Effect of linker variation on the stability, potency, and efficacy of carcinoma-reactive BR64-doxorubicin immunoconjugates

Cancer Research

Volumn 57, Issue 1, 1997, Pages 100-105

  Trail, Pamela A ^a   Willner, David ^b   Knipe, Jay ^b   Henderson, Arris J ^a   Lasch, Shirley J ^a   Zoeckler, Mary E ^b   Trailsmith, Mark D ^c   Doyle, Terrence W ^d   King, H Dalton ^b   Casazza, Anna Maria ^a   Braslawsky, Gary R ^e   Brown, Joseph ^g   Hofstead, Sandra J ^b   Greenfield, Robert S ^f   Firestone, Raymond A ^b   Mosure, Kathleen ^b   Kadow, Kathleen F ^b   Yang, Michael B ^a   Hellström, Karl Erik ^b   Hellström, Ingegerd ^b  

^a BRISTOL MYERS SQUIBB   (United States)

^b BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

^c WYETH AYERST RESEARCH   (United States)

^d Vion Pharmaceuticals Incorporated   (United States)

^e BIOGEN   (United States)

^f SymBiotech Incorporated   (United States)

^g NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY CONJUGATE; DISULFIDE; DOXORUBICIN; MONOCLONAL ANTIBODY; MONOCLONAL ANTIBODY BR 64; SULFIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIGEN EXPRESSION; ANTIGEN SPECIFICITY; ARTICLE; CARCINOMA; CHEMICAL BOND; COLORECTAL CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DISULFIDE BOND; DRUG BLOOD LEVEL; DRUG EFFICACY; DRUG POTENCY; DRUG STABILITY; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; HUMAN TISSUE; LUNG ADENOCARCINOMA; MOUSE; NONHUMAN; NUDE MOUSE; PRIORITY JOURNAL; TUMOR XENOGRAFT;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; ANTIBODIES, MONOCLONAL; ANTIGENS, NEOPLASM; COLONIC NEOPLASMS; DOXORUBICIN; DRUG SCREENING ASSAYS, ANTITUMOR; EPITOPES; FEMALE; HUMANS; IMMUNOCONJUGATES; LUNG NEOPLASMS; MICE; MICE, INBRED BALB C; MICE, NUDE; TRANSPLANTATION, HETEROLOGOUS; TUMOR CELLS, CULTURED;

