Antibody-directed enzyme prodrug therapy (ADEPT): A review

Advanced Drug Delivery Reviews

Volumn 26, Issue 2-3, 1997, Pages 151-172

  Niculescu Duvaz, I ^a   Springer, C J ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

ADEPT; Cancer chemotherapy; Enzyme antibody conjugates; Prodrug drug systems

Indexed keywords

ANTIBODIES; CELLS; ENZYMES; ONCOLOGY; SYNTHESIS (CHEMICAL);

ANTIBODY DIRECTED ENZYME PRODRUG THERAPY (ADEPT);

DRUG THERAPY;

ALKYLATING AGENT; AMYGDALIN; ANTHRACYCLINE; ANTIMETABOLITE; ANTINEOPLASTIC ANTIBIOTIC; CHLORMETHINE; CISPLATIN; DACTINOMYCIN; DOXORUBICIN; ENZYME; EPIRUBICIN; ETOPOSIDE; FLUOROURACIL; METHOTREXATE; MITOMYCIN; PRODRUG; RALTITREXED; TOXIN;

ANTIBODY DIRECTED ENZYME PRODRUG THERAPY; CANCER CHEMOTHERAPY; CONJUGATE; CYTOTOXICITY; DRUG TARGETING; HUMAN; NONHUMAN; PRIORITY JOURNAL; REVIEW;

EID: 0031558240     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-409X(97)00032-X     Document Type: Review

References (123)

1. M. Jarman, The development of anticancer drugs, Chem. Britain 25 (1989) 51-54.
2. K.D. Bagshawe, C.J. Springer, F. Searle, P. Antoniw, S.K. Sharma, R.G. Melton, R.F. Sherwood, A cytotoxic agent can be generated selectively at cancer sites, Br. J. Cancer 58 (1988) 700-703.
3. K.D. Bagshawe, Antibody directed enzymes revive anticancer prodrug concept, Br. J. Cancer 56 (1987) 531-532.
4. P.D. Senter, P.C.D. Su, T. Katsuragi, T. Sakai, W.L. Cosand, I. Hellström, K.E. Hellström, Generation of 5-fluorouracil from 5-fluorocytosine by monoclonal antibody-cytosine deaminase conjugates, Bioconjugate Chem. 2 (1991) 447-451.
5. P.M. Wallace, J.F. MacMaster, V.F. Smith, D.E. Kerr, P.D. Senter, W.L. Cosand, Intratumoral generation of 5-fluorouracil mediated by an antibody-cytosine deaminase conjugate in combination with 5-fluorocytosine, Cancer Res. 54 (1994) 2719-2723.
6. P.D. Senter, M.G. Saulnier, G.J. Schreiber, D.L. Hirshberg, J.P. Brown, I. Hellström, K.E. Hellström, Anti-tumor effects of antibody-alkaline phosphatase conjugates in combination with etoposide phosphate, Proc. Natl. Acad. Sci. USA 85 (1988) 4842-4846.
7. U. Sahin, F. Hartmann, P.D. Senter, C. Pohl, A. Engert, V. Dhiel, M. Pfreundschuh, Specific activation of the prodrug mitomycin phosphate by a bispecific anti-CD30/anti-alkaline phosphatase monoclonal antibody, Cancer Res. 50 (1990) 6944-6948.
8. B.M.E. Retta, P.J. Burke, A. Photiou, R.G. Melton, E. Enoamooquaye, Antibody-directed enzyme prodrug therapy (ADEPT)-evidence for a bystander effect in vitro, Int. J. Oncol. 9 (1996) 567-570.
9. K.D. Bagshawe, S.K. Sharma, C.J. Springer, P. Antoniw, Antibody-directed prodrug therapy (ADEPT): a pilot scale clinical therapy, Tumor Targeting 1 (1995) 17-29.
10. K.D. Bagshawe, S.K. Sharma, C.J. Springer, P. Antoniw, J.A. Boden, G.T. Rogers, P.J. Burke, R.G. Melton, R.F. Sherwood, Antibody-Directed Enzyme Prodrug Therapy (ADEPT): clinical report, Dis. Markers 9 (1991) 233-238.
11. K.D. Bagshawe, S.K. Sharma, C.J. Springer, P. Antoniw, G.T. Rogers, P.J. Burke, R. Melton, R. Sherwood, Antibody-enzyme conjugates can generate cytotoxic drugs from inactive precursors at tumor sites, Antibody Immunoconjugates Radiopharm. 4 (1991) 915-922.
