Reassessment of diethylenetriaminepentaacetic acid (DTPA) as a chelating agent for indium-111 labeling of polypeptides using a newly synthesized monoreactive DTPA derivative

Journal of Medicinal Chemistry

Volumn 39, Issue 18, 1996, Pages 3451-3460

  Arano, Yasushi ^a   Uezono, Takashi ^a   Akizawa, Hiromichi ^a   Ono, Masahiro ^a   Wakisaka, Kouji ^a   Nakayama, Morio ^b   Sakahara, Harumi ^a   Konishi, Junji ^a   Yokoyama, Akira ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY CONJUGATE; CHELATING AGENT; INDIUM 111; MALEIMIDE DERIVATIVE; MONOCLONAL ANTIBODY; PENTETIC ACID; PENTETIC ACID DERIVATIVE; POLYPEPTIDE;

ANTIGEN BINDING; ARTICLE; DRUG DESIGN; DRUG STABILITY; DRUG SYNTHESIS; HUMAN; ISOTOPE LABELING;

CHELATING AGENTS; DRUG STABILITY; HUMANS; INDIUM RADIOISOTOPES; ISOTOPE LABELING; PENTETIC ACID;

EID: 0029835370     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950949+     Document Type: Article

References (35)

1. Bakker, W. H.; Albert, R.; Bruns, C.; Breeman, W. A. P.; Hofland, L. J.; Marbach, P.; Pless, J.; Pralet, D.; Stolz, B.; Koper, J. W.; Lamberts, S. W. J.; Visser, T. J.; Krenning, E. P. (In-111-DTPA-D-Phe1)-Octreotide, a Potential Radiopharmaceutical for Imaging of Somatostatin Receptor-Positive Tumors - Synthesis, Radiolabeling and Invitro Validation. Life Sci. 1991, 49, 1583-1591.
2. Fischman, A. J.; Pike, M. C.; Kroon, D.; Fucello, A. J.; Rexinger, D.; Tenkate, C.; Wilkinson, R.; Rubin, R. H.; Strauss, H. W. Imaging Focal Sites of Bacterial Infection in Rats with Indium-111-Labeled Chemotactic Peptide Analogs. J. Nucl. Med. 1991, 32, 483-491.
3. Fischman, A. J.; Babich, J. W.; Strauss, H. W. A Ticket to Ride: Peptide Radiopharmaceuticals. J. Nucl. Med. 1993, 34, 2253-2263.
4. Krenning, E. P.; Bakker, W. H.; Kooij, P. P. M.; Breeman, W. A. P.; Oei, H. Y.; Dejong, M.; Reubi, J. C.; Visser, T. J.; Bruns, C.; Kwekkeboom, D. J.; Reijs, A. E. M.; Vanhagen, 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.
5. Krenning, E. P.; Kwekkeboom, D. J.; Bakker, W. H.; Breeman, W. A. P.; Kooij, P. P. M.; Oei, H. Y.; Vanhagen, M.; Postema, P. T. E.; Dejong, M.; Reubi, J. C.; Visser, T. J.; Reijs, A. E. M.; Hofland, L. J.; Koper, J. W.; Lamberts, S. W. J. Somatostatin Receptor Scintigraphy with [In-111-DTPA-D-Phe(1)]- and [I-123-Tyr(3)]-Octreotide - The Rotterdam Experience with More Than 1000 Patients. Eur. J. Nucl. Med. 1993, 20, 716-731.
6. Lambert, R.; Willenbrock, R.; Tremblay, J.; Bavaria, G.; Langlois, Y.; Hogan, K.; Tartaglia, D.; Flanagan, R. J.; Hamet, P. Receptor Imaging with Atrial Natriuretic Peptide. 1. High Specific Activity Iodine-123-Atrial Natriuretic Peptide. J. Nucl. Med. 1994, 35, 628-637.
7. Virgolini, I.; Kurtaran, A.; Raderer, M.; Leimer, M.; Angelberger, P.; Havlik, E.; Li, S.; Scheithauer, W.; Niederle, B.; Valent, P.; Eichler, H.-G. Vasoactive Intestinal Peptide Receptor Scintigraphy. J. Nucl. Med. 1995, 36, 1732-1739.
8. Brechbiel, M. W.; Gansow, O. A.; Atcher, R. W.; Schlom, J.; Esteban, J.; Simpson, D. E.; Colcher, D. Synthesis of 1-(pisothiocyanatobenzyl) Derivatives of DTPA and EDTA. Antibody Labeling and Tumor-Imaging Study. Inorg. Chem. 1986, 25, 2772-2781.
