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Title: Radiobrominated triphenylethylenes as estrogen receptor binding radiopharmaceuticals

Abstract

Estrogen receptor binding radiopharmaceuticals have potential for use in the diagnosis and treatment of cancers of the female reproductive system. Tamoxifen is an antiestrogen derived from the triphenylethylene skeleton which is used in the treatment of mammary carcinoma. Hydroxytamoxifen is a metabolite of tamoxifen which binds tightly to the estrogen receptor. Two triphenylethylene derivatives based on the structure of hydroxytamoxifen have been prepared: 1-bromo-1-phenyl-2- (2-dimethylamino)-4-ethoxyphenyl -2-(4-hydroxyphenyl) ethene (1) where the ethyl group of hydroxytamoxifen has been replaced by a bromine, and 1-bromo-1-phenyl-2,2-(4-hydroxyphenyl) ethene (2) with a similar substitution and also lacking the aminoethoxy side chain believed to confer antiestrogenicity. Both 1 and 2 bind strongly to the estrogen receptor. 2 has been labeled with the Auger electron emitting nuclide Br-80m in moderate yields in high specific activity using either N-bromosuccinimide or N-bromophthalimide and shows promise as a potential radiotherapy agent.

Authors:
; ; ;
Publication Date:
Research Org.:
Michael Reese Hospital and Medical Center, The Univ. of Chicago Medical Center, Chicago, IL
OSTI Identifier:
7030645
Report Number(s):
CONF-850611-
Journal ID: CODEN: JNMEA; TRN: 87-010789
Resource Type:
Conference
Journal Name:
J. Nucl. Med.; (United States)
Additional Journal Information:
Journal Volume: 26:5; Conference: 32. annual meeting of the Society of Nuclear Medicine, Houston, TX, USA, 2 Jun 1985
Country of Publication:
United States
Language:
English
Subject:
62 RADIOLOGY AND NUCLEAR MEDICINE; 38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY; BROMINE 80; RADIOCHEMISTRY; ESTROGENS; RECEPTORS; TAMOXIFEN; BROMINATION; CHEMICAL PREPARATION; STRUCTURE-ACTIVITY RELATIONSHIPS; AUGER EFFECT; BINDERS; BROMINE 88; CHEMICAL BONDS; CHEMICAL REACTION YIELD; DERIVATIZATION; DIAGNOSIS; ETHYLENE; FEMALE GENITALS; HYDROXY COMPOUNDS; IMIDES; LABELLING; NEOPLASMS; PHTHALIC ACID; RADIOACTIVATION; RADIOPHARMACEUTICALS; SUCCINIC ACID; ALKENES; BETA DECAY RADIOISOTOPES; BETA-MINUS DECAY RADIOISOTOPES; BETA-PLUS DECAY RADIOISOTOPES; BODY; BROMINE ISOTOPES; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; CHEMISTRY; DICARBOXYLIC ACIDS; DISEASES; DRUGS; ELECTRON CAPTURE RADIOISOTOPES; HALOGENATION; HORMONES; HOURS LIVING RADIOISOTOPES; HYDROCARBONS; INTERMEDIATE MASS NUCLEI; INTERNAL CONVERSION RADIOISOTOPES; ISOTOPES; LABELLED COMPOUNDS; MEMBRANE PROTEINS; MINUTES LIVING RADIOISOTOPES; NUCLEI; ODD-ODD NUCLEI; ORGANIC ACIDS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANS; PROTEINS; RADIOISOTOPES; SECONDS LIVING RADIOISOTOPES; STEROID HORMONES; SYNTHESIS; YIELDS; 550601* - Medicine- Unsealed Radionuclides in Diagnostics; 550604 - Medicine- Unsealed Radionuclides in Therapy- (1980-); 400700 - Radiochemistry & Nuclear Chemistry

Citation Formats

Seevers, R H, Meese, R C, Friedman, A M, and DeSombre, E R. Radiobrominated triphenylethylenes as estrogen receptor binding radiopharmaceuticals. United States: N. p., 1985. Web.
Seevers, R H, Meese, R C, Friedman, A M, & DeSombre, E R. Radiobrominated triphenylethylenes as estrogen receptor binding radiopharmaceuticals. United States.
Seevers, R H, Meese, R C, Friedman, A M, and DeSombre, E R. 1985. "Radiobrominated triphenylethylenes as estrogen receptor binding radiopharmaceuticals". United States.
@article{osti_7030645,
title = {Radiobrominated triphenylethylenes as estrogen receptor binding radiopharmaceuticals},
author = {Seevers, R H and Meese, R C and Friedman, A M and DeSombre, E R},
abstractNote = {Estrogen receptor binding radiopharmaceuticals have potential for use in the diagnosis and treatment of cancers of the female reproductive system. Tamoxifen is an antiestrogen derived from the triphenylethylene skeleton which is used in the treatment of mammary carcinoma. Hydroxytamoxifen is a metabolite of tamoxifen which binds tightly to the estrogen receptor. Two triphenylethylene derivatives based on the structure of hydroxytamoxifen have been prepared: 1-bromo-1-phenyl-2- (2-dimethylamino)-4-ethoxyphenyl -2-(4-hydroxyphenyl) ethene (1) where the ethyl group of hydroxytamoxifen has been replaced by a bromine, and 1-bromo-1-phenyl-2,2-(4-hydroxyphenyl) ethene (2) with a similar substitution and also lacking the aminoethoxy side chain believed to confer antiestrogenicity. Both 1 and 2 bind strongly to the estrogen receptor. 2 has been labeled with the Auger electron emitting nuclide Br-80m in moderate yields in high specific activity using either N-bromosuccinimide or N-bromophthalimide and shows promise as a potential radiotherapy agent.},
doi = {},
url = {https://www.osti.gov/biblio/7030645}, journal = {J. Nucl. Med.; (United States)},
number = ,
volume = 26:5,
place = {United States},
year = {Wed May 01 00:00:00 EDT 1985},
month = {Wed May 01 00:00:00 EDT 1985}
}

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