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 Chemistry

Volumn 7, Issue 6, 1996, Pages 628-637

  Arano, Yasushi ^a   Wakisaka, Kouji ^a   Ohmono, Yoshiro ^c   Uezono, Takashi ^a   Akizawa, Hiromichi ^a   Nakayama, Morio ^d   Sakahara, Harumi ^b   Tanaka, Chiaki ^c   Konishi, Junji ^b   Yokoyama, Akira ^a  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY FACULTY OF MEDICINE   (Japan)

^c OSAKA MEDICAL COLLEGE   (Japan)

^d KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BINDING ENERGY; BODY FLUIDS; DIAGNOSIS; ESTERS; ETHYLENEDIAMINETETRAACETIC ACID; HISTOLOGY; MAMMALS; RADIATION; RADIOACTIVITY; TUMORS;

DIAGNOSTIC APPLICATIONS; ESTER BONDS; HIPPURATES; OSTEOGENIC; POST INJECTION; RADIOACTIVITY LEVEL; RADIOIMMUNOIMAGING; RADIOIMMUNOTHERAPY; RADIOIODINATION; THERAPEUTIC APPLICATION;

MONOCLONAL ANTIBODIES;

EID: 0030294885     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc960058w     Document Type: Review

References (43)

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., and Masuho, Y. (1994) A Humanized Antibody Specific for the Platelet Integrin GpIIb/IIIa. J. Immunol. 152, 2968-2976.
2. Kobayashi, H., Sakahara, H., Saga, T., Hosono, M., Shirato, M., Kanda, H., Ishibashi, K., Watanabe, T., Endo, K., Ishiwata, I., and Konishi, J. (1993) A Human/Mouse Chimeric Monoclonal Antibody Against CA-125 for Radioimmunoimaging of Ovarian Cancer. Cancer Immunol. Immunother. 37, 143-149.
3. Yokota, T., Milenic, D. E., Whitlow, M., and Schlom, J. (1992) Rapid Tumor Penetration of a Single-Chain Fv and Comparison with Other Immunoglobulin Forms. Cancer Res. 52, 3402-3408.
4. Brechbiel, M. W., Gansow, O. A., Atcher, R. W., Schlom, J., Esteban, J., Simpson, D. E., and Colcher, D. (1986) Synthesis of 1-(p-isothiocyanatobenzyl) Derivatives of DTPA and EDTA. Antibody Labeling and Tumor-Imaging Study. Inorg. Chem. 25, 2772-2781.
5. Subramanian, R., Colony, J., Shaban, S., Sidrak, H., Haspel, M. V., Pomato, N., Hanna, M. G., and Mccabe, R. P. (1992) New Chelating Agent for Attaching Indium-111 to Monoclonal Antibodies - Invitro and Invivo Evaluation. Bioconjugate Chem. 3, 248-255.
6. Zalutsky, M. R., and Narula, A. S. (1987) A Method for the Radiohalogenation of Proteins Resulting in Decreased Thyroid Uptake of Radioiodine. Appl. Radiat. Isot. 38, 1051-1055.
7. Pietersz, G. A., and Krauer, K. (1994) Antibody-Targeted Drugs for the Therapy of Cancer. J. Drug Targeting 2, 183-215.
8. Arano, Y., Inoue, T., Mukai, T., Wakisaka, K., Sakahara, H., Konishi, J., and Yokoyama, A. (1994) 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. 35, 326-333.
9. 2 Fragments of Anti-Carcinoembryonic Antigen Antibody. 2. Comparative Pharmacokinetics and Biodistribution in Human Colorectal Carcinoma-Bearing Nude Mice. Nucl. Med. Biol. 20, 763-771.
10. 111In chelate conjugated anti-idiotype monoclonal antibody for radioimmunodetection of lymphoma in mice. Eur. J. Nucl. Med. 12, 455-460.
11. Meares, C. F., McCall, M. J., Deshpande, S. V., DeNardo, S., and Goodwin, D. A. (1988) Chelate Radiochemistry: Cleavable Linkers Lead to Altered Levels of Radioactivity in the Liver. Int. J. Cancer, Suppl. 2, 99-102.
12. Paik, C. H., Yokoyama, K., Reymonds, J. C., Quadri, S. M., Min, C. Y., Shin, S. Y., Maloney, P. J., Larson, S. M., and Reba, R. C. (1989) Reduction of Background Activities by Introduction of a Diester Linkage Between Antibody and a Chelate in Radioimmunodetection of Tumor. J. Nucl. Med. 30, 1693-1701.
