Recent advances in copper radiopharmaceuticals

Current Radiopharmaceuticals

Volumn 4, Issue 2, 2011, Pages 109-121

  Hao, Guiyang ^a   Singh, Ajay N ^a   Öz, Orhan K ^a   Sun, Xiankai ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

And molecular imaging; Bifunctional chelator; Copper radioisotope; Imaging probe; Immuno PET; Multivalent effect; Non standard PET nuclide; PET; Radioimmunoconjugate

Indexed keywords

1,4,7,10 TETRAAZACYCLODODECANE 1,4,7,10 TETRAACETIC ACID; ARGINYLGLYCYLASPARTIC ACID; BEVACIZUMAB; COPPER 60; COPPER 61; COPPER 62; COPPER 64; COPPER 67; COPPER CHLORIDE; COPPER COMPLEX; DIETHYLDITHIOCARBAMIC ACID; EDETIC ACID; FLUORODEOXYGLUCOSE F 18; MACROCYCLIC COMPOUND; METHOXY ISOBUTYL ISONITRILE TECHNETIUM TC 99M; MULTIDRUG RESISTANCE PROTEIN 1; PENTETIC ACID; PROTEOHEPARAN SULFATE; RADIOISOTOPE; UNCLASSIFIED DRUG; VASCULOTROPIN; VASCULOTROPIN RECEPTOR 1; VASCULOTROPIN RECEPTOR 2;

ABSORPTION SPECTROSCOPY; AUGER ELECTRON SPECTROSCOPY; BINDING AFFINITY; BLADDER CANCER; CANCER PATIENT; CHELATION; COLON CANCER; COLON CARCINOMA; COPPER METABOLISM; DOSIMETRY; DRUG HALF LIFE; ELECTROCHEMISTRY; HUMAN; HYPOXIA; IMMUNOHISTOCHEMISTRY; ISOTOPE LABELING; ISOTOPE TRACING; LEUKOPENIA; LIVER TUMOR; MENKES SYNDROME; NEOPLASM; NONHODGKIN LYMPHOMA; NONHUMAN; OUTCOME ASSESSMENT; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; POSITRON; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROSTATE CANCER; RADIATION DOSE FRACTIONATION; RADIOISOTOPE DECAY; REVIEW; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ACTIVITY RELATION; THERMODYNAMICS; THROMBOCYTOPENIA; TUMOR XENOGRAFT; WESTERN BLOTTING; WILSON DISEASE;

COPPER; COPPER RADIOISOTOPES; ELECTROCHEMISTRY; HUMANS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTORS, VASCULAR ENDOTHELIAL GROWTH FACTOR; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 79958264704     PISSN: 18744710     EISSN: 18744729     Source Type: Journal    
DOI: 10.2174/1874471011104020109     Document Type: Review

References (120)

1. Kodama, H.; Fujisawa, C. Copper metabolism and inherited copper transport disorders: molecular mechanisms, screening, and treatment. Metallomics, 2009, 1, 42-52.
2. Linder, M. C.; Goode, C. A. Biochemistry of copper. Plenum Press: New York, 1991.
3. Karlin, K. D.; Zubieta, J. Copper coordination chemistry: biochemical & inorganic perspectives. Adenine Press: New York, 1983.
4. Owen, C. A. Biochemical aspects of copper: copper proteins, ceruloplasmin, and copper protein binding. Noyes: New Jersy, 1982.
5. Owen, C. A. Wilson's disease: the etiology, clinical aspects, and treatment of inherited copper toxicosis. Noyes: New Jersy, 1981.
6. Lee, J.; Pena, M. M. O.; Nose, Y.; Thiele, D. J. Biochemical characterization of the human copper transporter CTR1. J. Biol. Chem., 2002, 277, 4380-4387.
