Evaluation of ketone-oxime method for developing therapeutic on-demand cleavable immunoconjugates

Bioconjugate Chemistry

Volumn 19, Issue 6, 2008, Pages 1313-1318

  Kumaresan, Pappanaicken R ^a   Luo, Juntao ^a   Song, Aimin ^a   Marik, Jan ^a   Lam, Kit S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL DETECTION; CONTROLLED DRUG DELIVERY; DISEASES; ELECTROPHORESIS; KETONES; MOLECULES; TARGETED DRUG DELIVERY;

ANTIBODY MOLECULES; CANCER CELLS; CANCER THERAPY; FUNCTIONAL MOIETIES; IMMUNOCONJUGATE; MEDICAL SCIENCE; MOLECULAR DETECTION; MOLECULAR TARGETING; ON DEMANDS; SMALL MOLECULES;

MONOCLONAL ANTIBODIES;

ANTIBODY CONJUGATE; KETONE; MONOCLONAL ANTIBODY; OXIME;

ARTICLE; CANCER CELL; CANCER THERAPY; DRUG DELIVERY SYSTEM; DRUG TARGETING; EVALUATION; IMMUNOASSAY; IMMUNOREACTIVITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; WESTERN BLOTTING;

EID: 45749145876     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800024v     Document Type: Article

References (30)

