Site specific conjugation of fluoroprobes to the remodeled Fc N-glycans of monoclonal antibodies using mutant glycosyltransferases: Application for cell surface antigen detection

Bioconjugate Chemistry

Volumn 20, Issue 6, 2009, Pages 1228-1236

  Boeggeman, Elizabeth ^a,b   Ramakrishnan, Boopathy ^a,b   Pasek, Marta ^a   Manzoni, Maria ^a   Puri, Anu ^a   Loomis, Kristin H ^a   Waybright, Timothy J ^a,b   Qasba, Pradman K ^a,c  

^a Structural Glycobiology Section   (United States)

^b SAIC FREDERICK INC   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOOXYACETIC ACID; AZIDE; BETA1,4 GALACTOSYLTRANSFERASE; BEVACIZUMAB; EPIDERMAL GROWTH FACTOR RECEPTOR 2; GALACTOSE; GALACTOSYLTRANSFERASE; GLYCAN DERIVATIVE; IMMUNOGLOBULIN G; INFLIXIMAB; KETONE; RITUXIMAB; TRASTUZUMAB; UNCLASSIFIED DRUG; URIDINE 5' DIPHOSPHO 5 ACETYLGALACTOSAMINE; URIDINE 5' DIPHOSPHO N ACETYL AZIDO GALACTOSAMINE; URIDINE DIPHOSPHATE; URIDINE DIPHOSPHATE GALACTOSE; VASCULOTROPIN;

ANTIGEN DETECTION; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG BINDING; DRUG EFFECT; ENZYME LINKED IMMUNOSORBENT ASSAY; FLUORESCENCE ACTIVATED CELL SORTING; GLYCOSYLATION; HUMAN; HUMAN CELL; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POLYACRYLAMIDE GEL ELECTROPHORESIS; STREPTOCOCCUS PNEUMONIAE;

STREPTOCOCCUS PNEUMONIAE;

EID: 67649206319     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc900103p     Document Type: Article

References (30)

