Enhanced aqueous Suzuki-Miyaura coupling allows site-specific polypeptide 18F-labeling

Journal of the American Chemical Society

Volumn 135, Issue 37, 2013, Pages 13612-13615

  Gao, Zhanghua ^a   Gouverneur, Véronique ^a   Davis, Benjamin G ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE-18; LIGAND SYSTEM; PROTEIN CHEMISTRY; RADIOLABELING; SITE-SPECIFIC; SMALL MOLECULES; SUZUKI-MIYAURA COUPLING; SUZUKI-MIYAURA CROSS-COUPLING;

LIGANDS; PALLADIUM; PROTEINS;

CHEMICAL REACTIONS;

4 FLUOROPHENYLBORONIC ACID F 18; FLUORINE 18; GUANIDINE; PALLADIUM; POLYPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DECOMPOSITION; GEL PERMEATION CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; RADIOCHEMISTRY; REACTION TIME; STOICHIOMETRY; SUZUKI REACTION;

BORONIC ACIDS; CATALYSIS; FLUORINE RADIOISOTOPES; HYDROCARBONS, FLUORINATED; ISOTOPE LABELING; LIGANDS; METHYLGUANIDINE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PALLADIUM; PEPTIDES; WATER;

EID: 84884469595     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja4049114     Document Type: Article

References (45)

