Homogeneous bispecifics by disulfide bridging

Bioconjugate Chemistry

Volumn 25, Issue 8, 2014, Pages 1395-1401

  Hull, Elizabeth A ^a   Livanos, Maria ^b   Miranda, Enrique ^b   Smith, Mark E B ^a   Chester, Kerry A ^b   Baker, James R ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

COVALENT BONDS; SULFUR COMPOUNDS;

% REDUCTIONS; ANTIBODY CONJUGATE; ANTIBODY-FRAGMENT; BINDING ACTIVITIES; CROSSLINKER; DISULPHIDE BONDS; IN-VITRO; SIMPLE++; SITE-SPECIFIC; SYNTHESISED;

ANTIBODIES;

BIS DIBROMOMALEIMIDE; BISPECIFIC ANTIBODY; CARCINOEMBRYONIC ANTIGEN; DISULFIDE; HOMODIMER; IMMUNOGLOBULIN F(AB) FRAGMENT; MALEIMIDE DERIVATIVE; SINGLE CHAIN FRAGMENT VARIABLE ANTIBODY; UNCLASSIFIED DRUG;

ANTIGEN BINDING; ARTICLE; BINDING AFFINITY; DIMERIZATION; DISULFIDE BOND; DISULFIDE BRIDGING; ENZYME LINKED IMMUNOSORBENT ASSAY; GEL PERMEATION CHROMATOGRAPHY; IN VITRO STUDY; POLYACRYLAMIDE GEL ELECTROPHORESIS; STEREOSPECIFICITY; ANTIBODY SPECIFICITY; CHEMISTRY; ENZYME SPECIFICITY; IMMUNOLOGY; PROTEIN MULTIMERIZATION; PROTEIN QUATERNARY STRUCTURE;

ANTIBODY SPECIFICITY; DISULFIDES; PROTEIN MULTIMERIZATION; PROTEIN STRUCTURE, QUATERNARY; SINGLE-CHAIN ANTIBODIES; SUBSTRATE SPECIFICITY;

EID: 84906335290     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc5002467     Document Type: Article

References (30)

