Synthesis and Evaluation of New Generation Cross-Bridged Bifunctional Chelator for 64Cu Radiotracers

Inorganic Chemistry

Volumn 54, Issue 17, 2015, Pages 8177-8186

  Dale, Ajit V ^a   An, Gwang Il ^b   Pandya, Darpan N ^a   Ha, Yeong Su ^a   Bhatt, Nikunj ^a   Soni, Nisarg ^a   Lee, Hochun ^c   Ahn, Heesu ^a   Sarkar, Swarbhanu ^a   Lee, Woonghee ^a   Huynh, Phuong Tu ^a   Kim, Jung Young ^b   Gwon, Mi Ri ^a   Kim, Sung Hong ^d   Park, Jae Gyu ^e   Yoon, Young Ran ^a   Yoo, Jeongsoo ^a  

^a Kyungpook National University   (South Korea)

^b Korea Institute of Radiation and Medical Science   (South Korea)

^c Daegu Gyeongbuk Institute of Science and Technology   (South Korea)

^d Korea Basic Science Institute (KBSI)   (South Korea)

^e Pohang Center of Evolution of Biomaterials   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATING AGENT; COPPER; ORGANOMETALLIC COMPOUND; RADIOPHARMACEUTICAL AGENT;

ANIMAL; ANIMAL MODEL; BAGG ALBINO MOUSE; CHEMICAL STRUCTURE; CHEMISTRY; MALE; MOUSE; POSITRON EMISSION TOMOGRAPHY; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; CHELATING AGENTS; COPPER RADIOISOTOPES; MALE; MICE; MICE, INBRED BALB C; MODELS, ANIMAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION;

EID: 84941236284     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/acs.inorgchem.5b01386     Document Type: Article

References (43)

