Tetraamine-coupled peptides and resulting 99mTc-radioligands: An effective route for receptor-targeted diagnostic imaging of human tumors

Current Topics in Medicinal Chemistry

Volumn 12, Issue 23, 2012, Pages 2655-2667

  Nock, Berthold A ^a   Maina, Theodosia ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

99mTc radiopeptide; Acyclic tetraamine; Receptor targeting; Tumor imaging

Indexed keywords

ALPHA INTERMEDIN; BOMBESIN; BOMBESIN DERIVATIVE; CHELATING AGENT; CHOLECYSTOKININ; DEMOBESIN 4 TC 99M; DEMOBESIN TC 99M; DEMOGASTRIN 2 TC 99M; DEMOTATE 1 TC 99M; DEMOTATE TC 99M; DEMOTENIN 6 TC 99M; DEPREOTIDE TC 99M; GASTRIN; GASTRIN DERIVATIVE; GONADORELIN; HYPOPHYSIS ADENYLATE CYCLASE ACTIVATING POLYPEPTIDE; MINIGASTRIN DERIVATIVE; NEUROTENSIN; NEUROTENSIN DERIVATIVE; OCTREOTIDE; OPIATE; PENTETREOTIDE; RADIOLIGAND; RADIOPHARMACEUTICAL AGENT; SOMATOSTATIN; SOMATOSTATIN DERIVATIVE; SUBSTANCE P; TECHNETIUM 99M; TETRAAMINE TC 99M; UNCLASSIFIED DRUG; VASOACTIVE INTESTINAL POLYPEPTIDE;

APOPTOSIS; CANCER LOCALIZATION; COST EFFECTIVENESS ANALYSIS; DIAGNOSTIC IMAGING; DIASTEREOISOMER; GEOMETRY; HUMAN; INTERNALIZATION; MOLECULARLY TARGETED THERAPY; NEOPLASM; NEUROENDOCRINE TUMOR; NONHUMAN; NUCLEAR MEDICINE; PROSTATE ADENOCARCINOMA; RADIOACTIVITY; RECEPTOR AFFINITY; REVIEW;

AMINES; CHELATING AGENTS; CLINICAL TRIALS AS TOPIC; DIAGNOSTIC IMAGING; HUMANS; LIGANDS; NEUROENDOCRINE TUMORS; OLIGOPEPTIDES; PANCREATIC NEOPLASMS; RADIOPHARMACEUTICALS; RADIOTHERAPY; RECEPTORS, PEPTIDE; TECHNETIUM;

EID: 84874955422     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026611212230003     Document Type: Review

References (128)

1. Dorsam, R.T.; Gutkind, J.S. G-protein-coupled receptors and cancer. Nat. Rev. Cancer, 2007, 7, 79-94.
2. Pierce, K.L.; Premont, R.T.; Lefkowitz, R.J. Seven-transmembrane receptors. Nat. Rev. Mol. Cell. Biol., 2002, 3, 639-650.
3. J.C. Peptide receptors as molecular targets for cancer diagnosis and therapy. Endocr. Rev., 2003, 24, 389-427.
4. Reubi, J.C. Old and new Peptide receptor targets in cancer: future directions. Recent Results Cancer Res, 2012, 194, 567-576.
5. Reubi, J.C.; Macke, H.R.; Krenning, E.P. Candidates for peptide receptor radiotherapy today and in the future. J. Nucl. Med., 2005, 46 (Suppl 1), 67S-75S.
6. de Jong, M.; Breeman, W.A.; Kwekkeboom, D.J.; Valkema, R.; Krenning, E.P. Tumor imaging and therapy using radiolabeled somatostatin analogues. Acc. Chem. Res., 2009, 42, 873-880.
7. van Vliet, E.I.; Teunissen, J.J.; Kam, B.L.; de Jong, M.; Krenning, E.P.; Kwekkeboom, D.J. Treatment of Gastroenteropancreatic Neuroendocrine Tumors with Peptide Receptor Radionuclide Therapy. Neuroendocrinology, 2013, 97 (1), 74-85.
8. 3]octreotide in patients with advanced gastroenteropancreatic neuroendocrine tumors. Semin. Nucl. Med., 2006, 36, 147-156.
