A novel radioiodination reagent for protein radiopharmaceuticals with L- lysine as a plasma-stable metabolizable linkage to liberate m-iodohippuric acid after lysosomal proteolysis

Journal of Medicinal Chemistry

Volumn 40, Issue 16, 1997, Pages 2643-2652

  Wakisaka, Kouji ^a   Arano, Yasushi ^a   Uezono, Takashi ^a   Akizawa, Hiromichi ^a   Ono, Masahiro ^a   Kawai, Keiichi ^d   Ohomomo, Yoshiro ^c   Nakayama, Morio ^b   Saji, Hideo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

^c OSAKA MEDICAL COLLEGE   (Japan)

^d UNIVERSITY OF MIYAZAKI   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CADAVERINE; IODOHIPPURIC ACID; LYSINE; RADIOPHARMACEUTICAL AGENT;

ARTICLE; DIAGNOSTIC VALUE; PROTEIN BINDING; PROTEIN DEGRADATION; PROTEIN STABILITY; RADIOACTIVITY; RADIOIODINATION; URINARY EXCRETION;

ALBUMINS; ANIMALS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HUMANS; INDICATORS AND REAGENTS; IODINE RADIOISOTOPES; IODOHIPPURIC ACID; LIGANDS; LYSINE; LYSOSOMES; MICE; MODELS, CHEMICAL; RADIOPHARMACEUTICALS; TISSUE DISTRIBUTION;

EID: 0030835389     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9606397     Document Type: Article

References (36)

