Generation of Cytotoxic Agents by Targeted Enzymes

Bioconjugate Chemistry

Volumn 4, Issue 1, 1993, Pages 3-9

  Senter, Peter D ^a   Wallace, Philip M ^a   Svensson, Hakan P ^a   Vrudhula, Vivekananda M ^a   Kerr, David E ^a   Hellström, Ingegerd ^a   Hellström, Karl Erik ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINE PHOSPHATASE; ANTINEOPLASTIC AGENT; DRUG CARRIER; ENZYME; GAMMA GLUTAMYL HYDROLASE; MONOCLONAL ANTIBODY; PRODRUG;

HUMAN; METABOLISM; REVIEW;

ALKALINE PHOSPHATASE; ANTIBODIES, MONOCLONAL; ANTINEOPLASTIC AGENTS; DRUG CARRIERS; ENZYMES; GAMMA-GLUTAMYL HYDROLASE; HUMANS; PRODRUGS;

EID: 0027357432     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc00019a001     Document Type: Review

References (76)

1. Zubrod, C. G. (1982) Principles of Chemotherapy. Cancer Med. (J. F. Holland, and E. Frei, Eds.) pp 627-632, Lea and Febiger, Philadelphia.
2. Thorpe, P. E. (1985) Antibody carriers of cytotoxic agents in cancer therapy. A review. Monoclonal Antibodies ‘84: Biological And Clinical Applications (A. Pinchera, G. Doria, F. Dammacco, and A. Bargellesi, Eds.) pp 475-506, Editrice Kurtis, Milan.
3. Vitetta, E. S., Fulton, R. J., May, T. D., Till, M., and Uhr, J. W. (1987) Redesigning nature's poisons to create anti-tumor reagents. Science 238, 1098-1104.
4. Wawrzynczak, E. J. (1991) Systemic immunotoxin therapy of cancer: advances and prospects. Br. J. Cancer 64, 624-630.
5. Pimm, M. V. (1988) Drug-monoclonal antibody conjugates for cancer therapy: potential and limitations. CRC Crit. Rev. Ther. Drug Carrier Syst. 5, 189-227.
6. Koppel, G. A. (1990) Recent advances with monoclonal antibody drug targeting for the treatment of human cancer. Bioconjugate Chem. 1, 13-23.
7. Weinstein, J. N., and van Osdol, W. (1992) Early intervention in cancer using monoclonal antibodies and other biological ligands: Micropharmacology and the “binding site barrier”. Cancer Res. 52, 2747s-2751s.
8. Del Vecchio, S., Reynolds, J. C., Carrasquillo, J. A., Blasberg, R. G., Neumann, R. D., Lotze, M. T., Bryant, G. J., Farkas, R. J., and Larson, S. M. (1989) Local distribution and concentration of intravenously injected 131I-9.2.27 monoclonal antibody in human malignant melanoma. Cancer Res. 49, 2783-2789.
9. Del Vecchio, S., Reynolds, J. C., Blasberg, R. G., Neumann, R. D., Carrasquillo, J. A., Hellström, I., and Larson, S. M. (1988) Measurement of local Mr 97,000 and 250,000 protein antigen concentration in sections of human melanoma tumor using in vitro quantitative autoradiography. Cancer Res. 48, 5475-5481.
10. Shockley, T. R., Lin, K., Nagy, J. A., Tompkins, R. G., Yarmush, M. L., and Dvorak, H. F. (1992) Spatial distribution of tumor-specific monoclonal antibodies in human melanoma xenografts. Cancer Res. 52, 367-376.
11. Jain, R. K., and Baxter, L. T. (1988) Mechanisms of heterogeneous distribution of monoclonal antibodies and other macromolecules in tumors: Significance of elevated interstitial pressure. Cancer Res. 48, 7022-7032.
12. Clauss, M. A. and Jain, R. K. (1990) Interstitial transport of rabbit and sheep antibodies in normal and neoplastic tissues. Cancer Res. 50, 3487-3492.
13. Mimnaugh, E. G., Dusre, L., Atwell, J., and Myers, C. E. (1989) Differential oxygen radical susceptibility of adriamycinsensitive and -resistant MCF-7 human breast tumor cells. Cancer Res. 49, 8-15.