EID: 0031031895     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

1. Hurwitz, E., Levy, R., Maron, R., Wilchek, M., Arnon, R., and Sela, M. The covalent binding of daunomycin and Adriamycin to antibodies with retention of both drug and antibody activities. Cancer Res., 35: 1175-1181, 1975.
2. Upeslacis, J., and Hinman, L. Chemical modification of antibodies for cancer chemotherapy. In: R. C. Allen (ed.) Annual Reports in Medicinal Chemistry, Vol. 23, pp. 151-160. San Diego, CA: Academic Press, Inc., 1988.
3. Trail, P. A., Willner, D., Lasch, S. J., Henderson, A. J., Hofstead, S. J., Casazza, A. M., Firestone, R. A., Hellström, I., and Hellström, K. E. Cure of xenografted human carcinomas by BR96-doxorubicin immunoconjugates. Science (Washington DC), 261: 212-215, 1993.
4. Trail, P. A., Willner, D., and Hellström, K. E. Site-directed delivery of anthracyclines for cancer therapy. Drug Dev. Res., 34: 196-209, 1995.
5. Goldenberg, D. M. Monoclonal antibodies in cancer detection and therapy. Am. J. Med., 94: 297-312, 1993.
6. Press, O. W., Eary, J. F., Appelbaum, F. R., Martin, P. J., Badger, C. C., Nelp, W. B., Glenn, S., Butchko, G., Fisher, D. P. B., Matthews, D. C., Fisher, L. D., and Bernstein, I. D. Radiolabeled-antibody therapy of B cell lymphoma with autologous bone marrow support. N. Engl. J. Med., 329: 1219-1268, 1993.
7. Senter, P. Activation of prodrugs by antibody-enzyme conjugates. Adv. Exp. Med. Biol., 305: 97-105, 1991.
8. Bagshawe, K. D., Sharma, S. K., Springer, C. J., and Rogers, G. T. Antibody directed enzyme prodrug therapy (ADEPT): a review of some theoretical, experimental and clinical aspects. Ann. Oncol., 5: 879-891, 1994.
9. Pastan, I. H., Willingham, M. C., and Fitzgerald, D. J. Immunotoxins. Cell, 47: 641-648, 1986.
10. Vitetta, E. S., and Thorpe, P. E. Immunotoxins containing ricin or its A chain. Semin. Cell Biol., 2: 47-58, 1991.
11. Hellström, I., Hellström, K. E., Siegall, C. B., and Trail, P. A. Immunoconjugates and immunotoxins for therapy of carcinomas. In: J. T. August, M. W. Anders, F. Murad, and J. T. Coyle (eds.), Advances in Pharmacology, Vol. 33, pp. 349-388. San Diego: Academic Press, 1995.
12. Friedman, P. N., McAndrew, S. J., Gawlak, S. L., Chace, D., Trail, P. A., Brown, J. P., and Siegall, C. B. BR96 sFv-PE40, a potent single-chain immunotoxin that selectively kills carcinoma cells. Cancer Res., 53: 334-339, 1993.
13. Starling, J. J., Maciak, R. S., Law, K. L., Hinson, N. A., Briggs, S. L., Laguzza, B. C., and Johnson, D. A. In vivo antitumor activity of a monoclonal antibody-vinca alkaloid immunoconjugate directed against a solid tumor membrane antigen characterized by heterogeneous expression and noninternalization of antibody-antigen complexes. Cancer Res., 51: 2965-2972, 1991.
14. Trail, P. A., Willner, D., Lasch, S. J., Henderson, A. J., Greenfield, R. S., King, D., Zoeckler, M. E., and Braslawsky, G. R. Antigen specific activity of carcinoma reactive BR64-Adriamycin conjugates evaluated in vitro and in human tumor xenograft models. Cancer Res., 52: 5693-5700, 1992.
15. Shih, L. B., Goldenberg, D. M., Xuan, H., Lu, W. Z. H., Mattes, M. J., and Hall, T. C. Internalization of an intact doxorubicin immunoconjugate. Cancer Immunol. Immunother., 38: 92-98, 1994.
16. Mueller, B. M., Reisfeld, R. A., Silviera, M. H., Duncan, J. D., and Wrasidlo, W. A. Pre-clinical therapy of human melanoma with morpholino-doxorubicin conjugated to a monoclonal antibody directed against an integrin of melanoma cells. Antibody Immunoconj. Radiopharm., 4: 99-106, 1991.
17. Hinman, L. M., Hamann, P. R., Wallace, R., Menendez, A. T., Durr, F. E., and Upeslacis, J. Preparation and characterization of monoclonal antibody conjugates of the calicheamicins: a novel and potent family of antitumor antibiotics. Cancer Res., 53: 3336-3342, 1993.
18. Trouet, A., Masquelier, M., Baurain, R., and Deprez-de Compeneere, D. A covalent linkage between daunorubicin and proteins that is stable in serum and reversible by lysosomal hydrolases, as required for a lysosomotropic drug-carrier conjugate: in vitro and in vivo studies. Proc. Natl. Acad. Sci. USA, 79: 626-629, 1982.