7. Hamza, I.; Schaefer, M.; Klomp, L. W.; Gitlin, J. D. Interaction of the copper chaperone HAH1 with the Wilson disease protein is essential for copper homeostasis. Proc. Nat. Acad. Sci. U.S.A., 1999, 96, 13363-13368.
8. Sun, X.; Anderson, C. J. Production and applications of copper-64 radiopharmaceuticals. Meth. Enzymol., 2004, 386, 237-261.
9. Shokeen, M.; Anderson, C. J. Molecular imaging of cancer with copper-64 radiopharmaceuticals and positron emission tomography (PET). Acc. Chem. Res., 2009, 42, 832-841.
10. 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.
11. 60/61/62/64Cu-ATSM: a hypoxia imaging agent for PET. Eur. J. Nucl. Med. Mol. Imaging, 2005, 32, 764-770.
12. McCarthy, D. W.; Bass, L. A.; Cutler, P. D.; Shefer, R. E.; Klinkowstein, R. E.; Herrero, P.; Lewis, J. S.; Cutler, C. S.; Anderson, C. J.; Welch, M. J. High purity production and potential applications of copper-60 and copper-61. Nucl. Med. Biol., 1999, 26, 351-358.
13. 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.
14. Hao, G.; Singh, A. N.; Liu, W.; Sun, X. PET with non-standard nuclides. Curr. Top. Med. Chem., 2010, 10, 1096-1112.
15. Kaim, W.; Rall, J. Copper - A "modern" bioelement. Angew. Chem. Int. Ed. Engl., 1996, 35, 43-60.
16. Santos, M. A.; Gaspar, M.; Goncalves, M. L. Electrochemistry of copper(II) complexes of dioxocyclam and dihydroxamate derivative. Electroanal., 2000, 12, 66-71.
17. Chaurin, V.; Constable, E. C.; Housecroft, C. E. What is the coordination number of copper(II) in metallosupramolecular chemistry? New J. Chem., 2006, 30, 1740-1744.
18. Murphy, B.; Hathaway, B. The stereochemistry of the copper(II) ion in the solid-state - some recent perspectives linking the Jahn- Teller effect, vibronic coupling, structure correlation analysis, structural pathways and comparative X-ray crystallography. Coord. Chem. Rev., 2003, 243, 237-262.
19. Halcrow, M. A. Interpreting and controlling the structures of sixcoordinate copper(II) centres - When is a compression really a compression? Dalton Trans., 2003, 4375-4384.
20. Elias, H. Kinetics and mechanism of metal complex formation with N-4-donor macrocycles of the cyclam type. Coord. Chem. Rev., 1999, 187, 37-73.
21. Busch, D. H. The Compleat Coordination Chemistry - One Practitioners Perspective. Chem. Rev., 1993, 93, 847-860.
22. Hancock, R. D.; Pattrick, G.; Wade, P. W.; Hosken, G. D. Structurally Reinforced Macrocyclic Ligands. Pure Appl. Chem., 1993, 65, 473-476.
23. Hancock, R. D.; Evers, A.; Ngwenya, M. P.; Wade, P. W. Structurally Reinforced Macrocyclic Ligands That Show Greatly Enhanced Selectivity for Metal-Ions on the Basis of the Match in Size between the Metal-Ion and the Macrocyclic Cavity. J. Chem. Soc. Chem. Comm., 1987, 1129-1130.
24. Di Bernardo, P.; Melchior, A.; Portanova, R.; Tolazzi, M.; Zanonato, P. L. Complex formation of N-donor ligands with group 11 monovalent ions. Coord. Chem. Rev., 2008, 252, 1270-1285.
25. 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.
26. 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.
27. Dong, Y.; Lawrance, G. A.; Lindoy, L. F.; Turner, P. Macrocyclic ligand design. Interaction of a series of successively N-benzylated derivatives of 1,4,8,11-tetraazacyclotetradecane (cyclam) with copper(II) and nickel(II). Dalton Trans., 2003, 1567-1576.
