Preparation of 18 F-labeled peptides using the copper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition

Nature Protocols

Volumn 6, Issue 11, 2011, Pages 1718-1725

  Gill, Herman S ^a   Marik, Jan ^a  

^a GENENTECH INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; BATHOPHENANTHROLINE DISULFONATE; COPPER; FLUORINE 18; MACROGOL; NUCLEOPHILE; PHENANTHROLINE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG; FLUORINE; PEPTIDE;

ARTICLE; CATALYSIS; CYCLOADDITION; DISULFIDE BOND; ELUTION; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; MICROWAVE RADIATION; PRIORITY JOURNAL; RADIOCHEMISTRY; REDUCTION; CHEMICAL STRUCTURE; CHEMISTRY;

ALKYNES; AZIDES; CATALYSIS; COPPER; FLUORINE RADIOISOTOPES; MOLECULAR STRUCTURE; PEPTIDES;

EID: 80054808224     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2011.390     Document Type: Article

References (47)

1. Kolb, H.C., Finn, M.G. & Sharpless, K.B. Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. Engl. 40, 2004-2021 (2001).
2. 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. Engl. 41, 2596-2599 (2002). (Pubitemid 34803480)
3. Tornoe, C.W., Christensen, C. & Meldal, M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecifc copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064 (2002). (Pubitemid 34457265)
4. Kolb, H.C. & Sharpless, K.B. The growing impact of click chemistry on drug discovery. Drug Discovery Today 8, 1128-1137 (2003). (Pubitemid 37547919)
5. Meldal, M. & Tornoe, C.W. Cu-catalyzed azide-alkyne cycloaddition. Chem. Rev. 108, 2952-3015 (2008).
6. Glaser, M. & Robins, E.G. 'Click labelling' in PET radiochemistry. J. Label. Compd. Radiopharm. 52, 407-414 (2009).
7. Sirion, U. et al. An effcient F-18 labeling method for PET study: Huisgen 1,3-dipolar cycloaddition of bioactive substances and F-18-labeled compounds. Tetrahedron Lett. 48, 3953-3957 (2007). (Pubitemid 46702266)
8. 18F]-labeled isatin sulfonamide. Proc. Natl. Acad. Sci. USA 106, 16375-16380 (2009).
9. 18F exemplifed by quantitative positron emission tomography of human epidermal growth factor receptor 2. J. Med. Chem. 52, 5816-5825 (2009).
10. Ramenda, T., Kniess, T., Bergmann, R., Steinbach, J. & Wuest, F. Radiolabelling of proteins with fuorine-18 via click chemistry. Chem. Commun. (Camb), 7521-7523 (2009).
11. 18F]fuoropeptides using Cu(I) catalyzed 1,3-dipolar cycloaddition. Tetrahedron Lett. 47, 6681-6684 (2006).
12. 18F] fuoroethylazide for positron emission tomography. Bioconjug. Chem. 18, 989-993 (2007). (Pubitemid 47010823)
13. 18F labeling of bioactive peptides. J. Label. Compd. Radiopharm. 51, 444-452 (2008).
14. 18F]fuoropropionyl-peptides. J. Med. Chem. 51, 5901-5904 (2008).
15. 18F-labeling of RGD peptides and microPET imaging of tumor integrin alphavbeta3 expression. Bioconjug. Chem. 18, 1987-1994 (2007). (Pubitemid 350220000)
16. Rodionov, V.O., Presolski, S.I., Diaz, D.D., Fokin, V.V. & Finn, M.G. Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: a mechanistic report. J. Am. Chem. Soc. 129, 12705-12712 (2007). (Pubitemid 350004482)
17. Rodionov, V.O., Presolski, S.I., Gardinier, S., Lim, Y.H. & Finn, M.G. Benzimidazole and related ligands for Cu-catalyzed azide-alkyne cycloaddition. J. Am. Chem. Soc. 129, 12696-12704 (2007). (Pubitemid 350004481)
18. Campbell-Verduyn, L.S., Mirfeizi, L., Dierckx, R.A., Elsinga, P.H. & Feringa, B.L. Phosphoramidite accelerated copper(I)-catalyzed [3 + 2] cycloadditions of azides and alkynes. Chem. Commun. (Camb), 2139-2141 (2009).
