Convenient synthesis of maleimido-derivatized lanthanide(III) chelates and their use in mercapto group conjugation

Bioconjugate Chemistry

Volumn 18, Issue 2, 2007, Pages 597-600

  Hovinen, Jari ^a  

^a PerkinElmer Finland Oy   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

EUROPIUM COMPOUNDS; ION EXCHANGE RESINS; LIGANDS; RARE EARTH ELEMENTS; SILICA GEL; TERBIUM COMPOUNDS;

ACIDOLYSIS; DEPROTECTION; HIGH PURITY; LABELINGS; LANTHANIDE(III) IONS; MERCAPTO GROUPS; SIMPLE++; STRONG CATION EXCHANGES;

CHELATION;

CATION EXCHANGE RESIN; CHELATE; EUROPIUM; LANTHANIDE; LIGAND; MALEIMIDE DERIVATIVE; SILICON DIOXIDE; TERBIUM; THIOL DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CONJUGATION; DEPROTECTION REACTION; HYDROPHILICITY; LUMINESCENCE; PURIFICATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33947657887     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060282d     Document Type: Article

References (28)

1. Hemmilä, I., and Mukkala, V.-M. (2001) Time-resolution in fluorometry technologies, labels, and applications in bioanalytical assays. Crit. Rev. Clin. Lab. Sci. 38, 441-519.
2. Hemmilä, I. (1991) Applications of Fluorescence in Immunoassays. In Chemical Analysis: A Series of Monographs on Analytical Chemistry and Its Applications, Vol. 117, John Wiley & Sons, Inc., New York.
3. Hemmilä, I., and Laitala, V. (2005) Progress in lanthanides as luminescent probes. J. Fluoresc. 15, 529-542.
4. Selvin, P. R. (1996) Lanthanide-based resonance energy transfer. IEEE J. Sel. Top. Quantum Electron. 2, 1077-1087.
5. Karvinen, J., Hurskainen, P., Gopalakrishnan, S., Burns, D., Warrior, U., and Hemmilä, I. (2002) Homogeneous time-resolved fluorescence quenching assay (LANCE) for caspase-3. J. Biomol. Screen. 7, 223-231.
6. Gopalakrishnan, S., Karvinen, J., Kofron, J., Burns, D., and Warrior, U. (2002) Application of micro arrayed compound screening (pcARCS) to identify inhibitors of caspase-3. J. Biomol. Screen. 7, 317-323.
7. Karvinen, J., Laitala, V., Mäkinen, M.-L., Mulari, O., Tamminen, J., Hermonen, J., Hurskainen, P., and Hemmilä, I. (2004) Fluorescence quenching-based assays for hydrolyzing enzymes. Application of time-resolved fluorometry in assays for caspase, helicase, and phosphatase. Anal. Chem. 76, 1429-1436.
8. Karvinen, J., Elomaa, A., Mäkinen, M.-L., Hakala, H., Mukkala, V.-M., Peuralahti, J., Hurskainen, P., Hovinen, J., and Hemmilä, I. (2004) Caspase multiplexing: simultaneous homogeneous time-resolved quenching assay (TruPoint) for caspases 1, 3, and 6. Anal. Biochem. 325, 317-325.
9. Wang, G., Yan, J., Hai, X., Matsumoto, K. (2006) Homogenous time-resolved fluoroimmunoassay of 3,5,3′-triiodo-L-thyronine in hyman serum by using europium fluorescence energy transfer Talanta 70, 133-138.
10. Ge, P., and Selvin, P. R. (2004) Carbostyril Derivatives as Antenna Molecules for Luminescent Lanthanide Chelates. Bioconjugate Chem. 15, 1088.
11. Ylikoski, A., Elomaa, A., Ollikka, P., Hakala, H., Mukkala, V.-M., Hovinen, J., and Hemmilä, I. (2004) A Homogenous time-resolved fluorescence quenching assay (TruPointTM) for genotyping. Clin. Chem. 50, 1943-1947.
