Mass spectrometric characterization of transglutaminase based site-specific antibody-drug conjugates

Bioconjugate Chemistry

Volumn 25, Issue 2, 2014, Pages 240-250

  Farias, Santiago E ^a   Strop, Pavel ^a   Delaria, Kathy ^a   Galindo Casas, Meritxell ^a   Dorywalska, Magdalena ^a   Shelton, David L ^a   Pons, Jaume ^a   Rajpal, Arvind ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMES; MONOCLONAL ANTIBODIES;

ANTIBODY-DRUG CONJUGATES; CYTOTOXIC; HETEROGENEOUS MIXTURES; POTENTIAL BENEFITS; SITE-SPECIFIC; SITE-SPECIFICITY; SMALL-MOLECULE DRUGS; THERAPEUTIC AGENTS; TRANSGLUTAMINASES; TUMOUR CELLS;

MASS SPECTROMETRY;

DRUG ANTIBODY; PROTEIN GLUTAMINE GAMMA GLUTAMYLTRANSFERASE;

ANTIBODY SPECIFICITY; ARTICLE; DRUG CONJUGATION; GEL PERMEATION CHROMATOGRAPHY; HYDROPHOBICITY; LIMIT OF DETECTION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MUTANT; PROTEIN PURIFICATION;

ANTIBODIES; CHROMATOGRAPHY, LIQUID; PHARMACEUTICAL PREPARATIONS; TANDEM MASS SPECTROMETRY; TRANSGLUTAMINASES;

EID: 84894450747     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc4003794     Document Type: Article

References (32)