12. H.H. Sedlacek, G. Seemann, D. Hoffmann, J. Czech, P. Lorenz, C. Kolar, K. Bosslet, Antibodies as Carriers of Cytotoxicity, Karger, Basel, 1992, pp. 208.
13. P.D. Senter, P.M. Wallace, H.P. Svensson, V.M. Vrudhula, D.E. Kerr, I. Hellström, K.E. Hellström, Generation of cytotoxic agents by targeted enzymes, Bioconjugate Chem. 4 (1993) 3-9.
14. M.P. Deonarain, A.A. Epenetos, Targeting enzymes for cancer therapy: old enzymes in new roles, Br. J. Cancer 70 (1994) 786-794.
15. C.J. Springer, I. Niculescu-Duvaz, Antibody-directed enzyme prodrug therapy (ADEPT) with mustard prodrugs, Anti-Cancer Drug Design 10 (1995) 361-372.
16. I. Niculescu-Duvaz, C.J. Springer, Antibody-directed enzyme prodrug therapy (ADEPT): a targeting strategy in chemotherapy, Curr. Med. Chem. 2 (1995) 687-706.
17. L.N. Jungheim, T.T. Shepherd, Design of antitumor pro-drugs: substrates for antibody targeted enzymes, Chem. Rev. 94 (1994) 1553-1566.
18. I. Niculescu-Duvaz, C.J. Springer, Development of prodrugs for ADEPT (antibody-directed enzyme prodrug therapy), Exp. Opin. Invest. Drugs 3 (1996) 289-308.
19. R.G. Melton, R.F. Sherwood, Antibody-enzyme conjugates for cancer therapy, J. Natl. Cancer Inst. 88 (1996) 153-165.
20. H.J. Haisma, E. Boven, M. van Muijen, J. de Jong, W.J.F. van der Vygh, H.M. Pinedo, A monoclonal antibody-β-glucuronidase conjugate as activator of the prodrug epirubicin-glucuronide for the specific treatment of cancer, Br. J. Cancer 66 (1992) 474-478.
21. P.D. Senter, H. Marquardt, A.T. Beth, B.T. Hammock, I.S. Frank, H.S. Svensson, The role of rat serum carboxylesterase in the activation of Paclitaxel and camptothecin prodrugs, Cancer Res. 56 (1996) 1471-1474.
22. P.D. Senter, Activation of prodrugs by antibody-enzyme conjugates: a new approach to cancer therapy, FASEB J. 4 (1990) 188-193.
23. D.L. Meyer, L.N. Jungheim, S.D. Mikolajczyk, T.A. Shepherd, J.J. Starling, C. Ahlem, Preparation and characterization of β-lactamase-Fab′ conjugates for the site specific activation of oncolytic agents, Bioconjugate Chem. 3 (1992) 42-48.
24. A.D. Tucker, S. Rowsell, R.G. Melton, R. Paauptit, A new crystal form of carboxypeptidase G2 from Pseudomonas sp. strain RS-16 which is more amenable to structure determination, Acta Crystallogr. Sect. D Biol. Crystallogr. D52 (1996) 890-892.
25. K. Bosslet, J. Czech, D. Hoffmann, Tumor-selective prodrug activation by fusion protein-mediated catalysis, Cancer Res. 54 (1994) 2151-2159.
26. K. Bosslet, J. Czech, G. Seeman, C. Monneret, D. Hoffmann, Fusion protein mediated prodrug activation (FMPA) in vivo, Cell Biophys. 24/25 (1994) 51-63.
27. S.C. Goshom, H.P. Svensson, D.E. Kerr, G.E. Somerville, P.D. Senter, H.P. Fell, Genetic construction, expression, and characterisation of a single chain anticarcinoma antibody fused to beta-lactamase, Cancer Res. 53 (1993) 2123-2127.
28. M.L. Rodrigues, L.G. Presta, C.E. Kotts, C. Wirth, C. Mordenti, G. Osaka, W.T. Wong, A. Nuijens, B. Blackburn, P. Carter, Development of a humanized disulfide-stabilized anti-p185HER Fv-β-lactamase fusion protein for activation of a cephalosporin doxorubicin prodrug, Cancer Res. 55 (1995) 63-70.
29. K. De Sutter, W. Fiers, A bifunctional murine: human chimeric antibody with one antigen binding arm replaced by bacterial beta-lactamase, Mol. Immunol. 31 (1994) 261-267.