1. Burke, B. P.; Archibald, S. J. Annu. Rep. Prog. Chem., Sect. A: Inorg. Chem. 2013, 109, 232-253 10.1039/c3ic90032k
2. Abiraj, K.; Jaccard, H.; Kretzschmar, M.; Helm, L.; Maecke, H. R. Chem. Commun. 2008, 3248-3250 10.1039/b805281f
3. Mansi, R.; Wang, X.; Forrer, F.; Kneifel, S.; Tamma, M.; Waser, B.; Cescato, R.; Reubi, J. C.; Maecke, H. R. Clin. Cancer Res. 2009, 15 (16) 5240-5249 10.1158/1078-0432.CCR-08-3145
4. Gaynor, D.; Griffith, D. M. Dalton Trans. 2012, 41, 13239-13257 10.1039/c2dt31601c
5. Cai, Z.; Anderson, C. J. J. Labelled Compd. Radiopharm. 2014, 57, 224-230 10.1002/jlcr.3165
6. Wadas, T. J.; Anderson, C. J.; Wong, E. H.; Weisman, G. R. Chem. Rev. 2008, 52, 185-192 10.1021/cr900325h
7. Shokeen, M.; Wadas, T. J. Med. Chem. 2011, 7, 413-429 10.2174/157340611796799177
8. Price, E. W.; Orvig, C. Chem. Soc. Rev. 2014, 43, 260-290 10.1039/C3CS60304K
9. Ramogida, C. F.; Orvig, C. Chem. Commun. 2013, 49, 4720-4739 10.1039/c3cc41554f
10. Bartholomä, M. D. Inorg. Chim. Acta 2012, 389, 36-51 10.1016/j.ica.2012.01.061
11. 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 10.1021/bc300037w
12. Stasiuk, G. J.; Long, N. J. Chem. Commun. 2013, 49, 2732-2746 10.1039/c3cc38507h
13. Anderson, C. J.; Dehdashti, F.; Cutler, P. D.; Schwarz, S. W.; Laforest, R.; Bass, L. A.; Lewis, J. S.; McCarthy, D. W. J. Nucl. Med. 2001, 42, 213-221
14. Prasanphanich, A. F.; Nanda, P. K.; Rold, T. L.; Ma, L.; Lewis, M. R.; Garrison, J. C.; Hoffman, T. J.; Sieckman, G. L.; Figueroa, S. D.; Smith, C. J. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 12462-12467 10.1073/pnas.0705347104
15. Pandya, D. N.; Kim, J. Y.; Park, J. C.; Lee, H.; Phapale, P. B.; Kwak, W.; Choi, T. H.; Cheon, G. J.; Yoon, Y. R.; Yoo, J. Chem. Commun. 2010, 46, 3517-3519 10.1039/b925703a
16. Pandya, D. N.; Bhatt, N.; Dale, A. V.; Kim, J. Y.; Lee, H.; Ha, Y. S.; Lee, J. E.; An, G. I.; Yoo, J. Bioconjugate Chem. 2013, 24, 1356-1366 10.1021/bc400192a
17. Wadas, T. J.; Anderson, C. J. Nat. Protoc. 2007, 1, 3062-3068 10.1038/nprot.2006.431
18. Pandya, D. N.; Dale, A. V.; Kim, J. Y.; Lee, H.; Ha, Y. S.; An, G. I.; Yoo, J. Bioconjugate Chem. 2012, 23, 330-335 10.1021/bc200539t
19. Pandya, D. N.; Bhatt, N.; An, G. I.; Ha, Y. S.; Soni, N.; Lee, H.; Lee, Y. J.; Kim, J. Y.; Lee, W.; Ahn, H.; Yoo, J. J. Med. Chem. 2014, 57, 7234-7243 10.1021/jm500348z
20. Ferdani, R.; Stigers, D. J.; Fiamengo, A. L.; Wei, L.; Li, B. T.; Golen, J. A.; Rheingold, A. L.; Weisman, G. R.; Wong, E. H.; Anderson, C. J. Dalton Trans. 2012, 41, 1938-1950 10.1039/C1DT11743B
21. Zeng, D.; Ouyang, Q.; Cai, Z.; Xie, X. Q.; Anderson, C. J. Chem. Commun. 2014, 50, 43-45 10.1039/C3CC45928D
22. Lewis, M. R.; Boswell, A.; Laforest, R.; Buettner, T. L.; Ye, D.; Connett, J. M.; Anderson, C. J. Cancer Biother.Radiopharm. 2001, 16, 483-494 10.1089/10849780152752083
23. Smith-Jones, P. M.; Fridrich, R.; Kaden, T. A.; Novak-Hofer, I.; Siebold, K.; Tschudin, D.; Maecke, H. R. Bioconjugate Chem. 1991, 2, 415-421 10.1021/bc00012a006
24. Parker, D. Chem. Soc. Rev. 1990, 19, 271-291 10.1039/cs9901900271