12. Mukkala, V.-M., Helenius, M., Hemmilä, I., Kankare, J., and Takalo, H. (1993) Development of luminescent europium(III) and terbium(III) chelates of 2,2′:6′,2″-terpyridine derivatives for protein labelling. Helv. Chim. Acta 76, 1361-1378.
13. Takalo, H., Mukkala, V.-M., Mikola, H., Liitti, P., and Hemmilä, I. (1994) Synthesis of europium(III) chelates suitable for labeling of bioactive molecules. Bioconjugate Chem. 5, 278-282.
14. Cooper, M. E., and Sammes, P. G. (2000) Synthesis and spectral properties of a new luminescent europium(III) terpyridyl chelate. J. Chem. Soc., Perkin Trans. 2 1695-1700.
15. Peuralahti, J., Puukka, K., Hakala, H., Mukkala, V.-M., Mulari, O., Hurskainen, P., and Hovinen, J. Synthesis of nonluminescent lanthanide(III) chelates tethered to an aminooxy function and their applicability to biomolecule derivatization. Bioconjugate Chem. 13, 876-880.
16. Hovinen, J. (2006) Synthesis of aminooxy chelates and their use in carbonyl group conjugation. Chem. Biodivers. 3, 296-303.
17. Hovinen, J. and Hakala, H. (2001) Versatile strategy for oligonucleotide derivatization. Introduction of lanthanide(III) chelates to oligonucleotides. Org. Lett. 3, 2473-2476.
18. Hakala, H., Ollikka, P., Degerholm, J., and Hovinen, J. (2002) Oligonucletide conjugates based on acyclonucleotides and their use in DNA hybridization assays. Tetrahedron 58, 8771-8777.
19. Jaakkola, L., Peuralahti, J., Hakala, H., Kunttu, J., Tallqvist, P., Mukkala, V.-M., Ylikoski, A., and Hovinen, J. (2005) Solid phase synthesis of oligonucleotides labeled with luminescent lanthanide(III) chelates. Bioconjugate Chem. 16, 700-709.
20. Peuralahti, J., Hakala, H., Mukkala, V.-M., Hurskainen, P., Mulari, O., and Hovinen, J. (2002) Introduction of lanthanide(III) chelates to oligopeptides on solid phase. Bioconjugate Chem. 13, 870-875.
21. Jaakkola, L., Peuralahti, J., Hakala, H., Mukkala, V.-M., Hurskainen, P., Hovinen, J. (2006) Labeling of oligopeptides and proteins with luminescent lanthanide(III) chelates. J. Pept. Sci. 19, 199-205.
22. Aslam, M., and Dent, A. Bioconjugation. Protein Coupling Techniques for the Biomedical Sciences, Macmillan Reference Ltd, London, G.B., 1998.
23. Chen, J., and Selvin, P. R. (1999) Thiol-reactive luminescent chelates of terbium and europium. Bioconjugate Chem., 10, 311-315.
24. Ge, P., and Selvin, P. R. (2003) Thiol-Reactive Luminescent Lanthanide Chelates: Part 2. Bioconjugate Chem. 14, 870-876.
25. Takalo, H., Hänninen, E., and Kankare, J. (1993) Luminescence of europium(III) chelates with 4-(arylethynyl)pyridines as ligands. Helv. Chim. Acta 76, 877-883.
26. Rodriques-Ubis, H., Takalo, H., and Mukkala, V.-M. (1999) Biospecific binding reactants labeled with luminescent lanthanide chelates. US Patent 5 859, 215.
27. Marchán, V. In Peptide-oligonucleotide conjugates: synthetic approaches and applications, Conference, Chemiedozententagung, Hamburg, Germany, March 19-22, 2006; A26.
28. Schelte, P., Boeckler, C., Frisch, B., and Schuber, F. (2000) Differential reactivity of maleimide and bromoacetyl functions with thiols: application to the preparation of liposomal diepitope constructs. Bioconjugate Chem. 11, 118-123.