Disulfide-linked antibody-maytansinoid conjugates: Optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage

Bioconjugate Chemistry

Volumn 22, Issue 4, 2011, Pages 717-727

  Kellogg, Brenda A ^a   Garrett, Lisa ^b   Kovtun, Yelena ^a   Lai, Katharine C ^a   Leece, Barbara ^a   Miller, Michael ^a   Payne, Gillian ^a   Steeves, Rita ^b   Whiteman, Kathleen R ^a   Widdison, Wayne ^a   Xie, Hongsheng ^c   Singh, Rajeeva ^a,d   Chari, Ravi V J ^a   Lambert, John M ^a   Lutz, Robert J ^a  

^a IMMUNOGEN INC   (United States)

^b Norfolk Agricultural School   (United States)

^c Acceleron Pharma   (United States)

^d Shire HGT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COVALENT BONDS; MAMMALS; PLASMA STABILITY; REDUCTION; SULFUR COMPOUNDS;

% REDUCTIONS; ANTITUMOUR ACTIVITY; DISULFIDE LINKAGES; DISULPHIDE BONDS; IN-VITRO; IN-VIVO; METHYL GROUP; OPTIMISATIONS; STERIC HINDRANCES; VIVO EFFICACIES;

ANTIBODIES;

ANTIBODY; ANTINEOPLASTIC AGENT; CARBON; DISULFIDE; DITHIOTHREITOL; MAYTANSINOID CONJUGATE; METHYL GROUP; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; AREA UNDER THE CURVE; ARTICLE; COLON CANCER; CYTOTOXICITY; DISULFIDE BOND; DRUG BLOOD LEVEL; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG HALF LIFE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; METABOLITE; MOUSE; NONHUMAN; PLASMA; STEREOSPECIFICITY; TUMOR CELL;

MUS;

EID: 79955022475     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc100480a     Document Type: Article

References (33)

