A one-pot three-component radiochemical reaction for rapid assembly of 125I-labeled molecular probes

Journal of the American Chemical Society

Volumn 135, Issue 2, 2013, Pages 703-709

  Yan, Ran ^a,d   Sander, Kerstin ^a   Galante, Eva ^a   Rajkumar, Vineeth ^b   Badar, Adam ^c   Robson, Mathew ^b   El Emir, Ethaar ^b   Lythgoe, Mark F ^c   Pedley, R Barbara ^b   Årstad, Erik ^a,d  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

^d ST THOMAS HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY CONJUGATE; BIO-CONJUGATION; BIOLOGICAL EVALUATION; BUILDING BLOCKES; COMBINATORIAL APPROACH; DEIODINATION; FLUORESCENT DYES; FUNCTIONALIZED; IN-VIVO; MEDIATED REACTIONS; MOLECULAR PROBES; NONINVASIVE MEASUREMENTS; NUCLEAR IMAGING; ONE POT; THREE-COMPONENT;

ACETYLENE; BIOACTIVITY; MOLECULAR BIOLOGY; NITROGEN COMPOUNDS;

PROBES;

5[125 IODINE]IODO 1,2,3 TRIAZOLE DERIVATIVE; ALKYNE; ANTIBODY CONJUGATE; AZIDE; FLUORESCENT DYE; IODINE 125; RADIOISOTOPE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CHEMICAL REACTION; CONJUGATION; DEIODINATION; IN VIVO STUDY; ISOTOPE LABELING; MOLECULAR IMAGING; MOLECULE; MOUSE; NONHUMAN; ONE POT SYNTHESIS; RADIOCHEMISTRY; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

IODINE RADIOISOTOPES; MOLECULAR PROBES; MOLECULAR STRUCTURE; RADIOCHEMISTRY; TIME FACTORS; TRIAZOLES;

EID: 84872523757     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307926g     Document Type: Article

References (31)

