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2Q6J

Crystal Structure of Estrogen Receptor alpha Complexed to a B-N Substituted Ligand

Summary for 2Q6J
Entry DOI10.2210/pdb2q6j/pdb
DescriptorEstrogen receptor, GRIP peptide, 4-[(DIMESITYLBORYL)(2,2,2-TRIFLUOROETHYL)AMINO]PHENOL, ... (4 entities in total)
Functional Keywordsprotein-ligand complex, transcription
Biological sourceHomo sapiens (human)
More
Cellular locationIsoform 1: Nucleus . Isoform 3: Nucleus. Nucleus: P03372
Nucleus : Q8BN74
Total number of polymer chains4
Total formula weight62811.59
Authors
Zhou, H.,Nettles, K.W.,Bruning, J.B.,Kim, Y.,Joachimiak, A.,Sharma, S.,Carlson, K.E.,Stossi, F.,Katzenellenbogen, B.S.,Greene, G.L.,Katzenellenbogen, J.A. (deposition date: 2007-06-05, release date: 2007-06-26, Last modification date: 2023-08-30)
Primary citationZhou, H.-B.,Nettles, K.W.,Bruning, J.B.,Kim, Y.,Joachimiak, A.,Sharma, S.,Carlson, K.E.,Stossi, F.,Katzenellenbogen, B.S.,Greene, G.L.,Katzenellenbogen, J.A.
Elemental isomerism: a boron-nitrogen surrogate for a carbon-carbon double bond increases the chemical diversity of estrogen receptor ligands
Chem.Biol., 14:659-669, 2007
Cited by
PubMed Abstract: To increase the chemical diversity of bioactive molecules by incorporating unusual elements, we have examined the replacement of a C=C double bond with the isoelectronic, isostructural B-N bond in the context of nonsteroidal estrogen receptor (ER) ligands. While the B-N bond was hydrolytically labile in the unhindered cyclofenil system, the more hindered anilino dimesitylboranes, analogs of triarylethylene estrogens, were easily prepared, hydrolytically stable, and demonstrated substantial affinity for ERs. X-ray analysis of one ERalpha-ligand complex revealed steric clashes with the para methyl groups distorting the receptor; removal of these groups resulted in an increase in affinity, potency, and transcriptional efficacy. These studies define the structural determinants of stability and cellular bioactivity of a B-N for C=C substitution in nonsteroidal estrogens and provide a framework for further exploration of "elemental isomerism" for diversification of drug-like molecules.
PubMed: 17584613
DOI: 10.1016/j.chembiol.2007.04.009
PDB entries with the same primary citation
Experimental method
X-RAY DIFFRACTION (2.7 Å)
Structure validation

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