Reduction of kidney uptake in radiometal labeled peptide linkers conjugated to recombinant antibody fragments. Site-specific conjugation of DOTA-peptides to a Cys-diabody

Bioconjugate Chemistry

Volumn 13, Issue 5, 2002, Pages 985-995

  Li, Lin ^a   Olafsen, Tove ^a   Anderson, Anne Line ^a   Wu, Anna ^a   Raubitschek, Andrew A ^a   Shively, John E ^a  

^a CITY OF HOPE NATIONAL MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ANTIBODIES; CHELATION;

AMINO GROUP; ANTIBODY-FRAGMENT; BIODISTRIBUTIONS; DIABODY; N-TERMINALS; NUDE MICE; PEPTIDE LINKERS; SYNTHESISED; TETRA PEPTIDE; WORKERS';

PEPTIDES;

MUS MUSCULUS;

ANTIBODY CONJUGATE; CROSS LINKING REAGENT; IMMUNOGLOBULIN FRAGMENT; INDIUM; PEPTIDE; RADIOPHARMACEUTICAL AGENT; RECOMBINANT PROTEIN;

ANIMAL; ANTIBODY SPECIFICITY; ARTICLE; CANCER TRANSPLANTATION; CHEMISTRY; COLON TUMOR; DRUG DESIGN; HUMAN; KIDNEY; METABOLISM; MOUSE; NUDE MOUSE; PATHOLOGY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TISSUE DISTRIBUTION; XENOGRAFT;

ANIMALS; COLONIC NEOPLASMS; CROSS-LINKING REAGENTS; DRUG DESIGN; HUMANS; IMMUNOCONJUGATES; IMMUNOGLOBULIN FRAGMENTS; INDIUM RADIOISOTOPES; KIDNEY; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; ORGAN SPECIFICITY; PEPTIDES; RADIOPHARMACEUTICALS; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION; TRANSPLANTATION, HETEROLOGOUS;

EID: 0036737972     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc025565u     Document Type: Article

References (48)