1. Lambert, J. M. (2010) Antibody-maytansinoid conjugates: A new strategy for the treatment of cancer Drugs Future 35, 471-480
2. Chari, R. V. (2008) Targeted cancer therapy: Conferring specificity to cytotoxic drugs Acc. Chem. Res. 41, 98-107
3. Erickson, H. E., Park, P. U., Widdison, W. C., Kovtun, Y. V., Garrett, L. M., Hoffman, K., Lutz, R. J., Goldmacher, V. S., and Blättler, W. A. (2006) Antibody-maytansinoid conjugates are activated in targeted cancer cells by lysosomal degradation and linker dependent intracellular processing Cancer Res. 66, 4426-4433
4. Lewis Phillips, G. D., Li, G., Dugger, D. L., Crocker, L. M., Parsons, K. L., Mai, E., Blättler, W. A., Lambert, J. M., Chari, R. V., Lutz, R. J., Wong, W. L., Jacobson, F. S., Koeppen, H., Schwall, R. H., Kenkare-Mitra, S. R., Spencer, S. D., and Sliwkowski, M. X. (2008) Targeting HER2-positive breast cancer with Trastuzumab-DM1, an antibody-cytotoxic drug conjugate Cancer Res. 68, 9280-9290
5. Krop, I. E., Beeram, M., Modi, S., Jones, S. F., Holden, S. N., Yu, W., Girish, S., Tibbitts, J., Yi, J. H., Sliwkowski, M. X., Jacobson, F., Lutzker, S. G., and Burris, H. A. (2010) Phase I study of trastuzumab-DM1, an HER2 antibody-drug conjugate, given every 3 weeks to patients with HER2-positive metastatic breast cancer J. Clin. Oncol. 28, 2698-2704
6. Xie, H., Audette, C., Hoffee, M., Lambert, J., and Blättler, W. (2004) Pharmacokinetics and biodistribution of the antitumor immunoconjugate, cantuzumab mertansine (huC242-DM1), and its two components in mice J. Pharmacol. Exp. Ther. 308, 1073-1082 (Pubitemid 38263984)
7. 2-(3-mercapto-1- oxopropyl)-maytansine against CD56+ multiple myeloma cells Cancer Res. 64, 4629-4636 (Pubitemid 38856937)
8. v Integrin-targeted immunoconjugates regress established human tumors in xenograft models Clin. Cancer Res. 13, 3689-3695 (Pubitemid 46955133)
9. Al-Katib, A. M., Aboukameel, A., Mohammad, R., Bissery, M. C., and Zuany-Amorim, C. (2009) Superior antitumor activity of SAR3419 to Rituximab in xenograft models for non-hodgkins lymphoma Clin. Cancer Res. 15, 4038-4045
10. Johansson, C., Nilsson, O., Baeckström, D., Jansson, E. L., and Lindholm, L. (1991) Novel epitopes on the CA50-carrying antigen: chemical and immunochemical studies Tumour Biol. 12, 159-170
11. a epitope on distinct core proteins J. Biol. Chem. 266, 21537-21547 (Pubitemid 121000217)
12. Thorpe, P. E., Wallace, P. M., Knowles, P. P., Relf, M. G., Brown, A. N., Watson, G. J., Knyba, R. E., Wawrzynczak, E. J., and Blakey, D. C. (1987) New coupling agents for the synthesis of immunotoxins containing a hindered disulfide bond with improved stability in vivo Cancer Res. 47, 5924-5931 (Pubitemid 18018731)
13. Thorpe, P. E., Wallace, P. M., Knowles, P. P., Relf, M. G., Brown, A. N., Watson, G. J., Blakey, D. C., and Newell, D. R. (1988) Improved antitumor effects of immunotoxins prepared with deglycosylated Ricin A-chain and hindered disulfide linkages Cancer Res. 48, 6396-6403
14. Flavell, D. J., Boehm, D. A., Okayama, K., Kohler, J. A., and Flavell, S. U. (1994) Therapy of human T-cell acute lymphoblastic leukemia in severe combined immunodeficient mice with two different anti-CD7-saporin immunotoxins containing hindered or non-hindered disulphide cross linkers Int. J. Cancer 58, 407-414 (Pubitemid 24254652)
15. Arpicco, S., Dosio, F., Brusa, P., Crosasso, P., and Cattel, L. (1997) New coupling reagents for the preparation of disulfide cross-linked conjugates with increased stability Bioconjugate Chem. 8, 327-337 (Pubitemid 27236497)
16. Dosio, F., Arpicco, S., Adobati, E., Canevari, S., Brusa, P., De Santis, R., Parente, D., Pignanelli, P., Negri, D. R., Colnaghi, M. I., and Cattel, L. (1998) Role of cross-linking agents in determining the biochemical and pharmacokinetic properties of Mgr6-Clavin immunotoxins Bioconjugate Chem. 9, 372-381 (Pubitemid 28222908)
17. Chari, R. V., Martell, B. A., Gross, J. L., Cook, S. B., Shah, S. A., Blättler, W. A., McKenzie, S. J., and Goldmacher, V. S. (1992) Immunoconjugates containing novel maytansinoids: promising anti-cancer drugs Cancer Res. 52, 127-131
