Synthesis, receptor binding and target-tissue uptake of carbon-11-labeled carbamate derivatives of estradiol and hexestrol.
Carbon-11-labeled estradiol and hexestrol derivatives were prepared via the reaction of [11C]ethylchloroformate with the 2- and 4-amino derivatives of estradiol, the 3'-amino derivatives of hexestrol, and the 1-aminophenoxy derivatives of hexestrol and 1-norhexestrol. The corresponding nonradioactive carbamates were prepared for chemical characterization and in vitro receptor binding assays. The positions of the substituents on the parent molecules were selected with a view to minimize interference with the receptor binding process. In spite of this, affinity for the estrogen receptor was strongly impaired for all carbamate derivatives. Likewise, in vivo, the [11C]carbamate analogs failed to localize in receptor rich tissue via an estrogen receptor mediated process.
Ali
H
H
MRC Group in the Radiation Sciences, Faculty of Medicine, University of Sherbrooke, Quebec, Canada.
Rousseau
J
J
Diksic
M
M
van Lier
J E
JE
D000588:Amines / Q000138:chemical synthesis / Q000378:metabolism; D000818:Animals; D001667:Binding, Competitive; D002219:Carbamates / Q000138:chemical synthesis* / Q000378:metabolism; D002250:Carbon Radioisotopes; D004958:Estradiol / Q000031:analogs & derivatives*; D005260:Female; D006589:Hexestrol / Q000031:analogs & derivatives*; D051381:Rats; D011919:Rats, Inbred Strains; D011960:Receptors, Estrogen / Q000378:metabolism*; D014599:Uterus / Q000378:metabolism / Q000648:ultrastructure
D000588:Amines; D002219:Carbamates; D002250:Carbon Radioisotopes; D011960:Receptors, Estrogen; D006589:Hexestrol; D004958:Estradiol