9. R.S. Paul Ehrlich's magic bullets. N. Engl. J. Med., 2004, 350, 1079-1080.
10. Maina T, Nock B.A. Radiolabeled peptides in receptor-targeted diagnosis and therapy of malignant tumors. In: Essays on Contemporary Peptide Science. Cordopatis, P. Ed.; Research Signpost: Kerala, India, 2011; Vol. 37/661 (2), pp. 113-136.
11. Reubi, J.C.; Eisenwiener, K.P.; Rink, H.; Waser, B.; Mäcke, H.R. A new peptidic somatostatin agonist with high affinity to all five somatostatin receptors. Eur. J. Pharmacol., 2002, 456, 45-49.
12. Capello, A.; Krenning, E.P.; Bernard, B.F.; Breeman, W.A.; van Hagen, M.P.; de Jong, M. Increased cell death after therapy with an Arg-Gly-Asp-linked somatostatin analog. J. Nucl. Med., 2004, 45, 1716-1720.
13. Dilworth, J.R.; Parrott, S.J. The biomedical chemistry of techne-tium and rhenium. Chem. Soc. Rev., 1998, 27, 43-55.
14. K. Technetium Radiopharmaceuticals - Fundamentals, Synthesis, Structure, and Development. Angew. Chem. Int. Ed., 1994, 33, 2258-2267.
15. Deutsch, E.; Heineman, W.R.; Zodda, J.P.; Gilbert, T.W.; Williams, C.C. Preparation of No-Carrier-Added Technetium-99m Complexes - Determination of the Total Technetium Content of Generator Eluents. Int. J. Appl. Radiat. Isotopes, 1982, 33, 843-848.
16. Deutsch, E.; Heineman, W.R.; Zodda, J.P. Preparation of No Carrier Added Tc-99m Complexes. Trans. Am. Nucl. Soc., 1981, 38, 55.
17. Kowalsky, R.J.; Perry, R. J. Radiopharmaceuticals in Nuclear Medicine Practice. Appleton and Lange, E Norwalk, CT: United States, 1987.
18. Breeman, W.A.; Fröberg, A.C.; de Blois, E.; van Gameren, A.; Melis, M.; de Jong, M.; Maina, T.; Nock, B.A.; Erion, J.L.; Mäcke, H.R.; Krenning, E.P. Optimised labeling, preclinical and initial clinical aspects of CCK-2 receptor-targeting with 3 radiolabeled peptides. Nucl. Med. Biol., 2008, 35, 839-849.
19. Tisato, F.; Porchia, M.; Bolzati, C.; Refosco, F.; Vittadini, A. The preparation of substitution-inert Tc-99 metal-fragments: Promising candidates for the design of new Tc-99m radiopharmaceuticals. Coord. Chem. Rev., 2006, 250, 2034-2045.
20. Bandoli, G.; Dolmella, A.; Porchia, M.; Refosco, F.; Tisato, F. Structural overview of technetium compounds (1993-1999). Coord. Chem. Rev., 2001, 214, 43-90.
21. Liu, S.; Edwards, D.S.; Harris, A.R.; Heminway, S.J.; Barrett, J.A. Technetium complexes of a hydrazinonicotinamide-conjugated cyclic peptide and 2-hydrazinopyridine: Synthesis and characterization. Inorg. Chem., 1999, 38, 1326-1335.
22. 99mTc-Labeled small peptides as diagnostic radiopharmaceuticals. Chem. Rev., 1999, 99, 2235-2268.
23. 99mTc-Labeling of highly potent small peptides. Bioconjugate Chem., 1997, 8, 621-636.
24. 99mTc-protein conjugates. Bioconjugate Chem., 1991, 2, 333-336.
25. 99mTc: a reflection on technetium core structures and a strategy for new chelate design. Nucl. Med. Biol., 2005, 32, 1-20.
26. Lahorte, C.M.; Vanderheyden, J.L.; Steinmetz, N.; Van de Wiele, C.; Dierckx, R.A.; Slegers, G. Apoptosis-detecting radioligands: current state of the art and future perspectives. Eur. J. Nucl. Med. Mol. Imaging, 2004, 31, 887-919.
27. 111In-octreotide. J. Nucl. Med., 2000, 41, 1114-1119.
28. 111In-labelled octreotide derivatives. Eur. J. Nucl. Med., 2000, 27, 1318-1325.
29. 99mTc by Amino Acid Side Chains Results in Improved Performance Both In Vitro and In Vivo. J. Nucl. Med., 2009, 50, 591-598.