1. Lambert, J. M. (2005) Drug-conjugated monoclonal antibodies for the treatment of cancer Curr. Opin. Pharmacol. 5, 543-9
2. Senter, P. D. (2009) Potent antibody drug conjugates for cancer therapy Curr. Opin. Chem. Biol. 13, 235-44
3. Junutula, J. R., Flagella, K. M., Graham, R. A., Parsons, K. L., Ha, E., Raab, H., Bhakta, S., Nguyen, T., Dugger, D. L., Li, G., Mai, E., Lewis Phillips, G. D., Hiraragi, H., Fuji, R. N., Tibbitts, J., Vandlen, R., Spencer, S. D., Scheller, R. H., Polakis, P., and Sliwkowski, M. X. (2010) Engineered thio-trastuzumab-DM1 conjugate with an improved therapeutic index to target human epidermal growth factor receptor 2-positive breast cancer Clin. Cancer Res. 16, 4769-78
4. Senter, P. D. and Sievers, E. L. (2012) The discovery and development of brentuximab vedotin for use in relapsed Hodgkin lymphoma and systemic anaplastic large cell lymphoma Nat. Biotechnol. 30, 631-7
5. Ricart, A. D. and Tolcher, A. W. (2007) Technology insight: cytotoxic drug immunoconjugates for cancer therapy Nat. Clin. Pract. Oncol. 4, 245-55
6. Ducry, L. and Stump, B. (2010) Antibody-drug conjugates: linking cytotoxic payloads to monoclonal antibodies Bioconjugate Chem. 21, 5-13
7. Doronina, S. O., Toki, B. E., Torgov, M. Y., Mendelsohn, B. A., Cerveny, C. G., Chace, D. F., DeBlanc, R. L., Gearing, R. P., Bovee, T. D., Siegall, C. B., Francisco, J. A., Wahl, A. F., Meyer, D. L., and Senter, P. D. (2003) Development of potent monoclonal antibody auristatin conjugates for cancer therapy Nat. Biotechnol. 21, 778-84
8. Lambert, J. M. (2012) Drug-conjugated antibodies for the treatment of cancer Br. J. Clin. Pharmacol. 76, 248-262
9. Wagner-Rousset, E., Janin-Bussat, M. C., Colas, O., Excoffier, M., Haeuw, J. F., Rilatt, I., Perez, M., Corvaia, N., and Beck, A. (2013) Antibody Drug Conjugate model fast characterization by LC-MS following IdeS proteolytic digestion. mAbs 6, DOI: 10.4161/mabs.26773.
10. Kellogg, B. A., Garrett, L., Kovtun, Y., Lai, K. C., Leece, B., Miller, M., Payne, G., Steeves, R., Whiteman, K. R., Widdison, W., Xie, H., Singh, R., Chari, R. V., Lambert, J. M., and Lutz, R. J. (2011) Disulfide-linked antibody-maytansinoid conjugates: optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage Bioconjugate Chem. 22, 717-27
11. Flygare, J. A., Pillow, T. H., and Aristoff, P. (2013) Antibody-drug conjugates for the treatment of cancer Chem. Biol. Drug Des. 81, 113-21
12. Wang, L., Amphlett, G., Blattler, W. A., Lambert, J. M., and Zhang, W. (2005) Structural characterization of the maytansinoid-monoclonal antibody immunoconjugate, huN901-DM1, by mass spectrometry Protein Sci. 14, 2436-46
13. Alley, S. C. and Anderson, K. E. (2013) Analytical and bioanalytical technologies for characterizing antibody-drug conjugates Curr. Opin. Chem. Biol. 17, 406-411
14. Shen, B. Q., Xu, K., Liu, L., Raab, H., Bhakta, S., Kenrick, M., Parsons-Reponte, K. L., Tien, J., Yu, S. F., Mai, E., Li, D., Tibbitts, J., Baudys, J., Saad, O. M., Scales, S. J., McDonald, P. J., Hass, P. E., Eigenbrot, C., Nguyen, T., Solis, W. A., Fuji, R. N., Flagella, K. M., Patel, D., Spencer, S. D., Khawli, L. A., Ebens, A., Wong, W. L., Vandlen, R., Kaur, S., Sliwkowski, M. X., Scheller, R. H., Polakis, P., and Junutula, J. R. (2012) Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates Nat. Biotechnol. 30, 184-9
15. Boswell, C. A., Mundo, E. E., Zhang, C., Bumbaca, D., Valle, N. R., Kozak, K. R., Fourie, A., Chuh, J., Koppada, N., Saad, O., Gill, H., Shen, B. Q., Rubinfeld, B., Tibbitts, J., Kaur, S., Theil, F. P., Fielder, P. J., Khawli, L. A., and Lin, K. (2011) Impact of drug conjugation on pharmacokinetics and tissue distribution of anti-STEAP1 antibody-drug conjugates in rats Bioconjugate Chem. 22, 1994-2004
16. Kozak, K. R., Tsai, S. P., Fourie-O'Donohue, A., Dela Cruz Chuh, J., Roth, L., Cook, R., Chan, E., Chan, P., Darwish, M., Ohri, R., Raab, H., Zhang, C., Lin, K., and Wong, W. L. (2013) Total antibody quantification for MMAE-conjugated antibody-drug conjugates: impact of assay format and reagents Bioconjugate Chem. 24, 772-779