28. Labuda, J.; Tarapcik, P.; Kotocova, A.; Sima, J. Ligand-Structure Effect on Electrochemical Reduction of Copper(II) Complexes. Monatsh. Chem., 1992, 123, 693-699.
29. Woodin, K. S.; Heroux, K. J.; Boswell, C. A.; Wong, E. H.; Weisman, G. R.; Niu, W. J.; 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, 4829-4833.
30. Vavere, A. L.; Lewis, J. S. Cu-ATSM: A radiopharmaceutical for the PET imaging of hypoxia. Dalton Trans., 2007, 4893-4902.
31. Aneetha, H.; Lai, Y. H.; Lin, S. C.; Panneerselvam, K.; Lu, T. H.; Chung, C. S. Copper(II) complexes of tetraaza macrocycles bearing pendant arms: syntheses, structures and properties. J. Chem. Soc. Dalton., 1999, 2885-2892.
32. 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.
33. 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.
34. Blower, P. J.; Went, M. J.; Martin, K. E.; Smith, G. E. Imaging hypoxia in vivo by controlling the electrochemistry of copper radionuclide complexes. J. Labelled Compd. Rad., 2007, 50, 354-359.
35. Lewis, J. S.; Laforest, R.; Buettner, T. L.; Song, S. K.; Fujibayashi, Y.; Connett, J. M.; Welch, M. J. Copper-64-diacetyl-bis(N-4- methylthiosemicarbazone): An agent for radiotherapy. Proc. Natl. Acad. Sci. U.S.A., 2001, 98, 1206-1211.
36. Dearling, J. L. J.; Lewis, J. S.; McCarthy, D. W.; Welch, M. J.; Blower, P. J. Redox-active metal complexes for imaging hypoxic tissues: structure-activity relationships in copper(II) bis(thiosemicarbazone) complexes. Chem. Commun., 1998, 2531-2532.
37. Subczynski, W. K.; Pasenkiewicz-Gierula, M.; Antholine, W. E.; Hyde, J. S. Oriented self-association of Copper(II) tetraphenylporphine in liquid-crystalline lipid bilayer membranes: An EPR study. J. Am. Chem. Soc., 1999, 121, 4054-4059.
38. Subczynski, W. K.; Antholine, W. E.; Hyde, J. S.; Petering, D. H. Orientation and Mobility of a Copper Square-Planar Complex in a Lipid Bilayer. J. Am. Chem. Soc., 1987, 109, 46-52.
39. Bernhardt, P. V.; Bramley, R.; Geue, R. J.; Ralph, S. F.; Sargeson, A. M. An expanded cavity hexaamine cage for copper(II). Dalton Trans., 2007, 1244-1249.
40. Creaser, I. I.; Harrowfield, J. M.; Lawrance, G. A.; Mulac, W.; Sangster, D.; Sargeson, A. M.; Schmidt, K.; Sullivan, J. C. Rapid Reduction of [CuII(Sarcophagine)]2+ Ion and Elimination of CuI from the Cage: a Pulse-Radiolysis Study. J. Coord. Chem., 1991, 23, 389-395.
41. Bell, C. A.; Bernhardt, P. V.; Gahan, L. R.; Martinez, M.; Monteiro, M. J.; Rodriguez, C.; Sharrad, C. A. Copper(II) Complexes of a Hexadentate Mixed-Donor N3S3 Macrobicyclic Cage: Facile Rearrangements and Interconversions. Chem-Eur. J., 2010, 16, 3166-3175.
42. Prakash, R.; Kandoi, S.; Srivastava, R. C. Electrochemical and spectroscopic studies of metal cyclam complexes with thiocyanate. Evidence for mixed ligand complex formation. Transit. Metal Chem., 2002, 27, 598-603.