30. King, R.C.; Surfraz, M.B.; Biagini, S.C.; Blower, P.J.; Mather, S.J. How do HYNIC-conjugated peptides bind technetium? Insights from LC-MS and stability studies. Dalton Trans., 2007, 4998-5007.
31. 1-octreotide. Eur. J. Nucl. Med., 2000, 27, 628-637.
32. 99mTc-EDDA/HYNIC-octreotate scintigraphy, an efficient method for the detection and staging of carcinoid tumours: results of 3 years' experience. Eur. J. Nucl. Med. Mol. Imaging, 2006, 33, 1123-1133.
33. 99mTc-TATE in identifying sites of disease in patients with proven GEP NETs. J. Nucl. Med., 2008, 49, 1060-1065.
34. Waibel, R.; Alberto, R.; Willuda, J.; Finnern, R.; Schibli, R.; Stichelberger, A.; Egli, A.; Abram, U.; Mach, J.P.; Pluckthun, A.; Schubiger, P.A. Stable one-step technetium-99m labeling of His-tagged recombinant proteins with a novel Tc(I)-carbonyl complex. Nat. Biotechnol., 1999, 17, 897-901.
35. 99mTc with an In Situ CO Source: Application to a Serotonergic Receptor Ligand. Angew. Chem. Int. Ed. Engl., 2001, 40, 3062-3066.
36. Maria, L.; Paulo, A.; Santos, I.C.; Santos, I.; Kurz, P.; Spingler, B.; Alberto, R. Very small and soft scorpionates: water stable technetium tricarbonyl complexes combining a bis-agostic (k(3)-H, H, S) binding motif with pendant and integrated bioactive molecules. J. Am. Chem. Soc., 2006, 128, 14590-14598.
37. + (M = Re, Tc) directed towards radiopharmaceutical application. Coord. Chem. Rev., 1999, 192, 901-919.
38. 2+ metal fragments (M = Tc, Re; PXP = diphosphine ligand). Inorg. Chem., 2004, 43, 8617-8625.
39. 2+ metal fragment: A technetium-nitrido synthon for use with biologically active molecules the N-(2-methoxyphenyl) piperazyl-cysteine analogues as examples. Bioconjugate Chem., 2003, 14, 1231-1242.
40. 2+ (PXP = diphosphine ligand). A novel tool for the selective labeling of small molecules. J. Am. Chem. Soc., 2002, 124, 11468-11479.
41. 2+ metal fragments (M = Tc, Re; PXP = diphosphine ligand). Inorg. Chem., 2004, 43 (26), 8617-8625.
42. +: A versatile precursor for the labelling of pharmacophores, amino acids and carbohydrates through a new ligand-centred labelling strategy. Chemistry, 2011, 17, 12967-12974.
43. W.C. Radiolabeling with technetium-99m to study high-capacity and low-capacity biochemical systems. Eur. J. Nucl. Med., 1995, 22, 249-263.
44. 99mTc-radiolabelled peptides for tumour imaging: present and future. Curr. Med. Chem., 2010, 17, 2656-2683.
45. 188Re in the development of radiolabeled peptide pharmaceuticals. Anticancer Agents Med. Chem., 2012, 12, 428-461.
46. Jones, A.G.; Davison, A.; Trop, H.S.; Depamphilis, B.V.; Orvig, C.; Davis, M.A. Oxotechnetium(V) Complexes. J. Nucl. Med., 1979, 20, 641-641.
47. Davison, A.; Orvig, C.; Trop, H.S.; Sohn, M.; Depamphilis, B.V.; Jones, A.G. Preparation of Oxobis(Dithiolato) Complexes of Tecnetium(V) and Rhenium(V). Inorg. Chem., 1980, 19, 1988-1992.
48. 99mTc renal tubular function agents: current status. Semin Nucl Med., 1990, 20 (1), 28-40.
49. Van de Wiele, C.; Dumont, F.; Vanden Broecke, R.; Oosterlinck, W.; Cocquyt, V.; Serreyn, R.; Peers, S.; Thornback, J.; Slegers, G.; Dierckx, R.A. Technetium-99m RP527, a GRP analogue for visualisation of GRP receptor-expressing malignancies: a feasibility study. Eur. J. Nucl. Med., 2000, 27, 1694-1699.
