Molecular imaging of cancer with copper-64 radiopharmaceuticals and positron emission tomography (PET)

Accounts of Chemical Research

Volumn 42, Issue 7, 2009, Pages 832-841

  Monica, Shokeen ^a   Anderson, Carolyn J ^a,b,c  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b University School of Medicine   (United States)

^c WASHINGTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHAVBETA5 INTEGRIN; CHELATING AGENT; COPPER; DIAGNOSTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR; RADIOPHARMACEUTICAL AGENT; SOMATOSTATIN RECEPTOR; TUMOR MARKER; VITRONECTIN RECEPTOR;

ANIMAL; ARTICLE; CHEMISTRY; HUMAN; METABOLISM; MOUSE; NEOPLASM; NUDE MOUSE; POSITRON EMISSION TOMOGRAPHY; SCINTISCANNING; TUMOR CELL CULTURE;

ANIMALS; CHELATING AGENTS; COPPER RADIOISOTOPES; HUMANS; MICE; MICE, NUDE; NEOPLASMS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTOR, EPIDERMAL GROWTH FACTOR; RECEPTORS, SOMATOSTATIN; RECEPTORS, VITRONECTIN; TUMOR CELLS, CULTURED; TUMOR MARKERS, BIOLOGICAL;

EID: 67651124762     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800255q     Document Type: Article

References (45)

