Copper-free click for PET: Rapid 1,3-dipolar cycloadditions with a fluorine-18 cyclooctyne

ACS Medicinal Chemistry Letters

Volumn 2, Issue 12, 2011, Pages 885-889

  Carpenter, Richard D ^a   Hausner, Sven H ^a   Sutcliffe, Julie L ^a,b,c  

^a University of California   (United States)

^b Department of Internal Medicine   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Copper free click chemistry; cycloaddition; cyclooctyne; fluorine 18; positron emission tomography

Indexed keywords

ALKYNE DERIVATIVE; AMINE; AZIDE; COPPER; CYCLOOCTYNE F 18; DYE; METAL DERIVATIVE; REAGENT; TRACER; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CLICK CHEMISTRY; CONJUGATION; CYCLOADDITION; DRUG SYNTHESIS; ISOTOPE LABELING; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOCHEMISTRY; REACTION ANALYSIS;

EID: 83455172909     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200187j     Document Type: Article

References (33)

1. El-Sagheer, A. H.; Brown, T. Click Chemistry with DNA Chem. Soc. Rev. 2010, 39, 1388-1405
2. 18F]fluoropeptides Using CuI Catalyzed 1,3-Dipolar Cycloaddition Tetrahedron Lett. 2006, 47, 6681-6684 (Pubitemid 44176106)
3. Lebedev, A. Y.; Holland, J. P.; Lewis, J. S. Clickable Bifunctional Radiometal Chelates for Peptide Labeling Chem. Commun. 2010, 46, 1706-1708
4. Hänni, K. D.; Leigh, D. A. The Application of CuAAC 'Click' Chemistry to Catenane and Rotaxane Synthesis Chem. Soc. Rev. 2010, 39, 1240-1251
5. Huisgen, R. Centenary Lecture: 1,3-Dipolar Cycloadditions Proc. Chem. Soc. 1961, 357-363
6. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem. 2002, 114, 2708-2711
7. Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. A Stepwise Huisgen Cycloaddition Process: Copper(I)-catalyzed Regioselective "Ligation" of Azides and Terminal Alkynes Angew. Chem., Int. Ed. 2002, 41, 2596-2599 (Pubitemid 34803480)
8. Torne, C. W.; Christensen, C.; Meldal, M. Peptidotriazoles on Solid-phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-catalyzed Cycloadditions of Terminal Alkynes to Azides J. Org. Chem. 2002, 67, 3057-3064 (Pubitemid 34457265)
9. Jewett, J. C.; Bertozzi, C. R. Cu-free Click Cycloaddition Reactions in Chemical Biology Chem. Soc. Rev. 2010, 39, 1272-1279
10. Hong, V.; Steinmetz, N. F.; Manchester, M.; Finn, M. G. Labeling Live Cells by Copper-catalyzed Alkyne-azide Click Chemistry Bioconjugate Chem. 2010, 21, 1912-1916
11. Soriano del Amo, D.; Wang, W.; Jiang, H.; Besanceney, C.; Yan, A. C.; Levy, M.; Liu, Y.; Marlow, F. L.; Wu, P. Biocompatible Copper(I) Catalysts for In Vivo Imaging of Glycans J. Am. Chem. Soc. 2010, 132, 16893-16899
12. Laughlin, S. T.; Baskin, J. M.; Amacher, S. L.; Bertozzi, C. R. In vivo Imaging of Membrane-associated Glycans in Developing Zebrafish Science 2008, 320, 664-667 (Pubitemid 351928348)
13. Poloukhtine, A. A.; Mbua, N. E.; Wolfert, M. A.; Boons, G.-J.; Popik, V. V. Selective Labeling of Living Cells by a Photo-triggered Click Reaction J. Am. Chem. Soc. 2009, 131, 15769-15776