50. 99mTc-RP527, a gastrin-releasing peptide (GRP) agonist for the visualization of GRP receptor-expressing malignancies. J. Nucl. Med., 2001, 42, 1722-1727.
51. 99mTc]technetium depreotide: a somatostatin receptor binding tumor imaging agent. J. Med. Chem., 2007, 50, 4295-4303.
52. 99mTc peptide targeted radiopharmaceuticals. Inorg. Chem., 2007, 46, 7326-7340.
53. Zuckman, S.A.; Freeman, G.M.; Troutner, D.E.; Volkert, W.A.; Holmes, R.A.; Vanderveer, D.G.; Barefield, E.K. Preparation and X-Ray Structure of Trans-Dioxo(1,4,8,11-Tetraazacyclotetrade cane)Technetium(V) Perchlorate Hydrate. Inorg. Chem., 1981, 20, 2386-2389.
54. Mantegazzi, D.; Ianoz, E.; Lerch, P.; Nicoló, F.; Chapuis, G. Preparation and Crystal-Structure of Polymeric Lithium[DioxoTc (V)Tetraazaundecane]-Bis(Trifluoromethanesulfonate) Complex. Inorg. Chim. Acta, 1990, 176, 99-105.
55. Thornback, J.R.; Theobald, A.E. Ethylenediamine-Tc-99m - a New Cationic Complex of Technetium. Int. J. Appl. Radiat. Isot., 1981, 32, 833-838.
56. Kremer, C; Kremer, E.; Dominguez, S.; Chinea, E.; Mederos, A.; Castineiras, A. Synthesis, characterization and potentiometric studies of trans-dioxorhenium(v) complexes. X-ray crystal structure of [ReO2(tn)2)]I-H2O. Polyhedron, 1996, 15, 4341-4347.
57. Gancheff, J.; Melian, C; Kremer, C; Dominguez, S.; Mederos, A.; Ventura, O.N.; Kremer, E. Synthesis, characterization and solution chemistry of new Re(V) dioxo complexes. J. Coord. Chem., 2001, 54, 285-296.
58. + Group from the Reactions of ReNCl2(PPh3)2, ReCl4(PPh3)2, and ReCl3(CH3cn) (PPh3)2 with Chelating Amines and Tetraazamacrocycles - Crystal-Structure of Trans-[ReO2(Cyclam)](PF6) (Cyclam = 1,4,8,11-Tetraazacyclotetradecane). Inorg. Chem., 1992, 31, 2595-2598.
59. Brewer, J.C.; Gray, H.B. Efficient Syntheses of Dioxorhenium(V) Complexes. Inorg. Chem., 1989, 28, 3334-3336.
60. Blake, A.J.; Greig, J.A.; Schröder, M. Rhenium Complexes of Tetra-Aza Macrocycles - the Synthesis and Single-Crystal X-Ray Structure of Trans-[Re(O)2(Cyclam)]Cl.2(BPh3.H2O). J. Chem. Soc.-Dalton Trans., 1988, 2645-2647.
61. +. Inorg. Chem., 1988, 27, 4127-4130.
62. 99mTc in Aqueous-Solutions by Ligand-Exchange. Int. J. Appl. Radiat. Isot., 1982, 33, 891-896.
63. Blauenstein, P.; Pfeiffer, G.; Schubiger, P.A.; Anderegg, G.; Zollinger, K.; May, K.; Proso, Z.; Ianovici, E.; Lerch, P. Chemical and Biological Properties of a Cationic Tc-Tetraamine Complex. Int. J. Appl. Radiat. Isot., 1985, 36, 315-317.
64. 99mTc-Labeled Organic Cations. J. Nucl. Med., 1992, 33, 2190-2195.
65. 1]octreotide, a new octreotide derivative with high affinity for somatostatin receptors. In: Technetium and Rhenium in Chemistry and Nuclear Medicine; M. Nicolini, G. Bandoli, U. Mazzi Ed; SGEditoriali: Padova, 1995; Vol 4, pp. 395-400.
66. 99mTc to tumors. In: Technetium and Rhenium in Chemistry and Nuclear Medicine; U. Mazzi Ed; SGEditoriali: Padova, 2006; Vol 7, pp. 277-282.
67. 3]octreotate analogue for the detection of somatostatin receptor-positive tumours: synthesis and preclinical results. Eur. J. Nucl. Med. Mol. Imaging, 2002, 29, 742-753.
