The role of inorganic chemistry in the development of radiometal agents for cancer therapy

Accounts of Chemical Research

Volumn 32, Issue 12, 1999, Pages 1053-1060

  Heeg, Mary Jane ^a,b   Jurisson, Silvia S ^a,b  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; COPPER 67; IODINE 131; MERTIATIDE TC 99M; RADIOACTIVE MATERIAL; RHODIUM; STRONTIUM 89; TECHNETIUM 99M; YTTRIUM 90;

ARTICLE; CANCER INHIBITION; CANCER RADIOTHERAPY; CHELATION; INORGANIC CHEMISTRY; ISOTOPE LABELING; LINEAR ENERGY TRANSFER; RADIOIMMUNOTHERAPY;

EID: 0033402734     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar980002c     Document Type: Article

References (83)

1. Cleaves, M. A. Radium Therapy. Med. Rec. 1903, 64, 601.
2. Brady, L. W.; Micaily, B.; Miyamoto, C. T.; Heilmann, H.-P.; Montemaggi, P. Innovations in Brachytherapy in Gynecologic Oncology. Cancer 1995, 76, 2143-2151.
3. Becker, D. V.; Sawin, C. T. Radioiodine and Thyroid Disease: The Beginning Semin. Nucl. Med. 1996, 26, 155-164.
4. Kusakabe, K.; Maki, M. Radionuclide Therapy of Thyroid Disease-Radioactive Iodine Therapy. Kaku Igaku [Jpn. J. Nucl. Med.] 1993, 30, 813-819.
5. Volkert, W. A.; Goeckler, W. F.; Ehrhardt, G. J.; Ketring, A. R. Therapeutic Radionuclides: Production and Decay Property Considerations. J. Nucl. Med. 1991, 32, 174-185.
6. Troutner, D. E. Chemical and Physical Properties of Radionuclides. Nucl. Med. Biol. 1987, 14, 171-176.
7. Srivastava, S. C.; Mease, R. C. Progress in Research on Ligands, Nuclides and Techniques for Labelling Monoclonal Antibodies. Nucl. Med. Biol. 1991, 18, 589-603.
8. Hnatowich, D. J. Antibody Labelling, Problems and Promises. Nucl. Med. Biol. 1990, 17, 49-55.
9. Goldenberg, D. M. Future Role of Radiolabelled Monoclonal Antibodies in Oncological Diagnosis and Therapy. Sem. Nucl. Med. 1989, 19, 332-339.
10. Woo, D. V.; Markoe, A. M.; Brady, L. W.; Koprowski, C.; Koprowski, H.; Heindel, N. D.; Mattis, J. Monoclonal-Antibodies for Use in Radiotherapy and Diagnosis. Am. J. Clin. Oncol. 1988, 11, 355-361.
11. Parker, D. Tumor Targeting with Radiolabelled Macrocycle-Antibody Conjugates. Chem. Soc. Rev. 1990, 19, 271-291.
12. Meares, C. F. Chelating Agents for the Binding of Metal Ions to Antibodies. Int. J. Rad. Appl. Instrum., Part B-Nucl. Med. Biol. 1986, 13, 311-318.
13. Liu, Y. F.; Wu, C. C. Radiolabeling of Monoclonal Antibodies with Metal Chelates. Pure Appl. Chem. 1991, 63, 427-463.
14. Schubiger, P. A., Alberto, R.; Smith, A. Vehicles, Chelators and Radionuclides: Choosing the "Building Blocks" of an Effective Therapeutic Radioimmunoconjugate. Bioconjugate Chem. 1996, 7, 165-179.
15. Jurisson, S.; Berning, D.; Jia, W.; Ma, D. Coordination Compounds in Nuclear Medicine. Chem. Rev. 1993, 93, 1137-1156.
16. 99mTc Labeling of Highly Potent Small Peptides. Bioconjugate Chem. 1997, 8, 621-636.
17. Dilworth, J. R.; Parrott, S. J. The Biomedical Chemistry of Technetium and Rhenium. Chem. Soc. Rev. 1998, 27, 43-55.
18. (a) Soloway, A. H.; Davis, M. A. Survey of Radiopharmaceuticals and Their Current Status. J. Pharm. Sci. 1974, 63, 647-665.
