Hydrolytically Stable Site-Specific Conjugation at the N-Terminus of an Engineered Antibody

Bioconjugate Chemistry

Volumn 26, Issue 10, 2015, Pages 2085-2096

  Thompson, Pamela ^a   Bezabeh, Binyam ^a   Fleming, Ryan ^a   Pruitt, Monica ^a   Mao, Shenlan ^a   Strout, Patrick ^a   Chen, Cui ^a   Cho, Song ^a   Zhong, Haihong ^a   Wu, Herren ^a   Gao, Changshou ^a   Dimasi, Nazzareno ^a  

^a MEDIMMUNE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CYTOTOXICITY;

AMINO-ACIDS; ANTIBODY-DRUG CONJUGATES; CYSTEINE RESIDUES; GLYCOSYLATED; KILLING ACTIVITIES; LYSINE RESIDUES; N TERMINUS; SITE-SPECIFIC; SPECIFIC CONJUGATIONS; TECHNOLOGY ADVANCEMENT;

ANTIBODIES;

MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY 1C1 SERINE MONOMETHYL AURISTATINE E CONJUGATE; SERINE DERIVATIVE; UNCLASSIFIED DRUG; ANTIBODY; ANTINEOPLASTIC AGENT; EPHRIN RECEPTOR A2; OXIME; SERINE;

AMINO TERMINAL SEQUENCE; ANTIBODY ENGINEERING; ARTICLE; CANCER INHIBITION; COMPLEMENTARITY DETERMINING REGION; CONTROLLED STUDY; CYTOTOXICITY; DRUG CONJUGATION; HUMAN; HYDROLYSIS; IN VITRO STUDY; IN VIVO STUDY; LIGHT CHAIN; MOUSE; NONHUMAN; TUMOR XENOGRAFT; ANIMAL; CHEMISTRY; DRUG SCREENING; IMMUNOLOGY; METABOLISM; NUDE MOUSE; PROCEDURES; PROTEIN ENGINEERING; PROTEIN STABILITY; RAT;

ANIMALS; ANTIBODIES; ANTINEOPLASTIC AGENTS; HUMANS; HYDROLYSIS; MICE, NUDE; OXIMES; PROTEIN ENGINEERING; PROTEIN STABILITY; RATS; RECEPTOR, EPHA2; SERINE; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84945419159     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.5b00355     Document Type: Article

References (30)

