., Cheng, G., Hartman, J., Tujague, M., Ström, A., Treuter, E., Warner, M., et al. (2007) · Physiological Reviews · doi:10.1152/physrev.00026.2006 · Cited by 1,857
Estrogen receptor signaling mechanisms
(2019) · Advances in Protein Chemistry and Structural Biology · doi:10.1016/bs.apcsb.2019.01.001 · Cited by 988
The pros and cons of phytoestrogens
Patisaul, H. B., & Jefferson, W. (2010) · Frontiers in Neuroendocrinology · doi:10.1016/j.yfrne.2010.03.003 · Cited by 746
Shanle, E. K., & Xu, W. (2011) · Chemical Research in Toxicology · doi:10.1021/tx100231n · Cited by 522
Metadata
- Authors
- Manas, E. S., Xu, Z. B., Unwalla, R. J., & Somers, W. S.
- Venue
- Structure
- Publisher
- Elsevier BV
- Published
- 2004-12
- Volume
- 12
- Issue
- 12
- Pages
- 2197-2207
- ISSN
- 0969-2126 (ISSN-L)
- OpenAlex
- W2150232801
- Cited by
- 188
- References
- 2
- FWCI
- 4.04
- Type
- journal article
- Language
- en
- Open access
- bronze
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- Manas, E. S., Xu, Z. B., Unwalla, R. J., & Somers, W. S. (2004). Understanding the Selectivity of Genistein for Human Estrogen Receptor-β Using X-Ray Crystallography and Computational Methods. Structure. https://doi.org/10.1016/j.str.2004.09.015
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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