Non-cross-bridged tetraazamacrocyclic chelator for stable 64Cu-based radiopharmaceuticals

ACS Medicinal Chemistry Letters

Volumn 4, Issue 10, 2013, Pages 927-931

  Dale, Ajit V ^a   Pandya, Darpan N ^a   Kim, Jung Young ^b   Lee, Hochun ^c   Ha, Yeong Su ^a   Bhatt, Nikunj ^a   Kim, Jonghee ^a   Seo, Jeong Ju ^a   Lee, Woonghee ^a   Kim, Sung Hong ^d   Yoon, Young Ran ^a   An, Gwang Il ^b   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)

Author keywords

Bifunctional chelator; copper complex; imaging agent; radiopharmaceutical

Indexed keywords

COPPER 64; MACROCYCLIC COMPOUND;

ARTICLE; ISOTOPE LABELING; PRIORITY JOURNAL;

EID: 84885462532     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400142s     Document Type: Article

References (29)

1. Wadas, T. J.; Wong, E. H.; Weisman, G. R.; Anderson, C. J. Coordinating radiometals of copper, gallium, indium, yttrium, and zirconium for PET and SPECT imaging of disease Chem. Rev. 2010, 110, 2858-2902
2. Zeglis, B. M.; Lewis, J. S. A practical guide to the construction of radiometallated bioconjugates for positron emission tomography Dalton Trans. 2011, 40, 6168-6195
3. Bhattacharyya, S.; Dixit, M. Metallic radionuclides in the development of diagnostic and therapeutic radiopharmaceuticals Dalton Trans. 2011, 40, 6112-6128
4. Paterson, B. M.; Donnelly, P. S. Copper complexes of bis(thiosemicarbazones): from chemotherapeutics to diagnostic and therapeutic radiopharmaceuticals Chem. Soc. Rev. 2011, 40, 3005-3018
5. Anderson, C. J.; Ferdani, R. Copper-64 radiopharmaceuticals for PET imaging of cancer: advances in preclinical and clinical research Cancer Biother. Radiopharm. 2009, 24, 379-393
6. Mewis, R. E.; Archibald, S. J. Biomedical applications of macrocyclic ligand complexes Coord. Chem. Rev. 2010, 254, 1686-1712
7. Wadas, T. J.; Wong, E. H.; Weisman, G. R.; Anderson, C. J. Copper chelation chemistry and its role in copper radiopharmaceuticals Curr. Pharm. Des. 2007, 13, 3-16
8. Bartholomä, M. D. Recent developments in the design of bifunctional chelators for metal-based radiopharmaceuticals used in positron emission tomography Inorg. Chim. Acta 2012, 389, 36-51
9. Liu, S. Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides Adv. Drug Delivery Rev. 2008, 60, 1347-1370
10. 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. Kinetic inertness and electrochemical behavior of copper(II) tetraazamacrocyclic complexes: possible implications for in vivo stability Eur. J. Inorg. Chem. 2005, 2005, 4829-4833
11. Cole, W. C.; DeNardo, S. J.; Meares, C. F.; McCall, M. J.; DeNardo, G. L.; Epstein, A. L.; O'Brien, H. A.; Moi, M. K. Comparative serum stability of radiochelates for antibody radiopharmaceuticals J. Nucl. Med. 1987, 28, 83-90
12. Bass, L. A.; Wang, M.; Welch, M. J.; Anderson, C. J. In vivo transchelation of copper-64 from TETA-octreotide to superoxide dismutase in rat liver Bioconjugate Chem. 2000, 11, 527-532
13. Boswell, C. A.; Sun, X.; Niu, W.; Weisman, G. R.; Wong, E. H.; Rheingold, A. L.; Anderson, C. J. Comparative in vivo stability of copper-64-labeled cross-bridged and conventional tetraazamacrocyclic complexes J. Med. Chem. 2004, 47, 1465-1474