19. (b) Feinendegen, L. E. Contributions of Nuclear Medicine to the Therapy of Malignant Tumors. Strahlenther. Onkol. 1991, 167, 619-627.
20. Krenning, E. P.; Bakker, W. H.; Kooij, P. P. M.; Breeman, W. A. P.; Oei, H. Y.; de Jong, M.; Reubi, J. C.; Visser, T. J.; Bruns, C.; Kwekkeboom, D. J.; Reijs, A. E. M.; van Hagen, P. M.; Koper, J. W.; Lamberts, S. W. J. 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.
21. Pless, J.; Bauer, W.; Briner, U.; Doepfner, W.; Marbach, P.; Maurer, R.; Petcher, T. J.; Reubi, J.-C.; Vonderscher J. Chemistry and Pharmacology of SMS 201-995, a Long-Acting Octapeptide Analogue of Somatostatin. Scand. J. Gastroent. 1986, 21 (Suppl. 119), 54-64.
22. del Pozo, E.; Neufeld, M.; Schluter, K.; Tortosa, F.; Clarenbach, P.; Bieder, E.; Wendel, L.; Nesch E.; Marbach, P.; Cramer, H.; Kerp, L. Endocrine Profile of a Long-Acting Somatostatin Derivative SMS 201-995. Study in Normal Volunteers Following Subcutaneous Administration. Acta Endocrinol. 1986, 111, 433-439.
23. Wheldon, T. E. Targeting Radiation to Tumours. Int. J. Radiat. Biol. 1994, 65, 109-116 and references therein.
24. Zweit, J. Radionuclides and Carrier Molecules for Therapy. Phys. Med. Biol. 1996, 41, 1905-1914.
25. Saha, G. B. Physics and Radiobiology of Nuclear Medicine; Springer-Verlag: New York, 1993.
26. Cole, A. Absorption of 20-eV to 50,000-eV Electron Beams in Air and Plastic. Radiat. Res. 1969, 38, 7-33.
27. 90Y. Radiother. Oncol. 1991, 21, 91-99.
28. Humm, J. L.; Cobb, L. M. Nonuniformity of Tumor Dose in Radioimmunotherapy. J. Nucl. Med. 1990, 31, 75-83.
29. O'Donoghue, J. A.; Wheldon, T. E. Targeted Radiotherapy Using Auger Electron Emitters. Phys. Med. Biol. 1996, 41, 1973-1992 and references therein.
30. McDevitt, M. R.; Sgouros, G.; Finn, R. D.; Humm, J. L.; Jurcic, J. G.; Larson, S. M.; Scheinberg, D. A. Radioimmunotherapy with Alpha-Emitting Nuclides. Eur. J. Nucl. Med. 1998, 25, 1341-1351.
31. Kassis, A. I.; Harapanhalli, R. S.; Adelstein, S. J. Comparison of Strand Breaks in Plasmid DNA After Positional Changes of Auger Electron-Emitting Iodine-125. Radiat. Res. 1999, 151, 167-176 and references therein.
32. Volkert, W. A.; Deutsch, E. A. Bone-Seeking Radiopharmaceuticals in Cancer Therapy. Adv. Metals Med. 1993, 1, 115-153.
33. Blake, G. M.; Zivanovic, M. A.; McEwan, A. J.; Ackery, D. M. Sr-89 Therapy: Strontium Kinetics in Disseminated Carcinoma of the Prostrate. Eur. J. Nucl. Med. 1986, 12, 447-454.
34. Volkert, W. A.; Simon, J.; Ketring, A. R.; Holmes, R. A.; Lattimer, L. C.; Corwin, L. A. Radiolabeled Phosphonic Acid Chelates: Potential Therapeutic Agents for Treatment of Skeletal Metastases. Drugs Future 1989, 14, 799-811.
35. 153Sm Chelates: Potential Therapeutic Bone Agents J. Nucl. Med. 1987, 28, 495-504.
36. Turner, J. H.; Claringbold, P. G. A Phase-II Study of Treatment of Painful Multifocal Skeletal Metastases with Single and Repeated Dose Sm-153 ethylenediaminetetramethylene phosphonate. Eur. J. Cancer 1991, 27, 1084-1086.
