Molecular imaging with copper-64 in the drug discovery and development area

Expert Opinion on Drug Discovery

Volumn 2, Issue 5, 2007, Pages 659-672

  Smith, Suzanne V ^a  

^a AUSTRALIAN NUCLEAR SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

Author keywords

64 Cu; Clinical trials; Drug development; Drug discovery; PET imaging

Indexed keywords

BROMINE 76; CARBON 11; COPPER 61; COPPER 64; COPPER DERIVATIVE; CYCLAM; CYCLAM DERIVATIVE; FLUORINE 18; GALLIUM; GALLIUM 66; GALLIUM 68; IODINE 124; NEW DRUG; OXYGEN 15; RUBIDIUM 82; TECHNETIUM 94M; TECHNETIUM DERIVATIVE; UNCLASSIFIED DRUG; YTTRIUM 86; ZINC 66; ZINC 68; ZINC DERIVATIVE;

ALGORITHM; CHEMICAL STRUCTURE; COMPLEX FORMATION; COST EFFECTIVENESS ANALYSIS; CYCLOTRON; DRUG BIOAVAILABILITY; DRUG HALF LIFE; DRUG RESEARCH; DRUG SYNTHESIS; IMAGE RECONSTRUCTION; ISOTOPE LABELING; LIGAND BINDING; MOLECULAR IMAGING; MOLECULAR STABILITY; NON INVASIVE PROCEDURE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RADIOCHEMISTRY; REVIEW; SENSITIVITY ANALYSIS; THERMODYNAMICS; THREE DIMENSIONAL IMAGING;

EID: 34447535507     PISSN: 17460441     EISSN: None     Source Type: Journal    
DOI: 10.1517/17460441.2.5.659     Document Type: Review

References (96)

