Development of Solid-Phase Site-Specific Conjugation and Its Application toward Generation of Dual Labeled Antibody and Fab Drug Conjugates

Bioconjugate Chemistry

Volumn 27, Issue 4, 2016, Pages 1030-1039

  Puthenveetil, Sujiet ^a   Musto, Sylvia ^b   Loganzo, Frank ^b   Tumey, L Nathan ^a   O'Donnell, Christopher J ^a   Graziani, Edmund ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b Pfizer Oncology Rinat R and D   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PURIFICATION;

ANTIBODY-DRUG CONJUGATES; COMBINATORIAL PROBLEM; DRUG-CONJUGATES; ITS APPLICATIONS; PHYSICOCHEMICAL PROPERTY; SITE-SPECIFIC; SOLID PHASIS; SOLID-PHASE; SPECIFIC CONJUGATIONS; THERAPEUTIC INDEX;

ANTIBODIES;

CYSTEINE DERIVATIVE; IMMUNOGLOBULIN F(AB) FRAGMENT; PROTEIN; PROTEIN A; PROTEIN L; UNCLASSIFIED DRUG; ANTIBODY; ANTIBODY CONJUGATE;

ANTIBODY LABELING; ARTICLE; DRUG CONJUGATION; DRUG PURIFICATION; DRUG SCREENING; IN VITRO STUDY; PHYSICAL CHEMISTRY; SOLID;

ANTIBODIES; IMMUNOCONJUGATES; IMMUNOGLOBULIN FAB FRAGMENTS;

EID: 84966377331     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.6b00054     Document Type: Article

References (34)