30. N.P. Michael, K.A. Chester, R.G. Melton, L. Robson, W. Nicholas, G.A. Boden, R.B. Pedley, R.H.J. Begent, R.F. Sherwood, N.P. Minton, In vitro and in vivo characterization of a recombinant carboxypeptidase G2 anti-CEA scFV fusion protein, Immunotechnol. J. 2 (1996) 47-57.
31. R.K. Jain, L.T. Baxter, Mechanisms of heterogeneous distribution of monoclonal antibodies and other macromolecules in tumors: significance of elevated interstitial pressure, Cancer Res. 48 (1988) 7022-7032.
32. R.K. Jain, Physiological barriers to delivery of monoclonal antibodies and others macromolecules in tumors, Cancer Res. 50 (1990) 814s-819s.
33. E.A. Swab, J. Wei, P.M. Gullino, Diffusion and convection in normal and neoplastic tissues, Cancer Res. 34 (1974) 2814-2822.
34. V.G. Stella, K.J. Himmelstein, Prodrugs and site-specific drug delivery, J. Med. Chem. 23 (1980) 1275-1282.
35. R.K. Jain, Transport of molecules in the tumor interstitium: a review, Cancer Res. 47 (1987) 3039-3051.
36. J. Yuan, L.T. Baxter, R.K. Jain, Pharmacokinetic analysis of two-step approaches using bifunctional and enzyme-conjugate antibodies, Cancer Res. 51 (1991) 3119-3130.
37. K.D. Bagshawe, S.K. Sharma, C.J. Springer, G.T. Rogers, Antibody-Directed Enzyme Prodrug Therapy (ADEPT): a review of some theoretical, experimental and clinical aspects, Anal. Oncol. 5 (1994) 879-891.
38. C.J. Springer, CMDA, an antineoplastic prodrug, Drugs Future 18 (1993) 212-215.
39. C.J. Springer, I. Niculescu-Duvaz, A.B. Mauger, T.A. Connors, P.J. Burke, D.H. Davies, R.I. Dowell, F.T. Boyle, D.C. Blakey, R.G. Melton, in: R. Begent, A. Hamlin (Eds.), New Antibody Technology and the Emergence of Useful Cancer Therapy, The Royal Society of Medicine Press, London, 1995, pp. 75-77.
40. J. Mann, M. Haase-Held, C.J. Springer, K.D. Bagshawe, Synthesis of an N-mustard prodrug, Tetrahedron 46 (1990) 5377-5382.
41. C.J. Springer, P. Antoniw, K.D. Bagshawe, F. Searle, G.M.F. Bisset, M. Jarman, Novel prodrugs which are activated to cytotoxic alkylating agents by carboxypeptidase G2, J. Med. Chem. 33 (1990) 677-681.
42. K.D. Bagshawe, Toward generating cytotoxic agents at cancer sites, Br. J. Cancer 60 (1989) 275-281.
43. E. Frei, B.A. Teicher, S.A. Holden, Preclinical studies and clinical correlation of the effect of alkylating drugs, Cancer Res. 48 (1988) 6417.
44. R.J. Du Frain, L.G. Littlefield, J.L. Wilmer, Cyclophosphamide induced SCEs in rabbit lymphocites, Environ. Mutagen. 1 (1979) 283-289.
45. B.A. Teicher, E. Frei III, Development of alkylating agent resistant human tumor cell lines, Cancer Chemother. Pharmacol. 21 (1988) 292-298.
46. C.J. Springer, P. Antoniw, K.D. Bagshawe, D.E.V. Wilman, Comparison of half-lives and cytotoxicity of N-mesyloxyethyl- and N-chloroethyl-4-amino benzoyl compounds, products of prodrugs in antibody-directed enzyme prodrug therapy (ADEPT), Anticancer Drug Design 6 (1991) 467-479.
47. C.J. Springer, I. Niculescu-Duvaz, R.B. Pedley, Novel prodrugs of alkylating agents derived from 2-fluoro- and 3-fluoro benzoic acids for antibody-directed enzyme prodrug therapy, J. Med. Chem. 37 (1994) 2361-2370.
48. C.J. Springer, D.C. Blakey, A.G. Mauger, I. Niculescu-Duvaz, P.J. Burke, D.H. Davies, R.I. Dowell, R.M. Melton, A novel bis-iodo phenol mustard prodrug for antibody-directed enzyme prodrug therapy (ADEPT), in: Proc 11th International Hammersmith Meeting: Advances in Applications of Monoclonal Antibodies in Clinical Oncology, Lesbos, Greece, 1994, 41.
49. C.J. Springer, I. Niculescu-Duvaz, C.J. East, R.I. Dowell, D.M. Davies, P.D. Burke, R.G. Melton, D.C. Blakey, A new clinical candidate for antibody-directed enzyme prodrug therapy (ADEPT), ZD 2767, in: Proc. 8th AEK Symposium, Heidelberg, 1995.