1. SERVICE RF: Surviving the blockbuster syndrome. Science(2004) 303(5665):1796-1799.
2. NUNN AD: The cost of developing imaging agents for routine clinical use. Invest. Radiol. (2006) 41(3):206-212.
3. DIMASI JA, HANSENR W, GRABOWSKI HG: The price of innovation: new estimates of drug development costs. J. Health Econ. (2003) 22:151-185.
4. FRANK RG: New estimates of drug development costs. J. Health Econ. (2003) 22:325-330.
5. PHILLIPS KA, VAN BEBBER S, ISSA AM: Diagnostics and biomarker development: priming the pipeline. Nat. Rev. Drug Discov. (2006) 5:469.
6. LAMERICHS R, SCHAFFER T, HAMISCH Y, POWERS J: Molecular imaging: the road to better healthcare. Medica Mundi (2003) 47(1):2-9.
7. SMITH SV: Challenges and opportunities for positron-emission tomography in personalized medicine. IDrugs (2005) 8(10):827-833.
8. CHERRY SR: Fundamental of positron emission tomography and application in preclinical drug development. J. Clin. Pharmacol. (2001) 41:482-491.
9. RUDIN M, WEISSLEDER R: Molecular imaging in drug discovery and development. Nat. Rev. Drug Discov. (2003) 2:123-131.
10. ZIEGLER SI: Development of a small-animal PET system. Proc. IEEE (2005) 93(4):763-770.
11. REPORT 240: The market for PET radiopharmaceuticals and PET imaging (2006) BIO-TECH Systems, Inc.
12. SANCHEZ-CRESPO A, ANDREO P, LARSSON SA: Positron flight in human tissues and its influence on PET image spatial resolution. Eur. J. Nucl. Med. Mol. Imaging(2004) 31:44-51.
13. HARVEY D: Time of flight - next-generation PET takes flight. Radiol. Today(2006) 7(16):20.
14. MUSHTAQ A, KARIM HMA, KHAN MA: Production of no-carrier-added copper-64 and copper-67 in a reactor. J. Radioanal. Nucl. Chem. (1990) 141(2):261-269.
15. SZELECSENYI F, BLESSING G, QAIM SM: Excitation functions of proton induced nuclear reactions on enriched nickel-61 and nickel-64: possibility of production of no-carrier- added copper-61 and copper-64 at a small cyclotron. Appl. Radiat. Isot. (1993) 44(3):575-580.
16. BOOTHE TE: Utilization of a hospital-based cyclotron for commercial radionuclide production. Nucl. Instrum. Meth. Phys. Res. Sect. B.- Beam Interact. Mater. Atoms (1991) B56-B57(Pt. 2):1266-1269.
17. HETHERINGTON EL, SORBY PJ, CAMAKARIS J: The preparation of high specific activity copper-64 for medical diagnosis. Appl. Radiat. Isot. (1986) 37(12):1242-1243.
18. SMITH SV, WATERS DJ, DI BARTOLO N: Separation of 64Cu from 67Ga waste products using anion exchange and low acid aqueous/organic mixtures. Radiochimica Acta (1996) 75(2):65-68.
19. MCCARTHY DW. SHEFER RE, KLINKOWSTEIN RE et al.: Efficient production of high specific activity 64Cu using a biomedical cyclotron. Nucl. Med. Biol. (1997) 24(1):35-43.
20. OBATA A, KASAMATSU S, MCCARTHY DW et al.: Production of therapeutic quantities of 64Cu using a 12 MeV cyclotron. Nucl. Med. Biol. (2003) 30(5):535-539.
21. BONARDI ML, GROPPI F, BIRATTARI C et al.: Thin-target excitation functions and optimization of simultaneous production of NCA copper-64 and gallium-66,67 by deuteron induced nuclear reactions on a natural zinc target. J. Radioanal. Nucl. Chem. (2003) 257(1):229-241.
22. HILGERS K, STOLL T, SKAKUN Y, COENEN HH, QAIM SM: Cross-section measurements of the nuclear reactions Zn-nat(d,x)Cu-64, Zn-66(d,α)Cu-64 and Zn-68(p,α n)Cu-64 for production of Cu-64 and technical developments for small-scale production of Cu-67 via the Zn-70(p,α)Cu-64 process. Appl. Radiat. Isot. (2003) 59(5-6):343-351.
23. TARKANYI F, TAKACS S, DITROI F et al.: Excitation functions of deuteron induced nuclear reactions on natural zinc up to 50 MeV. Nucl. Instrum. Meth. Phys. Res. Sect. B: Beam Interact. Mater. Atoms (2004) 217(4):531-550.
