Synthesis, receptor binding, and target-tissue uptake of carbon-11 labeled carbamate derivatives of estradiol and hexestrol

The reaction of ethyl chloroformate with amino compounds has been evaluated as a simple route to carbon-11 labeling of steroid hormone-receptor-based imaging agents. Both a 17 beta-amino analogue of estradiol and an aminoethyl derivative of the nonsteroidal estrogen hexestrol with potential affinity...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1984-04, Vol.27 (4), p.509-513
Main Authors: Ouellet, Rene, Rousseau, Jacques, Brasseur, Nicole, Van Lier, Johan E, Diksic, Mirko, Westera, Gerrit
Format: Article
Language:English
Subjects:
Animals
Carbamates - chemical synthesis
Carbamates - metabolism
Carbon Isotopes
Cattle
Chemistry
Cytosol - metabolism
Estradiol - metabolism
Exact sciences and technology
Female
Hexestrol - analogs & derivatives
Hexestrol - chemical synthesis
Hexestrol - metabolism
Indicators and Reagents
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Rats
Rats, Inbred F344
Receptors, Estradiol
Receptors, Estrogen - metabolism
Structure-Activity Relationship
Tissue Distribution
Uterus - metabolism
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Summary:The reaction of ethyl chloroformate with amino compounds has been evaluated as a simple route to carbon-11 labeling of steroid hormone-receptor-based imaging agents. Both a 17 beta-amino analogue of estradiol and an aminoethyl derivative of the nonsteroidal estrogen hexestrol with potential affinity for the estrogen receptor were studied. The unlabeled carbamate derivatives of the amino estrogens were prepared by standard methods, and the 11C-labeled analogues were synthesized from [11C]ethyl chloroformate, generated by purging ethanol with [11C]phosgene. Both carbamates showed weak in vitro binding affinity for the estrogen receptor, and only the 11C-labeled hexestrol exhibited a small but significant estrogen-responsive uterus uptake in immature rats.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00370a013