1. Brumlik, M. J., Daniel, B. J., Waehler, R., Curiel, D. T., Giles, F. J., and Curiel, T. J. (2008) Trends in immunoconjugate and ligand receptor-based targeting development for cancer therapy. Expert Opin. Drug Deliv. 5, 87-103. (Pubitemid 351234111)
2. Ross, J. S., Schenkein, D. P., Pietrusko, R., Rolfe, M., Linette, G. P., Stec, J., Stagliano, N. E., Ginsburg, G. S., Symmans, W. F., Pusztai, L., and Hortobagyi, G. N. (2004) Targeted therapies for cancer. Am. J. Clin. Pathol. 122, 598-609. (Pubitemid 39281258)
3. Hamann, P. R. (2005) Monoclonal antibody-drug conjugates. Expert Opin. Thera. Patents 15, 1087-1103. (Pubitemid 41358429)
4. Carter, P. J., and Senter, P. D. (2008) Antibody-drug conjugates for cancer therapy. Cancer J. 14, 154-169.
5. Trail, P. A., King, H. D., and Dubowchik, G. M. (2003) Monoclonal antibody drug immunoconjugates for targeted treatment of cancer. Cancer Immunol. Immunother. 52, 328-337. (Pubitemid 36578026)
6. Arnold, J. N., Dwek, R. A., Rudd, P. M., and Sim, R. B. (2006) Mannan binding lectin and its interaction with immunoglobulins in health and in disease. Immunol. Lett. 106, 103-110. (Pubitemid 44223746)
7. Jefferis, R. (2005) Glycosylation of recombinant antibody therapeutics. Biotechnol. Prog. 21, 11-16. (Pubitemid 40218466)
8. Holland, M., Yagi, H., Takahashi, N., Kato, K., Savage, C. O., Goodall, D. M., and Jefferis, R. (2006) Differential glycosylation of polyclonal IgG, IgG-Fc and IgG-Fab isolated from the sera of patients with ANCA-associated systemic vasculitis. Biochim. Biophys. Acta 1760, 669-677.
9. Hodoniczky, J., Zheng, Y. Z., and James, D. C. (2005) Control of recombinant monoclonal antibody effector functions by Fc N-glycan remodeling in vitro. Biotechnol. Prog. 6, 1644-1652. (Pubitemid 41778987)
10. Shinkawa, T., Nakamura, K., Yamane, N., Shoji-Hosaka, E., Kanda, Y., Sakurada, M., Uchida, K., Anazawa, H., Satoh, M., Yamasaki, M., Hanai, N., and Shitara, K. (2003) The absence of fucose but not the presence of galactose or bisecting N-acetylglucosamine of human IgG1 complex-type oligosaccharides shows the critical role of enhancing antibody-dependent cellular cytotoxicity. J. Biol. Chem. 278, 3466-3473. (Pubitemid 36801263)
11. Sharkey, R. M., and Goldenberg, D. M. (2008) Use of antibodies and immunoconjugates for the therapy of more accessible cancers. Adv. Drug Delivery Rev. 60, 1407-1420.
12. Byrne, J. D., Betancourt, T., and Brannon-Peppas, L. (2008) Active targeting schemes for nanoparticle systems in cancer therapeutics. Adv. Drug Delivery Rev. 60, 1615-1626.
13. Garnett, M. C. (2001) Targeted drug conjugates: principles and progress. Adv. Drug Delivery Rev. 53, 171-216.
14. O'Shannessy, D. J., and Quarles, R. H. (1971) Labeling of the oligosaccharide moieties of immunoglobulins. J. Immunol. Methods 99, 153-161. (Pubitemid 17089337)
15. Van Lenten, L., and Ashwell, G. (1971) Studies on the chemical and enzymatic modifications of glycoproteins. A general method for the tritiation of sialic-acid containing glycoprotein. J. Biol. Chem. 246, 1889-1894.
16. Chua, M., Fan, S., and Karush, F. (1984) Attachment of immunoglobulin to liposomal membrane via protein carbohydrate. Biochim. Biophys. Acta 800, 291-300. (Pubitemid 14033656)
17. Morell, A. G., Van den Hamer, C. J., Scheinberg, I. H., and Ashwell, G. (1966) Physical and chemical studies on ceruloplasmin. IV. Preparation of radioactive, sialic acid-free ceruloplasmin labeled with tritium on terminal D-galactose residues. J. Biol. Chem. 241, 3745-3749.
18. Wilchek, M., and Bayer, E. A. (1984) The avidin-biotin complex in immunology. Immunol. Today 5, 39-43.
19. Khidekel, N., Arndt, S., Lamarre-Vincent, N., Lippert, A., Poulin-Kerstien, K. G., Ramakrishnan, B., Qasba, P. K., and Hsieh-Wilson, L. C. (2003) A chemoenzymatic approach toward the rapid and sensitive detection of O-GlcNAc posttranslational modifications. J. Am. Chem. Soc. 125, 16162-16163. (Pubitemid 38020622)
20. Boeggeman, E., Ramakrishnan, B., Kilgore, C., Khidekel, N., Hsieh-Wilson, L. C., Simpson, J. T., and Qasba, P. K. (2007) Direct identification of nonreducing GlcNAc residues on Nglycans of glycoproteins using a novel chemoenzymatic method. Bioconjugate Chem. 18, 806-814. (Pubitemid 47010801)
21. Ramakrishnan, B., Boeggeman, E., and Qasba, P. K. (2007) Novel method for in vitro O-glycosylation of proteins: application for bioconjugation. Bioconjugate Chem. 18, 1912-1918. (Pubitemid 350219991)
22. Qasba, P. K., Boeggeman, E., and Ramakrishnan, B. (2008) Site-specific linking of biomolecules via glycan residues using glycosyltransferases. Biotechnol. Prog. 24, 520-526. (Pubitemid 351832706)
23. Boeggeman, E., Ramakrishnan, B., and Qasba, P. K. (2003) The N-terminal stem region of bovine and human ∃1,4-galactosyltransferase I increases the in vitro folding efficiency of their catalytic domain from inclusion bodies. Prot. Expres. Purif. 30, 219-220.
24. Ramakrishnan, B., and Qasba, P. K. (2002) Structure-based design of beta-1,4-galactosyltransferase-I (beta 4Gal-T1) with equally efficient N-Acetylgalactosaminyltransferase activity: point mutation broadens beta 4Gal-T1 donor specificity. J. Biol. Chem. 277, 20833-20839. (Pubitemid 34967390)
25. Snovida, S. I., and Perreault, H. (2007) A 2,5-dihydroxybenzoic acid/N, N-dimethylaniline matrix for the analysis of oligosaccharides by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun. Mass Spectrom. 21 (24), 3711-3715. (Pubitemid 350124641)
26. Bock, F., Onderka, J., Dietrich, T., Bachmann, B., Kruse, F. E., Paschke, M., Zahn, G., and Cursiefen, C. (2007) Bevacizumab as a potent inhibitor of inflammatory corneal angiogenesis and lymphangiogenesis. Invest. Ophthalmol. Vis. Sci. 48, 2545-2552. (Pubitemid 351261204)
27. Ramakrishnan, B., Boeggeman, E., and Qasba, P. K. (2008) Applications of glycosyltransferases in the site-specific conjugation of biomolecules and the development of a targeted drug delivery system and contrast agents for MRI. Expert Opin. Drug Delivery 5, 149-153. (Pubitemid 351308308)
28. Raju, T. S., Briggs, J. B., Borge, S. M., and Jones, A. J. (2000) Species-specific variation in glycosylation of IgG: evidence for the species-specific sialylation and branch-specific galactosylation and importance for engineering recombinant glycoprotein therapeutics. Glycobiology 10, 477-486. (Pubitemid 30216089)
29. Hama, Y., Urano, Y., Koyama, Y., Choyke, P. L., and Kobayashi, H. (2007) Activatable fluorescent molecular imaging of peritoneal metastases following pretargeting with a biotinylated monoclonal antibody. Cancer Res. 67, 3809-3817. (Pubitemid 46762168)
30. Koyama, Y., Barrett, T., Hama, Y., Ravizzini, G., Choyke, P. L., and Kobayashi, H. (2007) In vivo molecular imaging to diagnose and subtype tumors through receptor-targeted optically labeled monoclonal antibodies. Neoplasia 9, 1021-1029. (Pubitemid 350255349)