43. Hubin, T. J.; Alcock, N. W.; Morton, M. D.; Busch, D. H. Synthesis, structure, and stability in acid of copper(II) and zinc(II) complexes of cross-bridged tetraazamacrocycles. Inorg. Chim. Acta, 2003, 348, 33-40.
44. 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.
45. Heroux, K. J.; Woodin, K. S.; Tranchemontagne, D. J.; Widger, P. C. B.; 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.
46. Stigers, D. J.; Ferdani, R.; Weisman, G. R.; Wong, E. H.; Anderson, C. J.; Golen, J. A.; Moore, C.; Rheingold, A. L. A new phosphonate pendant-armed cross-bridged tetraamine chelator accelerates copper(II) binding for radiopharmaceutical applications. Dalton Trans., 2010, 39, 1699-1701.
47. Riesen, A.; Zehnder, M.; Kaden, T. A. Metal-Complexes of Macrocyclic Ligands.23. Synthesis, Properties, and Structures of Mononuclear Complexes with 12-Membered and 14-Membered Tetraazamacrocycle-N,N',N",N"'-Tetraacetic Acids. Helv. Chim. Acta, 1986, 69, 2067-2073.
48. 60Cu-ATSM PET scan. Dis. Colon Rectum., 2007, 50, 780-780.
49. 60Cu-labeled diacetyl-bis(N4-methylthiosemicarbazone). J. Nucl. Med., 2008, 49, 201-205.
50. 60Cu- ATSM in cancer of the uterine cervix. J. Nucl. Med., 2008, 49, 1177-1182.
51. 61Cu by proton irradiation of natZn at a medical cyclotron. Appl. Radiat. Isot., 2006, 64, 1563-1573.
52. Fukumura, T.; Okada, K.; Szelecsenyi, F.; Kovacs, Z.; Suzuki, K. Practical production of Cu-61 using natural Co target and its simple purification with a chelating resin for Cu-61-ATSM. Radiochim. Acta, 2004, 92, 209-214.
53. Liu, W.; Hao, G.; Long, M. A.; Anthony, T.; Hsieh, J. T.; Sun, X. Imparting multivalency to a bifunctional chelator: a scaffold design for targeted PET imaging probes. Angew. Chem. Int. Ed. Engl., 2009, 48, 7346-7349.
54. 60Cu-ATSM as a predictor of response and survival in patients undergoing Neoadjuvant chemoradiotherapy for rectal carcinoma: a pilot study. Dis. Colon Rectum, 2008, 51, 1641-1648.
55. 64Cu-PTSM in human and murine tumors is influenced by MDR1 protein expression. J. Nucl. Med., 2009, 50, 1332-1339.
56. Rice, G. C.; Ling, V.; Schimke, R. T. Frequencies of independent and simultaneous selection of Chinese hamster cells for methotrexate and doxorubicin (adriamycin) resistance. Proc. Natl. Acad. Sci. U.S.A., 1987, 84, 9261-9264.
57. Aratani, T.; Narabayashi, I.; Komori, T.; Utsunomiya, K.; Sueyoshi, K.; Tachibana, S.; Sasaki, S. Usefulness of Tc-99m MIBI SPECT in predicting multidrug resistance gene expression levels in non-small cell lung cancer-a preliminary report. Ann. Nucl. Med., 2001, 15, 313-319.
58. 99mTc-MIBI imaging as a predictor of therapy response in osteosarcoma compared with multidrug resistanceassociated protein and P-glycoprotein expression. J. Nucl. Med., 2003, 44, 1394-1401.
59. Cermik, T. F.; Altiay, G.; Firat, M. F.; Hatipoglu, O. N.; Berkarda, S. Assessment of Tc-99m sestamibi tumor tissue uptake under the influence of increased arterial oxygen saturation. Nucl. Med. Biol., 2005, 32, 165-170.
60. 99mTc-tetrofosmin uptake in MRP-expressing breast cancer cells under hypoxic conditions is independent of MRP function. Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 1529-1531.