14. Wong, E. H.; Weisman, G. R.; Hill, D. C.; Reed, D. P.; Rogers, M. E.; Condon, J. S.; Fagan, M. A.; Calabrese, J. C.; Lam, K.-C.; Guzei, I. A.; Rheingold, A. L. Synthesis and characterization of cross-bridged cyclams and pendant-armed derivatives and structural studies of their copper(II) complexes J. Am. Chem. Soc. 2000, 122, 10561-10572
15. Wadas, T. J.; Anderson, C. J. Radiolabeling of TETA- and CB-TE2A-conjugated peptides with copper-64 Nat. Protoc. 2006, 1, 3062-3068
16. 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. Revival of TE2A; a better chelate for Cu(II) ions than TETA? Chem. Commun. 2010, 46, 3517-3519
17. 2+ complex of 1,4,8,11-tetra-azacyclotetradecane-1,8-diacetic acid and the tricyclic lactam 15,18-dioxo-1,5,8,12-tetra-azatricyclo[10.2.2.25.8]tetradecane J. Chem. Soc., Chem. Commun. 1988, 16, 1094-1095
18. Chapman, J.; Ferguson, G.; Gallagher, J. F.; Jennings, M. C.; Parker, D. Copper and nickel complexes of 1,8-disubstituted derivatives of 1,4,8,11-tetraazacyclotetradecane J. Chem. Soc., Dalton Trans. 1992, 3, 345-353
19. Silversides, J. D.; Allan, C. C.; Archibald, S. J. Copper(II) cyclam-based complexes for radiopharmaceutical applications: synthesis and structural analysis Dalton Trans. 2007, 9, 971-978
20. Comparone, A.; Kaden, T. A. Copper(II) and nickel(II) complexes of trans-difunctionalized tetraaza macrocycles Helv. Chim. Acta 1998, 81, 1765-1772
21. 64Cu-radiolabeled bioconjugate Bioconjugate Chem. 2012, 23, 330-335
22. Royal, G.; Dahaoui-Gindrey, V.; Dahaoui, S.; Tabard, A.; Guilard, R.; Pullumbi, P.; Lecomte, C. New synthesis of trans-disubstituted cyclam macrocycles: elucidation of the disubstitution mechanism on the basis of X-ray data and molecular modeling Eur. J. Org. Chem. 1998, 1998, 1971-1975
23. 64Cu radiopharmaceuticals Nucl. Med. Biol. 2010, 37, 57-65
24. (177)Lu Inorg. Chem. 2012, 51, 12575-12589
25. 64Cu-labeled monocationic Copper(II) complex Nucl. Med. Biol. 2002, 29, 289-294
26. Yoo, J.; Reichert, D. E.; Welch, M. J. Comparative in vivo behavior studies of cyclen-based copper-64 complexes: regioselective synthesis, X-ray structure, radiochemistry, log P, and biodistribution J. Med. Chem. 2004, 47, 6625-6637
27. Kent Barefield, E. Coordination chemistry of N-tetraalkylated cyclam ligands: A status report Coord. Chem. Rev. 2010, 254, 1607-1627
28. Sprague, J. E.; Peng, Y.; Sun, X.; Weisman, G. R.; Wong, E. H.; Achilefu, S.; Anderson, C. J. Preparation and biological evaluation of copper-64-labeled Tyr3-octreotate using a cross-bridged macrocyclic chelator Clin. Cancer Res. 2004, 10, 8674-8682
29. Sprague, J. E.; Peng, Y.; Fiamengo, A. L.; Woodin, K. S.; Southwick, E. A.; Weisman, G. R.; Wong, E. H.; Golen, J. A.; Rheingold, A. L.; Anderson, C. J. Synthesis, characterization and in vivo studies of Cu(II)-64-labeled cross-bridged tetraazamacrocycle-amide complexes as models of peptide conjugate imaging agents J. Med. Chem. 2007, 50, 2527-2535