Folate-targeted enzyme prodrug cancer therapy utilizing penicillin-V amidase and a doxorubicin prodrug

Journal of Drug Targeting

Volumn 7, Issue 1, 1999, Pages 43-53

  Lu, J Y ^a   Lowe, D A ^b   Kennedy, M D ^a   Low, P S ^a  

^a PURDUE UNIVERSITY   (United States)

^b BRISTOL MYERS SQUIBB COMPANY   (United States)

Author keywords

Doxorubicin; Enzyme prodrug therapy; Folate targeting; Penicillin V amidase

Indexed keywords

AMIDASE; CELL RECEPTOR; DOXORUBICIN; DOXORUBICIN DERIVATIVE; DOXORUBICIN N 4 HYDROXYPHENOXYACETAMIDE; FOLATE RECEPTOR; FOLIC ACID; IODINE 125; PENICILLIN V AMIDASE; PRODRUG; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CANCER CHEMOTHERAPY; CANCER THERAPY; CELL DEATH; CELL KILLING; CELL STRAIN KB; CONTROLLED STUDY; COVALENT BOND; DRUG CLEARANCE; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG POTENCY; DRUG TARGETING; DRUG TRANSFORMATION; HUMAN; HUMAN CELL; INTRAVENOUS DRUG ADMINISTRATION; ISOTOPE LABELING; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; TUMOR CELL;

EID: 0032873312     PISSN: 1061186X     EISSN: None     Source Type: Journal    
DOI: 10.3109/10611869909085491     Document Type: Article

References (53)

