Design, Synthesis and Biological Properties of Fluorinated Estrogens, Progestins and Androgens, Potential Imaging Agents for Receptor-Positive Mammary and Prostate Tumors (fluorine-18)

Several estrogens fluorinated at the 17(alpha)- and 16(alpha)-positions were synthesized in the development of a potential fluorine-18 radiolabel useful as a means of quantifying estrogen receptor in receptor-positive mammary tumors. The affinities of the compounds for estrogen receptor were measured using competitive radiometric binding assays and 17(alpha)-fluoromethyl estradiol (17) and 17(alpha)-fluoropropynyl estradiol (18) found to bind to this receptor system with affinities 52% and 84% that of estradiol respectively. A method for rapidly and efficiently synthesizing 17(alpha)-fluoromethyl estradiol by fluoride ion cleavage of the corresponding C-17 spiro cyclic sulfate was developed by modifying the C-3 protecting group of the sulfate precursor and reaction time, temperature and solvent.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Brandes, Stephanie Jean

• Chemistry, Organic

Identifier

(UMI)AAI8701441

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70339