Synthesis of novel europium-labeled estradiol derivatives for time-resolved fluoroimmunoassays

Bioconjugate Chemistry

Volumn 10, Issue 3, 1999, Pages 325-331

  Meltola, Niko ^b   Jauria, Piitu ^a   Saviranta, Petri ^b   Mikola, Heikki ^b  

^a Innotrac Diagnostics Oy   (Finland)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

DRUG SYNTHESIS; ESTRADIOL DERIVATIVE; FLUOROIMMUNOASSAY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

BODY FLUIDS; EUROPIUM COMPOUNDS; MAMMALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMINOBUTYL; BOVINE SERUM ALBUMINS; CARBOXYMETHYL; EUROPIUM CHELATE; NMR-SPECTROSCOPY; SYNTHESISED; THIOETHER DERIVATIVES; TIME-RESOLVED FLUOROIMMUNOASSAY;

MONOCLONAL ANTIBODIES;

BOVINAE;

EID: 0033136580     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc980013q     Document Type: Article

References (23)

1. Pratt, J. J. (1978) Steroid immunoassay in clinical chemistry. Clin. Chem. 24, 1869-1890.
2. Tiefenauer, L. X., and Andres, R. Y. (1990) Biotinyl-estradiol derivatives in enzyme immunoassays: Structural requirements for optimal antibody binding. J. Steroid Biochem. 35, 633-639.
3. Mikola, H., and Miettinen, P. (1991) Preparation of europium labeled derivatives of cortisol for time-resolved fluoroimmunoassays. Steroids 56, 17-21.
4. Mikola H., Sundell, A.-C., and Hänninen, E. (1993) Labeling of estradiol and testosterone alkyloxime derivatives with a europium chelate for time-resolved fluoroimmunoassays. Steroids 58, 330-334.
5. Soini, E., and Lövgren, T. (1987) Time-resolved fluorescence of lanthanide probes and applications in biotechnology. CRC Crit. Rev. Anal. Chem. 18, 105-154.
6. Lövgren, T., Hemmilä, I., Pettersson, K., and Halonen, P. (1985) Time-resolved fluorometry in immunoassays. In Alternative immunoassays (W. P. Collins, Ed.) Wiley, Chichester, NY.
7. Lövgren, T. (1987) Time-resolved fluoroimmunoassays of steroid hormones. J. Steroid Biochem. 27, 47-51.
8. Tiefenauer, L. X., Bodmer, D. M., Frei, W., and Andres, R. Y. (1989) Prevention of bridge binding in immunoassays: a general estradiol tracer structure. J. Steroid Biochem. 32, 251-257.
9. Lamminmäki, U., Villoutreix, B. O., Jauria, P., Vihinen, M., Nilsson, L., Teleman, O., Saviranta, P., and Lövgren, T. (1997) Structural analysis of an anti-estradiol antibody. Mol. Immunol. 34, 1215-1226.
10. 125I-radioligands in the radio-immunoassay of progesterone. Steroids 32, 467-486.
11. Mukkala, V.-M., Mikola, H., and Hemmilä, I. (1989) The synthesis and use of activated N-benzyl derivatives of diethylenetriaminetetraacetic acids: Alternative reagents for labeling of antibodies with metal ions. Anal. Biochem. 176, 319-325.
12. Mikola, H., and Hänninen, E. (1992) Introduction of aliphatic amino and hydroxy groups to ketosteroids using O-substituted hydroxylamines. Bioconjugate Chem. 3, 182-186.
13. Mikola, H. (Unpublished results).
14. Scatchard, G. (1949) The attractions of proteins for small molecules and ions. Annals. N. Y. Acad. Sci. 51, 660-672.
15. Meltola, N., and Mikola, H. (unpublished results).
16. Lovely, C. J., and Brueggemeier, R. W. (1994) Synthesis of 2-substituted hydroxyalkyl and aminoalkyl estradiols. Tetrahedron Lett. 35, 8735-8738.
17. Pert, D. J., and Ridley, D. D. (1989) Formylation of oestrogens. Aust. J. Chem. 42, 405-419.
18. Xie, R., Chen, Q., Xie, J., and Zhao, H. (1990) A new efficient synthetic method for 2-and 4-hydroxy-17α-ethynylestradiol. Steroids 55, 488-490.
19. Mihailovic, M. Lj., Forsek, J., and Lorenc, Lj. (1977) A novel procedure for the aromatization of ring A in 19-nortestosterone. Tetrahedron 33, 235-237.
20. Le Quesne, P. W., Abdel-Baky, S., Durga, A. V., and Purdy, R. H. (1986) Active nonaromatic intermediates in conversion of the steroidal estrogens into catechol estrogens. Biochemistry 25, 2065-2072.
21. Ghaffari, M. A., and Abul-Hajj, Y. J. (1990) Reaction of thiol nucleophiles with 1,2-epoxy-and 4,5-epoxy-estrene-3-one-17β-ols. J. Steroid Biochem. Mol. Biol. 37, 237-244.
22. Gani, M., Coley, J., Piron, J., Humphrey, A. S., Arevalo, J., Wilson, I. A., and Taussig, M. J. (1994) Monoclonal antibodies against progesterone: effect of steroid-carrier coupling position on antibody specificity. J. Steroid Biochem. Mol. Biol. 48, 277-282.
23. Hoogenboom, H. R., Griffiths, A. D., Johnson, K. S., Chiswell, D. J., Hudson, P., and Winter, G. (1991) Multi-subunit proteins on the surface of filamentous phage: Methodologies for displaying antibody (Fab) heavy and light chains. Nucleic Acids Res. 19, 4133-4137.