1. Anderson, C. J., and Welch, M. J. Radiometal-labeled agents (non-technetium) for diagnostic imaging. (1999) Chem. Rev. 99, 2219-2234.
2. Gansow, O. A. Newer Approaches to the Radiolabeling of Monoclonal Antibodies by Use of Metal Chelates. (1991) Int. J. Radiat. Appl. Instrum. Part B Nucl. Med. Biol. 18, 369-381.
3. Meares, C. F. Chelating Agents for the Binding of Metal Ions to Antibodies. (1986) Int. J. Radiat. Appl. Instrum. Part B Nucl. Med. Biol. 13, 311-318.
4. Liu, S., and Edwards, D. S. Bifunctional chelators for therapeutic lanthanide radiopharmaceuticals. (2001) Bioconjugate Chem. 12, 7-34.
5. Bujis, W. C. A. M., Massuger, L. F. A. G., Claessens, R. A. M. J., Kenemans, P., and Corstens, F. H. M. Dosimetric evaluation of immunoscintigraphy using indium-111-labeled monoclonal antibody fragments in patients with ovarian cancer. (1992) J. Nucl. Med. 33, 1113-1120.
6. Govindan, S. V., Shih, L. B., Goldenberg, D. M., Sharkey, R. M., Karacay, H., Donnelly, J. E., Losman, M. J., Hansen, H. J., and Griffiths, G. L. 90Yttrium-labeled complementarity-determining-region grafted monoclonal antibodies for radioimmunotherpay: radiolabeling and animal biodistribution studies. (1998) Bioconjugate Chem. 9, 773-782.
7. Yemul, S., Leon, J. A., Pozniakoff, T., Esser, P. D., and Estabrook, A. Radioimmunoimaging of human breast carcinoma xenografts in nude mouse model with 111In labeled new monoclonal antibody EBA-1 and F(ab′)2 fragments. (1993) Nucl. Med. Biol. 20, 325-335.
8. Yokota, T., Milenic, D. E., Whitlow, M., and Schlom, J. Rapid tumor penetration of a single-chain Fv and comparison with other immunoglobulin forms. (1992) Cancer Res. 52, 3402-3408.
9. Yazaki, P. J., Wu, A. M., Tsai, S. W., Williams, L. E., Ikler, D. N., Wong, J. Y., Shively, J. E., and Raubitschek, A. A. Tumor targeting of radiometal labeled anti-CEA recombinant T84.66 diabody and T84.66 minibody: comparison to radioiodinated fragments. (2001) Bioconjugate Chem. 12, 220-8.
10. Colcher, D., Goel, A., Pavlinkova, G., Beresford, G., Booth, B., and Batra, S. K. Effects of genetic engineering on the pharmokinetics of antibodies. (1999) Q. J. Nucl. Med. 43, 132-139.
11. Buchegger, F. J., Haskell, C. M., Schreyer, M., Scazziga, B. R., Randin, S., Carrel, S., and Mach, J.-P. Radiolabeled Fragments of Monoclonal Antibodies Against Carcinoembryonic Antigen for Localization of Human Colon Carcinoma Grafted into Nude Mice. (1983) J. Exp. Med. 158, 413-427.
12. 2 Fragments are More Efficient and Less Toxic than Intact Anti-CEA Antibodies in Radioimmunotherapy of Large Human Colon Carcinoma Grafted in Nude Mice. (1990) J. Nucl. Med. 31, 1035-1044.
13. Lamki, L. M., Patt, Y. Z., Rosenblum, M. G., Shanken, L. J., Thompson, L. B., Scheighardt, S. A., Frincke, J. M., and Murray, J. L. Metastatic colorectal cancer: radioimmunoscintigraphy with a stabilized In-111-labeled F(ab′)2 fragment on an anti-CEA monoclonal antibody. (1990)Radiology 174, 147-151.
14. 2 fragments with the α-particle-emitting nuclide astatine-211: Preservation of immunoreactivity and in vivo localizing capacity. (1989) Proc. Natl. Acad. Sci. U.S.A. 86, 7149-7153.
15. Sharkey, R. M., Motta-Hennessy, C., Pawlyk, D., Siegel, J. A., and Goldenberg, D. M. Biodistribution and radiation dose estimates for yttrium and iodine labeled monoclonal antibody IgG and fragments in nude mice bearing humnan colonic tumor xenografts. (1990) Cancer Res. 50, 2330-2336.
16. Milenic, D. E., Yokota, T., Filupa, D. R., Finkelman, M. A. J., Dodd, S. W., Wood, J. F., Whitlow, M., Snoy, P., and Schlom, J. Construction, binding properties, metabolism, and tumor targeting of a single chain Fv derived from the pancarcinoma monoclonal antibody CC49. (1991) Cancer Res. 51, 6363-6371.
17. Huston, J. S., George, A. J. T., Adams, G. P., Stafford, W. F., Jamar, F., Tai, M. S., McCartney, J. E., H., O., Heelan, B. T., Peters, A. M., Houston, L. L., Bookman, M. A., Wolf, E. J., and Weiner, L. M. Single chain Fv radioimmunotargeting. (1996) Q. J. Nucl. Med. 40, 320-333.