37. Deutsch, E.; Libson, K.; Vanderheyden, J.-L.; Ketring, A. R.; Maxon, H. R. The Chemistry of Rhenium and Technetium as Related to the Use of Isotopes of These Elements in Therapeutic and Diagnostic Nuclear Medicine. Nucl. Med. Biol. 1986, 13, 465-477.
38. Hoefnagel, C. A. Radionuclide Therapy Revisited. Eur. J. Nucl. Med. 1991, 18, 408-431.
39. Pipes, D. W.; Deutsch, E. Rhenium Re-186 Etidronate Injection. Drugs Future 1993, 18, 520-524.
40. 186ReHEDP. Inorg. Chem. 1997, 36, 3055-3063.
41. 2O. Implications for the Chemistry of Technetium-99m-Diphosphonate Skeletal Imaging Agents. Inorg. Chem. 1983, 22, 1332-1338.
42. 4)-HEDP Mixtures Separated by Anion Exchange High Performance Liquid Chromatography. Int. J. Appl. Radiat. Isot. 1982, 33, 907-915.
43. (a) Pressman, D.; Keighly, G. The Zone of Activity of Antibodies as Determined by the Use of Radioactive Tracers; the Zone of Activity of Nephrotoxic Anti-Kidney Serum. J. Immunol. 1948, 59, 141-146.
44. (b) Pressman, D. Radiolabeled Antibodies. Ann. N.Y. Acad. Sci. 1957, 69, 644-650.
45. Kœhler, G.; Milstein, C. Continuous Culture of Fused Cells Secreting Antibody of Proven Defined Specificity. Nature 1975, 256, 495-497.
46. Kairemo, K. J. A. Radioimmunotherapy of Solid Cancers. Acta Oncol. 1996, 35, 343-355.
47. Wilder, R. B.; DeNardo, G. L.; DeNardo, S. J. Radioimmunotherapy: Recent Results and Future Directions. J. Clin. Oncol. 1996, 14, 1383-1400.
48. White, C. A.; Halpern, S. E.; Parker, B. A.; Miller, R. A.; Hupf, H. B.; Shawler, D. L.; Collins, H. A.; Royston, T. Radioimmunotherapy of Relapsed B-Cell Lymphoma with Yttrium 90 Anti-Idiotype Mno-clonal Antibodies. Blood 1996, 87, 3640-3649.
49. DeLand, F. H. A Perspective of Monoclonal Antibodies: Past, Present, and Future. Semin. Nucl. Med. 1989, 19, 158-165.
50. Goldenberg, D. M. Future Role of Radiolabeled Monoclonal Antibodies in Oncological Diagnosis and Therapy. Semin. Nucl. Med. 1989, 19, 332-339.
51. Goodwin, D. A.; Meares, C. F. Pretargeting General Principles; October 10-12 1996. Cancer 1997, 80, 2675-2680.
52. Paganelli, G.; Magnani, P.; Zito, F.; Villa, E.; Sudati, F.; Lopalco, L.; Rossetti, C.; Malcovati, M.; Chiolerio, F.; Seccamani, E.; Siccardi, A. G.; Fazio, F. Three-Step Monoclonal Antiody Tumor Targeting in Carcinoembryonic Antigen-Positive Patients. Cancer Res. 1991, 51, 5960-5966.
53. 111In-DTPA-Octreotide. Peptide Res. 1996, 9, 144-150.
54. 3-Octreotide in Baboons. Proceedings of the XII International Symposium on Radiopharmaceutical Chemistry, Uppsala, Sweden, June 15-19, 1997; pp 468-470 (abstract).
55. 188Re-RC-160 Somatostatin Analog: a Peptide for Local/Regional Radiotherapy. Appl. Radiat. Isot. 1997, 48, 305-309.
56. Zamora, P. O.; Bender, H.; Gulhke, S.; Marek, M. J.; Knapp, F. F.; Rhodes, B. A.; Biersack, H. J. Preclinical Experience with Re-188-RC-160, a Radiolabeled Somatostatin Analog for Use in Peptide-Targeted Radiotherapy. Anticancer Res. 1997, 17, 1803-1808.
57. Hoffman, T. J.; Li, N.; Sieckman, G. L.; Volkert, W. A. Uptake and Retention of a Rh-105 Labeled Bombesin Analogue in GRP Receptor Expressing Neoplasms: an in vitro Study. J. Nucl. Med. 1997, 30, 188P-189P (Suppl. S).