1. Antony, A.C., Kane, M.A., Portillo, R.M., Elwood, P.C. and Kolhouse, J.F. (1985) Studies of the role of a particulate folate-binding protein in the uptake of 5-methyltetrahydrofolate by cultured human KB cells. J. Biol. Chem., 260, 14911-14917.
2. Blakey, D.C., Burke, P.J., Davies, D.H., Dowell, R.I., Melton, R.G., Springer, C.J. and Wright, A.F. (1995) Antibody-directed enzyme prodrug therapy (ADEPT) for treatment of major solid tumor disease. Biochem. Soc. Trans., 23, 1047-1050.
3. Blakey, D.C., Burke, P.J., Davies, D.H., Dowell, R.I., East, S.J., Eckersley, K.P., Fitton, J.E., McDaid, J., Melton, R.G., Niculescu-Duvaz, I.A., Pinder, P.E., Sharma, S.K., Wright, A.F. and Springer, C.J. (1996) ZD2767, an improved system for antibody-directed enzyme prodrug therapy that results in tumor regressions in colorectal tumor xenografts. Cancer Res., 56, 3287-3292.
4. Calabresi, P. and Welch, A.D. (1994) Cytotoxic drugs, hormones and radioactive isotopes. In: L.S. Goodman and A. Gilman (Eds.), The Pharmacological Basis of Therapeutics (New York: Macmillan), pp. 1345-1393.
5. Cheng, T.-L., Chen, B.-M., Chan, L.-Y., Wu, P.-Y., Chern, J.-W. and Roffler, S.R. (1997) Poly(ethylene glycol) modification of β-glucuronidase-antibody conjugates for solid-tumor therapy by targeted activation of glucuronide prodrugs. Cancer Immunol. Immunother., 44, 305-315.
6. Chester, K.A. and Hawkins, R.E. (1996) Opportunities with phage technology and antibody engineering of fusion proteins. Adv. Drug Deliv. Rev., 22, 303-313.
7. Coney, L.R., Tomaselti, A., Carayannopoulos, L., Frasca, V., Kamen, B.A., Colnaghi, M.I. and Zurawski, V.R.J. (1991) Cloning of a tumor-associated antigen: MOv18 and MOv19 antibodies recognize a folate-binding protein. Cancer Res., 51, 6125-6132.
8. Eccles, S.A., Court, W.J., Box, G.A., Dean, C.J., Melton, R.G. and Springer, C.J. (1994) Regression of established breast carcinoma xenografts with antibody-directed enzyme prodrug therapy against c-erbB2 p185. Cancer Res., 54, 5171-5177.
9. Froesch, B.A., Stahel, R.A. and Zangemeister-Wittke, U. (1996) Preparation and functional evaluation of new doxorubicin immunoconjugates containing an acid-sensitive linker on small-cell lung cancer cells. Cancer Immunol. Immunother., 42, 55-63.
10. Garin-Chesa, P., Campbell, I., Saigo, P.E., Lewis, J.L.J., Old, L.I. and Rettig, W.J. (1993) Trophoblast and ovarian cancer antigen LK26. Sensitivity and specificity in immunopathology and molecular identification as a folate-binding protein. Am. J. Pathol., 142, 557-567.
11. Hortobagyi, G.N. (1997) Anthracyclines in the treatment of cancer. An overview. Drugs. 54 Suppl. 4, 1-7.
12. Houba, P.H.J., Boven, E. and Haisma, H.J. (1996) Improved characteristics of a human β-glucuronidase-antibody conjugate after deglycosylation for use in antibody-directed enzyme prodrug therapy. Bioconjug. Chem., 7, 606-611.
13. Kaneo, Y., Uemura, T., Tanaka, T. and Kanoh, S. (1997) Polysaccharides as drug carriers: biodisposition of fluorescein-labeled dextrans in mice. Biol. Pharm. Bull., 20(2), 181-187.
14. Kerr, D.E., Schreiber, G.J., Vrudhula, V.M., Svensson, H.P., Hellström, I., Hellström, K.E. and Senter, P.D. (1995) Regression and cures of melanoma xenografts following treatment with monoclonal antibody β-lactamase conjugates in combination with anticancer prodrugs. Cancer Res., 55, 3558-3563.
15. Kerr, D.E., Senter, P.D., Burnett, W.V., Hirschberg, D.L., Hellström, I. and Hellström, K.E. (1990) Antibody-penicillin-V-amidase conjugates kill antigen-positive tumor cells when combined with doxorubicin phenoxyacetamide. Cancer Immunol. Immunother., 31, 202-206.
16. Laemmli, U.K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature, 277, 680-685.
