Synthesis of dendrimer-based biotin radiopharmaceuticals to enhance whole-body clearance

Nuclear Medicine and Biology

Volumn 30, Issue 6, 2003, Pages 617-625

  Sato, Noriko ^a   Park, Chang W ^a   Kim, Hyung Sik ^a   Han, Eui Sik ^a   Wong, Karen J ^a   Paik, Ronald S ^a   Park, Luke S ^a   Yao, Zhengsheng ^a   Carrasquillo, Jorge A ^a   Paik, Chang H ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

Biotinylated; Iodinated dendrimer; Lysine co injection; Reduced renal and hepatic uptake; Succinylation

Indexed keywords

BIOTIN DERIVATIVE; IODOBENZOIC ACID DENDRIMER NORBIOTINAMIDOSUCCINIC ACID I 125; LYSINE; RADIOPHARMACEUTICAL AGENT; SUCCINIC ACID DERIVATIVE; SUCCINIC ANHYDRIDE; SUCCINIMIDE DERIVATIVE; TETRAFLUOROPHENYL NORBIOTINAMIDOSUCCINATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG CLEARANCE; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG RETENTION; DRUG SYNTHESIS; DRUG TISSUE LEVEL; DRUG UPTAKE; ISOTOPE LABELING; KIDNEY; MEAN RESIDENCE TIME; MOUSE; NONHUMAN;

EID: 0142106850     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(03)00052-0     Document Type: Article

References (35)