13. Quadri, S. M., Vriesendorp, H. M., Leichner, P. K., and Williams, J. R. (1993) Evaluation of Indium-111-Labeled and Yttrium-90-Labeled Linker-Immunoconjugates in Nude Mice and Dogs. J. Nucl. Med. 34, 938-945.
14. 99mTc-Radiolabeled Antibody Fab′-Chelator Conjugate. Bioconjugate Chem. 1, 431-437.
15. Arano, Y., Mukai, T., Uezono, T., Wakisaka, K., Motonari, H., Akizawa, H., Taoka, Y., and Yokoyama, A. (1994) A biological method to evaluate bifunctional chelating agents to label antibodies with metallic radionuclides. J. Nucl. Med. 35, 890-898.
16. Arano, Y., Mukai, T., Akizawa, H., Uezono, T., Motonari, H., Wakisaka, K., Kairiyama, C., and Yokoyama, A. (1995) Radiolabeled Metabolites of Proteins Play a Critical Role in Radioactivity Elimination from the Liver. Nucl. Med. Biol. 22, 555-564.
17. Duncan, J. R., and Welch, M. J. (1993) Intracellular Metabolism of Indium-111-DTPA-Labeled Receptor Targeted Proteins. J. Nucl. Med. 34, 1728-1738.
18. 111In-DTPA-∈-lysine as the Primary Metabolic and Excretory Product. Nucl. Med. Biol. 21, 1023-1034.
19. Arano, Y., Wakisaka, K., Ohmomo, Y., Uezono, T., Mukai, T., Motonari, H., Shiono, H., Sakahara, H., Konishi, J., Tanaka, C., and Yokoyama, A. (1994) Maleimidoethyl 3-(tri-n-butylstannyl)hippurate: A useful radioiodination reagent for protein radiopharmaceuticals to enhance target selective radioactivity localization. J. Med. Chem. 37, 2609-2618.
20. Boyle, C. C., Paine, A. J., and Mather, S. J. (1992) The Mechanism of Hepatic Uptake of a Radiolabelled Monoclonal Antibody. Int. J. Cancer 50, 912-917.
21. Sands, H., and Jones, P. L. (1987) Methods for the Study of the Metabolism of Radiolabeled monoclonal Antibodies by Liver and Tumor. J. Nucl. Med. 28, 390-398.
22. Deshpande, S. V., Subramanian, R., McCall, M. J., DeNardo, S. J., DeNardo, G. L., and Meares, C. F. (1990) Metabolism of Indium Chelates Attached to Monoclonal Antibody: Minimal Transchelation of Indium from Benzyl-EDTA chelate In Vivo. J. Nucl. Med. 31, 218-224.
23. Arano, Y., Mukai, T., Uezono, T., Motonari, H., Wakisaka, K., and Yokoyama, A. (1994) Biological Comparison of DTPA and SCN-Bz-EDTA as a Chelating Agent for Indium Labeling of Antibodies. J. Labelled Compd. Radiopharm. 35, 381-383.
24. 2 fragment labeled using N-succinimidyl 3-iodobenzoate and iodogen methods. Bioconjugate Chem. 6, 493-501.
25. 67Ga-labeled Antibodies for Immunoscintigraphy and Evaluation of Tumor Targeting of Drug-Antibody Conjugate in Mice. Cancer Res. 48, 1189-1194.
26. Sakahara, H., Endo, K., Koizumi, M., Nakashima, T., Kunimatsu, M., Watanabe, Y., Kawamura, Y., Nakamura, T., Ohta, H., Kotoura, Y., Yamamuro, T., Hosoi, S., Toyama, S., and Torizuka, K. (1988) Relationship Between In Vitro Binding Activity and In Vivo Tumor Accumulation of Radiolabeled Monoclonal Antibodies. J. Nucl. Med. 29, 235-240.
27. Hosoi, S., Nakamura, T., Higashi, S., Yamamuro, T., Toyama, S., Shinimiya, K., and Mikawa, H. (1982) Detection of human osteosarcoma-associated antigen(s) by monoclonal antibodies. Cancer Res. 42, 654-659.
28. Rousseaux, J., Rousseaux-Prevost, R., and Bazin, H. (1986) Optimal Conditions for the Preparation of Proteolytic Fragments from Monoclonal IgG of Different Rat IgG Subclasses, Methods Enzymol. 121, 663-669.
29. Meares, C. F., McCall, M. J., Reardan, D. T., Goodwin, D. A., Diamanti, C. I., and McTigue, M. (1984) Conjugation of Antibodies with Bifunctional Chelating Agents: Isothiocyanate and Bromoacetamide Reagents, Methods of Analysis, and Subsequent Addition of Metal Ions. Anal. Biochem. 142, 68-78.