14. Sartorelli, A. C. (1986) The role of mitomycin antibiotics in the chemotherapy of solid tumors. Biochem. Pharmacol. 35, 67-69.
15. Oberley, L. W., Lindgren, L. A., Baker, S. A., and Stevens, R. H. (1976) Superoxide ion as the cause of the oxygen effect. Radiat. Res. 68, 320-328.
16. Rossi, F. (1986) The O2-forming NADPH oxidase of the phagocytes: nature, mechanisms of activation and function. Biochim. Biophys. Acta 853, 69-89.
17. Philpott, G. W., Shearer, W. T., Bower, R. W., and Parker, C. W. (1973) Selective cytotoxicity of hapten-substituted cells with an antibody-enzyme conjugate. J. Immunol. III, 921-929.
18. Stanislawski, M., Rousseau, V., Goavec, M., and Ito, H. (1989) Immunotoxins containing glucose oxidase and lactoperoxidase with tumoricidal properties: in vitro killing effectiveness in a mouse plasmacytoma cell model. Cancer Res. 49, 5497-5504.
19. Muzykantov, V. R., and Danilov, S. M. (1991) Glucose oxidase conjugated with anti-endothelial monoclonal antibodies: in vitro and in vivo studies. Int. J. Radiat. Biol. 60, 11-15.
20. Ito, H., Morizet, J., Coulombel, L., Goavec, M., Rousseau, V., Bernard, A., and Stanislawski, M. (1989) An immunotoxin system intended for bone marrow purging composed of glucose oxidase and lactoperoxidase coupled to monoclonal antibody 097. Bone Marrow Transplant. 4, 519-527.
21. Ito, H., Morizet, J., Coulombel, L., and Stanislawski, M. (1990) T cell depletion of human bone marrow using an oxidaseperoxidase enzyme immunotoxin. Bone Marrow Transplant. 6, 395-398.
22. Kuppusamy, P., and Zweier, J. L. (1989) Characterization of free radical generation by xanthine oxidase. J. Biol. Chem. 264, 9880-9884.
23. Britigan, B. E., Pou, S., Rosen, G. M., Lilleg, D. M., and Buettner, G. R. (1990) Hydroxyl radical is not a product of the reaction of xanthine oxidase and xanthine. J. Biol. Chem. 265, 17533-17538.
24. Battelli, M. G., Abbondanza, A., Tazzari, P. L., Dinota, A., Rizzi, S., Grassi, G., Gobbi, M., and Stirpe, F. (1988) Selective cytotoxicity of an oxygen-radical-generating enzyme conjugated to a monoclonal antibody. Clin. Exp. Immunol. 73, 128- 133.
25. Dinota, A., Tazzari, P. L., Abbondanza, A., Battelli, M. G., Gobbi, M., and Stirpe, F. (1990) Bone marrow purging by a xanthine oxidase-antibody conjugate. Bone Marrow Transplant. 6, 31-36.
26. Muzykantov, V. R., Sakharov, D. V., Sinitsyn, V. V., Domogatsky, S. P., Goncharov, N. V., and Danilov, S. M. (1988) Specific killing of human endothelial cells by antibodyconjugated glucose oxidase. Anal. Chem. 169, 383-389.
27. Muzykantov, V. R., Trubetskaya, O. V., Puchnina, E. A., Sakharov, D. V., and Domogatsky, S. P. (1990) Cytotoxicity of glucose oxidase conjugated with antibodies to target cells: Killing efficiency depends on the conjugate internalization. Biochim. Biophys. Acta 1053, 27-31.
28. Basch, R. S., Lakow, E., Teng, M., and Buxbaum, J. N. (1984) Isolation of highly malignant Thy- 1-positive revertants from cultured cloned Thy-l-negative lymphoma cells of low tumorigenicity. Somatic Cell Mol. Genet. 10, 37-44.
29. Sakharov, D. V., Muzykantov, V. R., Domogatsky, S. P., and Danilov, S. M. (1987) Protection of cultured endothelial cells from hydrogen peroxide-induced injury by antibodyconjugated catalase. Biochim. Biophys. Acta 930, 140-144.