68. 99mTc targeting of sst2-expressing tumors by tetraamineoctreotide: first results in CA20948 cells and rat models. Anticancer Res., 2006, 26, 363-366.
69. 99mTc and preclinical comparison in AR4-2J cells and AR4-2J tumor-bearing mice. J. Pept. Sci., 2006, 12, 124-131.
70. 3]octreotate derivatives in DMSO: structure differentiation of peptide core due to chelate group attachment and biologically active conformation. Med. Chem., 2005, 1, 487-499.
71. 99mTc demotate 1: biodis tribution and elimination characteristics in rats. Nucl. Med. Commun., 2005, 26, 549-554.
72. 111In]DOTA-Tate. Eur. J. Nucl. Med. Mol. Imaging, 2006, 33, 831-840.
73. 99mTc]Demotate 1: A structure - Activity relationships study. J. Pept. Sci., 2008, 14, 152-153.
74. 99mTc]Demotate 1-4 in CA20948 cells and rats. Eur. J. Nucl. Med. Mol. Imaging, 2004, 31, S379.
75. 3]octreotate - Effects on target-tissue localization and kidney uptake. In: Technetium and Rhenium in Chemistry and Nuclear Medicine; M. Nicolini, G. Bandoli, U. Mazzi Ed; SGEditoriali: Padova, 2002; Vol 6, pp. 523-525.
76. 99mTc-Demotate 1: first data in tumour patients-results of a pilot/phase I study. Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 1211-1219.
77. 3]Octreotide: an intrapatient comparison of two novel Technetium-99m labeled tracers for somatostatin receptor scintigraphy. Cancer Biother. Radiopharm.,2004,19, 73-79.
78. 94mTc-Demotate 1. J. Nucl. Med.,2005,46, 1889-1897.
79. Ginj, M.; Chen, J.; Walter, M.A.; Eltschinger, V.; Reubi, J.C.; Maecke, H.R. Preclinical evaluation of new and highly potent analogues of octreotide for predictive imaging and targeted radiotherapy. Clin. Cancer Res., 2005, 11, 1136-1145.
80. 68Ga-DOTANOC: a first compound for PET imaging with high affinity for somatostatin receptor subtypes 2 and 5. Eur. J. Nucl. Med. Mol. Imaging, 2005, 32, 724.
81. Wild, D.; Schmitt, J.S.; Ginj, M.; Mäcke, H.R.; Bernard, B.F.; Krenning, E.; de Jong, M.; Wenger, S.; Reubi, J.C. DOTA-NOC, a high-affinity ligand of somatostatin receptor subtypes 2, 3 and 5 for labelling with various radiometals. Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 1338-1347.
82. Ginj, M.; Schmitt, J.S.; Chen, J.; Waser, B.; Reubi, J.C.; de Jong, M.; Schulz, S.; Maecke, H.R. Design, synthesis, and biological evaluation of somatostatin-based radiopeptides. Chem. Biol., 2006, 13, 1081-1090.
83. Ginj, M.; Zhang, H.; Eisenwiener, K.P.; Wild, D.; Schulz, S.; Rink, H.; Cescato, R.; Reubi, J.C.; Maecke, H.R. New pansomatostatin ligands and their chelated versions: affinity profile, agonist activity, internalization, and tumor targeting. Clin. Cancer Res., 2008, 14, 2019-2027.
84. 111In-DTPA-octreotide. Eur. J. Nucl. Med. Mol. Imaging, 2012, 39 (12), 1868-1875.
85. 99mTc-labeled N4-functionalized somatostatins with high affinity for all five human somatostatin receptor subtypes. Eur. J. Nucl. Med. Mol. Imaging, 2006, 33, S149.
86. 99mTc]Demonate 1 - Synthesis, radiolabeling and in vitro/in vivo evaluation. Eur. J. Nucl. Med. Mol. Imaging, 2006, 33, S149.
87. 99mTc-Labeled tetraamine-derivatized cyclic nona-peptides with pansomatostatin-like properties: Synthesis and comparative biological evaluation. J. Pept. Sci., 2008, 14, 152.
88. 99mTc-based tracers with pansomatostatin properties. In: Technetium and Rhenium in Chemistry and Nuclear Medicine; U. Mazzi Ed; SGEditoriali: Padova, 2006; Vol 7, pp. 321-322.