1. Chari, R. V., Miller, M. L., and Widdison, W. C. (2014) Antibody-drug conjugates: an emerging concept in cancer therapy Angew. Chem., Int. Ed. 53, 3796-3827 10.1002/anie.201307628
2. Beck, A. and Reichert, J. M. (2014) Antibody-drug conjugates: present and future MAbs 6, 15-17 10.4161/mabs.27436
3. Junutula, J. R., Raab, H., Clark, S., Bhakta, S., Leipold, D. D., Weir, S., Chen, Y., Simpson, M., Tsai, S. P., and Dennis, M. S. et al. 2008, Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index Nat. Biotechnol. 26, 925-932 10.1038/nbt.1480
4. Agarwal, P. and Bertozzi, C. R. (2015) Site-specific antibody-drug conjugates: the nexus of biorthogonal chemistry, protein engineering, and drug development Bioconjugate Chem. 26, 176-192 10.1021/bc5004982
5. Behrens, C. R. and Liu, B. (2014) Methods for site-specific drug conjugation to antibodies MAbs 6, 46-53 10.4161/mabs.26632
6. Panowski, S., Bhakta, S., Raab, H., Polakis, P., and Junutula, J. R. (2014) Site-specific antibody drug conjugates for cancer therapy MAbs 6, 34-45 10.4161/mabs.27022
7. Zhou, Q., Stefano, J. E., Manning, C., Kyazike, J., Chen, B., Gianolio, D. A., Park, A., Busch, M., Bird, J., and Zheng, X. et al. 2014, Site-specific antibody-drug conjugation through glycoengineering Bioconjugate Chem. 25, 510-520 10.1021/bc400505q
8. Li, X., Fang, T., and Boons, G. J. (2014) Preparation of well-defined antibody-drug conjugates through glycan remodeling and strain-promoted azide-alkyne cycloadditions Angew. Chem., Int. Ed. 53, 7179-7182 10.1002/anie.201402606
9. Van Geel, R., Wijdeven, M. A., Heesbeen, R., Verkade, J. M. M., Wasiel, A. A., van Berkel, S. S., and van Delft, F. L. (2015) Chemoenzymatic conjugation of toxic payloads to the globally conserved N-glycan of native mAbs provides homogeneous and highly efficacious antibody-drug conjugates Bioconjugate Chem. 10.1021/acs.bioconjchem.5b00224
10. Okeley, N. M., Toki, B. E., Zhang, X., Jeffrey, S. C., Burke, P. J., Alley, S. C., and Senter, P. D. (2013) Metabolic engineering of monoclonal antibody carbohydrates for antibody-drug conjugation Bioconjugate Chem. 24, 1650-1655 10.1021/bc4002695
11. Sutherland, M. S. K., Walter, R. B., Jeffrey, S. C., Burke, P. J., Yu, C., Kostner, H., Stone, I., Ryan, M. C., Sussman, D., and Lyon, R. P. et al. 2013, SGN-CD33A: a novel CD33-targeting antibody-drug conjugate using a pyrrolobenzodiazepine dimer is active in models of drug-resistant AML Blood 122, 1455-1463 10.1182/blood-2013-03-491506
12. Jeffrey, S. C., Burke, P. J., Lyon, R. P., Meyer, D. W., Sussman, D., Anderson, M., Hunter, J. H., Leiske, C. I., Miyamoto, J. B., and Nicholas, N. D. et al. 2013, A potent anti-CD70 antibody-drug conjugate combining a dimeric pyrrolobenzodiazepine drug with site-specific conjugation technology Bioconjugate Chem. 24, 1256-1263 10.1021/bc400217g
13. Lyon, R. P., Setter, J. R., Bovee, T. D., Doronina, S. O., Hunter, J. H., Anderson, M. E., Balasubramanian, C. L., Duniho, S. M., Leiske, C. I., Li, F., and Senter, P. D. (2014) Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates Nat. Biotechnol. 32, 1059-1062 10.1038/nbt.2968
14. Fontaine, S. D., Reid, R., Robinson, L., Ashley, G. W., and Santi, D. V. (2015) Long-term stabilization of maleimide-thiol conjugates Bioconjugate Chem. 26, 145-152 10.1021/bc5005262
15. Axup, J. Y., Bajjuri, K. M., Ritland, M., Hutchins, B. M., Kim, C. H., Kazane, S. A., Halder, R., Forsyth, J. S., Santidrian, A. F., and Stafin, K. et al. 2012, Synthesis of site-specific antibody-drug conjugates using unnatural amino acids Proc. Natl. Acad. Sci. U. S. A. 109, 16101-16106 10.1073/pnas.1211023109
16. Liu, C. C. and Schultz, P. G. (2010) Adding new chemistries to the genetic code Annu. Rev. Biochem. 79, 413-444 10.1146/annurev.biochem.052308.105824
17. Young, T. S. and Schultz, P. G. (2010) Beyond the canonical 20 amino acids: expanding the genetic lexicon J. Biol. Chem. 285, 11039-11044 10.1074/jbc.R109.091306
18. Geoghegan, K. F. and Stroh, J. G. (1992) Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Application to modification at N-terminal serine Bioconjugate Chem. 3, 138-146 10.1021/bc00014a008
19. Ning, X., Temming, R. P., Dommerholt, J., Guo, J., Ania, D. B., Debets, M. F., Wolfert, M. A., Boons, G. J., and van Delft, F. L. (2010) Protein modification by strain-promoted alkyne-nitrone cycloaddition Angew. Chem., Int. Ed. 49, 3065-3068 10.1002/anie.201000408
20. Colombo, M., Sommaruga, S., Mazzucchelli, S., Polito, L., Verderio, P., Galeffi, P., Corsi, F., Tortora, P., and Prosperi, D. (2012) Site-Specific Conjugation of ScFvs Antibodies to Nanoparticles by Bioorthogonal Strain-Promoted Alkyne-Nitrone Cycloaddition Angew. Chem. 124, 511-514 10.1002/ange.201106775
21. Jackson, D., Gooya, J., Mao, S., Kinneer, K., Xu, L., Camara, M., Fazenbaker, C., Fleming, R., Swamynathan, S., and Meyer, D. et al. 2008, A human antibody-drug conjugate targeting EphA2 inhibits tumor growth in vivo Cancer Res. 68, 9367-9374 10.1158/0008-5472.CAN-08-1933
22. Muller, P. Y. and Milton, M. N. (2012) The determination and interpretation of the therapeutic index in drug development Nat. Rev. Drug Discovery 11, 751-761 10.1038/nrd3801
23. Hinrichs, M. J. and Dixit, R. (2015) Antibody Drug Conjugates: Nonclinical Safety Considerations AAPS J. 17, 1055-1064 10.1208/s12248-015-9790-0
24. Zuberbuhler, K., Casi, G., Bernardes, G. J. L., and Neri, D. (2012) Fucose-specific conjugation of hydrazide derivatives to a vascular-targeting monoclonal antibody in IgG format Chem. Commun. 48, 7100-7102 10.1039/c2cc32412a
25. Liu, B., Burdine, L., and Kodadek, T. (2006) Chemistry of periodate-mediated cross-linking of 3,4-dihydroxylphenylalanine (DOPA)-containing molecules to proteins J. Am. Chem. Soc. 128, 15228-15235 10.1021/ja065794h
26. Agarwal, P., van der Weijden, J., Sletten, E. M., Rabuka, D., and Bertozzi, C. R. (2013) A Pictet-Spengler ligation for protein chemical modification Proc. Natl. Acad. Sci. U. S. A. 110, 46-51 10.1073/pnas.1213186110
27. Agarwal, P., Kudirka, R., Albers, A. E., Barfield, R. M., deHart, G. W., Drake, P. M., Jones, C. L., and Rabuka, D. (2013) Hydrazino-Pictet Spengler ligation as a biocompatible method for the generation of stable protein conjugates Bioconjugate Chem. 24, 846-851 10.1021/bc400042a
28. Dimasi, N., Gao, C., Fleming, R., Woods, R. M., Yao, X. T., Shirinian, L., Kiener, P. A., and Wu, H. (2009) The design and characterization of oligospecific antibodies for simultaneous targeting of multiple disease mediators J. Mol. Biol. 393, 672-692 10.1016/j.jmb.2009.08.032
29. Wendeler, M., Grinberg, L., Wang, X., Dawson, P. E., and Baca, M. (2014) Enhanced catalysis of oxime-based bioconjugations by substituted anilines Bioconjugate Chem. 25, 93-101 10.1021/bc400380f
30. Guide for the care and use of laboratory animals (1996) National Research Council, Washington, DC.