50. C.J. Springer, K.D. Bagshawe, S.K. Sharma, F. Searle, J.A. Boden, P. Antoniw, P.J. Burke, G.T. Rogers, R.F. Sherwood, R.G. Melton, Ablation of human choriocarcinoma xenografts in nude mice by Antibody-Directed Enzyme Prodrug Therapy (ADEPT) with three novel compounds, Eur. J. Cancer 27 (1991) 1361-1366.
51. S.K. Sharma, J.A. Boden, C.J. Springer, P.J. Burke, K.D. Bagshawe, Antibody-directed prodrug therapy (ADEPT). A three-phase study in ovarian tumour xenografts, Cell Biophys. 24/25 (1994) 219-228.
52. S. Eccles, W.J. Court, G.A. Box, C.J. Dean, R.G. Melton, C.J. Springer, Regression of established breast carcinoma xenografts with antibody-directed enzyme prodrug therapy against C-erbB2 p185, Cancer Res. 54 (1994) 5171-5177.
53. P. Antoniw, C.J. Springer, K.D. Bagshawe, F. Searle, R.G. Melton, G.T. Rogers, P.J. Burke, R.F. Sherwood, Disposition of the prodrug 4-[bis(2-chloroethyl)amino]benzoyl-L-glutamic acid and its active parent drug in mice, Br. J. Cancer 62 (1990) 909-914.
54. S.K. Sharma, K.D. Bagshawe, P.J. Burke, J.A. Boden, G.T. Rogers, P. Antoniw, C.J. Springer, R.G. Melton, R.F. Sherwood, Galactosylated antibodies and antibody-enzyme conjugates in ADEPT, Cancer 73 (1994) 1114-1120.
55. I. Niculescu-Duvaz, R.B. Pedley, C.J. Springer, New prodrugs for antibody-directed enzyme prodrug therapy, Proc. UICC Int. Cancer Congr. 4 (1994) 2779-2782.
56. I. Niculescu-Duvaz, C.J. Springer, Adamantylanyloxycarbonyl: a novel protecting group for phenols carrying strongly electron-withdrawing substituents. J. Chem. Res. (Suppl.) (1994) 242-243.
57. R. Dowell, C.J. Springer, D.H. Davies, E.M. Hadley, P.J. Burke, F.T. Boyle, R.G. Melton, T.A. Connors, D.C. Blakey, A.B. Mauger, New mustards prodrugs for antibody-directed prodrug therapy: alternative to the amide link, J. Med. Chem. 39 (1996) 1100-1105.
58. C.J. Springer, R.L. Dowell, P.J. Burke, E. Hadley, D.H. Davies, D.C. Blakey, R.G. Melton, I. Niculescu-Duvaz, Optimization of alkylating agents prodrugs derived from phenol and aniline mustards: a new clinical candidate prodrug (ZD2767) for ADEPT, J. Med. Chem. 38 (1995) 5051-5065.
59. D.C. Blakey, D.H. Davies, R.I. Dowell, C.J. East, P.J. Burke, S.K. Sharma, C.J. Springer, A.B. Mauger, R.G. Melton, Anti-tumour effect of an antibody-carboxypeptidase G2 conjugate in combination with phenol mustard prodrugs, Br. J. Cancer 72 (1995) 1083-1088.
60. D.C. Blakey, C.J. Springer, A.G. Mauger, D.H. Davies, R.I. Dowell, S.J. East, P.J. Burke, R.M. Melton, Tumour regressions caused by a bisiodo-phenol mustard prodrug in antibody-directed enzyme prodrug therapy (ADEPT), in: Proc 11th International Hammersmith Meeting: Advances in Applications of Monoclonal Antibodies in Clinical Oncology, Lesbos, Greece, 1994, 42.
61. D.C. Blakey, P.D. Burke, D.H. Davies, R.I. Dowell, S.J. East, K.P. Eckersley, J.E. Fitton, J. McDaid, R.G. Melton, I. Niculescu-Duvaz, P.E. Pinder, S.K. Sharma, A.F. Wright, C.J. Springer, ZD2767, an improved system for antibody-directed enzyme prodrug therapy that results in tumor regressions in colorectal tumor xenografts, Cancer Res. 56 (1996) 3287-3292.
62. P.M. Wallace, P.D. Senter, In vitro and in vivo activities of monoclonal antibody-alkaline phosphatase conjugates in combination with phenol mustard phosphate, Bioconjugate Chem. 2 (1991) 349-352.