1. Co, M. S.; Yano, S.; Hsu, R. K.; Landolfi, N. F.; Vasquez, M.; Cole, M.; Tso, J. T.; Bringman, T.; Laird, W.; Hudson, D.; Kawamura, K.; Suzuki, K.; Furuichi, K.; Queen, C.; Masuho, Y. A Humanized Antibody Specific for the Platelet Integrin GpIIb/ IIIa. J. Immunol. 1994, 152, 2968-2976.
2. Yokota, T.; Milenic, D. E.; Whitlow, M.; Schlom, J. Rapid Tumor Penetration of a Single-Chain Fv and Comparison with Other Immunogloblin Forms. Cancer Res. 1992, 52, 3402-3408.
3. 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-Phel〉-Octreotide, a Potential Radiopharmaceutical for Imaging of Somatostatin Receptor-Positive Tumors - Synthesis, Radiolabeling and In vitro Validation. Life Sci. 1991, 49, 1583-1591.
4. Fischman, A. J.; Babich, J. W.; Strauss, H. W. A Ticket to Ride: Peptide Radiopharmaceuticals. J. Nucl. Med. 1993, 34, 2253-2263.
5. Magnani, P.; Paganelli, G.; Songini, C.; Samuel, A.; Sudati, F.; Siccardi, A. G.; Fazio, F. Pretargeted Immunoscintigraphy in Patients with Medullary Thyroid Carcinoma. Br. J. Cancer 1996, 74, 825-831.
6. Paganelli, G.; Magnani, P.; Zito, F.; Lucignani, G.; Sudati, F.; Truci, G.; Motti, E.; Terreni, M.; Pollo, B.; Giovanelli, M.; Canal, N.; Scotti, G.; Comi, G.; Koch, P.; Maecke, H. R.; Fazio, F. Pre-Targeted Immunodetection in Glioma Patients - Tumour Localization and Single-Photon Emission Tomography Imaging of [Tc-99m]PnAo-Biotin. Eur. J. Nucl. Med. 1994, 21, 314-321.
7. Fritzberg, A. R.; Beaumier, P. L.; Bottino, B. J.; Reno, J. M. Approaches to Improved Antibody- and Peptide-Mediated Targeting for Imaging and Therapy of Cancer. J. Control. Release 1994, 28, 167-173.
8. Yao, Z. S.; Zhang, M. L.; Kobayashi, H.; Sakahara, H.; Nakada, H.; Yamashina, I.; Konishi, J. Improved Targeting of Radiolabeled Streptavidin in Tumors Pretargeted with Biotinylated Monoclonal Antibodies through an Avidin Chase. J. Nucl. Med. 1995, 36, 837-841.
9. 111In-Labeled Antibodies. Nucl. Med. Biol. 1989, 16, 839-845.
10. Motta-Hennessy, C.; Sharkey, R. M.; Goldenberg, D. M. Metabolism of Indium-111-Labeled Murine Monoclonal Antibody in Tumor and Normal Tissue of the Athymic Mouse. J. Nucl. Med. 1990, 31, 1510-1519.
11. 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.
12. 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.
13. 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.
14. Arano, Y.; Mukai, T.; Akizawa, H.; Uezono, T.; Motonari, H.; Wakisaka, K.; Kairiyama, C.; Yokoyama, A. Radiolabeled Metabolites of Proteins Play a Critical Role in Radioactivity Elimination from the Liver. Nucl. Med. Biol. 1995, 22, 555-564.
15. Duncan, J. R.; Welch, M. J. Intracellular Metabolism of Indium-111-DTPA-Labeled Receptor Targeted Proteins. J. Nucl. Med. 1993, 34, 1728-1738.
16. 111In-DTPA-ε-lysine as the Primary Metabolic and Excretory Product. Nucl. Med. Biol. 1994, 21, 1023-1034.
17. 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.
18. Alberts, B.; Bray, D.; Lewis, J.; Raff, M.; Roberts, K.; Watson, J. D. Membrane Transport of Macromolecules and Particles: Exocytosis and Endocytosis. Molecular Biology of The Cell; Garland Publishing Inc.: New York, 1983; pp 302-317.
19. Arano, Y.; Wakisaka, K.; Ohmomo, Y.; Uezono, T.; Akizawa, H.; Nakayama, M.; Sakahara, H.; Tanaka, C.; Konishi, J.; Yokoyama, A. Assessment of Radiochemical Design of Antibodies Using an Ester Bond as the Metabolizable Linkage: Evaluation of Maleimidoethyl 3-(Tri-n-butylstannyl)hippurate as a Radioiodination Reagent of Antibodies for Diagnostic and Therapeutic Applications. Bioconjugate Chem. 1996, 6, 628-637.
20. 2 Fragment Labeled Using N-Succinimidyl 3-Iodobenzoate and Iodogen Methods. Bioconjugate Chem. 1995, 6, 493-501.
21. Sands, H.; Jones, P. L. Methods for the Study of the Metabolism of Radiolabeled Monoclonal Antibodies by Liver and Tumor. J. Nucl. Med. 1987, 28, 390-398.
22. Boyle, C. C.; Paine, A. J.; Mather, S. J. The Mechanism of Hepatic Uptake of a Radiolabelled Monoclonal Antibody. Int. J. Cancer 1992, 50, 912-917.
23. Rogers, B. E.; Franano, F. N.; Duncan, J. R.; Edwards, W. B.; Anderson, C. J.; Connett, J. M.; Welch, M. J. Identification of Metabolites of In-111-Diethylenetriaminepentaacetic Acid Monoclonal Antibodies and Antibody Fragments In Vivo. Cancer Res. 1995, 55, S5714-S5720.
24. Zalutsky, M. R.; Naura, A. S. A Method for the Radiohalogenation of Proteins Resulting in Decreased Thyroid Uptake. Appl. Radiat. Isot. 1987, 38, 1051-1055.
25. Keller, O.; Rudinger, J. Preparation and Some Properties of Maleimido Acids and Maleoyl Derivatives of Peptides. Helv. Chim. Acta 1975, 58, 531-540.
26. Sogami, M.; Nagoka, S.; Era, S.; Honda, M.; Noguchi, K. Resolution of Human Mercapto- and Nonmercaptoalbumin by High Performance Liquid Chromatography. Int. J. Protein Res. 1987, 24, 96-103.
27. Grassetti, D. R.; Murray, J. F., Jr. Determination of Sulfhydryl Groups with 2,2′-or 4,4′-Dithiopyridine. Arch. Biochem. Biophys. 1967, 119, 41-49.
28. 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.
29. 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.
30. Arano, Y.; Inoue, T.; Mukai, T.; Wakisaka, K.; Sakahara, H.; Konishi, J.; Yokoyama, A. Discriminated Release of 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.
31. Arano, Y.; Uezono, T.; Akizawa, H.; Ono, M.; Wakisaka, K.; Nakayama, M.; Sakahara, H.; Konishi, J.; Yokoyama, A. Reassessment of Diethylenetriaminepentaacetic Acid (DTPA) as a Chelating Agent for Indium-111 Labeling of Polypeptides Using a Newly Synthesized Monoreactive DTPA Derivative. J. Med. Chem. 1996, 39, 3451-3460.
32. Arano, Y.; Wakisaka, K.; Mukai, T.; Uezono, T.; Motonari, H.; Akizawa, H.; Kairiyama, C.; Ohmomo, Y.; Tanaka, C.; Ishiyama, M.; Sakahara, H.; Konishi, J.; Yokoyama, A. Stability of a Metabolizable Ester Bond in Radioimmunoconjugates. Nucl. Med. Biol. 1996, 23, 129-136.
33. Lee, Y. C.; Stowell, C. P.; Krantz, M. J. 2-Imino-2-Methoxyethyl 1-Thioglycosides: New Reagents for Attaching Sugars to Proteins. Biochemistry 1976, 19, 3956-3963.
34. Stowell, C. P.; Lee, Y. C. Preparation of Some New Neoglycoproteins by Amidination of Bovine Serum Albumin Using 2-Imino-2-Methoxy 1-Thioglycosides. Biochemistry 1980, 19, 4899-4904.
35. Dubois, M.; Gilles, K. A.; Hamilton, J. K.; Robert, P. A.; Smith, F. Colorimetric Method for Determination of Sugars and Related Substances. Anal. Chem. 1956, 28, 350-356.
36. Imai, S.; Morimoto, J.; Tsubura, T.; Esaki, K.; Michalides, R.; Holms, R. S.; Deimling, O.; Higlgers, J. Genetic Marker Patterns and Endogenous Mammary Tumor Virus Genes in Inbred Mouse Strains in Japan. Exp. Anim. 1986, 35, 263-276.