61. 99mTc-HL91. Eur. J. Nucl. Med. Mol. Imaging, 2002, 29, 1006-1011.
62. Holmes, K.; Roberts, O. L.; Thomas, A. M.; Cross, M. J. Vascular endothelial growth factor receptor-2: structure, function, intracellular signalling and therapeutic inhibition. Cell. Signal., 2007, 19, 2003-2012.
63. Guo, S.; Colbert, L. S.; Fuller, M.; Zhang, Y.; Gonzalez-Perez, R. R. Vascular endothelial growth factor receptor-2 in breast cancer. Biochim. Biophys. Acta, 2010, 1806, 108-121.
64. Cai, W.; Chen, K.; Mohamedali, K. A.; Cao, Q.; Gambhir, S. S.; Rosenblum, M. G.; Chen, X. PET of vascular endothelial growth factor receptor expression. J. Nucl. Med., 2006, 47, 2048-2056.
65. Wang, H.; Cai, W.; Chen, K.; Li, Z. B.; Kashefi, A.; He, L.; Chen, X. A new PET tracer specific for vascular endothelial growth factor receptor 2. Eur. J. Nucl. Med. Mol. Imaging, 2007, 34, 2001-2010.
66. Haubner, R.; Wester, H. J. Radiolabeled tracers for imaging of tumor angiogenesis and evaluation of anti-angiogenic therapies. Curr. Pharm. Des., 2004, 10, 1439-1455.
67. Almutairi, A.; Rossin, R.; Shokeen, M.; Hagooly, A.; Ananth, A.; Capoccia, B.; Guillaudeu, S.; Abendschein, D.; Anderson, C. J.; Welch, M. J.; Frechet, J. M. Biodegradable dendritic positronemitting nanoprobes for the noninvasive imaging of angiogenesis. Proc. Natl. Acad. Sci. U.S.A., 2009, 106, 685-690.
68. Li, Z. B.; Cai, W.; Cao, Q.; Chen, K.; Wu, Z.; He, L.; Chen, X. (64)Cu-labeled tetrameric and octameric RGD peptides for smallanimal PET of tumor alpha(v)beta(3) integrin expression. J. Nucl. Med., 2007, 48, 1162-1171.
69. Montet, X.; Funovics, M.; Montet-Abou, K.; Weissleder, R.; Josephson, L. Multivalent effects of RGD peptides obtained by nanoparticle display. J. Med. Chem., 2006, 49, 6087-6093.
70. Boturyn, D.; Coll, J. L.; Garanger, E.; Favrot, M. C.; Dumy, P. Template assembled cyclopeptides as multimeric system for integrin targeting and endocytosis. J. Am. Chem. Soc., 2004, 126, 5730-5739.
71. 64Cu-labeled tetrameric RGD peptide. J. Nucl. Med., 2005, 46, 1707-1718.
72. Zhou, J.; Fan, J.; Hsieh, J. T. Inhibition of mitogen-elicited signal transduction and growth in prostate cancer with a small peptide derived from the functional domain of DOC-2/DAB2 delivered by a unique vehicle. Cancer Res., 2006, 66, 8954-8958.
73. Bucci, M.; Gratton, J. P.; Rudic, R. D.; Acevedo, L.; Roviezzo, F.; Cirino, G.; Sessa, W. C. In vivo delivery of the caveolin-1 scaffolding domain inhibits nitric oxide synthesis and reduces inflammation. Nat. Med., 2000, 6, 1362-1367.
74. Gratton, J. P.; Yu, J.; Griffith, J. W.; Babbitt, R. W.; Scotland, R. S.; Hickey, R.; Giordano, F. J.; Sessa, W. C. Cell-permeable peptides improve cellular uptake and therapeutic gene delivery of replication-deficient viruses in cells and in vivo. Nat. Med., 2003, 9, 357-362.