1. Hovinen, J. (2006) Synthesis of aminooxy-functionalized lanthanide(III) chelates for carbonyl-group conjugation. Chem. Biodiversity 3, 296-303.
2. Langenhan, J. M., and Thorson, J. S. (2005) Recent carbohydrate-based chemoselective ligation applications. Curr. Org. Synth. 2, 59-81.
3. 3 integrin. Mol. Cancer Ther. 3, 1593-604.
4. Zatsepin, T. S., Stetsenko, D. A., Arzumanov, A. A., Romanova, E. A., Gait, M. J., and Oretskaya, T. S. (2002) Synthesis of peptide-oligonucleotide conjugates with single and multiple peptides attached to 2′-aldehydes through thiazolidine, oxime, and hydrazine linkages. Bioconjugate Chem. 13, 822-30.
5. Kubler-Kielb, J., Liu, T. Y., Mocca, C., Majadly, F., Robbins, J. B., and Schneerson, R. (2006) Additional conjugation methods and immunogenicity of Bacillus anthracis poly-γ-D-glutamic acid-protein conjugates. Infect. Immunol. 74, 4744-9.
6. Gaertner, H. F., and Offord, R. E. (1996) Site-specific attachment of functionalized poly(ethylene glycol) to the amino terminus of proteins. Bioconjugate Chem. 7, 38-44.
7. Vilaseca, L. A., Rose, K., Werlen, R., Meunier, A., Offord, R. E., Nichols, C. L., and Scott, W. L. (1993) Protein conjugates of defined structure: synthesis and use of a new carrier molecule. Bioconjugate Chem. 4, 515-20.
8. Xu, Q., Miyamoto, S., and Lam, K. S. (2004) A novel approach to chemical microarray using ketone-modified macromolecular scaffolds: application in micro cell-adhesion assay. Mol. Diversity 8, 301-10.
9. Lemieux, G. A., and Bertozzi, C. R. (1998) Chemoselective ligation reactions with proteins, oligosaccharides and cells. Trends Biotechnol. 16, 506-513.
10. Lemieux, G. A., Yarema, K. J., Jacobs, C. L., and Bertozzi, C. R. (1999) Exploiting differences in sialoside expression for selective targeting of MRI contrast reagents. J. Am. Chem. Soc. 121, 4278-4279.
11. Scheck, R. A., and Francis, M. B. (2007) Regioselective labeling of antibodies through N-terminal transamination. ACS Chem. Biol. 2, 247-51.
12. Traut, R. R., Casiano, C., and Zecherle, N. (1989) Cross-linking of protein subunits and ligands by the introduction of disulfide bonds, in Protein Function-a Practical Approach (Creighton, T. E., Ed.) pp 101-133, IRL Press, Oxford University, Oxford, U.K.
13. Hermanson, T. G. (1996) Bioconjugates and applications, in Bioconjugate chemistry (Hermanson, T. G., Ed.), Academic Press, London.
14. Dixon, H. B. F. (1984) N-Terminal modification of proteins-a review. J. Protein Chem. 3, 99-108.
15. Gilmore, J. M., Scheck, R. A., Esser-Kahn, A. P., Joshi, N. S., and Francis, M. B. (2006) N-terminal protein modification through a biomimetic transamination reaction. Angew. Chem., Int. Ed. 45, 5307-5311.
16. Wu, P., and Brand, L. (1997) N-terminal modification of proteins for fluorescence measurements. Methods Enzymol. 278, 321-330.
17. Natarajan, A., Du, W. J., Xiong, C. Y., DeNardo, G. L., DeNardo, S. J., and Gervay-Hague, J. (2007) Construction of di-scFv through a trivalent alkyne-azide 1,3-dipolar cycloaddition. Chem. Commun. 695-697.
18. Kumaresan, P. R., Natarajan, A., Song, A. M., Wang, X. B., Liu, R. W., DeNardo, G., DeNardo, S., and Lam, K. S. (2007) Development of tissue plasminogen activator specific "on demand cleavable" (ODC) linkers for radioimmunotherapy by screening one-bead-one-compound combinatorial peptide libraries. Bioconjugate Chem. 18, 175-182.
19. Song, A. M., Wang, X. B., Zhang, J. H., Marik, J., Lebrilla, C. B., and Lam, K. S. (2004) Synthesis of hydrophilic and flexible linkers for peptide derivatization in solid phase. Bioorg. Med. Chem. Lett. 14, 161-165.
20. Fields, G. B., and Noble, R. L. (1990) Solid-phase peptide-synthesis utilizing 9-fluorenylmethoxycarbonyl amino-acids. Int. J. Pept. Protein Res. 35, 161-214.
21. Goodman, G. E., Hellstrom, I., Yelton, D. E., Murray, J. L., Ohara, S., Meaker, E., Zeigler, L., Palazollo, P., Nicaise, C., Usakewicz, J., and Hellstrom, K. E. (1993) Phase-I trial of chimeric (human-mouse) monoclonal-antibody L6 in patients with non-small-cell lung, colon, and breast-cancer. Cancer Immunol. Immunother. 36, 267-273.
22. Lee, J. H., Baker, T. J., Mahal, L. K., Zabner, J., Bertozzi, C. R., Wiemer, D. F., and Welsh, M. J. (1999) Engineering novel cell surface receptors for virus-mediated gene transfer. J. Biol. Chem. 274, 21878-84.
23. Jeffrey, S. C., Torgov, M. Y., Andreyka, J. B., Boddington, L., Cerveny, C. G., Denny, W. A., Gordon, K. A., Gustin, D., Haugen, J., Kline, T., Nguyen, M. T., and Senter, P. D. (2005) Design, synthesis, and in vitro evaluation of dipeptide-based antibody minor groove binder conjugates. J. Med. Chem. 48, 1344-58.
24. DeNardo, G. L., DeNardo, S. J., Peterson, J. J., Miers, L. A., Lam, K. S., Hartmann-Siantar, C., and Lamborn, K. R. (2003) Preclinical evaluation of cathepsin-degradable peptide linkers for radioimmunoconjugates. Clin. Cancer Res. 9, 3865S-72S.
25. Beeson, C., Butrynski, J. E., Hart, M. J., Nourigat, C., Matthews, D. C., Press, O. W., Senter, P. D., and Bernstein, I. D. (2003) Conditionally cleavable radioimmunoconjugates: a novel approach for the release of radioisotopes from radioimmunoconjugates. Bioconjugate Chem. 14, 927-33.
26. Falk, A., and Harbour, K. (2005) Tenecteplase in the treatment of thrombosed hemodialysis grafts. Cardiovasc. Interventional Radiol. 28, 472-475.
27. Guerra, D. R., Karha, J., and Gibson, C. M. (2003) Safety and efficacy of tenecteplase in acute myocardial infarction. Expert Opin. Pharmacother. 4, 791-798.
28. Wilde, M. I., Plosker, G. L., and Benfield, P. (1993) Fluvoxamine - an updated review of its pharmacology, and therapeutic use in depressive-illness. Drugs 46, 895-924.
29. Pozsgay, V., Kubler-Kielb, J., Schneerson, R., and Robbins, J. B. (2007) Effect of the nonreducing end of Shigella dysenteriae type 10-specific oligosaccharides on their immunogenicity as conjugates in mice. Proc. Natl. Acad. Sci. U.S.A. 104, 14478-14482.
30. Baskin, J. M., and Bertozzi, C. R. (2007) Bioorthogonal click chemistry: Covalent labeling in living systems. QSAR Comb. Sci. 26, 1211-1219.