25. Cox, J. P. L.; Craig, A. S.; Helps, I. M.; Jankowski, K. J.; Parker, D.; Eaton, M. A. W.; Millican, A. T.; Millar, K.; Beeley, N. R. A.; Boyce, B. A. J. Chem. Soc., Perkin Trans. 1 1990, 2567-2576 10.1039/p19900002567
26. Bass, L. A.; Wang, M.; Welch, M. J.; Anderson, C. J. Bioconjugate Chem. 2000, 11, 527-532 10.1021/bc990167l
27. Boswell, C. A.; Sun, X.; Niu, W.; Weisman, G. R.; Wong, E. H.; Rheingold, A. L.; Anderson, C. J. J. Med. Chem. 2004, 47, 1465-1474 10.1021/jm030383m
28. Di Bartolo, N. M.; Sargeson, A. M.; Donlevy, T. M.; Smith, S. V. J. Chem. Soc., Dalton Trans. 2001, 2303-2309 10.1039/b103242a
29. Ferreira, C. L.; Yapp, D. T.; Lamsa, E.; Gleave, M.; Bensimon, C.; Jurek, P.; Kiefer, G. E. Nucl. Med. Biol. 2008, 35, 875-882 10.1016/j.nucmedbio.2008.09.001
30. Boros, E.; Rybak-Akimova, E.; Holland, J. P.; Rietz, T.; Rotile, N.; Blasi, F.; Day, H.; Latifi, R.; Caravan, P. Mol. Pharmaceutics 2014, 11 (2) 617-629 10.1021/mp400686z
31. Royal, G.; Dahaoui-Gindrey, V.; Dahaoui, S.; Tabard, A.; Guilard, R.; Pullumbi, P.; Lecomte, C. Eur. J. Org. Chem. 1998, 1998, 1971-1975 10.1002/(SICI)1099-0690(199809)1998:9<1971::AID-EJOC1971>3.3.CO;2-4
32. Woodin, K. S.; Heroux, K. J.; Boswell, C. A.; Wong, E. H.; Weisman, G. R.; Niu, W.; Tomellini, S. A.; Anderson, C. J.; Zakharov, L. N.; Rheingold, A. L. Eur. J. Inorg. Chem. 2005, 2005, 4829-4833 10.1002/ejic.200500579
33. Dale, A. V.; Pandya, D. N.; Kim, J. Y.; Lee, H.; Ha, Y. S.; Bhatt, N.; Kim, J.; Seo, J. J.; Lee, W.; Kim, S. H.; Yoon, Y.-R.; An, G. I.; Yoo, J. ACS Med. Chem. Lett. 2013, 4, 927-931 10.1021/ml400142s
34. Maheshwari, V.; Dearling, J. L. J.; Treves, S. T.; Packard, A. B. Inorg. Chim. Acta 2012, 393, 318-323 10.1016/j.ica.2012.07.012
35. Juran, S.; Walther, M.; Stephan, H.; Bergmann, R.; Steinbach, J.; Kraus, W.; Emmerling, F.; Comba, P. Bioconjugate Chem. 2009, 20, 347-359 10.1021/bc800461e
36. Ferreira, C. L.; Holley, I.; Bensimon, C.; Jurek, P.; Kiefer, G. E. Mol. Pharmaceutics 2012, 9, 2180-2186 10.1021/mp300024c
37. Sun, X.; Wuest, M.; Kovacs, Z.; Sherry, A. D.; Motekaitis, R.; Wang, Z.; Martell, A. E.; Welch, M. J.; Anderson, C. J. JBIC, J. Biol. Inorg. Chem. 2003, 8, 217-225 10.1007/s00775-002-0408-5
38. Tanwar, J.; Datta, A.; Tiwari, A. K.; Thirumal, M.; Chuttani, K.; Mishra, A. K. Bioconjugate Chem. 2011, 22, 244-255 10.1021/bc100382c
39. Gano, L.; Marques, F.; Campello, M. P.; Balbina, M.; Lacerda, S.; Santos, I. Q. J. Nucl. Med. Mol. Imaging 2007, 51, 6-15
40. Vitha, T.; Kubicek, V.; Hermann, P.; Elst, L. V.; Muller, R. N.; Kolar, Z. I.; Wolterbeek, H. T.; Breeman, W. A. P.; Lukes, I.; Peters, J. A. J. Med. Chem. 2008, 51, 677-683 10.1021/jm7012776
41. Forsterova, M.; Jandurova, Z.; Marques, F.; Gano, L.; Lubal, P.; Vanek, J.; Hermann, P.; Santos, I. J. Inorg. Biochem. 2008, 102, 1531-1540 10.1016/j.jinorgbio.2008.02.002
42. Yoo, J.; Reichert, D. E.; Welch, M. J. J. Med. Chem. 2004, 47, 6625-6637 10.1021/jm0496990
43. Sprague, J. E.; Peng, Y.; Sun, X.; Weisman, G. R.; Wong, E. H.; Achilefu, S.; Anderson, C. J. Clin. Cancer Res. 2004, 10, 8674-8682 10.1158/1078-0432.CCR-04-1084