63. S.R. Roffler, S.M. Wang, J.W. Chern, M.Y. Yeh, E. Tung, Anti-neoplastic glucuronide prodrug treatment of human tumor cells targeted with a monoclonal antibody-enzyme conjugate, Biochem. Pharmacol. 42 (1991) 2062-2065.
64. S.M. Wang, J.W. Chern, M.Y. Yeh, J.C. Ng, E. Tung, S.R. Roffler, Specific activation of glucuronide prodrugs by antibody-targeted enzyme conjugates for cancer therapy, Cancer Res. 52 (1992) 4484-4491.
65. R.P. Alexander, N.R.A. Beeley, M. O'Driscoll, F.P. O'Neil, T.A. Millican, A.J. Pratt, F.W. Willenbrock, Cephalosporin nitrogen mustard carbamate prodrugs for 'ADEPT', Tetrahedron Lett. 32 (1991) 3269-3272.
66. H.P. Svensson, J.F. Kadow, V.M. Vrudhula, P.M. Wallace, P.D. Senter, Monoclonal antibody-β-lactamase conjugates for the activation of a cephalosporin mustard prodrug, Bioconjugate Chem. 3 (1992) 176-181.
67. H.P. Svensson, P.M. Wallace, P.D. Senter, Synthesis and characterisation of monoclonal antibody-β-lactamase conjugates, Bioconjugate Chem. 5 (1994) 262-267.
68. S. Hanessian, J. Wang, Design and synthesis of a cephalosporin-carboplatinum prodrug activatable by a β-lactamase, Can. J. Chem. 71 (1993) 896-906.
69. D.E. Kerr, G.J. Schreiber, V.M. Vrudhula, H.P. Svensson, J. Hellstrom, K.E. Hellstrom, P. Senter, Regressions and cures of melanoma xenografts following treatment with monoclonal antibody beta-lactamase conjugates in combination with anticancer prodrugs, Cancer Res. 55 (1995) 3558-3563.
70. V.M. Vrudhula, H.P. Svensson, P.D. Senter, Cephalosporin derivatives of doxorubicin as prodrugs for activation by monoclonal antibody-β-lactamase conjugates, J. Med. Chem. 38 (1995) 1380-1385.
71. L.M. Cobb, T.A. Connors, L.A. Elson, A.H. Khan, B.V.C. Mitschley, W.C.J. Ross, M.E. Whisson, 2,4-Dinitro-5-ethyl-eneiminobenzamide (CB 1954): a potent and selective inhibitor of growth of the Walker carcinoma 256, Biochem. Pharmacol. 18 (1969) 1519-1527.
72. J.J. Roberts, F. Friedlos, R.J. Knox, CB 1954 (2,4-dinitro-5-aziridinyl benzamide) becomes an DNA interstrand cross-linking agent in Walker tumour cells, Biochem. Biophys. Res. Commun. 140 (1986) 1073-1078.
73. R.J. Knox, F. Friedlos, P.J. Biggs, W.D. Fliter, M. Gaskell, P. Goddard, L. Davies, M. Jarman, Identification, synthesis and properties of 5-(aziridin-1-yl)-2-nitro-4-nitrosobenzamide, a novel DNA cross-linking agent derived from CB 1954, Biochem. Pharmacol. 46 (1993) 797-803.
74. L.C. Davies, Simple synthesis of the 5-O-benzoylriboside of 1,4-dihydronicotinic acid: a cofactor for DT diaphorase and nitroreductase enzymes, Nucleosides Nucleotides 14 (1995) 311-312.
75. H.H. Somani, D.E.V. Wilman, Novel analogues of CB 1954: their potential use in Antibody Directed Enzyme Therapy, Eur. J. Cancer 30A (1994) 9.
76. G.M. Anlezark, R.G. Melton, R.F. Sherwood, W.R. Wilson, W.A. Denny, B.D. Palmer, R.J. Knox, F. Friedlos, A. Williams, Bioactivation of dinitrobenzamide mustards by an Escherichia coli-B nitroreductase, Biochem. Pharmacol. 50 (1995) 609-618.
77. B.D. Palmer, W.R. Wilson, R.F. Anderson, M. Boyd, W.A. Denny, Hypoxia-selective antitumor agents. 14. Synthesis and hypoxic cell cytotoxicity of regioisomers of the hypoxia selective cytotoxin 5-[N,N-bis(2-chloroethyl)amino]-2,4-di-nitrobenzamide, J. Med. Chem. 39 (1996) 2518-2528.