1. Adam, M. J.; Wilbur, D. S. Chem. Soc. Rev. 2005, 34, 153-163
2. Seevers, R. H.; Counsell, R. E. Chem. Rev. 1982, 82, 575-590
3. Årstad, E.; Hoff, P.; Skattebøl, L.; Skretting, A.; Breistøl, K. J. Med. Chem. 2003, 46, 3021-3032
4. Vaidyanathan, G.; Zalutsky, M. R. Nat. Protoc. 2007, 2 (2) 282-286
5. Wu, Y. M.; Deng, J.; Li, Y.; Chen, Q. Y. Synthesis 2005, 18, 1314-1318
6. Yan, R.; El-Emir, E.; Rajkumar, V.; Robson, M.; Jathoul, A. P.; Pedley, R. B.; Årstad, E. Angew. Chem., Int. Ed. 2011, 50, 6793-6795
7. Kele, P.; Li, X.; Link, M.; Nagy, K.; Herner, A.; Krisztián, L.; Béni, S.; Wolfbeis, O. S. Org. Biomol. Chem. 2009, 7, 3486-3490
8. Stephen, A.; Hashmi, K.; Molinari, L.; Rominger, F.; Oeser, T. Eur. J. Org. Chem. 2011, 12, 2256-2264
9. Link, M.; Li, X.; Kleim, J.; Wolfbeis, O. S. Eur. J. Org. Chem. 2010, 36, 6922-6927
10. Glaser, M.; Årstad, E. Bioconjugate Chem. 2007, 18 (3) 989-993
11. Li, L.; Zhang, G.; Zhu, A.; Zhang, L. J. Org. Chem. 2008, 73, 3630-3633
12. Hein, J. E.; Tripp, J. C.; Krasnova, L. B.; Sharpless, K. B.; Fokin, V. V. Angew. Chem., Int. Ed. 2009, 48, 8018-8021
13. Zhou, Y.; Kim, Y. S.; Yan, X.; Jacobson, O.; Chen, X.; Liu, S. Mol. Pharm. 2011, 8, 1198-1208
14. Lesch, H. P.; Kaikkonen, M. U.; Pikkarainen, J. T.; Yla-Herttuala, S. Expert Opin. Drug Delivery 2010, 7 (5) 551-564
15. Mohsin, H.; Jia, F.; Bryan, J. N.; Sivaguru, G.; Cutler, C. S.; Ketring, A. R.; Miller, W. H.; Simón, J.; Frank, R. K.; Theodore, L. J.; Axworthy, D. B.; Jurisson, S. S.; Lewis, M. R. Bioconjugate Chem. 2011, 22, 2444-2452
16. Okamura, T.; Kikuchi, T.; Okada, M.; Toramatsu, C.; Fukushi, K.; Takei, M.; Irie, T. J. Cereb. Blood Flow Metab. 2009, 29, 504-511
17. Okamura, T.; Kikuchi, T.; Toramatsu, C.; Fuku-shi, K.; Irie, T. J. Med. Chem. 2009, 52, 7284-7288
18. Yoke, J. T.; Weiss, J. F.; Tollin, G. Inorg. Chem. 1963, 2 (6) 1210-1216
19. Weiss, J. F.; Tollin, G.; Yoke, J. T. Inorg. Chem. 1964, 3 (10) 1344-1348
20. Spiteri, C.; Moses, J. E. Angew. Chem., Int. Ed. 2010, 49, 31-33
21. Buckley, B. R.; Dann, S. E.; Heaney, H. Chem.-Eur. J. 2010, 16, 6278-6284
22. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39 (4) 1302-1315
23. Brotherton, W. S.; Clark, R. J.; Zhu, L. J. Org. Chem. 2012, 77, 6443-6455
24. El-Emir, E.; Qureshi, U.; Dearling, J. L. J.; Boxer, G. M.; Clatworthy, I.; Folarin, A. A.; Robson, M. P.; Konerding, M. A.; Nagl, S.; Pedley, R. B. Cancer Res. 2007, 67, 11896-11905
25. Fidarova, E. F.; El-Emir, E.; Boxer, G. M.; Qureshi, U.; Robson, M. P.; Dearling, J. L. J.; Trott, K. R.; Begent, R. H. J.; Pedley, R. B. Clin. Cancer Res. 2008, 14, 2639-2646
26. Meyer, T.; Gaya, A. M.; Dancey, G.; Stratford, M. R. L.; Othman, S.; Sharma, S. K.; Wellsted, D.; Taylor, N. J.; Stirling, J. J.; Poupard, L.; Folkes, L. K.; Chan, P.-S.; Pedley, R. B.; Chester, K. A.; Owen, K.; Violet, J. A.; Malaroda, A.; Green, A. J.; Buscombe, J.; Padhani, A. R.; Rustin, G. J.; Begent, R. H. Clin. Cancer Res. 2009, 15, 4484-4492
27. Cooper, M. S.; Ma, M. T.; Sunassee, K.; Shaw, K. P.; Williams, J. D.; Paul, R. L.; Donnelly, P. S.; Blower, P. J. Bioconjugate Chem. 2012, 23, 1029-1039
28. Tjuvajev, J. G.; Doubrovin, M.; Akhurst, T.; Cai, S. D.; Balatoni, J.; Alauddin, M. M.; Finn, R.; Bornmann, W.; Thaler, H.; Conti, P. S.; Blasberg, R. G. J. Nucl. Med. 2002, 43 (8) 1072-1083
29. Kim, E. J.; Hong, S. H.; Choi, T. H.; Lee, E. A.; Kim, K. M.; Lee, K. C.; An, G. I.; El-Gamal, M. I.; Cheon, G. J.; Choi, C. W.; Lim, S. M. Appl. Radiat. Isot. 2010, 68 (6) 971-978
30. Darwish, A.; Blacker, M.; Janzen, N.; Rathmann, S. M.; Czorny, S.; Hillier, S. M.; Joyal, J. L.; Babich, J. W.; Valliant, J. F. ACS Med. Chem. Lett. 2012, 3 (4) 313-316
31. Årstad, E.; Yan, R. Processes for producing radiohalogenated bioconjugates and products thereof. WO/2012/022932 (A1), 2012.