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Steroids. 2015 Apr;96:50-62. doi: 10.1016/j.steroids.2015.01.013. Epub 2015 Jan 29.

Synthesis and evaluation of 2-halogenated-1,1-bis(4-hydroxyphenyl)-2-(3-hydroxyphenyl)-ethylenes as potential estrogen receptor-targeted radiodiagnostic and radiotherapeutic agents.

Author information

1
Department of Chemistry and Chemical Biology, Northeastern University, 360 Huntington Avenue, Boston, MA 02115, United States.
2
The Ben May Institute for Cancer Research, The University of Chicago, 5846 S. Maryland Avenue, Chicago, IL 60637, United States.

Abstract

A series of three 1,1-bis(4-hydroxyphenyl)-2-(3-hydroxyphenyl)-ethylene derivatives was prepared and evaluated as potential estrogen receptor imaging agents. The compounds display high binding affinity compared to estradiol, with the 2-iodo and 2-bromo-derivatives expressing higher affinity than the parent 2-nonhalogenated derivative. Evaluation in immature female rats also indicate that the compounds were all full estrogenic agonists with potencies in the same order of activity (I∼Br>H). Computational analysis of the interactions between the ligands and ERα-LBD demonstrated positive contribution of halide to binding properties. In preparation for studies using the radiohalogenated analogs, the corresponding protected 2-(tributylstannyl) derivative was prepared and converted to the corresponding 2-iodo-product.

KEYWORDS:

Auger; Nonsteroidal estrogens; Relative binding affinity; Synthesis; Uterotrophic growth

PMID:
25637676
DOI:
10.1016/j.steroids.2015.01.013
[Indexed for MEDLINE]

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