75. Elson-Schwab, L.; Garner, O. B.; Schuksz, M.; Crawford, B. E.; Esko, J. D.; Tor, Y. Guanidinylated neomycin delivers large, bioactive cargo into cells through a heparan sulfate-dependent pathway. J. Biol. Chem., 2007, 282, 13585-13591.
76. Hao, G.; Zhou, J.; Guo, Y.; Long, M. A.; Anthony, T.; Stanfield, J.; Hsieh, J. T.; Sun, X. A cell permeable peptide analog as a potential-specific PET imaging probe for prostate cancer detection. Amino Acids, 2010, DOI: 10.1007/s00726-010-0515-5
77. Nakase, I.; Takeuchi, T.; Tanaka, G.; Futaki, S. Methodological and cellular aspects that govern the internalization mechanisms of arginine-rich cell-penetrating peptides. Adv. Drug Deliv. Rev., 2008, 60, 598-607.
78. Sanderson, R. D.; Yang, Y.; Suva, L. J.; Kelly, T. Heparan sulfate proteoglycans and heparanase--partners in osteolytic tumor growth and metastasis. Matrix Biol., 2004, 23, 341-352.
79. Sasisekharan, R.; Shriver, Z.; Venkataraman, G.; Narayanasami, U. Roles of heparan-sulphate glycosaminoglycans in cancer. Nat. Rev. Cancer, 2002, 2, 521-528.
80. Kirn-Safran, C.; Farach-Carson, M. C.; Carson, D. D. Multifunctionality of extracellular and cell surface heparan sulfate proteoglycans. Cell. Mol. Life Sci., 2009, 66, 3421-3434.
81. Alexander, C. M.; Reichsman, F.; Hinkes, M. T.; Lincecum, J.; Becker, K. A.; Cumberledge, S.; Bernfield, M. Syndecan-1 is required for Wnt-1-induced mammary tumorigenesis in mice. Nat. Genet., 2000, 25, 329-332.
82. Chen, D.; Adenekan, B.; Chen, L.; Vaughan, E. D.; Gerald, W.; Feng, Z.; Knudsen, B. S. Syndecan-1 expression in locally invasive and metastatic prostate cancer. Urology, 2004, 63, 402-407.
83. Datta, M. W.; Hernandez, A. M.; Schlicht, M. J.; Kahler, A. J.; DeGueme, A. M.; Dhir, R.; Shah, R. B.; Farach-Carson, C.; Barrett, A.; Datta, S. Perlecan, a candidate gene for the CAPB locus, regulates prostate cancer cell growth via the Sonic Hedgehog pathway. Mol. Cancer, 2006, 5, 9.
84. 64CuCl2. J. Nucl. Med., 2006, 47, 1649-1652.
85. Peng, F.; Liu, J.; Wu, J. S.; Lu, X.; Muzik, O. Mouse extrahepatic hepatoma detected on MicroPET using copper (II)-64 chloride uptake mediated by endogenous mouse copper transporter 1. Mol. Imaging Biol., 2005, 7, 325-329.
86. Scheinberg, I. H.; Sternlieb, I. Copper metabolism. Pharmacol. Rev., 1960, 12, 355-381.
87. Skromne-Kadlubik, G.; Diaz, J. F.; Celis, C. Basal ganglia scans in the human. J. Nucl. Med., 1975, 16, 787-788.
88. Turski, M. L.; Thiele, D. J. New roles for copper metabolism in cell proliferation, signaling, and disease. J. Biol. Chem., 2009, 284, 717-721.
89. Pedro-Segura, E.; Vergara, S. V.; Rodriguez-Navarro, S.; Parker, R.; Thiele, D. J.; Puig, S. The Cth2 ARE-binding protein recruits the Dhh1 helicase to promote the decay of succinate dehydrogenase SDH4 mRNA in response to iron deficiency. J. Biol. Chem., 2008, 283, 28527-28535.