58. Safavy, A.; Khazaeli, M. B.; Qin, H.; Buchsbaum, D. J. Synthesis of Bombesin Analogues for Radiolabeling with Rhenium-188. Cancer 1997, 80, 2354-2359 (Suppl.).
59. Griffiths, G. L.; Goldenberg, D. M.; Knapp, F. F.; Callahan, A. P.; Chang, C. H.; Hansen, H. J. Direct Radiolabeling of Monoclonal Antibodies with Generator-Produced Rhenium-188 for Radioimmunotherapy: Labeling and Animal Distribution Studies. Cancer Res. 1991, 51, 4595-4602.
60. Giblin, M. F.; Wang, N.; Hoffman, T. J.; Jurisson, S. S.; Quinn, T. P. Design and Characterization of α-Melanotropin Peptide Analogs Cyclized Through Rhenium and Technetium Metal Coordination. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12814-12818.
61. Boniface, G. R.; Izard, M. E.; Walker, K. Z.; McKay, D. R.; Sorby, P. J.; Turner, H.; Morris, J. G. Labeling of Monoclonal Antibodies with Samarium-153 for Combined Radioimmunoscintigraphy and Radioimmunotherapy. J. Nucl. Med. 1989, 30, 683-691.
62. Macklis, R. M.; Kinsey, B. M.; Kassis, A. I.; Ferrara, J. L. M.; Atcher, R. W.; Hines, J. J.; Coleman, C. N.; Adelstein, S. J.; Burakoff, S. J. Radioimmunotherapy with Alpha-Particle-Emitting Immunoconjugates. Science 1988, 240, 1024-1026.
63. Kozak, R. W.; Raubitschek, A.; Mirzadeh, S.; Brechbiel, M. W.; Junghaus, R.; Gansow, O. A.; Waldmann, T. A. Nature of the Bifunctional Chelating Agent Used for Radioimmunotherapy with Yttrium-90 Monoclonal Antibodies: Critical Factors in Determining in vivo Survival and Organ Toxicity. Cancer Res. 1989, 49, 2639-2644.
64. Deshpande, S. V.; DeNardo, S. J.; Kukis, D. L.; Moi, M. K.; McCall, M. J.; DeNardo, G. L.; Meares, C. F. Yttrium-90-Labeled Monoclonal Antibody for Therapy: Labeling by a New Macrocyclic Bifunctional Chelating Agent. J. Nucl. Med. 1990, 31, 473-479.
65. Junghans, R. P.; Dobbs, D.; Brechbiel, M. W.; Mirzadeh, S.; Raubitschek, A. A.; Gansow, O. A.; Waldmann, T. A. Pharmacokinetics and Bioactivity of 1,4,7,10-Tetra-azacyclododecane N,N′,N″,N‴-Tet-raacetic Acid (DOTA)-Bismuth-Conjugated Anti-Tac Antibody for Alpha-Emitter (Bi-212) Therapy. Cancer Res. 1993, 53, 5683-5689.
66. Ruegg, C. L.; Anderson-Berg, W. T.; Brechbiel, M. W.; Mirzadeh, S.; Gansow, O. A.; Strand, M. Improved in vivo Stability and Tumor Targeting of Bismuth-Labeled Antibody. Cancer Res. 1990, 50, 4221-4226.
67. Izard, M. E.; Boniface, G. R.; Hardiman, K. L.; Brechbiel, M. W.; Gansow, O. A.; Walkers, K. Z. An Improved Method for Labeling Monoclonal Antibodies with Samarium-153: Use of the Bifunctional Chelate 2-(p-Isothiocyanatobenzenzyl)-6-methyldiethylenetriaminepentaacetic Acid. Bioconjugate Chem. 1992, 3, 346-350.
68. 3OMe). Inorg. Chem. 1995, 34, 1764-1772.
69. Vanderheyden, J.-L.; Rao, T. N.; Kasina, S.; Wester, D.; Su, F.-M.; Fritzberg, A. R. Structural and Biological Equivalence of Technetium and Rhenium Diamide Dithiolate Complexes: Application to Antibody Labeling. In Technetium and Rhenium in Chemistry and Nuclear Medicine 3; Nicolini, M., Bandoli, G., Mazzi, U., Eds.; Cortina International: Verona, and Raven Press: New York, 1990; pp 624-629.
