Stable radioiodine conjugates and methods of their synthesis

Details Stable radioiodine conjugates and methods of their synthesis Stable radioiodine conjugates and methods of their synthesis

2006-12-12

2006-12-12

Shibuya, Mark (Department: 1639)

Drug, bio-affecting and body treating compositions

Conjugate or complex of monoclonal or polyclonal antibody,...

C424S179100, C514S012200, C530S324000, C530S345000, C930S021000

Reexamination Certificate

active

07147856

ABSTRACT:
Methods are described for conjugating radioiodinated peptides or carbohydrate structures to proteins with improved yields and qualities of conjugates. In one method, specially designed radioiodinated bifunctional peptides containing nonmetabolizable amide bonds are coupled to antibodies. In a second method, radioiodinated nonmetabolizable bifunctional peptides, which also contain aminopolycarboxylates, are coupled to antibodies. In a third method, radioiodinated bifunctional aminopolycarboxylates are coupled to antibodies. In a fourth method, a hydrazide-appended antibody is coupled to a radioiodinated carbohydrate or a thiolated antibody is coupled to a hydrazide-appended and radioiodinated carbohydrate. In a fifth method a monoderivatized cyanuric chloride is used to conjugate thiolated antibody. Radioiodinated residualizing antibody conjugates made by these methods are particularly stable in vivo and are suitable for radioimmunodetection and radioimmunotherapy.