19. Dillman, R. O., Johnson, D. E., Shawler, D. L., and Koziol, J. A. Superiority of an acid-labile daunorubicin-monoclonal antibody conjugate compared to free drug. Cancer Res., 48: 6097-6102, 1988.
20. Starling, J. J., Hinson, N. A., Marder, P., Maciak, R. S., and Laguzza, B. C. Rapid internalization of antigen-immunoconjugate complexes is not required for anti-tumor activity of monoclonal antibody-drug conjugates. Antibody Immunoconj. Radiopharm., 1: 311-324, 1988.
21. Greenfield, R. S., Kaneko, T., Daues, A., Edson, M. A., Fitzgerald, K. A., Olech, L., Grattan, J. A., and Braslawsky, G. R. Evaluation in vitro of Adriamycin: immunoconjugates synthesized using an acid sensitive hydrazone linker. Cancer Res., 50: 6600-6607, 1990.
22. 67Ga-labeled antibodies using deferoxamine as a bifunctional chelate. J. Immunol. Methods, 104: 93-102, 1987.
23. Thorpe, P. E., Wallace, P. M., Knowless, P. P., Relf, M. G., Brown, A. N. F., Watson, G. J., Knyba, R. E., Wawrzynczak, E. J., and Blakey, D. C. New coupling agents for the synthesis of immunotoxins containing a hindered disulfide bond with improved stability in vivo. Cancer Res., 47: 5924-5931, 1987.
24. Morgan, A. C., Sivam, G., Beaumier, and McIntyre, R., Bjorn, M, and Abrams, P. G. Immunotoxins of Pseudomonas exotoxin A (PE): effect of linkage on conjugate yield, potency, selectivity, and toxicity. Mol. Immunol., 27: 273-282, 1990.
25. y-related cell surface antigen. Cancer Res., 50: 2183-2190, 1990.
26. y specific antibody with potent anti-tumor activity is internalized and degraded in lysosomes. Am. J. Pathol., 142: 607-622, 1993.
27. Willner, D., Trail, P. A., Hofstead, S. J., King, H. D., Lasch, S. J., Braslawsky, G. R., Greenfield, R. S., Kaneko, T., and Firestone, R. A. (6-Maleimidocaproyl)hydrazone of doxorubicin: a new derivative for the preparation of immunoconjugates of doxorubicin. Bioconj. Chem., 4: 521-527, 1993.
28. Shinozawa, S., Mimaki, Y., Araki, Y., and Oda, T. Determination of the concentration of Adriamycin and its metabolites in the serum and tissues of Ehrlich carcinoma-bearing mice by high-performance liquid chromatography. J. Chromatogr., 196: 463-469, 1980.
29. Worrell, N. R., Cumber, A. J., Parnell, G. D., Mirza, A., Forrester, J. A., and Ross, W. C. J. Effect of linkage variation on pharmacokinetics of ricin A chain-antibody conjugates in normal rats. Anti-Cancer Drug Design, 1: 179-188, 1986.
30. Peeters, J. M., Hazendonk, T. G., Beuvery, E. C., and Tesser, G. I. Comparison of four bifunctional reagents for coupling peptides to protein and the effect of the three moieties on the immunogenicity of the conjugates. J. Immunol. Methods, 120: 133-143, 1989.
31. Hurwitz, E., Wilchek, M., and Pitha, J. Soluble molecules as carriers for daunorubicin. J. Appl. Biochem., 32: 25-35, 1980.
32. Arnon, R., and Sela, M. In vitro and in vivo efficacy of conjugates of daunomycin with anti-tumor antibodies. Immunol. Rev., 62: 5-27, 1982.
33. Kaneko, T., Willner, D., Monkovic, I., Knipe, J. O., Braslawsky, G. R., Greenfield, R. S., and Vyas, D. M. New hydrazone derivatives of Adriamycin and their immunoconjugates: a correlation between acid stability and cytotoxicity. Bioconj. Chem., 2: 133-141, 1991.
34. Shen, W. C., and Ryser, J. P. cis-Aconityl spacer between daunomycin and macro-molecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. Biochem. Biophys. Res. Commun., 102, 1048-1054, 1981.
35. Yang, H. M., and Reisfeld, R. A. Doxorubicin conjugated with a monoclonal antibody directed to a human melanoma-associated proteoglycan suppresses the growth of established tumor xenografts in nude mice. Proc. Natl. Acad. Sci. USA, 85: 1189-1193, 1988.
36. Sivam, G. P., Martin, P. J., Reisfeld, R. A., and Mueller, B. M. Therapeutic Efficacy of a doxorubicin immunoconjugate in a preclinical model of spontaneous metastatic human melanoma. Cancer Res., 55: 2352-2356, 1995.