90. Kim, B. E.; Nevitt, T.; Thiele, D. J. Mechanisms for copper acquisition, distribution and regulation. Nat. Chem. Biol., 2008, 4, 176-185.
91. Cobine, P. A.; Pierrel, F.; Bestwick, M. L.; Winge, D. R. Mitochondrial matrix copper complex used in metallation of cytochrome oxidase and superoxide dismutase. J. Biol. Chem., 2006, 281, 36552-36559.
92. Cobine, P. A.; Pierrel, F.; Winge, D. R. Copper trafficking to the mitochondrion and assembly of copper metalloenzymes. Biochim. Biophys. Acta, 2006, 1763, 759-772.
93. Linz, R.; Lutsenko, S. Copper-transporting ATPases ATP7A and ATP7B: cousins, not twins. J. Bioenerg. Biomembr., 2007, 39, 403-407.
94. Huster, D.; Lutsenko, S. Wilson disease: not just a copper disorder. Analysis of a Wilson disease model demonstrates the link between copper and lipid metabolism. Mol. Biosyst., 2007, 3, 816-824.
95. Linz, R.; Barnes, N. L.; Zimnicka, A. M.; Kaplan, J. H.; Eipper, B.; Lutsenko, S. Intracellular targeting of copper-transporting ATPase ATP7A in a normal and Atp7b-/- kidney. Am. J. Physiol. Renal Physiol., 2008, 294, F53-F61.
96. Lutsenko, S.; Barnes, N. L.; Bartee, M. Y.; Dmitriev, O. Y. Function and regulation of human copper-transporting ATPases. Physiol. Rev., 2007, 87, 1011-1046.
97. Lutsenko, S.; LeShane, E. S.; Shinde, U. Biochemical basis of regulation of human copper-transporting ATPases. Arch. Biochem. Biophys., 2007, 463, 134-148.
98. Bartee, M. Y.; Lutsenko, S. Hepatic copper-transporting ATPase ATP7B: function and inactivation at the molecular and cellular level. Biometals, 2007, 20, 627-637.
99. Huster, D.; Purnat, T. D.; Burkhead, J. L.; Ralle, M.; Fiehn, O.; Stuckert, F.; Olson, N. E.; Teupser, D.; Lutsenko, S. High copper selectively alters lipid metabolism and cell cycle machinery in the mouse model of Wilson disease. J. Biol. Chem., 2007, 282, 8343-8355.
100. West, E. C.; Prohaska, J. R. Cu, Zn-superoxide dismutase is lower and copper chaperone CCS is higher in erythrocytes of copperdeficient rats and mice. Exp. Biol. Med. (Maywood), 2004, 229, 756-764.
101. Penland, J. G.; Prohaska, J. R. Abnormal motor function persists following recovery from perinatal copper deficiency in rats. J. Nutr., 2004, 134, 1984-1988.
102. Prohaska, J. R.; Gybina, A. A. Intracellular copper transport in mammals. J. Nutr., 2004, 134, 1003-1006.
103. Menkes, J. H.; Alter, M.; Steigleder, G. K.; Weakley, D. R.; Sung, J. H. A sex-linked recessive disorder with retardation of growth, peculiar hair, and focal cerebral and cerebellar degeneration. Pediatrics, 1962, 29, 764-779.
104. Danks, D. M.; Campbell, P. E.; Walker-Smith, J.; Stevens, B. J.; Gillespie, J. M.; Blomfield, J.; Turner, B. Menkes' kinky-hair syndrome. Lancet, 1972, 1, 1100-1102.
105. Lazoff, S. G.; Rybak, J. J.; Parker, B. R.; Luzzatti, L. Skeletal dysplasia, occipital horns, diarrhea and obstructive uropathy- a new hereditary syndrome. Birth Defects Orig. Artic. Ser., 1975, 11, 71-74.
106. Wilson, S. A. K. Progressive lenticular degeneration: a familial nervous disease associated with cirrhosis of the liver. Brain, 1912, 34, 295-509.