9. Deshpande, S. V.; Subramanian, R.; McCall, M. J.; DeNardo, S. J.; DeNardo, G. L.; Meares, C. F. Metabolism of Indium Chelates Attached to Monoclonal Antibody: Minimal Transchelation of Indium from Benzyl-EDTA Chelate In Vivo. J. Nucl. Med. 1990, 31, 218-224.
10. Arano, Y.; Mukai, T.; Uezono, T.; Motonari, H.; Wakisaka, K.; Yokoyama, A. Biological Comparison of DTPA and SCN-Bz-EDTA as a Chelating Agent for Indium Labeling of Antibodies. J. Labelled Compd. Radiopharm. 1994, 35, 381-383.
11. Duncan, J. R.; Welch, M. J. Intracellular Metabolism of Indium-111-DTPA-Labeled Receptor Targeted Proteins. J. Nucl. Med. 1993, 34, 1728-1738.
12. Franano, F. N.; Edwards, W. B.; Welch, M. J., Duncan, J. R. Metabolism of receptor targeted In-111-DTPA-glycoproteins: Identification of In-111-DTPA-epsilon-lysine as the primary metabolic and excretory product. Nucl. Med. Biol. 1994, 21, 1023-1034.
13. Arano, Y.; Mukai, T.; Uezono, T.; Wakisaka, K.; Motonari, H.; Akizawa, H.; Taoka, Y.; Yokoyama, A. A biological method to evaluate bifunctional chelating agents to label antibodies with metallic radionuclides. J. Nucl. Med. 1994, 35, 890-898.
14. Lee, Y. C.; Stowell, C. P.; Krantz, M. J. S-Imino-2-methoxyethyl 1-Thioglycosides: New Reagents for Attaching Sugars to Proteins. Biochemistry 1976, 15, 3956-3963.
15. Reilly, R.; Lee, N.; Houle, S.; Law, J.; Marks, A. Invitro Stability of EDTA and DTPA Immunoconjugates of Monoclonal Antibody 2G3 Labeled with Indium-111. Appl. Radiat. Isot. 1992, 43, 961-967.
16. Maisano, F.; Gozzini, L.; Haen, C. D. Coupling of DTPA to Proteins: A Critical Analysis of the Cyclic Dianhydride Method in the Case of Insulin Modification. Bioconjugate Chem. 1991, 3, 212-217.
17. Maecke, H. R.; Riesen, A.; Ritter, W. The Molecular Structure of Indium-DTPA. J. Nucl. Med. 1989, 30, 1235-1239.
18. Edwards, W. B.; Fields, C. G.; Anderson, C. J.; Pajeau, T. S.; Welch, M. J.; Fields, G. B. Generally Applicable, Convenient Solid-Phase Synthesis and Receptor Affinities of Octreotide Analogs. J. Med. Chem. 1994, 37, 3749-3757.
19. Arano, Y.; Inoue, T.; Mukai, T.; Wakisaka, K.; Sakahara, H.; Konishi, J.; Yokoyama, A. Discriminated Release of a Hippurate-Like Radiometal Chelate in Nontarget Tissues for Target-Selective Radioactivity Localization Using pH-Dependent Dissociation of Reduced Antibody. J. Nucl. Med. 1994, 35, 326-333.
20. Arano, Y.; Wakisaka, K.; Ohmomo, Y.; Uezono, T.; Mukai, T.; Motonari, H.; Shiono, H.; Sakahara, H.; Konishi, J.; Tanaka, C.; Yokoyama, A. Maleimidoethyl 3-(tri-n-butylstannyl)hippurate: A Useful Radioiodination Reagent for Protein Radiopharmaceuticals to Enhance Target Selective Radioactivity Localization. J. Med. Chem. 1994, 37, 2609-2618.
21. Hnatowich, D. J.; Iayne, W. W.; Childs, R. L. The Preparation and Labeling of DTPA-coupled Albumin. Int. J. Appl. Radiat. Isot. 1982, 33, 327-332.
