Synthesis of 2-[131I]iodophenyl-metyrapone using Cu(I)-assisted nucleophilic exchange labelling: study of the reaction conditions.
2-Bromophenyl-metyrapone has been synthesized as a precursor for Cu(I)-assisted labelling with radioiodine. A labelling yield of > 95% was obtained and the specific activity of the purified product was 120 GBq/mumol. The iodo for bromo exchange requires an excess of reducing agents to maintain the Cu(I) redox potential. The effects of the amount of reactants, temperature and time were studied. The labelling yield showed a direct dependence on the amount of precursor and Cu(+)-catalyst used for the reaction, and an increase with reaction time (optimal at 60 min) and temperature (optimal at 100 degrees C). Studies of the stability, lipophilicity and binding of 2-[131I]iodophenyl-metyrapone to serum protein indicated high in vitro stability, high lipophilicity (log P = 2.19) and a loose association with serum proteins.
Yu
J
J
Univ. Klinik f. Nuclearmedizin, Allgemeines Krankenhaus, Vienna, Austria.
Zolle
I
I
Mertens
J
J
Rakias
F
F
D000818:Animals; D001798:Blood Proteins / Q000378:metabolism; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003300:Copper; D006801:Humans; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes / Q000097:blood; D007553:Isotope Labeling / Q000379:methods; D007700:Kinetics; D008797:Metyrapone / Q000031:analogs & derivatives* / Q000097:blood / Q000138:chemical synthesis / Q000302:isolation & purification; D015394:Molecular Structure; D011485:Protein Binding; D051381:Rats; D013329:Structure-Activity Relationship; D013997:Time Factors
C093930:2-iodophenylmetyrapone; D001798:Blood Proteins; D007202:Indicators and Reagents; D007457:Iodine Radioisotopes; D003300:Copper; D008797:Metyrapone