17. Leamon, C.P. and Low, P.S. (1991a) Cytotoxicity of momordin-folate conjugates in cultured human cells. J. Biol. Chem., 267, 24966-24971.
18. Leamon, C. and Low, P.S. (1991b) Delivery of macromolecules into living cells: a method that exploits folate receptor endocytosis. Pro. Natl. Acad. Sci. USA, 88, 5572-5576.
19. Lee, R.J. and Low, P.S. (1995) Folate-mediated tumor cell targeting of liposome-entrapped doxorubicin in vitro. Biochem. Biophys. Acta, 1233, 134-144.
20. Lowe, D.A., Romancik, G. and Elander, R.P. (1980) Penicillin acylases: a review of existing enzymes and the isolation of a new bacterial penicillin V acylase. Dev. Ind. Microbiol., 22, 163-180.
21. Lowe, D.A., Romancik, G. and Elander, R.P. (1986) Enzymatic hydrolysis of penicillin V to 6-aminopenicillanic acid by Fusarium Oxysporum. Biotechnol. Lett., 3, 151-156.
22. Mantovani, L.T., Miotti, S., Ménard, S., Canevari, S., Raspagliesi, F., Bottini, C. Bottero, F. and Colnaghi, M.I. (1994) Folate binding protein distribution in normal tissues and biological fluids from ovarian carcinoma patients as detected by the monoclonal antibodies MOv18 and MOv19. Eur. J. Cancer, 30A(3), 363-369.
23. Martin, J., Stribbling, S.M., Poon, G.K., Begent, R.H.J., Napier, M., Sharma, S.K. and Springer, C.J. (1997) Antibody-directed enzyme prodrug therapy: pharmacokinetics and plasma levels of prodrug and drug in a phase I clinical trial. Cancer Chemother. Pharmacol.,40, 189-201.
24. Mathias, C.J., Wang, S., Waters, D.J., Turek, J.J., Low, P.S. and Green, M.A. (1998) Indium-111-DTPA-folate as a potential folate-receptor-targeted radiopharmaceutical. J. Nucl. Med., 39, 1579-1585.
25. McHugh, M. and Chang, Y.C. (1979) Demonstration of a high affinity folate binder in human cell membrane and its characterization in cultured human KB cells. J. Biol. Chem., 254, 11312-11318.
26. Melton, R.G. and Sherwood. R.F. (1996) Antibody-enzyme conjugates for cancer therapy. J. Natl. Cancer Inst., 88, 153-165.
27. Meyer, D.L., Law, K.L., Payne, J.K., Mikolajczyk, S.D., Zarrinmayeh, H., Jungheim, L.N., Kling, J.K., Shepherd, T.A. and Starling, J.J. (1995) Site-specific prodrug activation by antibody-β-lactamase conjugates: preclinical investigation of the efficacy and toxicity of doxorubicin delivered by antibody directed catalysis. Bioconjug. Chem., 6, 440-446.
28. Milhaud, P.G., Machy, P., Lebleu, B. and Leserman, L. (1989) Antibody targeted liposomes containing poly(rI).poly(rC) exert a specific antiviral and toxic effect on cells primed with interferons alpha/beta or gamma. Biochim. Biophys. Acta, 987(1), 15-20.
29. Murray, J.C. and Carmichael. J. (1995) Targeting solid tumors: challenges, disappointments, and opportunities. Adv. Drug Deliv. Rev., 17, 117-127.
30. Noguchi, Y., Wu, J., Duncan, R., Strohalm, J., Ulbrich, K., Akaike, T. and Maeda, H. (1998) Early phase tumor accumulation of macromolecules: a great difference in clearance rate between tumor and normal tissues. Jpn. J. Cancer Res., 89, 307-314.
31. Panchal, R.G. (1998) Novel therapeutic strategies to selectively kill cancer cells. Biochem. Pharmacol., 55, 247-252.
32. Patrick, T.A., Kranz, D.M., van Dyke, T.A. and Roy, E.J. (1997) Folate receptors as potential therapeutic targets in choroid plexus tumors of SV40 transgenic mice. J. Neurooncol., 32, 111-123.
33. Perron, M.-J. and Page, M. (1996) Activation of methotrexate-phenylalanine by monoclonal antibody-carboxypeptidase A conjugate for the specific treatment of ovarian cancer in vitro. Br. J. Cancer, 73, 281-287.
34. Reddy, J.A. and Low, P.S. (1998) Folate-mediated targeting of therapeutic and imaging agents to cancers. Crit. Rev. Ther. Drug Deliv. Syst., 15, 587-627.