1. Wester, H. J.; Schottelius, M. In PET Chemistry: The Driving Force in Molecular Imaging; Schubiger, P. A., Lehmann, L., Friebe, M., Eds.; Springer: Berlin, 2007; pp 79-111.
2. Reubi, J. C.; Maecke, H. R. J. Nucl. Med. 2008, 49, 1735-1738
3. Lee, S.; Xie, J.; Chen, X. Chem. Rev. 2010, 110, 3087-3111
4. Tolmachev, V.; Stone-Elander, S. Biochim. Biophys. Acta 2010, 1800, 487-510
5. Wu, Z.; Kandeel, F. Curr. Pharm. Biotechnol. 2010, 11, 572-580
6. Smith, T. A. D. J. Labeled Compds. Radiopharm. 2012, 55, 281-288
7. Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501-1516
8. Cai, W.; Olafsen, T.; Zhang, X.; Cao, Q.; Gambhir, S. S.; Williams, L. E.; Wu, A. M.; Chen, X. J. Nucl. Med. 2007, 48, 304-310
9. Kostikov, A. P.; Chin, J.; Orchowski, K.; Schirrmacher, E.; Niedermoser, S.; Jurkschat, K.; Iovkova-Berends, L.; Wängler, C.; Wängler, B.; Schirrmacher, R. Nat. Protoc. 2012, 7, 1956-1963
10. Lang, L.; Eckelman, W. C. Appl. Radiat. Isot. 1997, 48, 169-173
11. Lang, L. X.; Eckelman, W. C. Appl. Radiat. Isot. 1994, 45, 1155-1163
12. Jeon, J.; Shen, B.; Xiong, L.; Miao, Z.; Lee, K. H.; Rao, J.; Chin, F. T. Bioconjugate Chem. 2012, 23, 1902-1908
13. Wängler, B.; Kostikov, A. P.; Niedermoser, S.; Chin, J.; Orchowski, K.; Schirrmacher, E.; Iovkova-Berends, L.; Jurkschat, K.; Wängler, C.; Schirrmacher, R. Nat. Protoc. 2012, 7, 1964-1969
14. Wuest, F.; Berndt, M.; Bergmann, R.; van den Hoff, J.; Pietzsch, J. Bioconjugate Chem. 2008, 19, 1202-1210
15. Chang, Y. S.; Jeong, J. M.; Lee, Y.-S.; Kim, H. W.; Rai, G. B.; Lee, S. J.; Lee, D.; Chung, J.; Lee, M. C. Bioconjugate Chem. 2005, 16, 1329-33
16. Cheng, Z.; De Jesus, O. P.; Namavari, M.; De, A.; Levi, J.; Webster, J. M.; Zhang, R.; Lee, B.; Syud, F. A.; Gambhir, S. S. J. Nucl. Med. 2008, 49, 804-813
17. Namavari, M.; Padilla De Jesus, O.; Cheng, Z.; De, A.; Kovacs, E.; Levi, J.; Zhang, R.; Hoerner, J.; Grade, H.; Syud, F.; Gambhir, S. Mol. Imaging Biol. 2008, 10, 177-181
18. Ramenda, T.; Kniess, T.; Bergmann, R.; Steinbach, J.; Wuest, F. Chem. Commun. 2009, 7521-7523
19. Gill, H. S.; Marik, J. Nat. Protoc. 2011, 6, 1718-1725
20. Sachin, K.; Jadhav, V. H.; Kim, E.-M.; Kim, H. L.; Lee, S. B.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Kim, D. W. Bioconjugate Chem. 2012, 23, 1680-1686
21. Liu, S.; Hassink, M.; Selvaraj, R.; Yap, L.-P.; Park, R.; Wang, H.; Chen, X.; Fox, J. M.; Li, Z.; Conti, P. S. Mol. Imaging 2013, 12, 121-8
22. Ting, R.; Adam, M. J.; Ruth, T. J.; Perrin, D. M. J. Am. Chem. Soc. 2005, 127, 13094-13095
23. Laverman, P.; McBride, W. J.; Sharkey, R. M.; Eek, A.; Joosten, L.; Oyen, W. J. G.; Goldenberg, D. M.; Boerman, O. C. J. Nucl. Med. 2010, 51, 454-461
24. Flavell, R. R.; Kothari, P.; Bar-Dagan, M.; Synan, M.; Vallabhajosula, S.; Friedman, J. M.; Muir, T. W.; Ceccarini, G. J. Am. Chem. Soc. 2008, 130, 9106-9112
25. Boutureira, O.; D'Hooge, F.; Fernandez-Gonzalez, M.; Bernardes, G. J. L.; Sanchez-Navarro, M.; Koeppe, J. R.; Davis, B. G. Chem. Commun. 2010, 46, 8142-8144
26. Chalker, J. M.; Bernardes, G. J. L.; Davis, B. G. Acc. Chem. Res. 2011, 44, 730-741
27. Chalker, J. M.; Wood, C. S. C.; Davis, B. G. J. Am. Chem. Soc. 2009, 131, 16346-7
28. Spicer, C. D.; Davis, B. G. Chem. Commun. 2011, 47, 1698-1700
29. Spicer, C. D.; Triemer, T.; Davis, B. G. J. Am. Chem. Soc. 2012, 134, 800-803
30. Dumas, A.; Spicer, C. D.; Gao, Z.; Takehana, T.; Lin, Y. A.; Yasukohchi, T.; Davis, B. G. Angew. Chem., Int. Ed. 2013, 52, 3916-3921
31. Spicer, C. D.; Davis, B. G. Chem. Commun. 2013, 49, 2747-2749
32. Knust, E. J.; Kupfernagel, C.; Müller-Platz, C.; Stöcklin, G. J. Fluorine Chem. 1980, 16, 535-536
33. Gao, Z.; Lim, Y. H.; Tredwell, M.; Li, L.; Verhoog, S.; Hopkinson, M.; Kaluza, W.; Collier, T. L.; Passchier, J.; Huiban, M.; Gouverneur, V. Angew. Chem., Int. Ed. 2012, 51, 6733-6737
34. Li, N.; Lim, R. K. V.; Edwardraja, S.; Lin, Q. J. Am. Chem. Soc. 2011, 133, 15316-15319
35. Li, S.; Lin, Y.; Cao, J.; Zhang, S. J. Org. Chem. 2007, 72, 4067-4072
36. Cutrera, J.; Dibra, D.; Xia, X.; Hasan, A.; Reed, S.; Li, S. Mol. Therapy 2011, 19, 1468-1477
37. Cardinale, J.; Ermert, J.; Coenen, H. H. Tetrahedron 2012, 68, 4112-4116
38. Ross, T. L.; Ermert, J.; Hocke, C.; Coenen, H. H. J. Am. Chem. Soc. 2007, 129, 8018-8025
39. Wüst, F. R.; Kniess, T. J. Labeled Compds. Radiopharm. 2003, 46, 699-713
40. Wüst, F. R.; Kniess, T. J. Labeled Compds. Radiopharm. 2004, 47, 457-468
41. Marcuccio, S. M.; Rodopoulos, M.; Weigold, H. (CSIRO, Australia). PCT WO9912940A1, 1999.
42. Molander, G. A.; Trice, S. L. J.; Dreher, S. D. J. Am. Chem. Soc. 2010, 132, 17701-17703
43. Molander, G. A.; Trice, S. L. J.; Kennedy, S. M.; Dreher, S. D.; Tudge, M. T. J. Am. Chem. Soc. 2012, 134, 11667-11673
44. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510
45. Steiniger, B.; Wuest, F. R. J. Labeled Compds. Radiopharm. 2006, 49, 817-827