22. Meares, C. F.; McCall, M. J.; Reardan, D. T.; Goodwin, D. A.; Diamanti, C. I.; McTigue, M. Conjugation of Antibodies with Bifunctional Chelating Agents: Isothiocyanate and Bromoacetamide Reagents, Methods of Analysis, and Subsequent Addition of Metal Ions. Anal. Biochem. 1984, 142, 68-78.
23. Paik, C. H.; Hong, J. J.; Ebbert, M. A.; Heald, S. C.; Reba, R. C.; Eckelman, W. C. Relative Reactivity of DTPA, Immunoreactive Antibody-DTPA Conjugates, and Nonimmunoreactive Antibody-DTPA Conjugates Toward Indium-111. J. Nucl. Med. 1985, 26, 482-487.
24. 99mTc Labeled protein Using Bifunctional Chelating Agent. Appl. Radiat, Isot. 1986, 37, 587-592.
25. Leung, C. S.-H.; Meares, C. F.; Goodwin, D. A. The Attachment of Metal-chelating Groups to Proteins: Tagging of Albumin by Diazonium Coupling and Use of the Diazonium Coupling and Use of the Products as Radiopharmaceuticals. Appl. Radiat. Isot. 1978, 29, 687-692.
26. Claessens, R. A. M. J.; Koenders, E. B.; Boerman, O. C.; Oyen, W. J. G.; Borm, G. F.; van der Meer, J. W. M.; Corstens, F. H. M. Dissociation of indium from indium-111-labelled diethylene triamine penta-acetic acid conjugated non-specific polyclonal human immunoglobulin G in inflammatory foci. Eur. J. Nucl, Med. 1995, 22, 212-219.
27. 111In-labeled Antibodies. Nucl. Med. Biol. 1989, 16, 839-845.
28. Hnatowich, D. J.; Griffin, T. W.; Kosciuczyk, C.; Rusckowski, M.; Childs, R. L.; Mattis, J. A.; Shealy, D.; Doherty, P. W. Pharmacokinetics of an Indium-111-Labeled Monoclonal Antibody in Cancer Patients. J. Nucl. Med. 1985, 26, 849-858.
29. Kinuya, S.; Jeong, J. M.; Garmestani, K.; Saga, T.; Camera, L.; Brechbiel, M. W.; Gansow, O. A.; Carrasquillo, J. A.; Neumann, R. D.; Paik, C. H. Effect of metabolism on retention of indium-111-labeled monoclonal antibody in liver and blood. J. Nucl. Med. 1994, 35, 1851-1857.
30. Hosoi, S.; Nakamura, T.; Higashi, S.; Yamamuro, T.; Toyama, S.; Shinomiya, K; Mikawa, H. Detection of human osteosarcomaassociated antigen(s) by monoclonal antibodies. Cancer Res. 1987, 42, 654-659,
31. Essien, H.; Lai, J. Y.; Hwang, K. J. Synthesis of Diethylenetri-aminepentaacetic Acid Conjugated Inulin and Utility for Cellular Uptake of Liposome. J. Med. Chem. 1988, 31, 898-901.
32. Arano, Y.; Matsushima, H.; Tagawa, M.; Koizumi, M.; Endo, K.; Konishi, J.; Yokoyama, A. A Novel Bifunctional Metabolizable Linker for the Conjugation of Antibodies with Radionuclides. Bioconjugate Chem. 1991, 2, 71-76.
33. Grassetti, D. R.; Murray, J. F., Jr. Determination of Sulfhydryl Groups with 2,2′- or 4,4′-Dithiodipyridine. Arch. Biochem. Biophys. 1967, 119, 41-49.
34. Paik, C. H.; Sood, V. K.; Le, N.; Cioloca, L.; Carrasquillo, J. A.; Reynolds, J. C.; Neumann, R. D.; Reba, R. C. Radiolabeled Products in Rat Liver and Serum After Administration of Antibody-Amide-DTPA-Indium-111. Nucl. Med. Biol. 1992, 19, 517-522.
35. Sakahara, H.; Endo, K.; Nakashima, T.; Koizumi, M.; Ohta, H.; Furukawa,T.; Ohmomo, Y.; Yokoyama, A.; Okada, K.; Yoshida, O.; Nishi, S. Effect of DTPA Conjugation on the Antigen Binding Activity and Biodistribution of Monoclonal Antibodies Against alpha-Fetoprotein. J. Nucl. Med. 1985, 26, 750-755.