70. Fritzberg, A. R.; Vanderheyden, J.-L.; Morgan, A. C.; Schroff, R. W.; Abrams, P. G. Rhenium-186/-188 Labeled Antibodies for Radioimmunotherapy. In Technetium and Rhenium in Chemistry and Nuclear Medicine 3; Nicolini, M., Bandoli, G., Mazzi, U., Eds.; Cortina International: Verona, and Raven Press: New York, 1990; pp 615-621.
71. Breitz, H. B.; Weiden, P. L.; Vanderheyden, J.-L.; Appelbaum, J. W.; Bjorn, M. J.; Fer, M. F.; Wolf, S. B.; Ratliff, B. A.; Seiler, C. A.; Foisie, D. C.; Fisher, D. R.; Schroff, R. W.; Fritzberg, A. R.; Abrams, P. G. Clinical Experience with Rhenium-186-Labeled Monoclonal Antibodies for Radioimmunotherapy: Results of Phase I Trials. J. Nucl. Med. 1992, 33, 1099-1112.
72. 2-Metal Conjugate. Bioconjugate Chem. 1994, 5, 182-193.
73. + Moiety for the Labeling of Biomolecules. Radiochim. Acta 1997, 79, 99-103.
74. Mausner, L. F.; Srivastava, S. C.; Kolsky, K. L.; Mease, R. C.; Joshi, V.; Meinken, G. E.; Kurczak, S.; Chatal, J. F.; Steplewski, Z. Development and Evaluation of Copper-67 Labeled DOTA and TETA Immunoconjugates for Radioimmunotherapy. J. Labelled Compd. Radiopharm. 1994, 35, 374-376.
75. Studer, M.; Meares, C. F. Synthesis of Novel 1,4,7-Triazacyclononane-N,N′,N″-triacetic Acid Derivatives Suitable for Protein Labeling. Bioconjugate Chem. 1992, 3, 337-341.
76. Rogers, B. E.; Anderson, C. J.; Connett, J. M.; Guo, L. W.; Edwards, W. B.; Sherman, E. L. C.; Zinn, K. R.; Welch, M. J. Comparison of Four Bifunctional Chelates for Radiolabeling Monoclonal Antibodies with Copper Radioisotopes: Biodistribution and Metabolism. Bioconjugate Chem. 1996, 7, 511-522.
77. 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 Complexes. Nucl. Med. Biol. 1998, 25, 523-530.
78. Anderson, C. J.; Pajeau, T. S.; Edwards, W. B.; Sherman, E. L. C.; Rogers, B. E.; Welch, M. J. In vitro and in vivo Evaluation of Copper-64-octreotide Complexes. J. Nucl. Med. 1995, 36, 2315-2325.
79. Efe, G. E.; Pillai, M. R. A.; Schlemper, E. O.; Troutner, D. E. Rhodium Complexes of 2 Bidentate Secondary Amine Oxime Ligands and Application to the Labeling of Proteins. Polyhedron 1991, 10, 1617-1624.
80. Kruper, W. J., Jr.; Pollock, D. K.; Fordyce, W. A.; Fazio, M. J.; Inbasekaram, M. N. Functionalized Polyamine Chelants and Radioactive Rhodium Complexes Thereof for Conjugation to Antibodies. U.S. Patent 4,994,560, Feb 19, 1991.
81. Venkatesh, M.; Goswami, N.; Volkert, W. A.; Schlemper, E. O.; Ketring, A. R.; Barnes, C. L.; Jurisson, S. An Rh-105 Complex of Tetrathiacyclohexadecane Diol with Potential for Formulating Bifunctional Chelates. Nucl. Med. Biol. 1996, 23, 33-40.
82. Goswami, N.; Alberto, R.; Barnes, C. L.; Jurisson, S. Rhodium(III) Complexes with Acyclic Tetrathioether Ligands. Effects of Backbone Chain Length on the Conformation of the Rh(III) Complex. Inorg. Chem. 1996, 35, 7546-7555.
83. 111In-DTPA-∈-Lysine as the Primary Metabolic and Excretory Product. Nucl. Med. Biol. 1994, 21, 1023-1034.