18. Adams, G. P., McCartney, J. E., Tai, M.-S., Oppermann, H., Huston, J. S., Stafford, W. F., III., Bookman, M. A., Fand, I., Houston, L. L., and Weiner, L. M. Highly specific in vivo tumor targeting by monovalent and divalent formns of 741F8 anti-c-erbB-2 single chain Fv. (1993) Cancer Res. 53, 4026-4034.
19. Adams, G. P., McCartney, J. E., Wolf, E. J., Eisenberg, J., Tai, M.-S., Huston, J. S., Stafford, W. F., III., Bookmann, M. A., and Weiner, L. M. Optimization of in vivo tumor targeting in SCID mice with divalent forms of 741F8 anti-c-erb-2 single chain Fv: effects of dose escalation and repeated i.v. administration. (1995) Cancer Immunol. Immunother. 40, 299-306.
20. Mueller, B. M., Reisfeld, R. A., and Gillies, S. D. Serum half-life and tumor localization of a chimeric antibody deleted of the CH2 domain and directed against the disialoganglioside GD2. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 5702-5705.
21. Ray, K., Embleton, M. J., Jailkhani, B. L., Bhan, M. K., and Kumar, R. Selection of single chain variable fragments (scFv) against the glycoprotein antigen of the rabies virus from a human synthetic scFv phage display library and their fusion with the Fc region of human IgG1. (2001) Clin. Exp. Immunol. 125, 94-101.
22. Li, S. L., Liang, S. J., Guo, N., Wu, A. M., and Fujita-Yamaguchi, Y. Single-chain antibodies against human insulin-like growth factor I receptor: expression, purification, and effect on tumor growth. (2000) Cancer Immunol. Immunother. 49, 243-52.
23. Shan, D., Press, O. W., Tsu, T. T., Hayden, M. S., and Ledbetter, J. A. Characterization of scFv-Ig constructs generated from the anti-CD20 mAb 1F5 using linker peptides of varying lengths. (1999) J. Immunol. 162, 6589-95.
24. Hu, S.-Z., Shively, L., Raubitschek, A., Sherman, M., Williams, L. E., Wong, J. Y. C., Shively, J. E., and Wu, A. M. Minibody: a novel engineered anti-carcinoembryonic antigen antibody fragment (single chain Fv-CH3) which exhibits rapid high level targeting of xenografts. (1996) Cancer Res. 56, 3055-3061.
25. Press, O. W., D., S., Howell-Clark, J., Eary, J., Appelbaum, F. R., Matthews, D., King, D. J., Haines, A., M., Hamann, P., Hinman, L., Shochat, D., and Bernstein, I. D. Comparative metabolism and retention of iodine-125, yttrium-90, and indium-111 radioimmunoconjugates by cancer cells. (1996) Cancer Res. 56, 2123-2129.
26. Rogers, B. E., Franano, F. N., Duncan, J. R., Edwards, W. B., Anderson, C. J., Connett, J. M., and Welch, M. J. Identification of metabolites of 111In-diethylenetriaminepentaacetic acid monoclonal antibodies and antibody fragments in vivo. (1995) Cancer Res. 55, 5714s-5720s.
27. Tsai, S. W., Li, L., Williams, L. E., Anderson, A.-L., Raubitschek, A. A., and Shively, J. E. Metabolism and renal clearance of 111In-labeled DOTA conjugated antibody fragments. (2001) Bioconjugate Chem. 12, 264-270.
28. Lang, L., Jagoda, E., Wu, C., Brechbiel, M. W., Gansow, O. A., Pastan, I., Paik, C. H., Carrasqillo, J. A., and Eckelman, W. C. Factors influencing the in vivo pharmokinetics of peptides and antibody fragments: the pharmokinetics of two PET-labeled low molecular weight proteins. (1997) Q. J. Nucl. Med. 41, 53-61.
29. Schott, M. E., Milenic, D. E., Yokota, T., Whitlow, M., Wood, J. F., Fordyce, W. A., Cheng, R. C., and Schlom, J. Differential metabolic patterns of iodinated versus radiometal chelated anticarcinoma single-chain Fv molecules. (1992) Cancer Res. 52, 6413-6417.
30. Williams, L. E., Wu, A. M., Yazaki, P. J., Liu, A., Raubitschek, A. A., Shively, J. E., and Wong, J. Y. Numerical selection of optimal tumor imaging agents with application to engineered antibodies. (2001) Cancer Biother. Radiopharm. 16, 25-35.
31. Solling, K. and Morgenson, C. E. Studies on the mechanism of renal tubular protein reabsorption. (1977) Proc. Eur. Dial. Transplant. Assoc. 14, 543-549.
32. Behr, T. M., Sharkey, R. M., Sgouros, G., Blumenthal, R. D., Dunn, R. M., Kolbert, K., Friffiths, G. L., Siegel, J. A., Becker, W. S., and Goldenberg, D. M. Overcoming the nephrotoxicity of radiometal labeled immunoconjugates. (1997) Cancer 80, 2591-2610.