89. R. Chemistry, Metabolism, and Biological Functions of Sialic Acids. Advances in Carbohydrate Chemistry and Biochemistry, 1982, 40, 131-234.
90. Rens-Domiano, S.; Reisine, T. Structural analysis and functional role of the carbohydrate component of somatostatin receptors. J. Biol. Chem., 1991, 266, 20094-20102.
91. el Battari, A.; Luis, J.; Martin, J.M.; Fantini, J.; Muller, J.M.; Marvaldi, J.; Pichon, J. The vasoactive intestinal peptide receptor on intact human colonic adenocarcinoma cells (HT29-D4). Evidence for its glycoprotein nature. Biochem. J., 1987, 242, 185-191.
92. Reubi, J.C.; Waser, B.; Schaer, J.C.; Laissue, J.A. Neurotensin receptors in human neoplasms: high incidence in Ewing's sarcomas. Int. J. Cancer, 1999, 82, 213-218.
93. Reubi, J.C.; Waser, B.; Friess, H.; Buchler, M.; Laissue, J. Neurotensin receptors: a new marker for human ductal pancreatic adenocarcinoma. Gut, 1998, 42, 546-550.
94. 99mTc. J. Med. Chem.,2006,49, 4767-4776.
95. 99mTc]Demotensin 5 and 6 in the NTS1-R-targeted imaging of tumours: synthesis and preclinical results. Eur. J. Nucl. Med. Mol. Imaging, 2007, 34, 1804-1814.
96. 99mTc]Demotensin VI: biodistribution and initial clinical results in tumor patients of a pilot/phase I study. Cancer Biother. Radiopharm., 2011, 26, 557-563.
97. 99mTc-NT-XI, evaluated in ductal pancreatic adenocarcinoma patients. J. Nucl. Med., 2003, 44, 1649-1654.
98. 111In-labelled DTPA- and DOTA-conjugated neurotensin analogues for imaging and therapy of exocrine pancreatic cancer. Eur. J. Nucl. Med. Mol/ Imaging, 2003, 30, 1134-1139.
99. J.C. Targeting CCK receptors in human cancers. Curr. Top. Med. Chem., 2007, 7, 1239-1242.
100. Schurrat, T.; Alfke, H.; Béhé, M.; Maina, T.; Nock, B.; Mäcke, H.; Heverhagen, J.T.; Klose, K.J.; Halling, H.; Behr, T.M.; Schramm, N. Molecular gastrin receptor localisation in mice using high-resolution SPET-MRI image fusion. Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 800.
101. 99mTc-labeled minigastrin analogs. J. Nucl. Med., 2005, 46, 1727-1736.
102. 111In-labeled CCK-2/gastrin receptor-specific peptides in rats. Anticancer Res., 2007,27, 907-912.
103. 99mTc-Demogastrin 1. Cancer Bioth. Radiopharm., 2012, 27, 169-174.
104. 99mTc]Demogastrin 2: effects on CCK-2/gastrin-R-interaction. In: Technetium and Rhenium in Chemistry and Nuclear Medicine; U. Mazzi Ed; SGEditoriali: Padova, 2006; Vol 7, pp. 323-324.
105. 99mTc]Demogastrin 4 - 6. In: Technetium and Rhenium in Chemistry and Nuclear Medicine; U. Mazzi Ed; SGEditoriali: Padova, 2006; Vol 7, pp. 325-326.
106. 111In-labelled gastrin/CCK2 receptor-targeting peptides. Eur. J. Nucl. Med. Mol. Imaging, 2011, 38, 1410-1416.
107. Fröberg, A.C.; de Jong, M.; Nock, B.A.; Breeman, W.A.P.; Erion, J.L.; Maina, T.; Verdijsseldonck, M.; de Herder, W.W.; van der Lugt, A.; Kooij, P.P.M.; Krenning, E.P. Comparison of three radiolabelled peptide analogues for CCK-2 receptor scintigraphy in medullary thyroid carcinoma. Eur. J. Nucl. Med. Mol. Imaging, 2009, 36, 1265-1272.
108. 99mTc-Demogastrin 2. Endocr. Rev., Suppl.1, 2010, 31 (3), S613; P1-538.
109. 99mTc-Demogastrin 2 for CCK 2-receptor scintigraphy in medullary thyroid carcinoma. Eur. J. Nucl. Med. Mol. Imaging, 2006, 33, S109.