30. Wilman, D. E. V. (1986) Prodrugs in cancer chemotherapy. Biochem. Soc. Trans. 14, 375-382.
31. Denny, W. A. (1988) New directions in the design and evaluation of anti-cancer drugs. Drug Des. Del. 3, 99-124.
32. Conners, T. A. (1986) Prodrugs in cancer chemotherapy. Xenobiotica 16, 975-988.
33. Senter, P. D. (1990) Activation of prodrugs by antibodyenzyme conjugates: A new approach to cancer therapy. FASEB 4, 188-193.
34. Senter, P. D., Saulnier, M. G., Schreiber, G. J., Hirschberg, D. L., Brown, J. P., Hellström, I., and Hellström, K. E. (1988) Anti-tumor effects of antibody-alkaline phosphatase conjugates in combination with etoposide phosphate. Proc. Natl. Acad. Sci. U.S.A. 85, 4842-4846.
35. Senter, P. D., Schreiber, G. J., Hirschberg, D. L., Ashe, S. A., Hellström, K. E., and Hellström, I. (1989) Enhancement of the in vitro and in vivo antitumor activities of phosphorylated mitomycin c and etoposide derivatives by monoclonal antibodyalkaline phosphatase conjugates. Cancer Res. 49, 5789-5792.
36. Haisma, H. J., Boven, E., van Muijen, M., De Vries, R., and Pinedo, H. M. (1992) Analysis of a conjugate between anticarcinoembryonic antigen monoclonal antibody and alkaline phosphatase for specific activation of the prodrug etoposide phosphate. Cancer Immunol. Immunother. 34, 343-348.
37. Wallace, P. M., and Senter, P. D. (1991) In vitro and in vivo activities of monoclonal antibody-alkaline phosphatase conjugates in combination with phenol mustard phosphate. Bioconjugate Chem. 2, 349-352.
38. Sahin, U., Hartmann, F., Senter, P., Pohl, C., Engert, A., Diehl, V., and Pfreundschuh, M. (1990) Specific activation of the prodrug mitomycin phosphate by a bispecific anti-CD30/anti-alkaline phosphatase monoclonal antibody. Cancer Res. 50, 6944-6948.
39. Bagshawe, K. D., Springer, C. J., Searle, F., Antoniw, P., Sharma, S. K., Melton, R. G., and Sherwood, R. F. (1988) A cytotoxic agent can be generated selectively at cancer sites. Br. J. Cancer 58, 700-703.
40. Springer, C. J., Antoniw, P., Bagshawe, K. D., Searle, F., Bisset, G. M. F., and Jarman, M. (1990) Novel prodrugs which are activated to cytotoxic alkylating agents by carboxypeptidase G2. J. Med. Chem. 33, 677-681.
41. Springer, C. J., Bagshawe, K. D., Sharma, S. K., Searle, F., Boden, J. A., Antoniw, P., Burke, P. J., Rogers, G. T., Sherwood, R. F., and Melton, R. G. (1991) Ablation of human choriocarcinoma xenografts in nude mice by antibody-directed enzyme prodrug therapy (ADEPT) with three novel compounds. Eur. J. Cancer 27, 1361-1366.
42. Antoniw, P., Springer, C. J., Bagshawe, K. D., Searle, F., Melton, R. G., Rogers, G. T., Burke, P. J., and Sherwood, R. F. (1990) Disposition of the prodrug 4-(bis(2-chloroethyl)- amino)benzoyl-L-glutamic acid and its active parent drug in mice. Br. J. Cancer 62, 909-914.
43. Sharma, S. K., Bagshawe, K. D., Burke, P. J., Boden, R. W., and Rogers, G. T. (1990) Inactivation and clearance of an anti- CEA carboxypeptidase G2 conjugate in blood after localisation in a xenograft model. Br. J. Cancer 61, 659-662.
44. Sharma, S. K., Bagshawe, K. D., Springer, C. J., Burke, P. J., Rogers, G. T., Boden, J. A., Antoniw, P., Melton, R. G., and Sherwood, R. F. (1991) Antibody directed enzyme prodrug therapy (ADEPT): A three phase system. Dis. Markers 9, 225-231.
45. Williams, C., Buskard, N., and Bussel, J. (1990) Plasma exchange in idiopathic thrombocytopenic purpura. Curr. Stud. Hematol. Blood. Transfus. 57, 131-151.
46. Sinitsyn, V. V., Mamontova, A. G., Checkneva, Y. Y., Shnyra, A. A., and Domogatsky, S. P. (1989) Rapid blood clearance of biotinylated lgG after infusion of avidin. J. Nucl. Med. 30, 66-69.