78. A.B. Mauger, P.J. Burke, H.H. Somani, F. Friedlos, R.J. Knox, Self-immolative prodrugs: candidates for antibody-directed enzyme prodrug therapy in conjunction with a nitroreductase enzyme, J. Med. Chem. 37 (1994) 3452-3458.
79. P.L. Carl, P.K. Chakravarty, J.A. Katzenellenbogen, A novel connector linkage applicable in prodrug design, J. Med. Chem. 24 (1981) 479-480.
80. D.E. Kerr, P.D. Senter, P.D. Burnett, D.L. Hirschberg, I. Hellstrom, K.E. Hellstrom, Antibody-penicillin-V-amidase conjugates kill antigen-positive tumor cells when combined with doxorubicin phenoxyacetamide, Cancer Immunol. Immunother. 31 (1990) 202-206.
81. M.E. Maier, Design of enediyne prodrugs, Synlett (1995) 13-26
82. K.C. Nicolaou, W.M. Dai, S.C. Tsai, V.A. Estevez, W. Wrasidlo, Designed enediyne - a new class of DNA-cleaving molecules with potent and selective anticancer activity, Science 256 (1992) 1172-1178.
83. M.P. Hay, W.R. Wilson, W.A. Denny, A novel enediyne prodrug as a substrate for antibody enzyme prodrug therapy (ADEPT) using E. coli-B nitroreductase, Bioorg. Med. Chem. Lett. 5 (1995) 2829-2834.
84. U. Kuefner, U. Lohrmann, Y.D. Montejano, K.S. Vitols, F.M. Huennekens, Carboxypeptidase-mediated release of methotrexate from methotrexate-α-peptides, Biochemistry 28 (1989) 2288-2297.
85. K.S. Vitols, Y. Montejano, U. Kuefner, F.M. Huennekens, Selective citotoxicity of carboxypeptidase-activated methotrexate α-peptides, Pteridines 1 (1989) 65-70.
86. K.S. Vitols, E. Haehseler, Y. Montejano, T. Baer, F.M. Huennekens, in: H.-C. Curtius, S. Ghisla and N. Blau (Eds.), Pteridines, Walter de Gruyer, Vol. 3, Berlin, 1992, pp 125-126.
87. E. Haenseler, A. Esswein, K.J. Vitols, Y. Montejano, B.M. Mueller, R.A. Reisfeld, M.F. Huennekens, Activation of methotrexate-α-alanine by carboxypeptidase A-monoclonal antibody conjugate, Biochemistry 31 (1992) 891-897.
88. F.M. Huennekens, Tumor targeting: activation of prodrugs by enzyme-monoclonal antibody conjugates, Trends Biotechnol. 12 (1994) 234-239.
89. K.S. Vitols, B. Haag-Zeino, T. Baer, Y.D. Montejano, F.M. Huennekens, Methotrexate-α-phenylalanine: optimization of methotrexate prodrug for activation by carboxypeptidase A-monoclonal antibody, Cancer Res. 55 (1995) 478-481.
90. R.M. Laethem, T.A. Blumenkopf, M. Cory, L. Elwell, C.P. Moxham, P.H. Ray, L.M. Walton, G.K. Smith, Expression and characterization of human pancreatic preprocarboxypeptidase A2, Arch. Biochem. Biophys. 332 (1996) 8-18.
91. L.A. Wolfe, R.J. Mullin, R. Laethem, T.A. Blumenkopf, M. Cory, J.F. Miller, B.R. Keith, J. Humphries, J.K. Smith, Am. Assoc. Cancer Res. (1996) 467.
92. C.J. Springer, V. Bavetsias, A.L. Jackman, R. Kimbell, F.T. Boyle, D. Marshall, R.B. Pedley, G.M.F. Bisset, Prodrugs of thymidylate synthase inhibitors: potential for antibody directed enzyme prodrug therapy (ADEPT), Anti-Cancer Drug Design (1996) 625-636.
93. M.A. Smal, L. Dong, H.T. Cheung, Y. Asano, L. Escoffier, M. Costello et al., Activation and cytotoxicity of 2-α-aminoacyl prodrugs of methotrexate, Biochem. Pharmacol. 49 (1995) 567-574.
94. R. Abraham, N. Aman, R. Von Borstel, M. Darsley, B. Kamireddy, J. Kenten, G. Morris, R. Titmas, Conjugates of COL-1 monoclonal antibody and β-galactosidase can specifically kill tumor cells by generation of 5-flourouridine from the prodrug β-D-galactosyl-5-fluorouridine, Cell Biophys. 24/25 (1994) 127-133.