110. Froeberg, A.C.; de Jong, M.; Nock, B.; Erion, J.; Breeman, W.A.P.; Kooji, P.P.M.; Melis, M.; Maina, T.; Krenning, E.P. Inconsistent renal uptake of CCK-2 receptor binding analogues in animals and humans. Eur. J. Nucl. Med. Mol. Imaging, 2010, 37, S299-S300.
111. Maina, T.; Nock, B.; Mather, S. Targeting prostate cancer with radiolabelled bombesins. Cancer Imaging, 2006, 6, 153-157.
112. 99mTc: A preclinical study. J. Med. Chem., 2005, 48, 100-110.
113. 99mTc]Demomedin C, a Radioligand Based on Human Gastrin Releasing Peptide(18-27): Synthesis and Preclinical Evaluation in Gastrin Releasing Peptide Receptor-Expressing Models. J. Med. Chem., 2012, 55, 8364-8374.
114. 99mTc]SAR-G1: A New Candidate for GRPR-Targeted Tumor Imaging. Eur. J. Nucl. Med. Mol. Imaging, 2010, 37, S228.
115. 99mTc-Neuromedin C Analogs. Eur. J. Nucl. Med. Mol. Imaging 2011, 38, S158-S159.
116. 99mTc: Synthesis and preclinical data. Eur. J. Nucl. Med., 2002, 29, S147.
117. 99mTc]Demobesin 1, a novel potent bombesin analogue for GRP receptor-targeted tumour imaging. Eur. J. Nucl. Med. Mol. Imaging, 2003, 30, 247-258.
118. Cescato, R.; Maina, T.; Nock, B.; Nikolopoulou, A.; Charalambidis, D.; Piccand, V.; Reubi, J.C. Bombesin receptor antagonists may be preferable to agonists for tumor targeting. J. Nucl. Med., 2008, 49, 318-326.
119. Fröberg, A.C.; Maina, T.; Erion, J.; de Swart, J.; de Jong, M.; Krenning, E.P. GRP-receptors are likely present in the human pancreas. J. Nucl. Med., 2006, 47, 429P.
120. 177Lu-AMBA Bombesin analogue in hormone refractory prostate cancer patients: A phase I escalation study with single-cycle administrations. Eur. J. Nucl. Med. Mol. Imaging, 2007, 34, S221.
121. Ginj, M.; Zhang, H.; Waser, B.; Cescato, R.; Wild, D.; Wang, X.; Erchegyi, J.; Rivier, J.; Mäcke, 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.
122. Mansi, R.; Wang, X.; Forrer, F.; Kneifel, S.; Tamma, M.L.; Waser, B.; Cescato, R.; Reubi, J.C.; Maecke, H.R. Evaluation of a 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraaceticacid-conjugated bombesin-based radioantagonist for the labeling with single-photon emission computed tomography, positron emission tomography, and therapeutic radionuclides. Clin. Cancer Res., 2009, 15, 5240-5249.
123. +-tumors. J. Pept. Sci., 2012, 18, S151.
124. Abiraj, K.; Mansi, R.; Tamma, M.L.; Forrer, F.; Cescato, R.; Reubi, J.C.; Akyel, K.G.; Maecke, H.R. Tetraamine-derived bifunctional chelators for technetium-99m labelling: synthesis, bioconjugation and evaluation as targeted SPECT imaging probes for GRP-receptor-positive tumours. Chemistry, 2010, 16, 2115-2124.
125. Abiraj, K.; Mansi, R.; Tamma, M.L.; Fani, M.; Forrer, F.; Nicolas, G.; Cescato, R.; Reubi, J.C.; Maecke, H.R. Bombesin antagonist-based radioligands for translational nuclear imaging of gastrin-releasing peptide receptor-positive tumors. J. Nucl. Med., 2011, 52, 1970-1978.
126. Fani, M.; Maecke, H.R.; Okarvi, S.M. Radiolabeled peptides: valuable tools for the detection and treatment of cancer. Theranostics, 2012, 2 (5), 481-501.
127. 188Re-complexes under mild conditions. Appl. Radiat. Isot., 2006, 64, 223-227.
128. Prakash, S.; Went, M.J.; Blower, P.J. Cyclic and acyclic polyamines as chelators of rhenium-186 and rhenium-188 for therapeutic use. Nucl. Med. Biol., 1996, 23, 543-549.