24. BONARDI ML, GROPPI F, MAINARDI HS et al.: Cross section studies on Cu-64 with zinc target in the proton energy range from 141 down to 31 MeV. J. Radioanal. Nucl. Chem. (2005) 264(1):101-105.
25. SZELECSENYI F, STEYN GF, KOVACS Z et al.: Investigation of the 66Zn(P,2pn)64Cu and 68Zn(p,x)64Cu nuclear processes up to 100 MeV: production of 64Cu. Nucl. Instrum. Meth. Phys. Res. Sect. B: Beam Interact. Mater. Atoms(2005) 240(3):625-637.
26. ABBAS K, KOZEMPEL J, BONARDIC M et al.: Cyclotron production of 64Cu by deuteron irradiation of 64Zn. Appl. Radiat. Isot. (2006) 64:1001-1005.
27. AL-ABYADA M, SPAHNA I, SUDA S et al.: Nuclear data for production of the therapeutic radionuclides 32P, 64Cu, 67Cu, 89Sr, 90Y and 153Sm via the (n,p) reaction: evaluation of excitation function and its validation via integral cross-section measurement using a 14MeV d(Be) neutron source. Appl. Radiat. Isot.(2006) 64:717-724.
28. ZWEIT J, SMITH AM, DOWNEY S et al.: Excitation functions for deuteron induced reactions in natural nickel: production of no-carrier-added copper-64 from enriched nickel-64 targets for positron emission tomography. Appl. Radiat. Isot.(1991) 42(2): 193-197.
29. TARKANYI F, DITROI F, CSIKAI J et al.: Activation cross-sections of long- lived products of proton-induced nuclear reactions on zinc. Appl. Radiat. Isot. (2005) 62(1):73-81.
30. ABBASI IA, ZAIDI JH, ARIF M et al.: Measurement of fission neutron spectrum averaged cross sections of some threshold reactions on zinc: small-scale production of no-carrier- added 64Cu in a nuclear reactor. Radiochimica Acta(2006) 94(2):63-67.
31. SMITH SV: Molecular imaging with copper-64. J. Inorg. Biochem. (2004) 98(11):1874-1901.
32. Directory of cyclotrons used for radionuclide production in member states. IAEA. Vienna (2006) ISBN 92-0-111506-7 IAEA-DCRP/2006 CD.
33. JONES-WILSON TM, DEAL KA, ANDERSON CJ et al.: The in vivo behavior of copper-64 labeled azamacrocyde complexes. Nucl. Med Biol.(1998) 25:523-530.
34. SUN X, WUEST M, WEISMAN GR et al.: Radiotabelling and in vivo behavior of copper-64-labeled cross-bridged cyclam ligands. J. Med. Chem. (2002) 45:469-477.
35. MOTEKAITIS RJ, ROGERS BE, REICHERT DE, MARTELL AF, WELCH MJ: Stability and structure of activated macrocycles. ligands with biological applications. Inorg. Chem. (1996) 35:3821-3827.
36. DI BARTOLO N, SARGESON AM, DONLEVY TM, SMITH SV: Synthesis of a new cage ligand, SarAr, and its complexation with selected transition metal ions for potential use in radioimaging. J. Chem. Soc. Dalton Trans. (2001) 15:2303-2309.
37. NOVAK-HOFER I, AMSTUTZ HP, MORGENTHALER JJ, SCHUBIGER PA. Internalization and degradation of monoclonal antibody chCE7 by human neutroblastoma cells. Int. J. Cancer (1994) 57(3):427-432.
38. NOVAK-HOFER I, ZIMMERMANN K, SCHUBIGER PA: Peptide linkers lead to modification of liver metabolism and improved tumor targeting of copper-67-labeled antibody fragments. Cancer Biother. Radiopharm. (2001) 16(6):469-481.
39. SMITH-JONES PM, KADEN FR et al.: Antibody labeling with copper-67 using the bifunctional macrocycle 4-[1,4,8,11 -tetraazacyclotetradec-1-yl) methyl]benzoiacid. Biconj. Chem. (1991) 2:415-421.
40. NOVAK HOFER I, AMSTUTZ HP MAECKE HR et al.: Cellular processing of copper-67-labeled monoclonal antibody chCET by human neumblastoma cells. Cancer Res.(1995) 55:46-50.
41. CHAVES S, DELGADO R, DASILVA J: The stability of the metal- complexes of cyclic tetra-aza tetraacetic acids. Talanta(1992) 39(3):249-254.