1. Linder, M. C. Biochemistry of Copper; Plenum Press: New York, 1991; Vol.10H.
2. Frieden, E. Perspectives on copper biochemistry. Clin. Physiol. Biochem. 1986, 4, 11-19. (Pubitemid 16147212)
3. Zinn, K. R.; Chaudhuri, T. R.; Cheng, T. P.; Morris, J. S.; Meyer, W. A. Production of no-carrier-added Cu-64 from zinc metal irradiated under boron shielding. Cancer 1994, 73, 774-778.
4. 64: Possibility of production of no-carrieradded 61Cu and 64Cu at a small cyclotron. Appl. Radiat. Isot. 1993, 44, 575-580. (Pubitemid 23069177)
5. 64Cu using a biomedical cyclotron. Nucl. Med. Biol. 1997, 24, 35-43.
6. 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. Serum stability of 67Cu chelates: Comparison with 111In and 57Co. Nucl. Med. Biol. 1986, 13, 363-368.
7. 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. (Pubitemid 38327472)
8. 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 Cu(II) tetraazamacrocyclic complexes: Possible implications for in vivo stability. Eur. J. Inorg. Chem. 2005, 23, 4829-4833.
9. Busch, D. H. The complete coordination chemistrysOne practitioner's perspective. Chem Rev 1993, 93, 847-860.
10. 2+ complex with a tetraaza macrocyclic tetraacetate. Acta Crystallogr. 1988, C44, 1740-1742.
11. 64Cu-labeled tetrameric RGD peptide. J. Nucl. Med. 2005, 46, 1707-1718. (Pubitemid 46211595)
12. 11), a cyclized peptide analogue of α-MSH. J. Med. Chem. 2005, 48, 2985-2992. (Pubitemid 40548110)
13. 3-integrin expression. J. Nucl. Med. 2004, 45, 1776-1783. (Pubitemid 47618490)
14. Moi, M. K.; Meares, C. F.; McCall, M. J.; Cole, W. C.; DeNardo, S. J. Copper chelates as probes of biological systems: Stable copper complexes with a macrocyclic bifunctional chelating agent. Anal. Biochem. 1985, 148, 249-253.
15. Anderson, C. J.; Pajeau, T. S.; Edwards, W. B.; Sherman, E. L.; Rogers, B. E.; Welch, M. J. In vitro and in vivo evaluation of copper-64-octreotide conjugates. J. Nucl. Med. 1995, 36, 2315-2325.
16. Anderson, C. J.; Jones, L. A.; Bass, L. A.; Sherman, E. L.; McCarthy, D. W.; Cutler, P. D.; Lanahan, M. V.; Cristel, M. E.; Lewis, J. S.; Schwarz, S. W. Radiotherapy, toxicity and dosimetry of copper-64-TETA-octreotide in tumor-bearing rats. J. Nucl. Med. 1998, 39, 1944-1951.
17. 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. (Pubitemid 30597722)
18. + complexation in a diamond-lattice cleft. J. Am. Chem. Soc. 1990, 112, 8604-8605.
19. Weisman, G. R.; Wong, E. H.; Hill, D. C.; Rogers, M. E.; Reed, D. P.; Calabrese, J. C. Synthesis and transition-metal complexes of new cross-bridged tetraamine ligands. Chem. Commun. 1996, 947-948. (Pubitemid 126425147)
20. Hubin, T. J.; McCormick, J. M.; Collinson, S. R.; Alcock, N. W.; Busch, D. H. Ultra rigid cross-bridged tetraazamacrocycles as ligands-the challenge and the solution. Chem. Commun. 1998, 1675-1676.
21. Hubin, T. J.; Alcock, N. W.; Busch, D. H. The square-pyramidal PdII complex of a cross-bridged tetraazamacrocycle. Acta Crystallogr. 1999, C55, 1404-1406.
22. Wong, E. H.; Weisman, G. R.; Hill, D. C.; Reed, D. P.; Rogers, M. E.; Condon, J. P.; 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.
23. Sun, X.; Wuest, M.; Weisman, G. R.; Wong, E. H.; Reed, D. P.; Boswell, C. A.; Motekaitis, R.; Martell, A. E.; Welch, M. J.; Anderson, C. J. Radiolabeling and in vivo behavior of copper-64-labeled cross-bridged cyclam ligands. J. Med. Chem. 2002, 45, 469-477. (Pubitemid 34073464)
24. Heroux, K. J.; Woodin, K. S.; Tranchemontagne, D. J.; Widger, P. C.; Southwick, E.; Wong, E. H.; Weisman, G. R.; Tomellini, S. A.; Wadas, T. J.; Anderson, C. J.; Kassel, S.; Golen, J. A.; Rheingold, A. L. The long and short of it: The influence of Ncarboxyethyl versus N-carboxymethyl pendant arms on in vitro and in vivo behavior of copper complexes of cross-bridged tetraamine macrocycles. Dalton Trans. 2007, 2150-2162. (Pubitemid 46791134)
25. Bauer, W.; Briner, U.; Doepfner, W.; Haller, R.; Huguenin, R.; Marbach, P.; Petcher, T. J.; Pless, J. SMS 201-995: A very potent and selective octapeptide analogue of somatostatin with prolonged action. Life Sci. 1982, 31, 1133-1140 (Pubitemid 13243115)
26. Krenning, E. P.; Bakker, W. H.; Kooij, P. P.; Breeman, W. A.; Oei, H. Y.; de Jong, M.; Reubi, J. C.; Visser, T. J.; Bruns, C.; Kwekkeboom, D. J.; et al. Somatostatin receptor scintigraphy with indium-111-DTPA-D-Phe-1-octreotide in man: Metabolism, dosimetry and comparison with iodine-123-Tyr-3-octreotide. J. Nucl. Med. 1992, 33, 652-658.
27. Anderson, C. J.; Dehdashti, F.; Cutler, P. D.; Schwarz, S. W.; Laforest, R.; Bass, L. A.; Lewis, J. S.; McCarthy, D. W. 64Cu-TETA-octreotide as a PET imaging agent for patients with neuroendocrine tumors. J. Nucl. Med. 2001, 42, 213-221. (Pubitemid 32150511)