18. Widdison, W. C., Wilhelm, S. D., Cavanagh, E. E., Whiteman, K. R., Leece, B. A., Kovtun, Y., Goldmacher, V. S., Xie, H., Steeves, R. M., Lutz, R. J., Zhao, R., Wang, L., Blättler, W. A., and Chari, R. V. (2006) Semisynthetic maytansine analogues for the targeted treatment of cancer J. Med. Chem. 49, 4392-4408 (Pubitemid 44036683)
19. Hermanson, G. T. (1996) Bioconjugate Techniques, Part I, Academic Press, San Diego.
20. Furth, E. E., Thilly, W. G., Pennan, B. W., Liber, H. L., and Rand, W. M. (1981) Quantitative assay for mutation in diploid human lymphoblasts using microtiter plates Anal. Biochem. 110, 1-8 (Pubitemid 11157545)
21. Morton, D. B., Abbot, D., and Barclay, R. (1993) Removal of blood from laboratory mammals and birds Lab. Anim. 27, 1-22
22. Worrell, N. R., Cumber, A. J., Parnell, G. D., Mirza, A., Forrester, J. A., and Ross, W. C. (1986) Effect of linkage variation on pharmacokinetics of ricin A chain-antibody conjugates in normal rats Anti-Cancer Drug Des. 1, 179-188 (Pubitemid 17213510)
23. Kovtun, Y. V., Audette, C. A., Ye, Y., Xie, H., Ruberti, M. F., Phinney, S. J., Leece, B. A., Chittenden, T., Blättler, W. A., and Goldmacher, V. S. (2006) Antibody-drug conjugates designed to eradicate tumors with homogeneous and heterogeneous expression of the target antigen Cancer Res. 66, 3214-3221
24. Erickson, H. K., Widdison, W. C., Mayo, M. F., Whiteman, K., Audette, C., Wilhelm, S. D., and Singh, R. (2010) Tumor delivery and in vivo processing of disulfide linked antibody-maytansinoid conjugates Bioconjugate Chem. 21, 84-92
25. Tolcher, A. W., Ochoa, L., Hammond, L. A., Patnaik, A., Edwards, T., Takimoto, C., Smith, L., de Bono, J., Schwartz, G., Mays, T., Jonak, Z. L., Johnson, R., DeWitte, M., Martino, H., Audette, C., Maes, K., Chari, R. V., Lambert, J. M., and Rowinsky, E. K. (2003) Cantuzumab Mertansine, a maytansinoid immunoconjugate directed to the CanAg antigen: A phase I, pharmacokinetic and biologic correlative study J. Clin. Oncol. 21, 211-222 (Pubitemid 46606149)
26. Helft, P. R., Schilsky, R. L., Hoke, F. J., Williams, D., Kindler, H. L., Sprague, E., DeWitte, M., Martino, H. K., Erickson, J., Pandite, L., Russo, M., Lambert, J. M., Howard, M., and Ratain, M. J. (2004) A phase I study of Cantuzumab Mertansine administered as a single intravenous infusion once weekly in patients with advanced solid tumors Clin. Cancer Res. 10, 4363-4368 (Pubitemid 38878875)
27. Rodon, J., Garrison, M., Hammond, L. A., de Bono, J., Smith, L., Forero, L., Hao, D., Takimoto, C., Lambert, J. M., Pandite, L., Howard, M., Xie, H., and Tolcher, A. W. (2008) Cantuzumab mertansine in a three-times a week schedule: a phase I and pharmacokinetic study Cancer Chemother. Pharmacol. 62, 911-919
28. Mills, B. J. and Lang, C. A. (1996) Differential distribution of free and bound glutathione and cysteine in human blood Biochem. Pharmacol. 52, 401-406 (Pubitemid 26233582)
29. Jain, R. K. (1994) Barriers to drug delivery in solid tumours Sci. Am. 271, 59-65
30. Minchinton, A. I. and Tannock, I. F. (2006) Drug penetration in solid tumours Nat. Rev. Cancer 6, 583-592 (Pubitemid 44140857)
31. 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
32. Giles, F., Morariu-Zamfir, R., Lambert, J., Verstovsek, S., Thomas, D., Ravandi, F., and Deangelo, D. (2006) Phase I study of AVE9633, an antiCD33 maytansinoid immunoconjugate, administered as an intravenous infusion in patients with refractory/relapsed CD33 positive acute myeloid leukemia (AML). Blood (ASH Annual Meeting Abstracts) 106, Abstract 4548.
33. Ikeda, H., Hideshima, T., Fulciniti, M., Lutz, R. J., Yasui, H., Okawa, Y., Kiziltepe, T., Vallet, S., Pozzi, S., Santo, L., Perrone, G., Tai, Y. T., Cirstea, D., Raje, N. S., Uherek, C., Dälken, B., Aigner, S., Osterroth, F., Munshi, N., Richardson, P., and Anderson, K. C. (2009) The monoclonal antibody nBT062 conjugated to cytotoxic maytansinoids has selective cytotoxicity against CD138-positive multiple myeloma cells in vitro and in vivo Clin. Cancer Res. 15, 4028-4037