42. MARTELL AE, SMITH RM: Critical Stability Constants. Plenum, New York, USA (1989) 6(Suppl. 2):183.
43. CLARKE ET, MARTELL AE, Stabilities of the alkaline earth and divalent transition metal complexes of the tetraazarnacrocyclic tetraacetic acid ligands. Inog. Chim. Acta (1991) 190:27-36.
44. CABBINESS DK, MARGERUM DW: Macrocyclic effect on Cu(II) complexes of tetraamine complexes. J. Am. Chem. Soc. (1969) 91:6540.
45. KODAMA M, KIMURA E: Kinetic and equilibrium studies on copper(iI) complom of a 9-membered macrocyctic triamine, 1,4,7-triazacydononane8 and a 14-membered macrocyclic tetra-amine, 1,4,8,1 1-tetra-azacyclotetradecane. J. Chem Soc. Dalton Trans. (1977):1473-1478.
46. GRØNDAHL L, HAMMERSHØI A, SARGESON AM, THÖM VJ: Stability and kinetics of acid and anion-assisted dissociation reactions of hexaamine macrobicyclic mercury(II) complexes. Inorg. Chem. (1997) 36(23):5396-5403.
47. DI BARTOLO N, SARGESON AM, SMITH SV: New Cu-64 PET imaging agents for personalised medicine and drug development using the hexa-aza cage, SarAr. Org. Biomol. Chem. (2006) 4(17):3350-3357.
48. LEWIS MR, BOSWELL A, LAFOREST R et al.: Conjugation of monoclonal antibodies with tem using activated esters: biological comparison of 64Cu-TETA-1A3 with 64Cu-BAT-21T-1A3. Cancer Biother. Radiopharm. (2001) 16(6):483-494.
49. NOVAK-HOFER I, SCHUBIGER PA: Copper-67 as a therapeutic nuclide for radioimmunotherapy. Eur. J. Nucl. Med. (2002) 29:821-830.
50. SPRAGUE JE, PENG Y, SUN X et al.: Preparation and biological evaluation of copper-64 labelled Tyr3-octreotate using a cross-bridged macrocyclic chelator. Can. Cancer Res. (2004) 10:8674-8682.
51. CAI WB, WU Y, CHEN K et al.: In vitro and in vivo characterization of Cu-64-labeled Abegrin (TM) a humanized monoclonal antibody against integrin α(v)β(3). Cancer Res. (2006) 66(19):9673-9681.
52. MORPHY JR. PARKER D, KATAKY R et al.: Towards turnour targeting with copper-radiolabelled macrocycles-andbody conjugates: synthesis, antibody linkage and complexation behaviour. J. Chem Soc. Perkins Thans. (1990) 573-585.
53. CHAKRABARTI A, ARUVA MR. SAJANKILA SP, THAKUR ML, WICKSTROM E: Synthesis of novel peptide nucleic acid-peptide chimera for non-invasive imaging of cancer. Nucleosides Nucleotides Nucleic Acids (2005) 24(5-7):409-414.
54. CHEN XY, HOU YP, TOHME M et al.: Pegylated Arg-Gly-Asp peptide: Cu-64 labeling and PET imaging of brain tumor α(v)β(3)-integrin expression. J. Nucl. Med. (2004) 45(10):1776-1783.
55. CHEN XY, LIU S, HOU YP et al.: MicroPET imaging of breast cancer α(v)-integrin expression with Cu-64-labeled dimeric RGD peptides. Mol. Imaging Biol. (2004) 6(5)-350-359.
56. CHEN XY, PARK R, HOU YP et al.: MicroPET and autoradiographic imaging of GRP receptor expression with Cu-64-DOTA-[Lys(3)]bombesin in human prostate adenocarcinoma xenografts. J. Nucl. Med. (2004) 45(8):1390-1397.
57. CHEN XY, PARK R. TOHME M et al.: MicroPET and autoradiographic imaging of breast cancer α(v)-integrin expression using F-18-and Cu-64-labeled RGD peptide. Bioconjug. Chem. (2004) 15(1):41-49.
58. CHEN XY, SIEVERS E, HOU YP et al.: Integrin α(V)β(3)-targeted imaging of lung cancer. Neoplasia (2005) 7(3):271-279.
59. GRUNBERG J, NOVAK-HOFER I, HONER M et al.: In vivo evaluation of Lu-177-and Cu-67/64-labelled recombinant fragments of antibody chCE7 fin radioimmunotherapy and PET imaging of L1-CAM-positive tumors. Clin. Cancer Res. (2005) 11(14):5112-5120.
60. KE CY, MATHIAS CJ, GREEN MA: Folate-receptor-targeted radionuclide imaging agents. Adv. Drug Deliv. Rev. (2004) 56(8):1143.1160.