47. Kerr, D. E., Senter, P. D., Burnett, W. V., Hirschberg, D. L., Hellström, I., and Hellström, K. E. (1990) Antibodypenicillin-V-amidase conjugates kill antigen-positive tumor cells when combined with doxorubicin phenoxyacetamide. Cancer Immunol. Immunother. 31, 202-206.
48. Haenseler, E., Esswein, A., Vitols, K. S., Montejano, Y., Mueller, B. M., Reisfeld, R. A., and Huennekens, F. M. (1992) Activation of methotrexate-α-alanine by carboxypeptidase A-monoclonal antibody conjugate. Biochemistry 31, 891-897.
49. Kuefner, U., Lohrmann, U., Montejano, Y. D., Vitols, K. S., and Huennekens, F. M. (1989) Carboxypeptidase-mediated release of methotrexate from methotrexate-α-peptides. Biochemistry 28, 2288-2297.
50. Esswein, A., Hanseler, E., Montejano, Y., Vitols, K. S., and Huennekens, F. M. (1991) Construction and chemotherapeutic potential of carboxypeptidase-A/monoclonal antibody conjugate. Ado. Enzyme Regul. 31, 3-12.
51. Senter, P. D., Su, P. C. D., Katsuragi, T., Sakai, T., Cosand, W. L., Hellström, I., and Hellström, K. E. (1991) Generation of 5-fluorouracil from 5-fluorocytosine by monoclonal antibodycytosine deaminase conjugates. Bioconjugate Chem. 2, 447-451.
52. Rowlinson-Busza, G., Bamias, A., Krausz, T., and Epenetos, A. A. (1992) Antibody-guided enzyme nitrile therapy (Agent): in vitro cytotoxicity and in vivo tumour localisation. Monoclonal Antibodies. Applications in Clinical Oncology, (A. A. Epenetos, Ed.) Chapman and Hall, London.
53. Roffler, S. R., Wang, S.-M., Chem. J.-W., Yeh, M.-Y., and Tung, E. (1991) Anti-neoplastic glucuronide prodrug treatment of human tumor cells targeted with a monoclonal antibodyenzyme conjugate. Biochem. Pharmacol. 42, 2062-2065.
54. Wang, S.-M., Chern, J.-W., Yeh, M.-Y., Ng, J. C., Tung, E., and Roffler, S. R. (1992) Specific activation of glucuronide prodrugs by antibody-targeted enzyme conjugates for cancer therapy. Cancer Res. 52, 4484-4491.
55. Alexander, R. P., Beeley, N. R. A., O'Driscoll, M., O'Neill, F. P., Millican, T. A., Pratt, A. J., and Willenbrock, F. W. (1991) Cephalosporin nitrogen mustard carbamate prodrugs for “ADEPT”. Tetrahedron Letts. 32, 3269-3272.
56. Svensson, H. P., Kadow, J. F., Vrudhula, V. M., Wallace, P. M., and Senter, P. D. (1992) Monoclonal antibody-β- lactamase conjugates for the activation of a cephalosporin mustard prodrug. Bioconjugate Chem. 3, 176-181.
57. Bignami, G. S., Senter, P. D., Grothaus, P. G., Fischer, K. J., Humphreys, T., and Wallace, P. M. (1992) N-(4′-Hydroxyphenylacetyl)palytoxin: A palytoxin prodrug that can be activated by a monoclonal antibody-penicillin-G amidase conjugate, Cancer Res., in press.
58. Bock, K. W. (1991) Roles of UDP-glucuronosyltransferases in chemical carcinogenisis. Crit. Reo. Biochem. Mol. Biol. 26, 129-150.
59. Shepherd, T. A., Jungheim, L. N., Meyer, D. L., and Starling, J. J. (1991) A novel targeted delivery system utilizing a cephalosporinoncolytic prodrug activated by an antibody β-lactamase conjugate for the treatment of cancer. Bioorg. Med. Chem. Letts. 1, 21-26.
60. Meyer, D. L., Jungheim, L. N., Mikolajczyk, S. D., Shepherd, T. A., Starling, J. J., and Ahlem, C. (1992) Preparation and characterization of β-lactamase-Fab′ conjugates for the site specific activation of oncolytic agents. Bioconjugate Chem. 3, 42-48.