1. Behr T.M., Sharkey R.M., Juweid M.E., Blumenthal R.D., Dunn R.M., Griffiths G.L., Bair H.J., Wolf F.G., Becker W.S., Goldenberg D.M. Reduction of the renal uptake of radiolabeled monoclonal antibody fragments by cationic amino acids and their derivatives. Cancer Res. 1995:1995;3825-3834.
2. Behr T.M., Becker W.S., Sharkey R.M., Juweid M.E., Dunn R.M., Bair H.J., Wolf F.G., Goldenberg D.M. Reduction of renal uptake of monoclonal antibody fragments by amino acid infusion. J Nucl Med. 1996:1996;829-833.
3. 18F-labeled anti-tac disulfide-stabilized Fv. Cancer Res. 1998:1998;2612-2617.
4. Cremonesi M., Ferrari M., Chinol M., Stabin M.G., Grana C., Prisco G., Robertson C., Tosi G., Paganelli G. Three-step radioimmunotherapy with yttrium-90 biotin dosimetry and pharmacokinetics in cancer patients . Eur J Nucl Med. 1999:1999;110-120.
5. 177Lu]alpha-[2-(4-aminophenyl) ethyl]-1,4,7,10-tetraaza-cyclodecane- 1,4,7,10-tetraacetic acid-CC49 Fab radioimmunoconjugate. Cancer Res. 1995:1995;5288-5295.
6. Del Rosario R.B., Wahl R.L. Biotinylated iodo-polylysine for pretargeted radiation delivery. J Nucl Med. 1993:1993;1147-1151.
7. Fang Q.W., Jeong J.M., Lee J.T., Saga T., Le N., Park S.G., Sood V.K., Carrasquillo J.A., Neumann R.D., Reynolds J.C., Reba R.C., Paik C.H. Use of polylysine as a linker for Tc-99m chelate and biotin. J Nucl Med. 34:(Suppl):1993;233.
8. Freitas C.H., Gross M.D., Ripley S., Shapiro B. Radionuclide diagnosis and therapy of thyroid cancer: current status report. Semin Nucl Med. 1985:1985;106-131.
9. Foulon C.F., Alston K.L., Zalutsky M.R. Synthesis and preliminary biological evaluation of (3-iodobenzoyl)norbiotinamide and ((5-iodo-3-pyridinyl) carbonyl)- norbiotinamide two radioiodinated biotin conjugates with improved stability . Bioconjug Chem. 1997:1997;179-186.
10. Foulin C.F., Alston K.L., Zalutsky M.R. Astatine-211-labeled biotin conjugates resistant to biotinidase for use in pretargeted radioimmunotherapy. Nucl Med Biol. 1998:1998;81-88.
11. Goodwin D.A. Pharmacokinetics and antibodies. J Nucl Med. 1987:1987;1358-1362.
12. Goodwin D.A. Tumor pretargeting almost the bottom line . J Nucl Med. 1995:1995;876-879.
13. Green N.M. A spectrophotometric assay for avidin and biotin based on binding of dyes by avidin. Biochem J. 1965:1965;23c-24c.
14. 99mTc labeled polylysine-based biotin radiopharmaceuticals. J Labeled Cpd Radiopharm. 42:(Suppl):1999;S592-594.
15. 99mTc- mercaptoacetyltriglycine-biocytin as a new hepatobiliary imaging agent in mice coinjected with bilirubin. Nucl Med Biol. 1999:1999;43-49.
16. 99mTc-labeled anti-Tac monoclonal antibody Fab by chemical modifications. Nucl Med Biol. 2002:2002;139-146.
17. 99mTc-labeled anti-Tac dsFv. Cancer Res. 1996:1996;3788-3795.
18. Kobayashi H., Wu C., Kim M.K., Paik C.H., Carrasquillo J.A., Brechbiel M.W. Evaluation of the in vivo biodistribution of indium-111 and yttrium-88 labeled dendrimer-1B4M-DTPA and its conjugation with anti-Tac monoclonal antibody. Bioconjug Chem. 1999:1999;103-111.
19. Kobayashi H., Sato N., Saga T., Nakamoto Y., Ishimori T., Toyama S., Togashi K., Konishi J., Brechbiel M.W. Monoclonal antibody-dendrimer conjugates enable radiolabeling of antibody with markedly high specific activity with minimal loss of immunoreactivity. Eur J Nucl Med. 2000:2000;1334-1339.
20. Kobayashi H., Sato N., Hiraga A., Saga T., Nakamoto Y., Ueda H., Konishi J., Togashi K., Brechbiel M.W. 3D-micro-MR angiography of mice using macromolecular MR contrast agents with polyamidoamine dendrimer core with reference to their pharmacokinetic properties. Magn Reson Med. 2001:2001;454-460.
21. Maack T., Park C.H., Camargo M.J.F. Renal filtration, transport, and metabolism of proteins. Seldin D.W., Giebisch G. The kidney physiology and pathophysiology . 1992;3005-3038 Raven Press Ltd, New York, NY.
22. Mogensen C.E., Vittinghus E., Slooing K. Abnormal albumin excretion after two provocative renal tests in diabetes physical exercise and lysine injection . Kidney Int. 1979:1979;385-393.
23. 211At]astato-3-pyridinecarboxylate. Nucl Med Biol. 1999:1999;405-411.
24. Sato N., Kobayashi H., Hiraga A., Saga T., Togashi K., Konishi J., Brechbiel M.W. Pharmacokinetics and enhancement patterns of macromolecular MR contrast agents with various sizes of polyamidoamine dendrimer cores. Magn Reson Med. 2001:2001;1169-1173.
25. Sato N., Kobayashi H., Saga T., Nakamoto Y., Ishimori T., Togashi K., Fujibayashi Y., Konishi J., Brechbiel M.W. Tumor targeting and imaging of intraperitoneal tumors by use of antisense oligo-DNA complexed with dendrimers and/or avidin in mice. Clin Cancer Res. 2001:2001;3606-3612.
26. Schuster J.M., Garg P.K., Bigner D.D., Zalutsky M.R. Improved therapeutic efficacy of a monoclonal antibody radioiodinated using N-succinimidyl-3-(tri-n-butylstannyl)-benzoate. Cancer Res. 1991:1991;4164-4169.
27. Szalecki W. Synthesis of norbiotinamine and its derivatives. Bioconjug Chem. 1996:1996;271-273.
28. Tomalia D.A., Naylor A.M., Goddard W.A. Starburst dendrimers Molecular-level control of size, shape, surface chemistry, topology, and flexibility from atoms to macroscopic matter . Angew Chem Int Ed Engl. 1990:1990;138-175.
29. 99Tc-MAG3-biotin conjugates for antibody pretargeting strategies. Nucl Med Biol. 1998:1998;611-619.
30. Wiener E.C., Brechbiel M.W., Brothers H., Magin R.L., Gansow O.A., Tomalia D.A., Lauterbur P.C. Dendrimer-based metal chelates a new class of magnetic resonance imaging contrast agents . Magn Reson Med. 1994:1994;1-8.
31. Wilbur D.S., Pathare P.M., Hamlin D.K., Buhler K.R., Vessella R.L. Biotin reagents for antibody pretargeting. 3. Synthesis, radioiodination, and evaluation of biotinylated starburst dendrimers. Bioconjug Chem. 1998:1998;813-825.
32. Wu C., Brechbiel M.W., Kozak R.W., Gansow O.A. Metal-chelate-dendrimer- antibody constructs for use in radioimmunotherapy and imaging. Bioorg Med Chem Lett. 1994:1994;449-454.
33. Yoo T.M., Chang H.K., Choi C.W., Webber K.O., Le N., Kim I.S., Eckelman W.C., Pastan I., Carrasquillo J.A., Paik C.H. Technetium-99m labeling and biodistribution of anti-TAC disulfide-stabilized Fv fragment. J Nucl Med. 1997:1997;294-300.
34. Zalutsky M.R., Narula A.S. A method for the radiohalogenation of proteins resulting in decreased thyroid uptake of radioiodine. Int J Rad Appl Instrum [A]. 1987:1987;1051-1055.
35. Zalutsky M.R., Noska M.A., Colapinto E.V., Garg P.K., Bigner D.D. Enhanced tumor localization and in vivo stability of a monoclonal antibody radioiodinated using N-succinimidyl 3-(tri-n-butylstannyl) benzoate. Cancer Res. 1989:1989;5543-5549.