61. LI M, MEARES CF: Synthesis, metal chelate stability studies and enzyme digestion of a peptide linked DOTA derivative and its corresponding radiolabelled immunoconjugate. Bioconjug. Chem. (1993) 4:275-283.
62. LEWIS JS, LEWIS MR, SRINIVASAN A et al.: Comparison of four Cu-64-labeled somatostatin analogues in vitro and in a tumor-bearing rat model: evaluation of new derivatives for positron emission tomography imaging and targeted radiotherapy. J. Med. Chem. (1999) 42(8):1341-1347.
63. LEWIS MR, WANG M, AXWORTHY DB et al.: In vivo evaluation of pretargeted Cu-64 for tumor imaging and therapy. J. Nucl. Med. (2003) 44(8):1284-1292.
64. LI WP, LEWIS JS, LAN S, ANDERSON CJ: Cu-64-DOTA-CTTHWGFTLC, a selective gelatinase inhibitor for tumor imaging. J. Nucl. Med. (2002) 43(5):277P-278P.
65. MCQUADE P, KNIGHT LC, WELCH MJ: Evaluation of Cu-64-and I-125-radiolabeled bitistatin as potential agents for targeting α(v)β(3) integrins in tumor angiogenesis. Bioconjug. Chem. (2004) 15(5):988-996.
66. MCQUADE P, MIAO YB, YOO J et al.: Imaging of melanoma using Cu-64- and Y-86-DOTA-ReCCMSH(Arg(11)), a cyclized peptide analogue of α-MSH. J. Med. Chem. (2005) 48(8):2985-2992.
67. NOVAK-HOFER I, HONER M, AMETAMEY S et al.: Imaging of renal carcinoma xenografts with Cu-64-labelled anti-L1-CAM antibody chCE7. Eur. J. Nucl. Med. Mol. Imaging (2003) 30(7):1066.
68. ROGERS BE, BIGOTT HM, MCCARTHY DW et al.: MicroPET imaging of a gastrin-releasing peptide receptor-positive tumor in a mouse model of human prostate cancer using a Cu-64-labeled bombesin analogue. Bioconjug. Chem. (2003) 14(4):756-763.
69. SPRAGUE JE, LI WP, LIANG KX, ACHILEFU S, ANDERSON CJ: In vitro and in vivo investigation of matrix metalloproteinase expression in metastatic tumor models. Nucl. Med. Biol. (2006) 33(2):227-237.
70. THAKUR ML, ARUVA MR, GARIEPY J et al.: PET imaging of oncogene overexpression using Cu-64-vasoactive intestinal peptide (VIP) analog: comparison with Tc-99m-VIP analog. J. Nucl. Med. (2004) 45(8):1381-1389.
71. WU AM, YAZAKI PJ, TSAI SW et al.: High-resolution microPET imaging of carcino-embryonic antigen-positive xenografts by using a copper-64-labeled engineered antibody fragment. Proc. Nat. Acad. Sci. USA (2000) 97(15):8495-8500.
72. WU Y, ZHANG XZ, XIONG ZM et al.: MicroPET imaging of glioma integrin α(V)β(3) expression using Cu-64-labeled tetrameric RGD peptide. J. Nucl. Med. (2005) 46(10):1707-1718.
73. ZIMMERMANN K, GRUNBERG J, HONER M et al.: Targeting of renal carcinoma with (CU)-C-67/64-labeled anti-L1-CAM antibody chCE7: selection of copper ligands and PET imaging. Nucl. Med. Biol. (2003) 30(4):417-427.
74. WU AM, YAZAKI PJ, TSAI SW et al.: High-resolution microPET imaging of carcino-embryonic antigen-positive xenografts by using a copper-64-labeled engineered antibody fragment. Proc. Nat. Acad. Sci. USA (2000) 97(15):8495-8500.
75. YANG YS, ZHANG XZ, XIONG ZM, CHEN XY. Comparative in vitro and in vivo evaluation of two Cu-64-labeled bombesin analogs in a mouse model of human prostate adenocarcinoma. Nucl. Med. Biol. (2006) 33(3):371-380.
76. BURGMAN P, O'DONOGHUE JA, LEWIS JS et al.: Cell line-dependent differences in uptake and retention of the hypoxia-selective nuclear imaging agent Cu-ATSM. Nucl. Med. Biol. (2005) 32(6):623-630.
77. CASTLE TC, MAURER RI, SOWREY FE et al.: Hypoxia-targeting copper bis(selenosemicarbazone) complexes: comparison with their sulfur analogues. J. Am. Chem. Soc. (2003) 125(33):10040-10049.
78. DEARLING JLJ, LEWIS JS, MULLER GED, WELCH MJ, BLOWER PJ: Copper bis(thiosemicarbazone) complexes as hypoxia imaging agents: structure-activity relationships. J. Biol. Inorg. Chem. (2002) 7(3):249-259.