33. Arano, Y. Strategies to reduce renal radioactivity levels of antibody fragments. (1998) Quart. J. Nucl. Med. 42, 262-270.
34. Behr, T. M., Sharkey, R. M., Juweid, M. E., Blumenthal, R. D., Dunn, R. M., Griffiths, G. L., Bait, H. J., Wolf, F. G., Becket, W. S., and Goldenberg, D. M. Reduction of the renal uptake of radiolabeled monoclonal antibody fragments by cationic amino acids and their derivatives. (1995) Cancer Res. 55, 3825-3834.
35. Behr, T. M., Becker, W. S., Sharkey, R. M., Juweid, M. E., Dunn, R. M., Bair, H. J., Wolf, F. G., and Goldenberg, D. M. Reduction of renal uptake of monoclonal antibody fragments by amino acid infusion. (1996) J. Nucl. Med. 37, 829-833.
36. Arano, Y., Mukai, T., Uezono, T., Wakisaka, K., Motonari, H., Akizawa, H., Taoka, Y., and Yokoyama, A. A biological method to evaluate bifunctional chelating agents to label antibodies with metallic radionuclides. (1994) J. Nucl. Med. 35, 890-898.
37. Arano, Y., Wakisaka, K., Ohmono, Y., Uezono, T., Akizawa, H., Nakayama, M., Sakahara, H., Tanaka, C., Konishi, J., and Yokoyama, A. Assessment of radiochemical design of antibodies using an ester bond as the metabolizable linkage: evaluation ofmaleimidoethyl 3-(tri-n-butylstannyl)hippurate as a radioiodination reagent of antibodies for diagnostic and therapeutic applications. (1996) Bioconjugate Chem. 7, 628-637.
38. ε-maleoyl-L-lysine (HML)-conjugated Fab fragments. (2001) Bioconjugate Chem. 12, 178-185.
39. Arano, Y., Fujioka, Y., Akizawa, H., Ono, M., Uehara, T., Wakisaka, K., Nakayama, M., Sakahara, H., J., K., and Saji, H. Chemical design of radiolabeled antibody fragments for low renal radioactivity levels. (1999) Cancer Res. 59, 128-134.
40. Wu, A. M.,Williams, L. E., Zieran, L., Padma, A., Sherman, M., Bebb, G. G., Odom-Maryon, T., Wong, J. Y. C., Shively, J. E., and Raubitschek, A. A. Anti-carcinoembryonic antigen (CEA) diabody for rapid tumor targeting and imaging. (1999) Tumor Targeting 4, 1-12.
41. Lewis, M. R., and Shively, J. E. Maleimidocysteineamido-DOTA derivatives: new reagents for radiometal chelate conjugation to antibody sulfhydryl groups undergo pH-dependent cleavage reactions. (1998) Bioconjugate Chem. 9, 72-86.
42. Yazaki, P. J., Shively, L., Clark, C., Cheung, C. W., Le, W., Szpikowska, B., Shively, J. E., Raubitschek, A. A., and Wu, A. M. Mammalian expression and hollow fiber bioreactor production of recombinant anti-CEA diabody and minibody for clinical applications. (2001) J. Immunol. Methods 253, 195-208.
43. Li, M., and Meares, C. F. Synthesis, Metal Chelate Stability Studies, and Enzyme Digestion of a Peptide-Linked DOTA Derivative and its Corresponding Radiolabeled Immunoconjugates. (1993) Bioconjugate Chem. 4, 275-283.
44. 90Y-Labeled DOTA and Maleimidocysteineamido-DOTA Conjugated to Chimeric Anti-Carcinoembryonic Antigen Antibody in Xenograft-Bearing Nude Mice: Comparison of Stable and Chemically Labile Linker Systems. (1998) Bioconjugate Chem. 9, 87-93.
45. Meares, C. F., McCall, M. J., Reardan, D. T., Goodwin, D. A., Diamanti, C. I., and McTigue, M. Conjugation of Antibodies with Bifunctional Chelating Agents: Isothiocyanate and Bromoacetamide Reagents, Methods of Analysis, and Subsequent Addition of Metal Ions. (1984) Anal. Biochem. 142, 68-78.
46. Li, L., Tsai, S. W., Anderson, A.-L., Keire, D. A., Raubitschek, A. A., and Shively, J. E. Vinyl sulfone bifunctional derivatives of DOTA allow sulfhydryl or amino directed coupling to antibodies. Conjugates retain immunoreactivity and have similar biodistributions. (2002) Bioconjugate Chem. 13, 110-115.
47. Duncan, J. R., Stephenson, M. T., Wu, H. P., and Anderson, C. J. Indium-111-diethylenetriamine pentaacetic acid octreotide is delivered in vivo to pancreatic, tumor cell, renal, and hepatocyte lysosomes. (1997) Cancer Res. 57, 659-671.
48. Kim, I. S., Yoo, T. M., Kobayashi, H., Kim, M. K., Le, N., Wang, Q. C., Pastan, I., Carrasqillo, J. A., and Paik, C. H. Chemical modification to reduce renal uptake of disulfide bonded variable region fragment of anti-Tac monoclonal antibody labeled with 99mTc. (1999) Bioconjugate Chem. 10, 447-453.