REFERENCES:
patent: 5273738 (1993-12-01), Matthews et al.
patent: 5274076 (1993-12-01), Barbet et al.
patent: 5554745 (1996-09-01), Chiu et al.
patent: 0 419 387 (1991-03-01), None
patent: 0 492 478 (1992-07-01), None
patent: 2 109 407 (1983-06-01), None
patent: 03173900 (1991-07-01), None
patent: WO 95/29707 (1995-11-01), None
patent: WO 96/16677 (1996-06-01), None
patent: WO 9808548 (1998-03-01), None
patent: WO 99/11294 (1999-03-01), None
Stein et al., “Effects of Radiolabeling Monoclonal Antibodies with a Residualizing Iodine Radiolabel on the Accretion of Radioisotope in Tumors”, Cancer Research, vol. 55(14):3132-3139, (1995).
Devys et al., “Comparative Targeting of Human Colon-Carcinoma Multicell Spheriods using One- and Two-step (Bispecific Antibody) Techniques”, Chemical Abstracts, vol. 125(23):883-891, (1996).
Bianchi, Chemical Abstracts, 1-Pharmacology, vol. 1, (1998), pp. 1, 404-405.
Dumas et al., Biochim, et Biophys. Acta, vol. 293, pp. 36-47.
Goldenberg, et al., “Monoclonal Antibodies in Cancer Detection and Therapy”,The American Journal of Medicine, vol. 94, pp. 297-312. Mar. 1993.
Strobel, et al., “I-Glycocojugate Labels for Indentifying Sites of Protein Catabolismin Vivo: Effect of Structure and Chemistry of Coupling to Protein on Label Entrapment in Cells after Protein Degradation”,Archives of Biochemistry and Biophysics, vol. 240, No. 2, pp. 635-645, Aug. 1985.
Franano, et al., “Metabolism of Receptor Targeted111In-DTPA-Glycoproteins: Identification of111In-DTPA-ε-lysine as the Primary Metabolic and Excretory Product”,Nucl. Med. Biol. vol. 21, No. 8, pp. 1023-1034, 1994.
Dumas, et al., “Specificite De L'Iodotyrosine Desiodase Des Microsomes Thyroidiens Et Hepatiques”,Biochimica et Biophysics Acta, vol. 293, pp. 36-47, 1973.
Ali, et al., “Improving the Tumor Retention of Radioiodinated Antibody: Aryl Carbohydrate Adducts”,Cancer Research(Suppl.), vol. 50, pp. 783-788, Feb. 1990.
Pawlak-Byczkowska, et al. “Two New Monoclonal Antibodies, EPB-1 and EPB-2, Reactive with Human Lymphoma”,Cancer Research, vol. 49, pp. 4568-4577, Aug. 1989.
Wilbur, et al., “Development of a Stable Radioiodinating Reagent to Label Monocloncal Antibodies for Radiotherapy of Cancer”,The Journal of Nuclear Medicine, vol. 30, pp. 216-226, 1989.
Stein, et al., “Murine Monoclonal Antibodies Raised against Human Non-Small Cell Carcinoma of the Lung: Specificity and Tumor Targeting”,Cancer Research, vol. 50, pp. 1330-1336, Feb. 1990.
Stein, et al., “Effects of Radiolabeling Monoclonal Antibodies with a Residualizing Iodine Radiolabel on the Accretion of Radioisotope in Tumors”,Cancer Research, vol. 55, pp. 3132-3139, Jul. 1995.
Govindan, et al., “Thiolations,99mTc Labelings, and AnimalIn VivoBiodistributions of Divalent Monoclonal Antibody Fragments”,ARTICLES: Bioconjugate Chem., vol. 7, pp. 290-297, 1996.
Hansen, et al., “Characterization of Second-Generation Monoclonal Antibodies Against Carcinoemnbryonic Antigen”,Cancer, vol. 71, No. 11, pp. 3478-3485, Jun. 1993.
Lee, H. et al., “Development of a Kit-Form Analog of Metaiodobenzylguanidine”, The Journal of Nuclear Medicine, vol. 27, pp. 256-267 (1986).
Stein, R., et al., “Improved Iodine Radiolabels for Monoclonal Antibody Therapy”, Cancer Research, vol. 63, pp. 111-118 (2003).
Weadock, K.S., et al., “Evaluation of a Remote Radioiodination System for Radioimmunotherapy”, The Journal of Nuclear Medicine, vol. 31, No. 4, pp. 508-510 (1990).
Govindan, Serengulam, et al., “Labeling of Monoclonal Antibodies with Diethylenetriaminepentaacetic Acid-Appended Radioiodinated Peptides Containing D-Amino Acds” Bioconjugate Chem. 1999, 10, 231-240.
Sharkey, Robert M., et al., “Advantage of residualizing radiolabels for an internalizing antibody against the B-cell lymphoma antigen, CD22” Cancer Immunol Immunother (1997) 44: 179-188 XP-002202223.
Shih, Lisa, “Localization of an antibody to CD74 (MHC class II invariant chain) to human B cell lymphoma xenografts in nude mice” Cancer Immunol Immunother (2000) 49:208-216 XP-002202222.
Shih, Lisa B., et al., “The Processing and Fate of Antibodies and Their Radiolabels Bound to the Surface of Tumor Cells In Vitro: A Comparison of Nine Radiolabels” The Journal of Nuclear Medicine, vol. 35, No. 5, May 1994.
Seham A., et al., “Synthesis and Radioiodiination of Tyramine Cellobiose for Labeling Monoclonal Antibodies” Nucl. Med. Biol. vol. 15, No. 5, pp. 557-561, 1988.
Stein, Rhoma, et al., “Targeting Human Cancer Xenografts with Monoclonal Antibodies Labeled Using Radioiodinated, Diethylenetriaminepentaacetic Acid-appended Peptides” vol. 5, 3079s-3087s Oct. 1999 (Suppl.) Clinical Cancer Research 3079s XP-001118209.
Pearson, Randall K., et al., “Establishment of a New Short, Protease-Resistant, Affinity Labeling Reagent for the Cholecystokinin Receptor” Biochemical and Biophysical Reserach Communications, vol. 147, No. 1, 1987 Aug. 31, 1987, pp. 346-353.
Thorpe, Suzanne R, et al., “The design and application of residualizing labels for studies of protein catabolism” The FASEB Journal, 400 vol. 7, Mar. 1993, pp. 399-405.

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