107. Kodama, H.; Sato, E.; Gu, Y. H.; Shiga, K.; Fujisawa, C.; Kozuma, T. Effect of copper and diethyldithiocarbamate combination therapy on the macular mouse, an animal model of Menkes disease. J. Inherit. Metab. Dis., 2005, 28, 971-978.
108. Roberts, E. A.; Schilsky, M. L. Diagnosis and treatment of Wilson disease: an update. Hepatology, 2008, 47, 2089-2111.
109. 64Cu in foetal and adult tissues in mice: influence of sodium diethyldithiocarbamate treatment. Acta Pharmacol. Toxicol. (Copenh), 1985, 57, 262-270.
110. Diez, M.; Arroyo, M.; Cerdan, F. J.; Munoz, M.; Martin, M. A.; Balibrea, J. L. Serum and tissue trace metal levels in lung cancer. Oncology, 1989, 46, 230-234.
111. Gupta, S. K.; Shukla, V. K.; Vaidya, M. P.; Roy, S. K.; Gupta, S. Serum and tissue trace elements in colorectal cancer. J. Surg. Oncol., 1993, 52, 172-175.
112. Connett, J. M.; Anderson, C. J.; Guo, L. W.; Schwarz, S. W.; Zinn, K. R.; Rogers, B. E.; Siegel, B. A.; Philpott, G. W.; Welch, M. J. Radioimmunotherapy with a Cu-64-labeled monoclonal antibody: A comparison with Cu-67. Proc. Natl. Acad. Sci. U.S.A., 1996, 93, 6814-6818.
113. Anderson, C. J.; Jones, L. A.; Bass, L. A.; Sherman, E. L. C.; 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.
114. O'Donnell, R. T.; DeNardo, G. L.; Kukis, D. L.; Lamborn, K. R.; Shen, S.; Yuan, A. N.; Goldstein, D. S.; Carr, C. E.; Mirick, G. R.; DeNardo, S. J. A clinical trial of radioimmunotherapy with Cu-67- 2IT-BAT-Lym-1 for non-Hodgkin's lymphoma. J. Nucl. Med., 1999, 40, 2014-2020.
115. Delaloye, A. B.; Delaloye, B.; Buchegger, F.; Vogel, C. A.; Gillet, M.; Mach, J. P.; Smith, A.; Schubiger, P. A. Comparison of copper- 67- and iodine-125-labeled anti-CEA monoclonal antibody biodistribution in patients with colorectal tumors. J. Nucl. Med., 1997, 38, 847-853.
116. Hughes, O. D. M.; Bishop, M. C.; Perkins, A. C.; Wastie, M. L.; Denton, G.; Price, M. R.; Frier, M.; Denley, H.; Rutherford, R.; Schubiger, P. A. Targeting superficial bladder cancer by the intravesical administration of copper-67-labeled anti-MUC1 mucin monoclonal antibody C595. J. Clin. Oncol., 2000, 18, 363-370.
117. Liu, X.; Laforest, R. Quantitative small animal PET imaging with nonconventional nuclides. Nucl. Med. Biol., 2009, 36, 551-559.
118. Laforest, R.; Liu, X. Image quality with non-standard nuclides in PET. Q. J. Nucl. Med. Mol. Imaging, 2008, 52, 151-158.
119. Shokeen, M.; Fettig, N. M.; Rossin, R. Synthesis, in vitro and in vivo evaluation of radiolabeled nanoparticles. Q. J. Nucl. Med. Mol. Imaging, 2008, 52, 267-277.
120. Fukukawa, K.; Rossin, R.; Hagooly, A.; Pressly, E. D.; Hunt, J. N.; Messmore, B. W.; Wooley, K. L.; Welch, M. J.; Hawker, C. J. Synthesis and characterization of core-shell star copolymers for in vivo PET imaging applications. Biomacromol., 2008, 9, 1329-1339.