79. LAFOREST R, DEHDASHTI F, LEWIS JS, SCHWARZ SW: Dosimetry of Cu-60/61/62/ 64-ATSM: a hypoxia imaging agent for PET Eur. J. Nucl. Med. Mol. Imaging (2005) 32(7):764-770.
80. LEWIS JS, CONNETT JM, GARBOW JR et al.: Copper-64-pyruvaldehyde-bis (N-4-methylthiosemicarbazone) for the prevention of tumor growth at wound sites following laparoscopic surgery: monitoring therapy response with microPET and magnetic resonance imaging. Cancer Res. (2002) 62(2):445-449.
81. MCQUADE P, MARTIN KE, CASTLE TC et al.: Investigation into Cu-64-labeled bis(selenosemicarbazone) and bis(thiosemicarbazone) complexes as hypoxia imaging agents. Nucl. Med. Biol. (2005) 32(2):147-156.
82. MYERSON RJ, SINGH AK, BIGOTT HM et al.: Monitoring the effect of mild hyperthermia on turnout hypoxia by Cu-ATSM PET scanning. Int. J. Hyperthermia (2006) 22(2):93-115.
83. PACKARD AB, KRONAUGE JF, BARBARICS E, KIANI S, TREVES ST. Synthesis and biodistribution of a lipophilic (CU)-C-64-labeled monocationic copper(II) complex. Nucl. Med. Biol. (2002) 29(3):289-294.
84. YUAN H, SCHROEDER T, BOWSHER JE et al: Intertumoral differences in hypoxia selectivity of the PET imaging agent Cu-64(11)-diacetyl-bis(N-4-methylthiosemicarbazone). J. Nucl. Med. (2006) 47(6):989-998.
85. PAGEL JM, HEDIN N, SUBBIAH K et al.: Comparison of anit-CD20 anad anti CD 45 antibodies for conventional and precargeted radioimmunotherapy of B-cell lymphomas. Blood (2003) 101:2340-2348.
86. SUN XK, FANG HF, LI XX et al.: MicroPET imaging of MCF-7 tumors in mice via unr mRNA-targeted peptide nucleic acids. Bioconjug. Chem. (2005) 16(2):294-305.
87. TIAN XB, CHAKRABARTI A, AMIRKHANOV NV et al.: External imaging of CCND1, MYC, and KRAS oncogene mRNAs with tumor-targeted radionuclide-PNA-peptide chimeras. In: Tumor Progression and Therapeutic Resistance (2005):106-144.
88. TIAN XB, WINTER R., ARUVA MR et al.: CCND1 mRNA visualized in human estrogen receptor negative breast cancer xenografts by PET imaging of antisense Cu-64-DOTA-PNA-peptide. Clin. Cancer Res. (2005) 11(24):9130S-9130S.
89. SUN X ROSSIN R, TURNER JL et al.: An assessment of die effects of shell cross-linked nanoparcticle size, core composition, and surface PEGylation on in vivo biodistribution. Biomacromolecules (2005) 6:2541-2554.
90. ROSSIN R, PAN DPJ, QI K et al.: Cu-64-labeled folate-conjugated shell cross-linked nanoparticles fbr tumor imaging and radiotherapy: synthesis, radiolabeling, and biologic evaluation. J. Nucl. Med. (2005) 46(7):1210-1218.
91. SHANTHLY N, ARUVA MR, ZHANG K et al.: Stem cells: a regenerative pharmaceutical. Q. J. Nucl. Med. Mol. Imaging (2006) 50:205-216.
92. ADONAI N, NGUYEN KN, WALSH J et al.: Ex vivo cell labelling with 64Cu-pyruvaldehyde-bis (N4-methylthiosemicarbazone) for imaging cell trafficking in mice with positron emission tomography. Proc. Natl. Acad. Sci. USA (2002) 99:3030-3035.
93. CZERNIN J, WEBER VA, HERSCHMAN HR: Molecular imaging in the development of cancer therapeutics. Annu. Rev. Med. (2006) 57:99-118.
94. LEE CC, MACKAY JA, FRECHET JM et al.: Designing dendrimers for biological applications. Nat. Biotech. (2005) 23:1517-1526.
95. OBERDÖRSTER G, OBERDÖRSTER E, OBERDÖRSTER J: Nanotoxicology: an emerging discipline evolving from studies of ultrafine particles. Environ. Health Perspect. (2005) 113:823-839.
96. OBERDÖRSTER G, MAYNARD A. DONALDSON K et al.: Principles for characterizing the potential human health effects from exposure to nanomaterials: elements of screening strategy. Particle Fibre Toxicol. (2005) 2:8-111.