35. HER2 Fv-β-lactamase fusion protein for activation of a cephalosporin doxorubicin prodrug. Cancer Res., 55, 63-70.
36. Ross, J.F., Chaudhuri, P.K. and Ratnam, M. (1994) Differential regulation of folate receptor isoforms in normal and malignant tissues in vivo and in established cell lines. Physiologic and clinical implications. Cancer, 73, 2432-2443.
37. Senter, P.D. and Svensson, H.P. (1996) A summary of monoclonal antibody-enzyme/prodrug. Adv. Drug Deliv. Rev., 22, 341-349.
38. Sharma, S.K. (1996) Immune response in ADEPT. Adv. Drug Deliv. Rev., 22, 369-376.
39. Sherwood, R. F. (1996) Advanced drug delivery reviews: enzyme prodrug therapy. Adv. Drug Deliv. Rev., 22, 269-288.
40. Smith, G.K., Banks, S., Blumenkopf, T.A., Cory, M., Humphreys, J., Laethem, R.M., Miller, J., Moxham, C.P., Mullin, R., Ray, P.H., Walton, L.M. and Wolfe III, L.A. (1997) Toward antibody-directed enzyme prodrug therapy with the T268G mutant of human carboxypeptidase Al and novel in vivo stable prodrugs of methotrexate. J. Biol. Chem., 272, 15804-15816.
41. Springer, C.J., Bavetsias, V., Jackman, A.L., Boyle, F.T., Marshall, D., Pedley, R.B. and Bisset, G.M.F. (1996) Prodrugs of thymidylate synthase inhibitors: potential for antibody directed enzyme prodrug therapy (ADEPT). Anti-Cancer Drug Des., 11, 625-636.
42. Stribbling, S.M., Martin, J., Pedley, R.B., Boden, J.A., Sharma, S.K. and Springer, C.J. (1997) Biodistribution of an antibody -enzyme conjugate for antibody-directed enzyme prodrug therapy in nude mice bearing a human colon adenocarcinoma xenograft. Cancer Immunol. Immunother., 40, 277-284.
43. Svensson, H.P., Vrudhula, V.M., Emswiler, J.E., MacMaster, J.F., Cosand, W.L., Senter, P.D. and Wallace, P.M. (1995) In vitro and in vivo activities of a doxorubicin prodrug in combination with monoclonal antibody β-lactamase conjugates. Cancer Res., 55, 2357-2365.
44. Takakura, Y., Fujita, T., Hashida, M. and Sezaki, H. (1990) Disposition characteristics of macromolecules in tumor-bearing mice. Pharm. Res., 7, 339-346.
45. Thoren, L. (1980) The dextrans - clinical data. Dev. Biol. Stand., 48, 157-167.
46. Vitols, K.S., Haag-Zeino, B., Baer, T., Montejano, Y.D. and Huennekens, F.M. (1995) Methotrexate-α-phenylalanine: optimization of methotrexate prodrug for activation by carboxypeptidase A-monoclonal antibody conjugate. Cancer Res., 55, 478-481.
47. Vrudhula, V.M., Senter, P.D., Fischer, K.J. and Wallace, P.M. (1993) Prodrugs of doxorubicin and melphalan and their activation by a monoclonal antibody-penicillin-G amidase conjugate. J. Med. Chem. 36, 919-923.
48. 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. Bioconjug. Chem., 2, 349-352.
49. Wang, S.-M., Chern, J.-W., Yeh, M.-Y., Co Ng, J., Tung, E. and Roffler, S.R. (1992) Specific activation of glucuronide by antibody-targeted enzyme prodrug conjugates for cancer therapy. Cancer Res., 52, 4484-4491.
50. Wang, S., Lee, R.J., Cauchon, G., Gorenstein, D.G. and Low, P.S. (1995) Delivery of antisense oligodeoxyribonucleotides against the human epidermal growth factor receptor into cultured KB cells with liposomes conjugated to folate via polyethylene glycol. Proc. Natl. Acad. Sci. USA, 92, 3318-3322.
51. 111In]DTPA-folate for use as a tumor-targeted radiopharmaceutical. Bioconjug., 8, 673-679.
52. Weitman, S.D., Lark, R.H., Coney, L.R., Fort, D.W., Frasca, V., Zurawski, V.R.J. and Kamen, B.A. (1992a) Distribution of the folate receptor GP38 in normal and malignant cell lines and tissues. Cancer Res., 52, 3396-3401.
53. Weitman, S.D., Weinberg, A.G., Coney, L.R., Zurawski, V.R., Jennings, D.S. and Kamen, B.A. (1992b) Cellular localization or the folate receptor: potential role in drug toxicity and folate homeostasis. Cancer Res., 52, 6708-6711.