30. Grassetti, D. R., and Murray, Jr., J. F. (1967) Determination of Sulfhydryl Groups with 2,2′- or 4,4′-Dithiodipyridine. Arch. Biochem. Biophys. 119, 41-49.
31. Wilbur, D. S., Hadley, S. W., Grant, L. M., and Hylarides, M. D. (1991) Radioiodinated Iodobenzoyl Conjugates of a Monoclonal Antibody Fab Fragment. In Vivo Comparisons with Chloramine-T-Labeled Fab. Bioconjugate Chem. 2, 111-116.
32. Paik, C. H., Hong, J. J., Ebbert, M. A., Heald, S. C., Reba, R. C., and Eckelman, W. C. (1985) Relative Reactivity of DTPA, Immunoreactive Antibody-DTPA Conjugates, and Nonimmunoreactive Antibody-DTPA Conjugates Toward Indium-111. J. Nucl. Med. 26, 482-487.
33. Paik, C. H., Sood, V. K., Le, N., Cioloca, L., Carrasquillo, J. A., Reynolds, J. C., Neumann, R. D., and Reba, R. C. (1992) Radiolabeled Products in Rat Liver and Serum After Administration of Antibody-Amide-DTPA-Indium-111. Nucl. Med. Biol. 19, 517-522.
34. Sakahara, H., Endo, K., Nakashima, T., Koizumi, M., Ohta, H., Furukawa, T., Ohmomo, Y., Yokoyama, A., Okada, K., Yoshida, O., and Nishi, S. (1985) Effect of DTPA Conjugation on the Antigen Binding Activity and Biodistribution of Monoclonal Antibodies Against alpha-Fetoprotein. J. Nucl. Med. 26, 750-755.
35. Imai, S., Morimoto, J., Tsubura, T., Esaki, K., Michalides, R., Holmes, R. S., Deimling, O., and Hilgers, J. (1986) Genetic marker patterns and endogenous mammary tumor virus genes in inbred mouse strains in Japan. Exp. Anim. 35, 263-273.
36. Arano, Y., Uezono, T., Akizawa, H., Ono, M., Wakisaka, K., Nakayama, M., Sakahara, H., Konishi, J., and Yokoyama, A. (1996) 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. 39, 3451-3460.
37. Dykes, P. W., Bradwell, A. R., Chapman, C. E., and Vaughan, A. T. N. (1987) Radioimmunotherapy of cancer: clinical studies and limiting factors. Cancer Treat. Rev. 14, 87-106.
38. Gallinger, S., Reilly, R. M., Kirsh, J. C., Odze, R. D., Schmocker, B. J., Hay, K., Polihronis, J., Damani, M. T., Shpitz, B., and Stern, H. S. (1993) Comparative Dual Label Study of First and Second Generation Antitumor-associated Glycoprotein-72 Monoclonal Antibodies in Colorectal Cancer Patients. Cancer Res. 53, 271-278.
39. Bormans, G., Nerom, C. V., Hoogmartens, M., Roo, M. D., and Verbruggen, A. (1989) Metabolism of Tc-99m ECD in Isolated Rat Organs. J. Nucl. Med. 30, 743 (Abstract).
40. Himmelsbach, M., and Wahl, R. L. (1989) Studies on the Metabolic Fate of 111In-labeled Antibodies. Nucl. Med. Biol. 16, 839-845.
41. Motta-Hennessy, C., Sharkey, R. M., and Goldenberg, D. M. (1990) Metabolism of Indium-111-Labeled Murine Monoclonal Antibody in Tumor and Normal Tissue of the Athymic Mouse. J. Nucl. Med. 31, 1510-1519.
42. Kobayashi, H., Sakahara, H., Hosono, M., Yao, Z. S., Toyama, S., Endo, K., and Konishi, J. (1994) Improved clearance of radiolabeled biotinylated monoclonal antibody following the infusion of avidin as a "chase" without decreased accumulation in the target tumor. J. Nucl. Med. 35, 1677-1684.
43. Sakahara, H., Endo, K., Kunimatsu, M., Kawamura, Y., Ohta, H., Nakamura, T., Tanaka, H., Kotoura, Y., Yamamuro, T., Hosoi, S., Toyama, S., and Torizuka, K. (1987) Localization of Human Osteogenic Sarcoma Xenografts in Nude Mice by a Monoclonal Antibody Labeled with Radioiodine and Indium-111. J. Nucl. Med. 28, 342-348.