17. Strop, P., Liu, S. H., Dorywalska, M., Delaria, K., Dushin, R. G., Tran, T. T., Ho, W. H., Farias, S., Casas, M. G., Abdiche, Y., Zhou, D., Chandrasekaran, R., Samain, C., Loo, C., Rossi, A., Rickert, M., Krimm, S., Wong, T., Chin, S. M., Yu, J., Dilley, J., Chaparro-Riggers, J., Filzen, G. F., O'Donnell, C. J., Wang, F., Myers, J. S., Pons, J., Shelton, D. L., and Rajpal, A. (2013) Location matters: site of conjugation modulates stability and pharmacokinetics of antibody drug conjugates Chem. Biol. 20, 161-7
18. McDonagh, C. F., Turcott, E., Westendorf, L., Webster, J. B., Alley, S. C., Kim, K., Andreyka, J., Stone, I., Hamblett, K. J., Francisco, J. A., and Carter, P. (2006) Engineered antibody-drug conjugates with defined sites and stoichiometries of drug attachment Protein Eng. Des. Sel. 19, 299-307
19. Sun, M. M., Beam, K. S., Cerveny, C. G., Hamblett, K. J., Blackmore, R. S., Torgov, M. Y., Handley, F. G., Ihle, N. C., Senter, P. D., and Alley, S. C. (2005) Reduction-alkylation strategies for the modification of specific monoclonal antibody disulfides Bioconjugate Chem. 16, 1282-90
20. 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., Nicholas, N. D., Okeley, N. M., Sanderson, R. J., Stone, I. J., Zeng, W., Gregson, S. J., Masterson, L., Tiberghien, A. C., Howard, P. W., Thurston, D. E., Law, C. L., and Senter, P. D. (2013) A potent anti-CD70 antibody-drug conjugate combining a dimeric pyrrolobenzodiazepine drug with site-specific conjugation technology Bioconjugate Chem. 24, 1256-1263
21. Kung Sutherland, M. S., Walter, R. B., Jeffrey, S. C., Burke, P. J., Yu, C., Kostner, H., Stone, I., Ryan, M. C., Sussman, D., Lyon, R. P., Zeng, W., Harrington, K. H., Klussman, K., Westendorf, L., Meyer, D., Bernstein, I. D., Senter, P. D., Benjamin, D. R., Drachman, J. G., and McEarchern, J. A. (2013) SGN-CD33A: a novel CD33-targeting antibody-drug conjugate utilizing a pyrrolobenzodiazepine dimer is active in models of drug-resistant AML Blood 122, 1455-1463
22. 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
23. 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., Stafin, K., Lu, Y., Tran, H., Seller, A. J., Biroc, S. L., Szydlik, A., Pinkstaff, J. K., Tian, F., Sinha, S. C., Felding-Habermann, B., Smider, V. V., and Schultz, P. G. (2012) Synthesis of site-specific antibody-drug conjugates using unnatural amino acids Proc. Natl. Acad. Sci. U.S.A. 109, 16101-6
24. Ohtsuka, T., Sawa, A., Kawabata, R., Nio, N., and Motoki, M. (2000) Substrate specificities of microbial transglutaminase for primary amines J. Agric. Food Chem. 48, 6230-3
25. Yokoyama, K., Nio, N., and Kikuchi, Y. (2004) Properties and applications of microbial transglutaminase Appl. Microbiol. Biotechnol. 64, 447-54
26. Jeger, S., Zimmermann, K., Blanc, A., Grunberg, 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. Engl. 49, 9995-7
27. Sato, H. (2002) Enzymatic procedure for site-specific pegylation of proteins Adv. Drug Delivery Rev. 54, 487-504
28. Dai, L., Preston, R., Bacica, M., Kinhikar, A., Bolaños, B., and Murphy, R. E. (2012) Development of a potential high-throughput workflow to characterize sites of bioconjugation by immuno-affinity capture coupled to MALDI-TOF mass spectrometry Bioconjugate Chem. 24, 53-62
29. Vanderlinden, L. A., Saba, L. M., Kechris, K., Miles, M. F., Hoffman, P. L., and Tabakoff, B. (2013) Whole brain and brain regional coexpression network interactions associated with predisposition to alcohol consumption PloS One 8, e68878
30. Hafko, R., Villapol, S., Nostramo, R., Symes, A., Sabban, E. L., Inagami, T., and Saavedra, J. M. (2013) Commercially available angiotensin II At2 receptor antibodies are nonspecific PLoS One 8, e69234
31. Moskvina, V., Harold, D., Russo, G., Vedernikov, A., Sharma, M., Saad, M., Holmans, P., Bras, J. M., Bettella, F., Keller, M. F., Nicolaou, N., Simon-Sanchez, J., Gibbs, J. R., Schulte, C., Durr, A., Guerreiro, R., Hernandez, D., Brice, A., Stefansson, H., Majamaa, K., Gasser, T., Heutink, P., Wood, N., Martinez, M., Singleton, A. B., Nalls, M. A., Hardy, J., Owen, M. J., O'Donovan, M. C., Williams, J., Morris, H. R., and Williams, N. M. (2013) Analysis of genome-wide association studies of Alzheimer disease and of Parkinson disease to determine if these 2 diseases share a common genetic risk JAMA Neurol. 70, 1268-1276
32. Alley, S. C., Benjamin, D. R., Jeffrey, S. C., Okeley, N. M., Meyer, D. L., Sanderson, R. J., and Senter, P. D. (2008) Contribution of linker stability to the activities of anticancer immunoconjugates Bioconjugate Chem. 19, 759-65