28. 64Cu-labeled somatostatin analogues in vitro and in a tumorbearing rat model: Evaluation of new derivatives for positron emission tomography imaging and targeted radiotherapy. J. Med. Chem. 1999, 42, 1341-1347. (Pubitemid 29200869)
29. de Jong, M.; Breeman, W. A.; Bakker, W. H.; Kooij, P. P.; Bernard, B. F.; Hofland, L. J.; Visser, T. J.; Srinivasan, A.; Schmidt, M. A.; Erion, J. L.; Bugaj, J. E.; Macke, H. R.; Krenning, E. P. Comparison of (111)In-labeled somatostatin analogues for tumor scintigraphy and radionuclide therapy. Cancer Res. 1998, 58, 437-441. (Pubitemid 28087403)
30. 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. (Pubitemid 40053436)
31. Wadas, T. J.; Anderson, C. J. Radiolabeling of TETA-and CB-TE2A-conjugated peptides with copper-64. Nat. Protoc. 2006, 1, 3062-3068.
32. de Jong, M.; Bakker, W. H.; Krenning, E. P.; Breeman, W. A.; van der Pluijm, M. E.; Bernard, B. F.; Visser, T. J.; Jermann, E.; Behe, M.; Powell, P.; Macke, H. R. Yttrium-90 and indium-111 labelling, receptor binding and biodistribution of [DOTA0,d-Phe1, Tyr3]octreotide, a promising somatostatin analogue for radionuclide therapy. Eur. J. Nucl. Med. 1997, 24, 368-371. (Pubitemid 27183039)
33. de Jong, M.; Bernard, B. F.; de Bruin, E.; van Gameren, A.; Bakker, W. H.; Visser, T. J.; Maecke, H. R.; Krenning, E. P. Internalization of radiolabelled [DTPA0]octreotide and [DOTA0, Tyr3]octreotide: Peptides for somatostatin receptortargeted scintigraphy and radionuclide therapy. Nucl. Med. Commun. 1998, 19, 283-288. (Pubitemid 28198201)
34. Ginj, M.; Zhang, H.; Waser, B.; Cescato, R.; Wild, D.; Wang, X.; Erchegyi, J.; Rivier, J.; Macke, H. R.; Reubi, J. C. Radiolabeled somatostatin receptor antagonists are preferable to agonists for in vivo peptide receptor targeting of tumors. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 16436-16441. (Pubitemid 44715214)
35. Wadas, T. J.; Eiblmaier, M.; Zheleznyak, A.; Sherman, C. D.; Ferdani, R.; Liang, K.; Achilefu, S.; Anderson, C. J. Preparation and biological evaluation of 64Cu-CBTE2A-sst2-ANT, a somatostatin antagonist for PET imaging of somatostatin receptor-positive tumors. J. Nucl. Med. 2008, 49, 1819-1827.
36. Laskin, J. J.; Sandler, A. B. Epidermal growth factor receptors: A promising target in solid tumors. Cancer Treat. Rev. 2004, 30, 1-17. (Pubitemid 38240085)
37. Fan, Z.; Masui, H.; Altas, I.; Mendelsohn, J. Blockage of epidermal growth factor receptor function by bivalent and monovalent fragments of C225 anti-epidermal growth factor receptor monoclonal antibodies. Cancer Res. 1993, 53, 4322-4328. (Pubitemid 24146785)
38. Li, W. P.; Meyer, L. A.; Capretto, D. A.; Sherman, C. D.; Anderson, C. J. Receptorbinding, biodistribution, and metabolism studies of 64Cu-DOTA-cetuximab, a PETimaging agent for epidermal growth-factor receptor-positive tumors. Cancer Biother. Radiopharm. 2008, 23, 158-171.
39. Eiblmaier, M.; Meyer, L. A.; Watson, M. A.; Fracasso, P. M.; Pike, L. J.; Anderson, C. J. Correlating EGFR expression with receptor-binding properties and internalization of 64Cu-DOTA-cetuximab in 5 cervical cancer cell lines. J. Nucl. Med. 2008, 49, 1472-1479.
40. Hood, J. D.; Cheresh, D. A. Role of integrins in cell invasion and migration. Nat. Rev. Cancer 2002, 2, 91-100. (Pubitemid 37328796)
41. Haubner, R.; Decristoforo, C. Radiolabelled RGD peptides and peptidomimetics for tumour targeting. Front. Biosci. 2009, 14, 872-886.
42. Horton, M. A. The alpha v beta 3 integrin "vitronectin receptor". Int. J. Biochem. Cell Biol. 1997, 29, 721-725.
43. Sprague, J. E.; Kitaura, H.; Zou, W.; Ye, Y.; Achilefu, S.; Weilbaecher, K. N.; Teitelbaum, S. L.; Anderson, C. J. Noninvasive imaging of osteoclasts in parathyroid hormone-induced osteolysis using a 64Cu-labeled RGD peptide. J. Nucl. Med. 2007, 48, 311-318. (Pubitemid 47555359)
44. Yates, A. J.; Gutierrez, G. E.; Smolens, P.; Travis, P. S.; Katz, M. S.; Aufdemorte, T. B.; Boyce, B. F.; Hymer, T. K.; Poser, J. W.; Mundy, G. R. Effects of a synthetic peptide of a parathyroid hormone-related protein on calcium homeostasis, renal tubular calcium reabsorption, and bone metabolism in vivo and in vitro in rodents. J. Clin. Invest. 1988, 81, 932-938. (Pubitemid 18079748)
45. Jones-Wilson, T. M.; Deal, K. A.; Anderson, C. J.; McCarthy, D. W.; Kovacs, Z.; Motekaitis, R. J.; Sherry, A. D.; Martell, A. E.; Welch, M. J. The in vivo behavior of copper-64-labeled azamacrocyclic compounds. Nucl. Med. Biol. 1998, 25, 523-530. (Pubitemid 28378424)