1. Kim, E. G. and Kim, K. M. (2015) Strategies and Advancement in Antibody-Drug Conjugate Optimization for Targeted Cancer Therapeutics Biomol. Ther. 23, 493-509 10.4062/biomolther.2015.116
2. Wu, A. M. and Senter, P. D. (2005) Arming antibodies: prospects and challenges for immunoconjugates Nat. Biotechnol. 23, 1137-1146 10.1038/nbt1141
3. Tian, F., Lu, Y., Manibusan, A., Sellers, A., Tran, H., Sun, Y., Phuong, T., Barnett, R., Hehli, B., and Song, F. et al. 2014, A general approach to site-specific antibody drug conjugates Proc. Natl. Acad. Sci. U. S. A. 111, 1766-1771 10.1073/pnas.1321237111
4. Mack, F., Ritchie, M., and Sapra, P. (2014) The next generation of antibody drug conjugates Semin. Oncol. 41, 637-652 10.1053/j.seminoncol.2014.08.001
5. 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
6. 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
7. Shen, B.-Q., Xu, K., Liu, L., Raab, H., Bhakta, S., Kenrick, M., Parsons-Reponte, K. L., Tien, J., Yu, S.-F., and Mai, E. et al. 2012, Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates Nat. Biotechnol. 30, 184-189 10.1038/nbt.2108
8. Strop, P., Liu, S.-H., Dorywalska, M., Delaria, K., Dushin, R. G., Tran, T.-T., Ho, W.-H., Farias, S., Casas, M. G., and Abdiche, Y. et al. 2013, Location Matters: Site of Conjugation Modulates Stability and Pharmacokinetics of Antibody Drug Conjugates Chem. Biol. (Oxford, U. K.) 20, 161-167 10.1016/j.chembiol.2013.01.010
9. Lhospice, F., Bregeon, D., Belmant, C., Dennler, P., Chiotellis, A., Fischer, E., Gauthier, L., Boedec, A., Rispaud, H., and Savard-Chambard, S. et al. 2015, Site-Specific Conjugation of Monomethyl Auristatin E to Anti-CD30 Antibodies Improves Their Pharmacokinetics and Therapeutic Index in Rodent Models Mol. Pharmaceutics 12, 1863-1871 10.1021/mp500666j
10. Jackson, D., Atkinson, J., Guevara, C. I., Zhang, C., Kery, V., Moon, S. J., Virata, C., Yang, P., Lowe, C., and Pinkstaff, J. et al. 2014, In vitro and in vivo evaluation of cysteine and site specific conjugated herceptin antibody-drug conjugates PLoS One 9, e83865 10.1371/journal.pone.0083865
11. Dorywalska, M., Strop, P., Melton-Witt, J. A., Hasa-Moreno, A., Farias, S. E., Galindo Casas, M., Delaria, K., Lui, V., Poulsen, K., and Loo, C. et al. 2015, Effect of attachment site on stability of cleavable antibody drug conjugates Bioconjugate Chem. 26, 650-659 10.1021/bc5005747
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. Acchione, M., Kwon, H., Jochheim, C. M., and Atkins, W. M. (2012) Impact of linker and conjugation chemistry on antigen binding, Fc receptor binding and thermal stability of model antibody-drug conjugates mAbs 4, 362-372 10.4161/mabs.19449
14. Li, X., Patterson, J. T., Sarkar, M., Pedzisa, L., Kodadek, T., Roush, W. R., and Rader, C. (2015) Site-Specific Dual Antibody Conjugation via Engineered Cysteine and Selenocysteine Residues Bioconjugate Chem. 26, 2243-2248 10.1021/acs.bioconjchem.5b00244
15. Azhdarinia, A., Ghosh, P., Ghosh, S., Wilganowski, N., and Sevick-Muraca, E. M. (2012) Dual-labeling strategies for nuclear and fluorescence molecular imaging: a review and analysis Molecular imaging and biology: MIB: the official publication of the Academy of Molecular Imaging 14, 261-276 10.1007/s11307-011-0528-9
16. Maruani, A., Smith, M. E., Miranda, E., Chester, K. A., Chudasama, V., and Caddick, S. (2015) A plug-and-play approach to antibody-based therapeutics via a chemoselective dual click strategy Nat. Commun. 6, 6645 10.1038/ncomms7645
17. Nath, N., Godat, B., Benink, H., and Urh, M. (2015) On-bead antibody-small molecule conjugation using high-capacity magnetic beads J. Immunol. Methods 426, 95-103 10.1016/j.jim.2015.08.008
18. Lyon, R. P., Meyer, D. L., Setter, J. R., and Senter, P. D. (2012) Conjugation of anticancer drugs through endogenous monoclonal antibody cysteine residues Methods Enzymol. 502, 123-138 10.1016/B978-0-12-416039-2.00006-9
19. Doroski, M. D., Maderna, A., O'Donnell, C. J., Subramanyam, C., Vetelino, B. C., Dushin, R. G., Strop, P., and Graziani, E. I. (Pfizer) (2013) Cytotoxic peptides and antibody drug conjugates thereof. Pat. Appl. WO 2013/072813 A2.
20. Maderna, A., Doroski, M., Subramanyam, C., Porte, A., Leverett, C. A., Vetelino, B. C., Chen, Z., Risley, H., Parris, K., and Pandit, J. et al. 2014, Discovery of cytotoxic dolastatin 10 analogues with N-terminal modifications J. Med. Chem. 57, 10527-10543 10.1021/jm501649k
21. Deisenhofer, J. (1981) Crystallographic refinement and atomic models of a human Fc fragment and its complex with fragment B of protein A from Staphylococcus aureus at 2.9- and 2.8-A resolution Biochemistry 20, 2361-2370 10.1021/bi00512a001
22. Guex, N. and Peitsch, M. C. (1997) SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling Electrophoresis 18, 2714-2723 10.1002/elps.1150181505
23. Jeger, S., Zimmermann, K., Blanc, A., Gruenberg, J., Honer, M., Hunziker, P., Struthers, H., and Schibli, R. (2010) Site-Specific and Stoichiometric Modification of Antibodies by Bacterial Transglutaminase Angew. Chem., Int. Ed. 49, 9995-9997 10.1002/anie.201004243
24. Deonarain, M. P., Yahioglu, G., Stamati, I., and Marklew, J. (2015) Emerging formats for next-generation antibody drug conjugates Expert Opin. Drug Discovery 10, 463-481 10.1517/17460441.2015.1025049
25. Dorywalska, M., Strop, P., Melton-Witt, J. A., Hasa-Moreno, A., Farias, S. E., Galindo Casas, M., Delaria, K., Lui, V., Poulsen, K., and Sutton, J. et al. 2015, Site-Dependent Degradation of a Non-Cleavable Auristatin-Based Linker-Payload in Rodent Plasma and Its Effect on ADC Efficacy PLoS One 10, e0132282 10.1371/journal.pone.0132282
26. Conner, K. P., Rock, B. M., Kwon, G. K., Balthasar, J. P., Abuqayyas, L., Wienkers, L. C., and Rock, D. A. (2014) Evaluation of near infrared fluorescent labeling of monoclonal antibodies as a tool for tissue distribution Drug Metab. Dispos. 42, 1906-1913 10.1124/dmd.114.060319
27. Hallam, T. (2013) Producing Homogeneous ADCs with Combination Warheads. World ADC Summit, San Francisco, CA.
28. Yokota, T., Milenic, D. E., Whitlow, M., and Schlom, J. (1992) Rapid tumor penetration of a single-chain Fv and comparison with other immunoglobulin forms Cancer Res. 52, 3402-3408
29. Kim, K. M., McDonagh, C. F., Westendorf, L., Brown, L. L., Sussman, D., Feist, T., Lyon, R., Alley, S. C., Okeley, N. M., and Zhang, X. et al. 2008, Anti-CD30 diabody-drug conjugates with potent antitumor activity Mol. Cancer Ther. 7, 2486-2497 10.1158/1535-7163.MCT-08-0388
30. Okeley, N. M., Miyamoto, J. B., Zhang, X., Sanderson, R. J., Benjamin, D. R., Sievers, E. L., Senter, P. D., and Alley, S. C. (2010) Intracellular Activation of SGN-35, a Potent Anti-CD30 Antibody-Drug Conjugate Clin. Cancer Res. 16, 888-897 10.1158/1078-0432.CCR-09-2069
31. Brown, M. P. and Staudacher, A. H. (2014) Could bystander killing contribute significantly to the antitumor activity of brentuximab vedotin given with standard first-line chemotherapy for Hodgkin lymphoma? Immunotherapy 6, 371-375 10.2217/imt.14.13
32. Polson, A. G., Calemine-Fenaux, J., Chan, P., Chang, W., Christensen, E., Clark, S., de Sauvage, F. J., Eaton, D., Elkins, K., and Elliott, J. M. et al. 2009, Antibody-Drug Conjugates for the Treatment of Non-Hodgkin's Lymphoma: Target and Linker-Drug Selection Cancer Res. 69, 2358-2364 10.1158/0008-5472.CAN-08-2250
33. Marquette, K., Bennett, E., Tchistiakova, L., and Tumey, N. (2013) Engineered antibody constant regions for site-specific conjugation and methods and uses therefor. Pat. Appl. WO 2013/093809 A1.
34. Loganzo, F., Tan, X., Sung, M., Jin, G., Myers, J. S., Melamud, E., Wang, F., Diesl, V., Follettie, M. T., and Musto, S. et al. 2015, Tumor cells chronically treated with a trastuzumab-maytansinoid antibody-drug conjugate develop varied resistance mechanisms but respond to alternate treatments Mol. Cancer Ther. 14, 952-963 10.1158/1535-7163.MCT-14-0862