19. Lewis, W.G., Magallon, F.G., Fokin, V.V. & Finn, M.G. Discovery and characterization of catalysts for azide-alkyne cycloaddition by fuorescence quenching. J. Am. Chem. Soc. 126, 9152-9153 (2004). (Pubitemid 38989411)
20. Chan, T.R., Hilgraf, R., Sharpless, K.B. & Fokin, V.V. Polytriazoles as copper(I)-stabilizing ligands in catalysis. Org. Lett. 6, 2853-2855 (2004). (Pubitemid 39178025)
21. Soriano Del Amo, D. et al. Biocompatible copper(I) catalysts for in vivo imaging of glycans. J. Am. Chem. Soc. 132, 16893-16899.
22. Sen Gupta, S. et al. Accelerated bioorthogonal conjugation: a practical method for the ligation of diverse functional molecules to a polyvalent virus scaffold. Bioconjug. Chem. 16, 1572-1579 (2005).
23. 18F]labelled peptides for positron emission tomography. Bioorg. Med. Chem. Lett. 10, 1501-1503 (2000). (Pubitemid 30449705)
24. 18F-labelled linear peptides. Eur. J. Nucl. Med. Mol. Imaging 29, 754-759 (2002).
25. 18F]fuoropropionyl peptides. Bioconjug. Chem. 17, 1017-1021 (2006).
26. 18F]fuorobenzylidene) aminooxyhexyl]maleimide. Nucl. Med. Biol. 34, 5-15 (2007). (Pubitemid 46038147)
27. 18F-fuorobenzamido)ethyl] maleimide, and synthesis of RGD peptide-based tracer for PET imaging of alpha v beta 3 integrin expression. J. Nucl. Med. 47, 1172-1180 (2006). (Pubitemid 47544912)
28. 18F-labeling agent. Bioconjug. Chem. 14, 1253-1259 (2003). (Pubitemid 37451774)
29. 18F]SFB). Amino Acids 36, 283-295 (2009).
30. 18F]fuoropropanethiol. Amino Acids 37, 717-724 (2009).
31. 18F]fuorinated aldehyde-containing prosthetic groups. Bioconjug. Chem. 19, 951-957 (2008). (Pubitemid 351614549)
32. 18F]fuorobenzaldehyde via oxime chemistry. Mol. Imaging Biol. 10, 177-181 (2008).
33. 18F]FDG. Bioconjug. Chem. 20, 432-436 (2009).
34. 18F-fuorinated aldehydes. Nucl. Med. Biol. 33, 173-183 (2006).
35. Olberg, D.E. et al. A novel prosthetic group for site-selective labeling of peptides for positron emission tomography. Bioconjug. Chem. 19, 1301-1308 (2008). (Pubitemid 351874953)
36. 18F-N- methylaminooxy-containing prosthetic group to a vinylsulfone modifed peptide. J. Label. Compd. Radiopharm. 52, 571-575 (2009).
37. 18F-labeling of N-amino-oxy derivatized peptides. Bioconjug. Chem. 18, 2085-2089 (2007). (Pubitemid 350220012)
38. 18F-labeling of peptides by means of an organosilicon-based fuoride acceptor. Angew. Chem. Int. Ed. Engl. 45, 6047-6050 (2006). (Pubitemid 44408699)
39. 18F radiolabeling for PET. J. Nucl. Med. 50, 991-998 (2009).
40. 18F-fuorine. J. Nucl. Med. 51, 454-461 (2010).
41. 18F labeling of peptides with a fuoride-aluminum-chelate complex. Bioconjug. Chem. 21, 1331-1340 (2010).
42. Hong, V., Presolski, S.I., Ma, C. & Finn, M.G. Analysis and optimization of copper-catalyzed azide-alkyne cycloaddition for bioconjugation. Angew. Chem. Int. Ed. Engl. 48, 9879-9883 (2009).
43. Berridge, M.S., Apana, S.M. & Hersh, J.M. Tefon radiolysis as the major source of carrier in fuorine-18. J. Label. Compd. Radiopharm. 52, 543-548 (2009).
44. 18O]water target. Nuklearmedizin 47, 116-119 (2008). (Pubitemid 351881406)
45. Kaiser, E., Colescott, R.L., Bossinger, C.D. & Cook, P.I. Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal. Biochem. 34, 595-598 (1970).
46. Patgiri, A., Menzenski, M.Z., Mahon, A.B. & Arora, P.S. Solid-phase synthesis of short α-helices stabilized by the hydrogen bond surrogate approach. Nat. Protoc. 5, 1857-1865 (2010).
47. Chan, W.C. & White, P.D. (eds.) Fmoc Solid Phase Peptide Synthesis: A Practical Approach (Oxford University Press, 2000)