95. B.A. Chabner, in: H.M. Pinedo, D.L. Longo, B.A. Chabner (Eds.), Cancer Chemotherapy and Biological Response Modifiers, Vol. 13, Elsevier, Amsterdam, London, New York, Tokyo, 1992, pp. 69-74.
96. B.A. Chabner, in: H.M. Pinedo, D.L. Longo, B.A. Chabner (Eds.), Cancer Chemotherapy and Biological Response Modifiers, Vol. 15, Elsevier, Amsterdam, London, New York, Tokyo, 1994, pp. 58-67.
97. L.F. Liu, Topoisomerase poisons as antitumor drugs, Annu. Rev. Biochem. 58 (1989) 351-375.
98. G. Rowlinson-Busza, A. Bamias, T. Krausz, D.J. Evans, A.A. Epenetos, in: A.A. Epenetos (Ed.), Monoclonal Antibodies. Application in Clinical Oncology, Vol. 1, Chapman & Hall, London, 1991, pp. 179-184.
99. G. Rowlinson-Busza, A. Bamias, T. Krausz, D.J. Evans, A.A. Epenetos, in: A.A. Epenetos (Ed.), Monoclonal Antibodies. Application in Clinical Oncology, Vol. 2, Chapman & Hall, London, 1992, pp. 111-118.
100. H.P. Svensson, V.M. Vrudhula, J.E. Emswiler, J.F. MacMaster, W.L. Cosand, P.D. Senter, P.M. Wallace, In vitro and in vivo activities of a doxorubicin prodrug in combination with monoclonal antibody β-lactamase conjugates, Cancer Res. 55 (1995) 2357-2363.
101. P.D. Senter, H.P. Svensson, G.J. Schreiber, J.L. Rodriguez, V.M. Vrudhula, Poly(ethylene glycol)-doxorubicin conjugates containing β-lactamase-sensitive linkers, Bioconjugate Chem. 6 (1995) 389-394.
102. L.N. Jungheim, T.A. Shepherd, J.K. Kling, Synthesis of a cephalosporin-doxorubicin antitumor prodrug: a substrate for an antibody-targeted enzyme, Heterocycles 35 (1993) 339-348.
103. T.W. Hudyma, K. Bush, K. Colson, R.A. Firestone, H.D. King, Synthesis and release of doxorubicin from a cephalosporin based prodrug by a β-lactamase conjugate, Bioorg. Med. Chem. Lett. 3 (1993) 323-328.
104. D.L. Meyer, K.L. Law, J.K. Payne, S.D. Mikolajczyk, H. Zarrinmayeh, L.N. Jungheim, J.K. Kling, T.A. Shepherd, J.J. Starling, Site-specific drug activation by antibody-β-lactamase conjugates: preclinical investigation of the efficacy and toxicity of doxorubicin delivered by antibody directed catalysis, Bioconjugate Chem. 6 (1995) 440-446.
105. S. Andrianomenjanahary, X. Dong, J.C. Florent, G. Gaudel, J.P. Gesson, J.C. Jacquesy, M. Koch, S. Michel, M. Mondon, C. Monneret, P. Petit, B. Renoux, F. Tillequin, Synthesis of novel targeted pro-drugs of anthracyclines potentially activated by a monoclonal antibody galactosidase conjugate (Part 1), Bioorg. Med. Chem. Lett. 2 (1992) 1093-1096.
106. J.P. Gesson, J.C. Jacquesy, M. Mondon, P. Petit, B. Renoux, S. Andrianomenjanahary, H. Dufat-Trinh Van, M. Koch, S. Michel, F. Tillequin, J.C. Florent, C. Monneret, K. Bosslet, J. Czech, D. Hoffmann, Prodrugs of anthracyclines for chemotherapy via enzyme-monoclonal antibody conjugates, Anti-Cancer Drug Design 9 (1994) 409-423.
107. M. Azoulay, J.C. Florent, C. Monneret, G.P. Gesson, G.P. Jacquesy, F. Tillequin, M. Koch, K. Bosslet, J. Czech, D. Hoffman, Prodrugs of anthracycline antibiotics suited for tumor-specific activation, Anti-Cancer Drug Design 10 (1995) 441-450.
108. H.J. Haisma, M. Van Muijen, H.M. Pinedo, E. Boven, Comparison of two anthracycline-based produgs for activation by a monoclonal antibody-β-glucuronidase conjugate in specific treatment of cancer, Cell Biophys. 24/25 (1994) 185-192.