61. Jungheim, L. N., Shepherd, T. A., and Meyer, D. L. (1992) Synthesis of acylhydrazido-substituted cephems. Design of cephalosporin-vinca alkaloid prodrugs: Substrates for an antibody-targeted enzyme. J. Org. Chem. 57, 2334-2340.
62. Byers, V. S., Rodvien, R., Grant, K., Durrant, L. G., Hudson, K. H., Baldwin, R. W., and Scannon, P. J. (1989) Phase I study of monoclonal antibody-ricin A chain immunotoxin XomaZyme-791 in patients with metastatic colon cancer. Cancer Res. 49, 6153-6160.
63. Oratz, R., Speyer, J. L., Wernz, J. C., Hochster, H., Meyers, M., Mischak, R., and Spitler, L. E. (1990) Anti-melanoma monoclonal antibody-ricin A chain immunoconjugate (XMMME-001-RTA) plus cyclophosphamide in the treatment of metastatic malignant melanoma: Results of a phase II trial. J. Biol. Respons. Mod. 9, 345-354.
64. Bagshawe, K. D., Sharma, S. K., Springer, C. J., Antoniw, P., Rogers, G. T., Burke, P. J., Melton, R., and Sherwood, R. (1991) Antibody-enzyme conjugates can generate cytoxic drugs from inactive precursors at tumor sites. Antibody Imm. Radiopharm. 4, 915-922.
65. Lederman, J. A., Begent, R. H. J., Bagshawe, K. D., Riggs, S. J., Searle, F., Glaser, M. G., Green, A. J., and Dale, R. G. (1988) Repeated anti-tumor antibody therapy in man with suppression of the host response by cyclosporin A. Br. J. Cancer 58, 654-657.
66. Pai, L. H., Fitzgerald, D. J., Tepper, M., Schacter, B., Spitalny, G., and Pastan, I. (1990) Inhibition of antibody response to Pseudomonas exotoxin and an immunotoxin containing Pseudomonas exotoxin by 15-deoxyspergualin in mice. Cancer Res. 50, 7750-7753.
67. Sehon, A. H. (1989) Modulation of antibody responses by conjugates of antigens with monomethoxypolyethylene glycol. Adv. Exp. Med. Biol. 251, 341-351.
68. Schultz, P. G., Lerner, R. A., and Benkovic, S. J. (1990) Catalytic antibodies. Chem. Eng. News 68, May 28, 26-40.
69. Brinkley, M. (1992) A brief survey of methods for preparing protein conjugates with dyes, haptens, and cross-linking reagents. Bioconjugate Chem. 3, 2-13.
70. Dewerchin, M., and Collen, D. (1991) Enhancement of the thrombolytic potency of plasminogen activators by conjugation with clot-specific monoclonal antibodies. Bioconjugate Chem. 2, 293-300.
71. Hayzer, D. J., Lubin, I. M., and Runge, M. S. (1991) Conjugation of plasminogen activators and fibrin-specific antibodies to improve thrombolytic therapeutic agents. Bioconjugate Chem. 2, 301-308.
72. Haber, E., Quertermous, T., Matsueda, G. R., and Runge, M. S. (1989) Innovative approaches to plasminogen activator therapy. Science 243, 51-56.
73. Bosslet, K., Czech, J., Lorenz, P., Sedlacek, H. H., Schuermann, M., and Seemann, G. (1992) Molecular and functional characterisation of a fusion protein suited for tumour specific prodrug activation. Br. J. Cancer 65, 234-238.
74. Yuan, F., Baxter, L. T., and Jain, R. K. (1991) Pharmacokinetic analysis of two-step approaches using bifunctional and enzyme-conjugated antibodies. Cancer Res. 51, 3119-3130.
75. Sowek, J. A., Singer, S. B., Ohringer, S., Malley, M. F., Dougherty, T. J., Gougoutas, J. Z., and Bush, K. (1991) Substitution of lysine at position 104 or 240 of TEM-pTZ18R β-lactamase enhances the effect of serine-164 substitution on hydrolysis or affinity for cephalosporins and the monobactam aztreonam. Biochemistry 30, 3179-3188.
76. Dube, D. K. and Loeb, L. A. (1989) Mutants generated by the insertion of random oligonucleotides into the active site of the β-lactamase gene. Biochemistry 28, 5703-5707.