"Click labeling" with 2-[18F]fluoroethylazide for positron emission tomography

Bioconjugate Chemistry

Volumn 18, Issue 3, 2007, Pages 989-993

  Glaser, Matthias ^a   Årstad, Erik ^a  

^a Hammersmith Imanet Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPOUNDS; COPPER POWDER; DISTILLATION; HYDROCARBONS;

CLICK REACTION; HUISGEN CYCLOADDITION; LABELINGS; MODEL PEPTIDES; NUCLEOPHILIC FLUORINATION; RADIOCHEMICAL YIELD; TERMINAL ALKYNE;

POSITRON EMISSION TOMOGRAPHY;

1,2,3 TRIAZOLE DERIVATIVE; 2 AZIDOETHYL 4 TOLUENESULFONATE; ASCORBIC ACID; AZIDE; COPPER ION; FLUORINE 18; FLUOROETHYLAZIDE F 18; N BENZYLPROPYNAMIDE; PROPANE; TOLUENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; ENVIRONMENTAL TEMPERATURE; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POSITRON EMISSION TOMOGRAPHY; PRODUCT RECOVERY; QUANTITATIVE ANALYSIS; RADIOCHEMISTRY;

EID: 34347338806     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc060301j     Document Type: Article

References (25)

1. Stahl, A., Wieder, H., Piert, M., Wester, H.-J., Senekowitsch-Schmidtke, R., and Schwaiger, M. (2004) Positron emission tomography as a tool for translational research in oncology. Mol. Imaging Biol. 6, 214-224.
2. Welch, M. J., and Redvanly, C. S. (2003) Handbook of Radiopharmaceuticals, Radiochemistry and Applications, John Wiley & Sons Ltd, Chichester.
3. Heiss, W.-D., and Herholz, K. (2006) Brain receptor imaging. J. Nucl. Med. 47, 302-312.
4. Stoecklin, G. (1998) Is there a future for clinical fluorine-18 radiopharmaceuticals (excluding FDG)? Eur. J. Nucl. Med. 25, 1612-1616.
5. 123I. Appl. Radiat. Isot. 37, 803-810.
6. Adam, M. J., and Wilbur, D. S. (2005) Radiohalogens for imaging and therapy. Chem. Soc. Rev. 34, 153-163.
7. Wester, H.-J., Hamacher, K., and Stoecklin, G. (1996) A comparative study of NC. A. Fluorine-18 labeling of proteins via acylation and photochemical conjugation. Nucl. Med. Biol. 23, 365-372.
8. 18F-labeled RGD and Octreotide analogs. J. Nucl. Med. 45, 892-902.
9. Tornøe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper-(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064.
10. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 41, 2596-2599.
11. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: diverse chemical function from a few good reactions. Angew. Chem., Int. Ed. 40, 2004-2021.
12. Pagliai, F., Pirali, T., Grosso, E. D., Brisco, R. D., Tron, G. C., Sorba, G., and Genazzani, A. A. (2006) Rapid synthesis of triazole-modified Resveratrol analogues via click chemistry. J. Med. Chem. 49, 467-470.
13. Burley, G. A., Gierlich, J., Mofid, M. R., Nir, H., Tal, S., Eichen, Y., and Carell, T. (2006) Directed DNA metallization. J. Am. Chem. Soc. 128, 1398-1399.
14. Whiting, M., Muldoo, J., Lin, Y.-C., Silverman, S. M., Lindstrom, W., Olson, A. J., Kolb, H. C., Finn, M. G., Sharpless, K. B., Elder, J. H., and Fokin, V. V. (2006) Inhibitors of HIV-1 protease by using in situ click chemistry. Angew. Chem., Int. Ed. 45, 1435-1439.
15. Krasinski, A., Radic, Z., Manetsch, R., Raushel, J., Taylor, P., Sharpless, K. B., and Kolb, H. C. (2005) In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors. J. Am. Chem. Soc. 127, 6686-6692.
16. Agard, N. J., Prescher, J. A., and Bertozzi, C. R. (2004) A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J. Am. Chem. Soc. 126, 15046-15047.
17. I-Catalyzed alkyne-azide "Click" cycloadditions form a mechanistic and synthetic perspective. Eur. J. Org. Chem. 51-68.
18. I catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett. 47, 6681-6684).
19. van Velzen, E. U. T., Engbersen, J. F. J., and Reinhoudt, D. T. (1995) Synthesis of self-assembling resorcin[4]arene tetrasulfide adsorbates. Synthesis 989-997.
20. Coppola, G. M., and Damon, R. E. (1993) Acetylenic amides, i: synthesis of N-substituted-2-propynamide. Synth. Commun. 23, 2003-2010.
21. Jacobi, P. A., Brielmann, H. L., and Hauck, S. I. (1996) Toward the synthesis of biologically important chlorines, isobacteriochlorins, and corrins. Cyclic enamides from acetylenic amides. J. Org. Chem. 61, 5013-5023.
22. Hashmi, A. S. K., Weyrauch, J. P., Frey, W., and Bats, J. W. (2004) Gold catalysis: mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects. Org. Lett. 6, 4391-4394.
23. Demko, Z. P., and Sharpless, K. B. (2001) An intramolecular [2+3] cycloaddition route to fused 5-heterosubstituted tetrazoles. Org. Lett. 3, 4091-4094.
24. Himo, F., Lovell, T., Hilgraf, R., Rostovtsev, V. V., Noodleman, L., Sharpless, K. B., and Fokin, V. V. (2004) Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J. Am. Chem. Soc. 127, 210-216.
25. 18F]2 in 5% TFA solution only.