109. R.G.G. Leenders, H.W. Scheeren, Synthesis and evaluation of novel daunomycin-phosphate, sulfate, β-glucuronide and β-glucoside for application in ADEPT, Bioorg. Med. Chem. Lett. 5 (1995) 2975-2980.
110. V.M. Vrudhula, P.D. Senter, K.J. Fischer, P.M. Wallace, Prodrugs of doxorubicin and melphalan and their activation by a monoclonal antibody-Penicillin-G-Amidase conjugate, J. Med. Chem. 36 (1993) 919-923.
111. M.V. Vrudhula, P.D. Senter, K. Fischer, P.M. Wallace, Prodrugs of doxorubicin and melphalan and their activation by a monoclonal antibody-penicillin-G amidase conjugate, J. Med. Chem. 36 (1993) 919-923.
112. R.J. Knox, F. Friedlos, R.F. Sherwood, R.G. Melton, G.M. Anlezark, The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954). II. A comparison of an Escherichia coli nitroreductase and Walker DT-diaphorase, Biochem. Pharmacol. 44 (1992) 2297-2301.
113. P.D. Senter, G.J. Schreiber, D.L. Hirshberg, S.A. Ashe, K.E. Hellström, I. Hellström, Enhancement of the in vitro and in vivo antitumor activities of phosphorylated mitomycin C and etoposide derivatives by monoclonal antibody-alkaline phosphatase conjugates, Cancer Res. 49 (1989) 5789-5792.
114. H.J. Haisma, E. Boven, M. van Muijen, R. De Vries, H.M. Pinedo, Analysis of a conjugate between anticarcinoembryonic antigen and alkaline phosphatase for specific activation of the prodrug etoposide phosphate, Cancer Immmunol. Immunother. 34 (1992) 343-348.
115. L.N. Jungheim, T.A. Shepherd, D.L. Meyer, Synthesis of acylhydrazido-substituted cephems. Design of cephalosporin-vinca alkaloid prodrugs: substrates for an antibody-targeted enzyme, J. Org. Chem. 57 (1992) 2334-2340.
116. T.A. Shepherd, L.N. Jungheim, D.L. Meyer, J.J. Starling, A novel targeted delivery system utilizing a cephalosporin oncolytic prodrug activated by an antibody β-lactamase conjugate for the treatment of cancer, Bioorg. Med. Chem. Lett. 1 (1991) 21-26.
117. D.L. Meyer, L.N. Jungheim, K.L. Law, S.D. Mikolajczyk, T.A. Shepherd, D.G. Mackensen, S.L. Briggs, J.J. Starling, Site-specific prodrug activation by antibody-β-lactamase conjugates: regression and long-term growth inhibition by human colon carcinoma xenograft models, Cancer Res. 53 (1993) 3956-3963.
118. M.L. Rodrigues, P. Carter, C. Wirth, S. Mullins, A. Lee, B.K. Blackburn, Synthesis and β-lactamase-mediated activation of a cephalosporin-taxol prodrug, Chem. Biol. 2 (1995) 223-227.
119. G.S. Bignani, P.D. Senter, P.G. Grothaus, K.J. Fischer, T. Humphreys, P.M. Wallace, N-(4′-Hydroxyphenylacetyl)palytoxin: a palytoxin prodrug that can be activated by a monoclonal antibody-penicillin-G amidase conjugate, Cancer Res. 52 (1992) 5759-5764.
120. R.C. Werlen, M. Lankinen, K. Rose, D. Blakey, H. Shuttleworth, R. Melton, R.E. Offord, Site specific conjugation of an enzyme and an antibody fragment, Bioconjugate Chem. 5 (1994) 411-417.
121. H. Miyashita, Y. Karaki, M. Kinichi, I. Fujii, Prodrug activation via catalytic antibodies, Proc. Natl. Acad. Sci. USA 90 (1993) 5337-5340.
122. P. Wentworth, A. Datta, D. Blakey, T. Boyle, L.J. Partidge, G.M. Blackburn, Toward antibody-directed 'abzyme' therapy, ADAPT: carbamate prodrug activation by a catalytic antibody and its in vitro application to human tumor cell killing, Proc. Natl. Acad. Sci. USA 93 (1996) 799-803.
123. M.H. Vingerhoeds, H.J. Haisma, S.O. Belliot, R.H.P. Smit, D.J.A. Crommelin, G. Storm, Immunoliposomes as enzyme carriers (Immuno-Enzymosomes) for antibody-directed enzyme prodrug therapy (ADEPT): optimization of prodrug activating capacity, Pharm. Res. 13 (1996) 604-610.