1. Heiss, M. M., Murawa, P., Koralewski, P., Kutarska, E., Kolesnik, O. O., Ivanchenko, V. V., Dudnichenko, A. S., Aleknaviciene, B., Razbadauskas, A., Gore, M., Ganea-Motan, E., Ciuleanu, T., Wimberger, P., Schmittel, A., Schmalfeldt, B., Burges, A., Bokemeyer, C., Lindhofer, H., Lahr, A., and Parsons, S. L. (2010) The trifunctional antibody catumaxomab for the treatment of malignant ascites due to epithelial cancer: Results of a prospective randomized phase II/III trial Int. J. Cancer 127, 2209-21
2. Byrne, H., Conroy, P. J., Whisstock, J. C., and O'Kennedy, R. J. (2013) A tale of two specificities: bispecific antibodies for therapeutic and diagnostic applications Trends Biotechnol. 31, 621-32
3. Schmidt, S. R. (2009) Fusion proteins as biopharmaceuticals-applications and challenges Curr. Opin. Drug Discovery Dev. 12, 284-295
4. Baggio, L. L., Huang, Q., Brown, T. J., and Drucker, D. J. (2004) A recombinant human glucagon-like peptide (GLP)-1-albumin protein (Albugon) mimics peptidergic activation of GLP-1 receptor-dependent pathways coupled with satiety, gastrointestinal motility, and glucose homeostasis Diabetes 53, 2492-2500
5. Chames, P. and Baty, D. (2009) Bispecific antibodies for cancer therapy: the light at the end of the tunnel? mAbs 1, 539-47
6. Schmiedl, A., Breitling, F., Winter, C. H., Queitsch, I., and Dübel, S. (2000) Effects of unpaired cysteines on yield, solubility and activity of different recombinant antibody constructs expressed in E. coli J. Immunol. Methods 242, 101-14
7. Junutula, J. R., Raab, H., Clark, S., Bhakta, S., Leipold, D. D., Weir, S., Chen, Y., Simpson, M., Tsai, S. P., Dennis, M. S., Lu, Y., Meng, Y. G., Ng, C., Yang, J., Lee, C. C., Duenas, E., Gorrell, J., Katta, V., Kim, A., McDorman, K., Flagella, K., Venook, R., Ross, S., Spencer, S. D., Lee Wong, W., Lowman, H. B., Vandlen, R., Sliwkowski, M. X., Scheller, R. H., Polakis, P., and Mallet, W. (2008) Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index Nat. Biotechnol. 26, 925-32
8. Albrecht, H., Burke, P. A., Natarajan, A., Xiong, C.-Y., Kalicinsky, M., DeNardo, G. L., and DeNardo, S. J. Production of soluble ScFvs with C-terminal-free thiol for site-specific conjugation or stable dimeric ScFvs on demand. Bioconjugate Chem. 15, 16-26.
9. Hudak, J. E., Barfield, R. M., de Hart, G. W., Grob, P., Nogales, E., Bertozzi, C. R., and Rabuka, D. (2012) Synthesis of heterobifunctional protein fusions using copper-free click chemistry and the aldehyde tag Angew. Chem., Int. Ed. 51, 4161-4165
10. Kim, C. H., Axup, J. Y., Dubrovska, A., Kazane, S. A., Hutchins, B. A., Wold, E. D., Smider, V. V., and Schultz, P. G. (2012) Synthesis of bispecific antibodies using genetically encoded unnatural amino acids J. Am. Chem. Soc. 134, 9918-21
11. Loscha, K. V., Herlt, A. J., Qi, R., Huber, T., Ozawa, K., and Otting, G. (2012) Multiple-site labeling of proteins with unnatural amino acids Angew. Chem., Int. Ed. 51, 2243-6
12. Liebscher, S., Schöpfel, M., Aumüller, T., Sharkhuukhen, A., Pech, A., Höss, E., Parthier, C., Jahreis, G., Stubbs, M. T., and Bordusa, F. (2014) N-terminal protein modification by substrate-activated reverse proteolysis Angew. Chem., Int. Ed. 53, 3024-8
13. Fodje, M. N. and Al-Karadaghi, S. (2002) Occurrence, conformational features and amino acid propensities for the α-helix Protein Eng., Des. Sel. 15, 353-358
14. Adem, Y. T., Schwarz, K. A., Duenas, E., Patapoff, T. W., Galush, W. J., and Esue, O. (2014) Auristatin antibody drug conjugate physical instability and the role of drug payload Bioconjugate Chem. 25, 656-64
15. Ellerman, D. and Scheer, J. M. (2011) Generation of Bispecific Antibodies by Chemical Conjugation. In Bispecific Antibodies (Kontermann, R. E., Ed.) pp 47-63, Chapter 3, Springer.
16. Smith, M. E. B., Schumacher, F. F., Ryan, C. P., Tedaldi, L. M., Papaioannou, D., Waksman, G., Caddick, S., and Baker, J. R. (2010) Protein modification, bioconjugation, and disulfide bridging using bromomaleimides J. Am. Chem. Soc. 132, 1960-5
17. Schumacher, F. F., Nobles, M., Ryan, C. P., Smith, M. E. B., Tinker, A., Caddick, S., and Baker, J. R. (2011) In situ maleimide bridging of disulfides and a new approach to protein PEGylation Bioconjugate Chem. 22, 132-6
18. Ryan, C. P., Smith, M. E. B., Schumacher, F. F., Grohmann, D., Papaioannou, D., Waksman, G., Werner, F., Baker, J. R., and Caddick, S. (2011) Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis Chem. Commun. 47, 5452-4
19. Khalili, H., Godwin, A., Choi, J., Lever, R., and Brocchini, S. (2012) Comparative binding of disulfide-bridged PEG-Fabs Bioconjugate Chem. 23, 248-263
20. Schumacher, F. F., Sanchania, V. A., Tolner, B., Wright, Z. V. F., Ryan, C. P., Smith, M. E. B., Ward, J. M., Caddick, S., Kay, C. W. M., Aeppli, G., Chester, K. A., and Baker, J. R. (2013) Homogeneous antibody fragment conjugation by disulfide bridging introduces "spinostics" Sci. Rep. 3, 1525
21. Castañeda, L., Maruani, A., Schumacher, F. F., Miranda, E., Chudasama, V., Chester, K. A., Baker, J. R., Smith, M. E. B., and Caddick, S. (2013) Acid-cleavable thiomaleamic acid linker for homogeneous antibody-drug conjugation Chem. Commun. 49, 8187-9
22. Palanki, M. S. S., Bhat, A., Bolanos, B., Brunel, F., Del Rosario, J., Dettling, D., Horn, M., Lappe, R., Preston, R., Sievers, A., Stankovic, N., Woodnut, G., and Chen, G. (2013) Development of a long acting human growth hormone analog suitable for once a week dosing Bioorg. Med. Chem. Lett. 23, 402-6
23. Marculescu, C., Kossen, H., Morgan, R. E., Mayer, P., Fletcher, S. A., Tolner, B., Chester, K. A., Jones, L. H., and Baker, J. R. (2014) Aryloxymaleimides for cysteine modification, disulfide bridging and the dual functionalization of disulfide bonds Chem. Commun. 54, 4-7
24. Castañeda, L., Wright, Z. V. F., Marculescu, C., Tran, T. M., Chudasama, V., Maruani, A., Hull, E. A., Nunes, J. P. M., Fitzmaurice, R. J., Smith, M. E. B., Jones, L. H., Caddick, S., and Baker, J. R. (2013) A mild synthesis of N-functionalised bromomaleimides, thiomaleimides and bromopyridazinediones Tetrahedron Lett. 54, 3493-3495
25. Goldstein, M. J. and Mitchell, E. P. (2005) Carcinoembryonic antigen in the staging and follow-up of patients with colorectal cancer Cancer Invest. 23, 338-351
26. Khalili, H., Godwin, A., Choi, J., Lever, R., Khaw, S. P., and Brocchini, S. (2013) Fab-PEG-Fab as a potential antibody mimetic Fab-PEG-Fab as a potential antibody mimetic Bioconjugate Chem. 24, 1870-1882
27. Karpovsky, B. Y. B., Titus, J. A., Stephany, D. A., and Segal, D. M. (1984) Production of target-specific effector cells using hetero-cross-linked aggregates containing anti-target cell and anti-Fc gamma receptor antibodies J. Exp. Med. 160, 1686-1701
28. Reusch, U., Sundaram, M., Davol, P. A., Olson, S. D., Davis, J. B., Demel, K., Nissim, J., Rathore, R., Liu, P. Y., and Lum, L. G. (2006) Anti-CD3 x anti-epidermal growth factor receptor (EGFR) bispecific antibody redirects T-cell cytolytic activity to EGFR-positive cancers in vitro and in an animal model Clin. Cancer Res. 12, 183-90
29. Lee, R. J., Fang, Q., Davol, P. a, Gu, Y., Sievers, R. E., Grabert, R. C., Gall, J. M., Tsang, E., Yee, M. S., Fok, H., Huang, N. F., Padbury, J. F., Larrick, J. W., and Lum, L. G. (2007) Antibody targeting of stem cells to infarcted myocardium Stem cells 25, 712-7
30. Hudis, C. A. (2007) Trastuzumab-mechanism of action and use in clinical practice N. Eng. J. Med. 357, 39-51