14. Jewett, J. C.; Sletten, E. M.; Bertozzi, C. R. Rapid Cu-free Click Chemistry with Readily Synthesized Biarylazacyclooctynones J. Am. Chem. Soc. 2010, 132, 3688-3690
15. Sletten, E. M.; Nakamura, H.; Jewett, J. C.; Bertozzi, C. R. Difluorobenzocyclooctyne: Synthesis, Reactivity, and Stabilization by 8-Cyclodextrin J. Am. Chem. Soc. 2010, 132, 11799-11855
16. Kuzmin, A.; Poloukhtine, A.; Wolfert, M. A.; Popik, V. V. Surface Functionalization Using Catalyst-free Azide-alkyne Cycloaddition Bioconjugate Chem. 2010, 21, 2076-2085
17. Schultz, M. K.; Parameswarappa, S. G.; Pigge, F. C. Synthesis of a DOTA-biotin Conjugate for Radionuclide Chelation via Cu-free Click Chemistry Org. Lett. 2010, 12, 2398-2341
18. Martin, M. E.; Parameswarappa, S. G.; ODorisio, M. S.; Pigge, F. C.; Schultz, M. K. A DOTA-peptide Conjugate by Copper-free Click Chemistry Bioorg. Med. Chem. Lett. 2010, 20, 4805-4807
19. Rossin, R.; Verkerk, P. R.; van den Bosch, S. M.; Vulders, R. C. M.; Verel, I.; Lub, J.; Robillard, M. S. In Vivo Chemistry for Pretargeted Tumor Imaging in Live Mice Angew. Chem. 2010, 122, 3308-3311
20. Rossin, R.; Verkerk, P. R.; van den Bosch, S. M.; Vulders, R. C. M.; Verel, I.; Lub, J.; Robillard, M. S. In Vivo Chemistry for Pretargeted Tumor Imaging in Live Mice Angew. Chem., Int. Ed. 2010, 49, 3375-3378
21. 18F-PARP1 Inhibitors ChemMedChem 2011, 6, 424-427
22. 18F Labeled Probes Chem. Commun. 2010, 46, 8043-8045
23. Ametamey, S. M.; Honer, M. J.; Schubiger, P. A. Molecular Imaging with PET Chem. Rev. 2008, 108, 1501-1516 (Pubitemid 351796395)
24. Lee, S.; Xie, J.; Chen, X. Peptides and Peptide Hormones for Molecular Imaging and Disease Diagnosis Chem. Rev. 2010, 110, 3087-3111
25. 18F]fluoropropionyl Peptides J. Med. Chem. 2008, 51, 5901-5904
26. 18F Radiolabeling for PET J. Nucl. Med. 2009, 50, 991-998
27. 18F-radiochemistry: Syntheses and Applications Mini Rev. Org. Chem. 2007, 4, 317-329
28. Turner, R. B.; Jarrett, A. D.; Goebel, P.; Mallon, B. J. Heats of Hydrogenation. IX. Cyclic Acetylenes and Some Miscellaneous Olefins J. Am. Chem. Soc. 1973, 95, 790-792
29. 18F] fluorobenzoate Using a Siemens/CTI Chemistry Process Unit (CPCU) Appl. Radiat. Isot. 2007, 65, 199-203 (Pubitemid 44828500)
30. 18F]fluoropropionyl Peptides Bioconjugate Chem. 2006, 17, 1017-1021 (Pubitemid 44162621)
31. Clark, J. S.; Hodgson, P. B.; Goldsmith, M. D.; Street, L. J. Rearrangement of Ammonium Ylides Produced by Intramolecular Reaction of Catalytically Generated Metal Carbenoids. Part 1. Synthesis of Cyclic Amines J. Chem. Soc., Perkin Trans. 1 2001, 3312-3324 (Pubitemid 35290936)
32. 18F Nat. Protoc. 2006, 1, 1655-1661 (Pubitemid 46773286)
33. Robins, L. I.; Carpenter, R. D.; Fettinger, J. C.; Haddadin, M. J.; Tinti, D. S.; Kurth, M. J. Diazocinones: Synthesis and Conformational Analysis J. Org. Chem. 2006, 71, 2480-2485