Synthesis of Novel Europium-Labeled Estradiol Derivatives for Time-Resolved Fluoroimmunoassays

The O-(5-carboxypentyl)-, O-(4-aminobutyl)-, O-(6-aminohexyl)oximes of 2- and 4-formylestradiol as well as the 4-carboxyethylthioether derivative of estradiol were synthesized. These estradiol derivatives were characterized using IR-, 1H-, and 13C NMR spectroscopy. All synthesized estradiol derivati...

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Bibliographic Details
Published in:Bioconjugate chemistry 1999-05, Vol.10 (3), p.325-331
Main Authors: Meltola, Niko, Jauria, Piitu, Saviranta, Petri, Mikola, Heikki
Format: Article
Language:English
Subjects:
Antibodies, Monoclonal - immunology
Estradiol - analogs & derivatives
Estradiol - analysis
Estradiol - chemistry
Estradiol - immunology
Europium - chemistry
Fluoroimmunoassay - methods
Magnetic Resonance Spectroscopy
Time Factors
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Summary:The O-(5-carboxypentyl)-, O-(4-aminobutyl)-, O-(6-aminohexyl)oximes of 2- and 4-formylestradiol as well as the 4-carboxyethylthioether derivative of estradiol were synthesized. These estradiol derivatives were characterized using IR-, 1H-, and 13C NMR spectroscopy. All synthesized estradiol derivatives were labeled with europium chelates. These “tracers” were purified and tested in a competitive time-resolved fluoroimmunoassay with monoclonal antibody (SSI 57-2) raised against the 6-O-(carboxymethyl)oxime-bovine serum albumin derivative of estradiol. All the tested europium-labeled estradiol-4-derivatives were bound by the antibody, whereas tracers linked via position 2 were not recognized by this antibody. It was observed that tracers conjugated via C-4 gave more sensitive standard curves than tracers conjugated via C-6. Especially, the estradiol-4-thioether derivative was found to be highly useful in time-resolved fluoroimmunoassays of estradiol while using this antibody.
ISSN:1043-1802
1520-4812
DOI:10.1021/bc980013q